The Sales Hiring Playbook

Before building Close, we ran an outsourced sales business. We helped startups develop their sales efforts, which gave us firsthand experience hiring and coaching reps for different sales motions.

Think Amazon AWS for Sales.

Our mission was simple: never again should a great company fail because of a lack of sales.

We started hiring top sales talent, opening offices and signing up clients within the first few weeks. It was clear that there was massive demand for this service out there. Much more than we were capable of handling at the time. We didn’t have a huge sales team with hundreds of reps readily available. We needed to hire more people, fast.

However, there was no experienced VP of Sales around to manage this. We had to figure things out on the fly. How could we quickly scale our sales team and get all those new reps productive in minimum time?

We didn’t know “the right way” to do this. We didn’t know what the best practices for sales hiring were or how to properly recruit, interview and train sales reps.

So we hacked the whole process and discovered new shortcuts to building a high-performance sales team. What started out as a motley assortment of tactics over time evolved into a more coherent system for hiring sales reps.

For the first time, I’m sharing our playbook in a well-structured and actionable way so that you can build out your team much faster than ever before.

There’s only one thing I ask of you: commit to taking action.

All the knowledge in the world is of no use if you don’t act upon it. So whenever you come across something in this book that makes you think, “Hmm, we should be doing this”, either put the book aside and do it right then and there or write it down and make time in your schedule to execute the task.

If you have questions, comments or encounter a specific challenge in the course of hiring salespeople that I don’t address in this book, just send me an email. At the end of this book, you’ll find how to get in touch with me.

With all that out of the way, let’s get started!

Steli Efti, CEO of Close

During my sales office hours, I often talk with startup founders who are beginning to see success. They’ve developed their product to a point where the few customers they have keep using it regularly. Their retention rates are okay and they have early signs of revenue growth.

It’s time to ask the question: Should I hire salespeople?

These four stages describe a useful progression of responsibilities. The timing depends on your sales motion, workload, and ability to support the team, not a fixed headcount.

Stage #1: Founder-driven sales (founders only)

The first person to sell your product should be you (the founder) and your co-founders. Even if you hate sales and suck at it. Even if you don’t have any sales experience and know-how. Do customer development yourself, and be as close to your prospects as you can.

Begin with the low-hanging fruit and tap into your network:

• Friends and acquaintances
• Co-workers
• Past employers
• Alumni
• And always ask for introductions left and right

At this point, the objective is not closing deals. Instead, focus on early stage sales exploration:

• Gain insights into your market
• Understand and listen to your customers better
  • What objections do they have?
  • How do they describe their problems?
  • What are their pain points?
  • How do they respond to your solution?
• Figure out which metrics truly matter for your sales outreach and your business
• Test different strategies, methods, and tactics to make sales and drive business
• Get started with cold emails
• Learn sales hacking 101
• Write a sales phone script

This phase is all about getting your hands dirty in the startup hustle and figuring out what works in the real world. It’s all about lean sales and validating your idea with the power of the hustle. The experience you gain will help you later evaluate salespeople.

Stage #2: Founder-led sales team

Once you have some success (made some sales, generated some revenue), the question you will ask yourself next is, “How do I grow this? How can I take this to the next level?”

This is challenging, because you still need to focus on developing your product further as well. Balancing these two responsibilities isn’t easy.

Consider the first sales hires when you have a motion they can learn, enough opportunity to support the role, and time to coach them. Early revenue alone does not answer all three questions.

Don’t make age or a “hungry” persona your hiring filter. For an early sales hire, look for curiosity, follow-through, coachability, and evidence they can learn your customers and repeat the founder’s emerging sales motion. Hire the number of reps you can support and compare fairly.

When does hiring more than one rep help?

If you can fund and coach two reps, there are potential advantages:

1. Friendly competition
2. Less dependence on individual performance
3. More data for future sales recruiting
4. More firepower

More than one rep can give you more opportunities to learn. It also adds cost and coaching work. Choose the hiring pace your pipeline and management capacity can support.

Now you have a sales team, you’re responsible and accountable for them. Sales thrives in this kind of competitive environment and team spirit. And staying afloat in an ocean of rejection will be a lot easier with a supportive team, too.

If an approach works for one rep but not another, investigate why. Lead quality, territory, timing, experience, and execution may all contribute. One comparison does not establish the cause.

Compare conversations and opportunities as well as outcomes. A small team gives you useful observations, but not enough evidence to blame the rep or declare a method proven.

At this stage, you still need to be deeply involved. You’re managing and leading this team. You’re still pitching, doing outbound and inbound, working with your sales reps, listening to feedback.

You can’t outsource this. There are still too many critical decisions to be made. You need all these one-on-one experiences with customers, different sales channels, and lead generation methods. It’s not enough to monitor numbers. You need to be living them.

Goals you should accomplish before transitioning into the next stage:

• Try and test cold email templates
• Use an effective sales lead management system
• Be experienced at negotiating deals and know how to handle discount inquiries
• Use drip marketing emails to convert leads better
• Have the ability to see early levels of predictability in your sales funnel

Stage #3: Dedicated sales management

At this point, your sales exploration has matured: Results are a lot more predictable. You’ve established an effective sales funnel. You’re generating consistent growth. It’s not about exploration anymore, it’s about time you start focusing on sales execution.

Let’s bring in some experienced sales leadership: a sales manager or sales director.

What should this sales manager accomplish for your company?

• Fine-tune the rough sales approaches you’ve developed
• Expand on the things you’ve learned
• Grow and manage your sales team
• Set up quotas, train, and coach your reps

Look for a leader who has built the capabilities you need next, such as coaching, forecasting, hiring, or improving a repeatable sales motion. Relevant experience can come from different company sizes and paths; test how they would apply it to your stage and constraints.

A useful signal is having grown from direct selling into leadership, but it is not a requirement. Ask candidates to show how they coached a team, what changed in the results, and what they learned when the approach did not work.

Some managers excel at improving an established process; others are strong at building one. Ask for evidence of the specific work you need instead of inferring it from a title.

Stage #4: Leadership across teams

As multiple teams, managers, or sales motions make coordination more complex, consider whether you need a leader responsible for the whole sales organization.

You’ll need a senior sales leader, a VP of Sales who can manage a few sales managers/directors.

Look for a leader whose results and operating approach match the scale and sales motion you expect to build. Ask for examples, understand their role in those outcomes, and probe what they would do differently at your current stage.

A VP of Sales will work on sales strategy, scaling and expanding your sales channels and partnerships, and moving your customer base upstream as well as improving your unit economics. The VP will:

• Build an organizational structure for the sales team
• Develop hiring and training plans
• Reorganize your commission structure
• Groom sales talent to sales management positions
• Open new offices
• Add new channels like field sales to your inside sales team
• Close larger deals

To bring such a person on board, you’ll need to throw a lot of money and some equity at them, that’s why this is such a crucial hire, and one that you shouldn’t make light-heartedly. They will guide your sales team on a journey that can either make or break your startup.

It’s hard, but it’s worth it

Startup sales is tough. Nothing about it is easy. If you focus on the right things and hire the right people at the right time, you’re going to be able to see your startup go from sales exploration to sales execution and ultimately sales scale.

One of the most useful frameworks for assessing a potential sales hire is something I learned a long time ago from reading a book by Jack Welch, former chairman and CEO of General Electric.

CEOs of giant corporations like General Electric usually aren’t admired much in the startup world. However, ever since I’ve learned about this concept, it has stuck with me and been a guiding principle in all my hiring decisions.

He had a quadrant in which he would place each of his hires, categorizing them by their capability and willingness: capable and willing, incapable and willing, capable and unwilling, and incapable and unwilling.

Let’s look at each of these in more detail.

Capable and willing

These are people who can do the work and show behaviors that support the team’s goals. Look for role-relevant skills, sound judgment, follow-through, and examples of collaborating well across functions.

You want to have them in your organization, and they can really propel your company forward.

When you find one of these people, do your best to hire and empower them.

Incapable and unwilling

If someone lacks a skill the role requires and does not show willingness to learn or take feedback, do not hire them. For a current employee, be clear about the gap, support, and expectations before deciding on next steps.

For an existing employee, make the expectations and available support explicit, then decide on next steps from documented performance.

Incapable and willing

If someone is still developing a skill the role needs but shows relevant strengths and coachability, ask whether the gap is teachable and whether you can provide the support and ramp time. Avoid using “culture fit” as a substitute for job-related evidence.

This is a tough decision. Personally, it’s one of my weak spots, because I myself have been in this quadrant for much of my professional life.

Why you should hire them

With a clear learning plan, practice, and feedback, a developing candidate may grow into the role. Look for evidence that they apply feedback and improve, rather than assuming enthusiasm alone will translate into results.

Why you shouldn’t hire them

If they don’t learn fast enough, or if the gap between their qualifications and your needs is too large, they will slow your company down.

If progress stalls, discuss the specific expectations that are not being met, identify obstacles, and agree on support and a review date. Consistent standards matter, and so does giving people a fair chance to understand and meet them.

With an incapable but willing person, consider these questions:

• How much training, time and money are you willing to invest into bringing that person up to speed?
• How much training, time and money do you have to invest into bringing that person up to speed?
• Do you already have a strategy in place to develop their skills?
• Who will take responsibility for training them?
• How quickly do you need a strong performance from them?
• How will you evaluate their performance and provide them with feedback?

You can’t answer all these questions with 100% accuracy, it’s impossible to know what’s required to develop talent. But just take a couple of hours to think this through and then make your best guess.

Capable and unwilling

These are capable people whose behavior may conflict with how the team needs to work. Strong results do not excuse dishonesty, disrespect, or conduct that harms customers or colleagues.

If their behavior is disrespectful or undermines colleagues, that can harm collaboration and customer outcomes even when they hit quota.

What do you do with these people?

If you’re a small company, you might feel you can’t afford to be finicky. It’s tough to pass on smart and talented people.

A little voice in the back of your head will tell you, “Yeah, this guy might be a highly qualified douchebag, but we need someone with his skill set, and none of the other candidates have it. Just hire him to drive growth. We can keep looking for someone with the same level of expertise and a better attitude.”

Don’t listen to that voice.

Do not use “culture fit” as a vague veto. Define the role’s values as observable behaviors, then assess candidates against the same job-related criteria.

Early hires can influence team norms, so be explicit about the behaviors you expect and model them consistently from the start.

7 ways bad culture fit hires can screw up your startup

1. If you bring in someone who treats others disrespectfully, schemes against colleagues to rise up the ranks, lies and closes bad deals to earn commissions or get on top of the leaderboard, these misaligned behaviors will spread throughout your company because other team members will conclude they’re acceptable, even if you verbally condemn them.
2. Office politics can lead to separate factions that are divided from your core company culture.
3. A highly skilled person has plenty of career opportunities. If they’re not aligned with your culture, they’ll probably leave your company as soon as a better option pops up, and you’re again faced with the task of recruiting someone for their position.
4. A hiring process needs more than a vague sense of “fit.” Define the behaviors required for the role and assess them through structured questions and work samples.
5. Hiring mistakes cost tens of thousands of dollars (and sometimes, even equity when it comes to startups,).
6. They will demoralize your highly engaged and fully aligned employees.
7. They can take away the joy you gain from your own company. (Nowadays, Tony Hsieh, the CEO of Zappos, is famous for his focus on workplace culture. However, do you know why he made it his number 1 priority? Because he had previously founded LinkExchange, a very successful company that grew to hundreds of employees and was worth hundreds of millions of dollars ... but dreaded getting out of bed in the morning because the culture of his own company made his stomach turn. He didn’t want the same thing to happen with Zappos.)

There are plenty of other ways how hiring unwilling high-performers can cause havoc, but rather than making this into an endless list, let’s focus on ...

The benefits of a strong company culture

It’s important to differentiate company culture from some mission statement or a written list of values that’s never put into practice.

A strong company culture is incredibly valuable for a startup. It will inspire and motivate each team member to produce the best work they can, rather than just the required minimum. And its value increases exponentially when things go wrong (which they always do in startups).

Think of all the time, money and resources you spend on recruiting and developing people. It’s a huge investment, and its ROI increases the longer your employees stay at your company.

How to assess the culture fit of a job candidate?

Start by naming the work behaviors that help your team succeed, such as sharing context, following through, learning from feedback, and treating customers fairly. Ask every candidate for specific examples against the same criteria.

Candidates are presenting their strongest case, as are you. Use the same structured questions and realistic work sample for everyone, then compare specific evidence rather than trying to “break through” a persona.

Let’s say a sales rep tells you he cares about always creating win-wins. Ask him to share a specific situation where he could have earned a big commission, but advised a prospect not to buy. Ask for details and see if it’s a credible story.

If a candidate struggles to recall an example, ask a follow-up or use a realistic scenario. Treat the answer as one data point, and avoid judging sincerity from presentation style alone.

Take everything with a grain of salt

If someone seems to be a promising candidate, don’t hire them right away. Get to know each other in steps. I’ve outlined this in a later chapter, “Hiring for startups: How to recruit the un-recruitable.”

Have them visit the office, work on a small project together, and if it all seems promising, have them join your team on a trial basis for a number of weeks or months. Get to know them in different environments and situations before you make long-term commitments to each other.

And if you make a wrong hiring decision despite all these precautions ... fire fast!

What’s the right attitude, mindset, and energy to sell SaaS products?

One useful sales principle is to combine warmth with clear guidance. Focus on the behaviors a buyer needs: thoughtful questions, an informed recommendation, and a direct next step.

People communicate in different ways. The goal is to be respectful and empathetic while still helping the buyer evaluate options and make a decision.

Salespeople need to be warm and assertive: understand the customer’s situation, explain a useful point of view, and ask for a clear next step. People can demonstrate this in different styles.

Two unhelpful extremes show up in sales:

• Pushing for a signature without checking whether the purchase makes sense for the customer.
• Offering information without helping the customer weigh the options or agree on a next step.

Either extreme can get in the way: pressure can produce poor-fit deals, while avoiding a recommendation can leave a buyer without useful guidance.

Let’s compare two common approaches and why a balanced, customer-centered approach works better in SaaS sales.

High-pressure selling

A high-pressure seller pushes for a close without enough regard for the buyer’s needs, timing, or ability to benefit. That can win a signature while damaging trust and the chance of a lasting customer relationship.

In a subscription business, a deal that quickly cancels may not cover the cost of selling, onboarding, and support. Evaluate sales quality through retention and customer outcomes as well as bookings.

And more importantly, that sales modus operandi is just unhealthy. You don’t want an asshole, it’s not worth it. They might be the number one closer but that doesn’t count for much if it hurts your business.

Low-assertiveness selling

At the other extreme, a rep may avoid influencing the conversation or asking for a decision, even when the customer would benefit from clear guidance.

A helpful sales approach still needs a point of view, clear recommendations, and confident next steps. Influence comes from relevant evidence and good questions, not power over the buyer.

Being considerate does not make someone weak, and it does not predict which customers they will attract. Assess whether they can listen, explain tradeoffs, set boundaries, and ask for a decision.

Consultative sales?

Many self-proclaimed sales experts advise salespeople to take a consultative sales approach. They say selling has changed.

Which is all well and fine, but in the real world, too many people use this explanation as an excuse to avoid doing uncomfortable things.

If a salesperson is a consultant, their job is not just to dispense advice. A salesperson’s job is to:

1. Figure out what needs to be done
2. Find a way to get it done
3. And make sure it actually gets done

If a salesperson isn’t doing that, their “consultation” has no value.

The trusted guide

I think a salesperson should act like a trusted guide: understand the customer’s goals, share a clear recommendation, and respect the customer’s decision.

A trusted guide has the customer’s interests in mind and communicates with confidence:

• They give clear directions
• They confidently take charge of the conversation
• They lead with clarity

Imagine a customer is about to make a decision that could create a serious problem for their business.

You would explain the risk clearly, ask what they are trying to accomplish, and recommend a safer option.

Be direct about the risk, then make space for the customer to consider the evidence and choose.

A trusted guide adapts the explanation to help the customer make an informed decision, without taking away their agency.

Customers are adults and equals. A salesperson can still bring useful product knowledge and a clear point of view.

A salesperson may have seen similar challenges before, but should ask questions before assuming the customer’s situation is the same.

A good salesperson may have useful product and market knowledge. They should share it clearly, check their assumptions, and treat the customer as the expert on their own business.

A good salesperson can respectfully challenge assumptions, explain the risks, and help the buyer choose a sound next step.

A good salesperson sells with friendly strength.

Before she became a household name on the show Shark Tank, Barbara Corcoran built The Corcoran Group, a $6 billion real estate business. For Barbara, there are two simple traits that differentiated the top performers from the underperformers in her sales team:

1. Having something to prove or a chip on your shoulder.
2. Being able to emotionally deal with rejection.

In her organization, Corcoran emphasized persistence through rejection. Treat this as an anecdote about her team, not a universal explanation for the gap between sales outcomes.

It doesn’t matter if they’re selling real estate or SaaS; salespeople must embrace rejection.

If rejection is so awesome, why does it feel so bad?

It’s one thing to talk about embracing rejection and logically understand the concept. It’s a completely different thing to translate this idea into behavior.

We’re hardwired to fear and avoid rejection. When our ancestors still lived in caves, being rejected from our tribe, and cast out on our own was akin to a death sentence. The desire to belong, and avoid rejection, is deeply programmed into our brains.

Most people struggle to deal with rejection.

However, if you want to hire the best salespeople, you need to find salespeople who can handle rejection.

Can you train salespeople to embrace rejection?

Look for evidence that a candidate can recover from setbacks, learn from a lost deal, and continue their work without becoming careless or cynical.

Some resilience helps in sales, but it can be coached. Use role-play and past examples to assess how candidates respond to rejection, and plan coaching for the skills they are still building.

A candidate who can reflect on setbacks may respond well to coaching. Avoid equating sensitivity or communication style with an inability to sell.

Why salespeople need to handle rejection well

While hearing the word “no” is never fun, think about it this way: If everyone said yes, there wouldn’t be a need for salespeople. The reason why salespeople have a job is because people say “no,” all the time.

Strong salespeople can hear “no,” learn what it means, and continue with sound judgment. Look for steady follow-through, not a claim that they love rejection or need to beat everyone else.

How can a cash-conscious startup find strong sales candidates? Use several recruiting channels and a consistent evaluation process.

Job boards, recruiting sites, and LinkedIn can all produce useful candidates. Referrals and targeted outreach can widen your pool too; use a consistent process to assess everyone.

You know who the only salespeople are who are actively looking for sales jobs?

Avoid treating active job search as evidence of poor sales ability.

A candidate’s employment status does not tell you whether they can sell. Assess their results, role in those results, customer approach, and ability to learn your motion.

If you want to get good professional salespeople, you need great compensation plans, big bonuses, expensive perks, predictable and scalable sales models, a brand, and operational infrastructure.

As an early-stage startup, you most likely can’t offer that.

Don’t look for salespeople, look for salespeople material

Look for people who have the emotional and mental blueprint of a great startup hustler. This kind of person typically doesn’t want to be a salesperson, though. They usually have other goals and aspirations in life.

Help them view the sales job at your startup as a step that brings them closer to achieving their long-term goals. Many startup hustlers have founder aspirations in the long-term.

Look for people who can learn quickly, take initiative, communicate well, and follow through. Assess those behaviors with examples and a realistic work sample, regardless of age or career path.

Characteristics of great startup hustlers

These are the key questions you need to ask yourself:

• Can they explain how they set priorities, take initiative, and complete work?
• Do they have an entrepreneurial spirit?
• Can they connect personal goals to the responsibilities and growth path this role actually offers?
• Are they competitive and do they enjoy a good challenge?
• Do they enjoy communicating and interacting with others?
• How do they respond to a setback, learn from it, and keep a thoughtful process moving?

Are they open to feedback? Ask for an example of how they changed their approach after coaching.

Where do you find startup sales hustlers?

Referrals can be a useful source, but do not limit the search to personal networks. Post the role in relevant communities and use targeted outreach so qualified candidates have a fair path to apply.

Hire for attitude, not experience

Hire for the capabilities the role needs, and distinguish skills you can teach from experience that is essential on day one.

The two main pillars of great salesmanship are being competitive and compassionate.

This isn’t a contradiction.

To excel in sales, salespeople need to be hyper-competitive.

• They need to compare themselves against others.
• They need to keep score of revenue generated, commissions earned, deals closed.
• They need to be driven by this. They need to look at the leaderboard and feel an intense desire to be number one, to be the best, to be better than everyone else.

But if they want to achieve true sales mastery, it can’t just be about them. It has to be about something bigger than them. Ultimately, they need to be driven by a mission to make the world better and help others.

Sales people need compassion. Tons of it.

• They need to care intensely about their customers.
• They need to believe in what they sell, and have a more encompassing understanding of how their product/service helps people to solve a problem or improve their life or business.
• They need to be mission-driven. They passionately feel responsible for empowering others with their solution. This is one of the biggest differences between true masters of the sales game and everyone else.

Why does mission matter so much?

Salespeople who are stuck in the old school used car salesman mentality are ego-driven and selfish. They just care about their commissions, their quotas, and their paychecks. They’re in it because of greed.

Being mission-driven is almost like possessing a superpower in the world of sales. It’s a secret source of strength. If your sales reps ever fall on hard times, it’s their mission that will compel them to keep pushing, rather than giving up as most people do.

The people who improve over time usually keep practicing through setbacks. Consistency matters, but perseverance should stay connected to learning and healthy boundaries.

Which brings me to the next big thing ...

Daily defiance

Every single day, your sales reps need to resist the temptation of complacency. Every single day, they need to push themselves one step further. They always have at least one leg outside their comfort zone.

Most people don’t have it in themselves. They don’t want it bad enough. They want a break from all the pressure. Everybody feels that way, it’s normal. But normal won’t lead to excellence.

Your salespeople must condition themselves to thrive at this. In sales, the score starts at zero every single day. No matter what they have accomplished in the past, what matters today is only what they achieve today. Nobody gets a head start.

Sales is like a sport. Every time your reps walk into the arena, it’s a completely new game.

Every single day, they need to get back in the ring, take the hits and throw their punches.

Relevant examples, not tenure alone

Most people think too short-term. Because they don’t have the patience. And they don’t want to put in their 10,000 hours.

Sales skills develop through practice, feedback, and experience. Evaluate what a candidate has learned and delivered, rather than using years in a role as a proxy.

Do what’s difficult

Great sales reps take on jobs that others shy away from. They avoid “easy money” jobs and low-hanging fruit.

They can sell things that are hard to sell. They will find the best people in these markets and learn from them.

They would even go into areas where they have to be really great just to survive. They might go broke, but desperation can turn them into a totally different kind of beast. It’s going to give them the muscle, the strength and the energy to go into a market where things are easier and totally crush it there.

Seek out risk

Great salespeople ask themselves, “What am I still afraid of? Where are opportunities outside of my reach?”

They’re comfortable taking risks and going for things others are scared of.

“To improve is to change; to be perfect is to change often.” , Winston Churchill

Lifelong learning

Great salespeople study communication. Read as much as they can. Learn. Practice. Constantly sharpen their saw. Listen to audiobooks. Go to seminars. Find mentors. Become students of human behavior. Master the art of the pitch. Work in places with the best sales culture and surround themselves with other great salespeople.

Deliberate practice can help people improve, but there is no universal hour count that guarantees mastery. Encourage regular practice with feedback and opportunities to apply what was learned.

They stay motivated and both intellectually and emotionally engaged on the path to sales mastery.

How to recruit your first top-notch sales rep

Most startups suck at outbound sales recruiting.

They recruit either too early, or too late. Too aggressively, or too passively. They pursue the wrong candidates or no candidates at all (FYI: good salespeople are not going to come to you).

The good news is they don’t have to. Create an outbound recruiting machine and you’ll have a pipeline of high-quality sales candidates. Here are the steps you can take to start building your recruiting process today.

When is the right time to hire a salesperson?

Hiring your first full-time salesperson is a huge step. Are you sure the timing is right? Too soon and you risk losing touch with your market.

Ask yourself these three questions to find out if your startup is ready for a full-time sales hire:

1. Is the expected customer value and gross margin sufficient to support the role’s fully loaded cost and ramp period? Model a range of outcomes before hiring; $1,000 CLTV is not a universal threshold.
2. Are my larger customers struggling to convert? If larger trial accounts convert at the same rate as smaller accounts, you don’t need a salesperson.
3. Is there complexity in the sales process for my larger accounts? A salesperson probably won’t make a difference in a frictionless sales process.

If you can answer “yes” to all three questions, you’re ready for a salesperson! But where do you start?

Talent trumps experience

A candidate’s years of experience can help frame questions, but it is not a qualification by itself. Focus on evidence that matches the sales motion, customer, and responsibilities you need.

Don’t! That’s the biggest mistake startups make with their first sales hire.

A job board is one source of candidates, not a quality signal by itself. Review each person’s actual experience and use structured questions and work samples to check their claims.

Instead of looking for sales experience, look for sales talent. Here are some of the key characteristics of successful startup hustlers:

• A compassionate and competitive nature
• Excellent communication skills
• A high tolerance for rejection
• Charisma and charm
• Shamelessness

Your network can be a useful starting point, but referrals are only one recruiting channel. Share the role broadly enough to reach candidates beyond your immediate circle.

How to recruit sales talent within your network

Who in your network might have skills relevant to this role?

Relevant skills can come from many occupations. Consider candidates from adjacent fields, then assess their communication, learning, and customer problem-solving with the same process you use for everyone.

If you can’t find anyone in your immediate network, then ask for referrals. Explain what you’re looking for in a salesperson and ask your contacts for introductions.

If that doesn’t work, start looking outside your network.

How to recruit sales talent outside of your network

When reaching beyond your network, look at companies with a similar customer, sales motion, or stage. Job boards and recruiting channels can also help you find candidates with relevant experience.

Find one with an established and successful sales team and reach out to one of their junior reps. Say:

“Hey Janet, this is Steli from Close. I really admire what your company is doing and I’m hoping you could help me out. You’re part of an incredible sales team and we’re trying to hire amazing sales talent like you for our inside sales CRM. Would you be willing to hop on a call with me this week and tell me what you were looking for when you joined a company?”

Most reps will be flattered and take the call. Use that opportunity to explore whether or not they’d be a good fit. If it seems like a match, be upfront. Say:

“This might sound crazy, but is there any chance you’d join our company? You’re exactly what we’re looking for.”

If they’re interested, keep the momentum going by setting up a formal interview. If they aren’t, thank them for their time and ask one final question.

Turn rejections into referrals

Some of the best hires start as referrals.

If the rep rejects your job offer, that’s okay. Thank them for their time and, just before you get off the phone, ask for a referral that’s totally out of your league. For example:

“Thanks for your insights, Janet. Before I let you go, I have one more question. Now that you know what we’re looking for in a salesperson, who do you know that’s so insanely talented at sales that they’d probably never work for us?”

This twist on the standard, “Who do you know who would be interested?” makes people really think and leads to higher-quality referrals.

Create long-term relationships

When you reach out to this referral, keep in mind that the goal isn’t to hire them on the spot. If you rush it, you’ll lose the opportunity. Approach the conversation like this:

“Hi Cathy, this is Steli from Close. I was speaking with Janet about building an amazing sales team and she said you’re the best salesperson she knows. She also said that I’d never be able to hire you, so I’m not even going to try. But would you be willing to talk with me about your sales experience?”

If you’d be interested in working with this person in the future, start building a relationship immediately. Find a way that you can provide lasting value on a consistent basis and check in with them once or twice a month.

It may take a while (I knew my Close co-founders for five years before I could convince them to start a company with me), but if you’re willing to invest the time no one else is, you’ll win them over.

And if you don’t? You still developed a powerful relationship that can be valuable in other ways.

Always be recruiting

Outbound recruiting is a lot like outbound sales.

You identify a prospect, qualify them, and go for the close. If you don’t get it on the first try, you follow up relentlessly.

And if you don’t start looking for prospects until you really need them, you’re in trouble. Don’t wait until you need to hire to start recruiting. If you start making those connections today, you’ll have a list of highly qualified candidates when you need them.

Like sales, recruiting is a never-ending cycle. Start preparing today for tomorrow’s crisis, and there won’t be a crisis at all.

Startup recruiting is hard. The challenge is twofold: finding incredible talent and then making them want to join your team.

I’ve been doing the impossible task of hiring way above my “talent class” for over a decade. And here’s what I’ve learned about startup recruiting.

Little steps, not giant leaps

Don’t ask amazing people to make a life-changing decision like coming to work for your company right away. That’s a giant leap. It’s too easy to reject that.

In fact, the type of person you want to hire should reject that. You probably don’t want to hire anyone you can hire that easily just by throwing out an offer.

Instead, make the first step compellingly small.

Relationships progress in increments. Deepen the commitment step by step, rather than requesting someone go full in before they’ve even had a chance to fall in love with your startup.

“A journey of a thousand miles must begin with a single step.” , Lao Tzu

Make it noncommittal, seemingly small and insignificant.

Step #1: Say hello

When you deal with rock star talent, you need to get on the phone with them as soon as possible. As I talked about in the last chapter, the goal is not to offer them a job right away, but to get to know each other and start building a relationship. Make sure you keep it casual so people can put their guard down. Here’s what you say.

“Hey, Mike! We just hired your friend Bob. Every time we make a new hire, we have a conversation and ask:

Who’s the most amazing person you know who would never ever change what they’re doing to consider joining us?

You know who Bob thought of first? Yep, you!

I know you’re happy and there is no way you would come and work here right now, and that’s fine. All I want to do is get to know each other since Bob made me very curious. :)

You are one of the most impressive people that Bob knows, so now I want to get to know you as well.

And in full disclosure, obviously, if there is ever even a glimpse of hope, I’m probably gonna attempt to hire you. But for now, let’s just put that aside. Let’s just get to know each other.”

Ask them questions:

• What are their goals in life?
• What do they want to accomplish?
• What are they passionate about?
• Etc.

Once you’ve gotten to know them, and you sense a potentially good match, initiate the next small step.

“I’d love you to just stop by our office at some point, meet the team, and give us some feedback. You seem to be really creative and really cool.”

With this process, it’s all about small steps. You go from a first phone call (first tiny step) to the next step (come in and meet the team, and give us a chance to meet you).

Step #2: Dating

The first meeting is usually them stopping by the office and spending time with the team, anywhere from an hour to a whole day.

Do you sense there’s a great connection? Are both sides getting more engaged and excited?

Now is the time to come clean and tell your potential superstar hire your intentions:

“I told you I would not attempt to hire you. I know there’s not much hope. But I’m a bit of a romantic. It seems like this could be really great for both parties. Maybe there is a way for us to work together and get to know each other better before making any long-term decisions.”

You indicate that you are interested, but you’re not asking them to join full-time just yet! It’s too early.

Remember, little steps, not giant leaps. It would be too easy to refuse your offer at this point and both sides have to do a bit more homework in order to really know that this is a great fit.

Instead, you say this:

“Hey, why don’t you come for a whole weekend? We can work on a little project together. That would be fun!”

Step #3: Small commitments

The conversations have gone well, but “culture fit” can be hard to define. Before deciding, compare specific examples against the same role criteria you use for every candidate.

This step can be bigger. You’ve built some emotional momentum. Mike has already committed some of his time to your company. The steps progressively get bigger and all ultimately lead to the giant leap of making an offer.

Two good ways to do that would be to ask them to work with you:

• On a part-time basis
• Or as a three-month contractor or consultant

Here is your pitch:

If a short paid work trial is appropriate and permitted by your company’s process, define the scope, compensation, time commitment, and evaluation criteria in advance. A structured work sample can also assess the same skills without an open-ended trial.

That way we are both getting a chance to evaluate if this might really be the right next step for you, and for us. There is no way to really know until we’ve worked with each other for at least a little while. What do you say?”

If the role, expectations, and working relationship are a strong match, that should become clearer through structured conversations and work samples. Avoid relying on a candidate’s growing attachment to the company as proof of fit.

If they do, you simply pitch them to take the final giant leap and do the unthinkable of joining your company now that they know they can’t live without it anymore :)

What if it’s a position they don’t want ... like a “sales job”?

Sales hiring is particularly challenging because as a startup, you should not hire experienced sales professionals. You should hire talented people who understand business. And many of them don’t find the prospect of being a “sales rep” very tempting.

Sales doesn’t enjoy a particularly good reputation.

When you think of “sales” or “selling”, what’s the first word that comes to mind?

When Dan Pink, the author of To Sell Is Human: The Surprising Truth About Moving Others, surveyed people, he got replies like “pushy”, “sleazy”, “manipulative”, “dishonest and annoying.”

Make it clear that it’s about your team and your vision, and not about “a sales job.”

Be clear about both the company and the actual job. Explain the sales responsibilities, expectations, and support so the candidate can make an informed choice.

Understand their big goals, and their motivation for wanting to be in business. Help them realize how their goals and your job offer align.

Be rigorous

Hiring great people is difficult. The easiest thing is to lower your standards, find someone who is subpar, talk yourself into believing that they “have it” and just give them the job.

Don’t do that. Don’t rush it just because you need to find someone quickly. In the end, hiring the wrong person will cost you more time than taking the time it takes to hire the right one.

Especially in the early days of a startup, you want to have a team of superstars. The process I shared with you now can help you hire the kind of talent that would usually decline the invitation to interview with you in the first place. And that’s a massive competitive advantage.

If you’re about to hire sales reps, how should you conduct a job interview to figure out whether a candidate is a great fit or not? What interview questions should you ask to determine if they’re a great salesperson?

The real answer is interview questions are rarely reliable indicators of future sales performance. (Although sometimes, they make great stories.)*

How can you find out if someone is a great basketball player? Do you:

• Interview him and ask a lot of well thought out questions?
• Or watch him play?

Watching him perform is a much more reliable indicator of skill and talent.

Some people are great at interviews, and suck at sales

I learned this while interviewing a candidate for our earlier outsourced sales business. He came highly recommended by one of our best-performing sales reps.

I like to think that my judgment of people is pretty good, especially when it comes to assessing their sales mojo.

When I interviewed this guy, I was sure he’d be a great salesperson! He was charismatic, sold himself well and just seemed to “have it.”

And then we put him in front of a phone.

Meltdown.

He dialed the first number and when he started talking, it was as if he’d become a different person. He had a massive meltdown, started sweating, stuttering. It was horrible.

* Like when Dick Harrison interviewed Mark Cranney and asked him, “Do you think you could kick my ass?”

He kept trying for a while, but he just disintegrated minute by minute in front of our eyes.

At the end of it, he looked at me and said, “All right, this is not for me.”

He was great at presenting himself but when it came to performing, he fell short.

Doing cold calls and exposing yourself to potential rejection can create a lot of psychological pressure, and it just deflated that guy.

This was a guy who appeared to have the chops, but he didn’t. He was the anti-Mark Cranney (bad at interviews, lacking a winning personality, but a top sales producer). Read Chapter 5 of Ben Horowitz’ The Hard Thing About Hard Things if you haven’t done so yet.

And then there’s another kind of person ...

Some people could be great salespeople, but won’t

We had other candidates who were great on their first call ... but ultimately didn’t turn into great salespeople.

Why? They had the skills, they could handle the pressure... but they lacked consistency. They couldn’t perform day in and day out.

How to find out if someone is a great salesperson?

Give people a chance to perform.

Reserve your judgment not for how great they are when you first meet them, or the first day, week or month. Judge them on how great and consistent their performance is day in and day out.

As I’ve said before, there’s no such thing as a perfect interview question.

There’s no single question you can ask to figure out whether someone is the right candidate and will be amazing at sales.

Questions won’t give you all the answers. However, when you’re asking questions, you’re collecting data. And what you want to do is collect enough data so that you can make a judgment call: Will this person be worth investing in?

Giving people practical tests and throwing them into the fire and seeing how they react will normally give you more answers than your standard interview questions. But since practical tests aren’t always possible, here’s a set of 10 interview questions that’ll help you find your next sales hire.

Remember, a lot of people will have weak answers to some of these questions. This doesn’t mean they’ll be bad at the job.

1. Why sales?

This is the most fundamental question when hiring salespeople. Ask the candidate why they’ve chosen sales as a career. Why have they been doing it and why do they keep doing it? What is it about selling that attracts them? What is it about selling that makes them want to be in this profession? How did they get into it? What’s the reason? What motivates them?

In sales, motivation is crucial to performance. What drives a person, what’s their purpose and what gets them going? What are they striving for? If you know these things, you’ll be able to provide them with the support they need in their journey and help them get to that goal.

Ask how the candidate’s goals connect to the work and growth path you can offer. A match is useful evidence, but it does not replace assessing their ability to do the role.

2. Why do you want to sell this product?

This may seem like an obvious question, but a lot of companies neglect to ask their candidates, “Why do you want to sell this particular product?”

This is a good question to ask because you’ll find out if they’re thoughtful. Is there a purpose behind them sitting here or did they just apply to a bunch of jobs to see what would happen?

If they have a reason or a pre-existing relationship with your company or product, it increases the chances of the candidate being good at the job.

3. What do you know about our customers?

This is another fundamental question to ask during the early interview stages that a lot of sales managers miss.

You want to figure out if the person did their homework. How well do they understand your customer? They might have been misinformed as to who your customer is. If that’s the case, this is your opportunity to clarify that.

Next, it’s time to figure out if this candidate will care about your customer. Why do they think they can communicate well with this person? Why do they think they can influence them? Can they relate to them?

What do you know about our competitors?

Do they know what the competitive landscape looks like? Do they know the companies you’re up against?

Have they done their research to see who else is in this space? Do they know what sets your company and product apart? Why do they think they could win selling against these people?

If they don’t know the answers, it’s not the end of the world. Most candidates won’t know your competitors very well; it doesn’t necessarily make them a bad fit.

5. When was the last time you were really stressed out and how did you deal with it?

This is a powerful question because you want to know how people act under pressure. This is when you can uncover both the really good sides and really terrible sides to a person.

Potential sales hires most likely won’t be prepared for this question. This means their answer might be complete BS and just something that they’ll say to make them look good.

Whatever the reason, work-related or personal, how did this person deal with that situation? What was it that stressed them out? This is a simple question that can be really revealing.

Look at the situation they describe. Is it a situation you can relate to or does it seem really trivial?

By asking this, you’ll get an idea of how this person might react in stressful situations, when being put under pressure, or faced with challenges.

Lastly, how do they handle that stress in the workplace?

6. When was the last time you took a big risk and it didn’t pan out?

This is another question most sales hires are unlikely to be prepared for. It will reveal if they’re comfortable and secure in themselves, two crucial ingredients for a good salesperson.

Ask for an example of a thoughtful risk or difficult decision. Focus on how they weighed the evidence and what they learned, not on whether they took a risk in a prescribed time window.

The example can come from work or another setting. Listen for sound judgment, initiative, and willingness to learn; risk-taking by itself does not predict sales performance.

Don’t forget to ask how they responded when that situation didn’t pan out.

7. When was the last time you lost a deal?

“I’ve never lost a deal.”

If someone says this, it’s very likely not true. But it might also mean they’re not taking enough risks with their prospects.

You want to know how often the potential sales hire loses deals, but you also want to know the reasons as to why this deal didn’t work out. You want to hear them analyze themselves.

If they’re good at analyzing what happened and why the deal didn’t work out, it shows a certain level of maturity and indicates that they’ll have a good understanding of a prospect’s situation.

If they have that understanding, it also means they’ll know what needs to happen in order to close that deal.

They’ll know what they need to work on in order to improve at selling.

8. When was the last time you won a deal?

You don’t just want to know how they cope in more sticky situations. You also want to know about their successes. You want to see if they get excited, passionate and motivated when they talk about the deals they’ve closed. How do they talk about their wins? How much energy do they bring? How much motivation and inspiration do they gain from these wins?

And the same questions goes, do they know why they won this deal?

9. What was the last sales tactic that you learned?

When was the last time this person learned something, either from a book, a course, a blog post, someone else, a workshop, anything. How did they apply what they learned to their job?

It doesn’t matter if it worked or not. This question explores whether this person is a learner. Are they coachable and do they want to continuously grow and get better at what they do?

The best salespeople in the world are lifelong learners. They never stop trying to find new ways to get better at their jobs and close more deals.

10. How do you think this interview is going so far?

This is an opportunity for the person to be self-aware and self-reflective with you as a prospect.

The product they’re selling is themselves, and you’re the potential customer. Now is when you want to see what this person thinks it takes to close this deal and make you hire him or her.

How good are they at reading other people and can they make a good judgment based on the conversation you’re having?

This will translate to their sensibilities when they talk to prospects and how much they can influence the process. Do they understand what’s going on? Maybe they think they killed it at a question where you were underwhelmed. If the gap in your perceptions is too big, it’s likely that this is not a very good salesperson.

Two questions for the interviewer

These questions will help you uncover the likelihood that this person will be amazing at selling your product to your potential customers.

Remember, no single question can point to if you should hire someone or not. But what you should ask yourself is:

1. Do I like this person?
2. Would I buy from this person?

If the answers raise concerns, ask follow-up questions and compare them with other evidence. A single yes-or-no answer should not decide whether someone belongs on your team.

If the answer is “yes,” then move forward with them.

Hiring people for your startup is hard. There’s no way around that. Whether you’re a little unknown startup nobody ever heard of, or a hotshot rocket ship making headlines in the tech press, figuring out which candidates to hire is really difficult.

How can you assess which applicants would add the most value to your startup? (And whom you should avoid like the plague?)

Conducting a hiring interview

I have an unorthodox opinion on the topic of job interviews. Interviewing people isn’t my primary way of judging whether someone is a good fit for our company.

Beware of “job interview experts”

I’ve learned from experience that some of the best interviewees make the worst employees, and some of the best employees are the worst interviewees.

Making a good impression during a job interview is a skill that can be learned and some people invest a great amount of time and effort into developing their job interview skills. Time and effort they could have invested into developing the skills they’re actually hired for.

You don’t want to hire this kind of people, because they tend to be the ones who are also good at playing office politics and claiming credit for other people’s achievements.

But even if you take these extreme cases aside ...

Every job applicant packages himself favorably

Many founders fail to look beyond the packaging. They see the big bold letters on the box, and the shiny colors and make a judgment call: “Oh, this candidate looks good!” Or “No way am I going to hire this person!”

If they think it’s a good one, they’ll remind themselves: “Do your due diligence. This is an important decision!”

So they turn the package around and carefully study the fine print on the side. “Well, this still looks good! I’ll hire this person!”

The problem is they haven’t actually opened up the box and looked at what’s inside.

To get insights into what’s in the box, you need to get through the superficial layer of bullshit and have a real interaction.

If that sounds like a lot of work, don’t worry. You don’t need a Ph.D. in psychology. There’s a super simple hiring hack for this.

How to interview someone so they reveal their real self

Ask them whatever questions you need to ask them. There are no standard “great interview questions.” It really depends on your startup’s needs, and you must do your homework and figure out what the best questions to ask are.

So, come up with a list of questions you want to ask, and then follow up on each of the interviewee’s answers by asking “why” three times in a row.

Interviewer: (Asks initial question.)

Interviewee: “That’s a great question, and I’m happy to share with you that blah, blah, blah [insert a couple of bullshit phrases that make a great-sounding answer].”

Interviewer: “That’s good! Why?”

Interviewee: “Because I really blah, blah, blah [insert more bullshit].”

Interviewer: “Oh, interesting. Why do you think that is?”

Interviewee: “Well, hm ...” [at this point you can often see the wheels inside their head turning, and the answers aren’t as slick and polished anymore] “so blah, blah, blah [still contains a good percentage of bullshit].”

Interviewer: “Oh, this is good. Why?”

Interviewee: “Uh, oh, well ...” [Some serious mental processing is going on. They might be a little less articulate, and more introspective. That’s a good sign!] “Ok, so I think this ... [Depending on where the conversation went, they demonstrate their level of expertise, or reveal how their thought process works, or what drives them, or they bring up formative experiences that made lasting impressions on them.]”

Getting real

Now, these are the insights you’re looking for. You’ve opened the box and got a glimpse of what’s inside.

These deeper insights provide a better foundation to build your judgment on than the slick answers you’ll get with standard interview questions.

What if, after three why’s, you’re still not getting “real” answers?

Some smooth interviewees will try to circumvent the answer. They’ll tell you something like, “Well, that’s a really good question, let me think about it, I don’t really know, but let me get back later to you on that.”

Here’s how you respond to those people: “Take a guess. If you had to guess an answer, what would be your first guess?”

Don’t let them off the hook. Push until you move the conversation beyond the level of “things people say at job interviews.”

When I interview someone for a job, I want to know a) what they want from life, and b) why they want it.

So, I ask the candidate the first question, and follow up with “why” until they get real.

How Zappos asks questions that get candidates off script

Another way to dig below the surface during an interview is to ask questions for which a candidate isn’t prepared, rather than just the typical “job interview questions.”

The Zappos hiring process includes a lot of these, for example:

• What is something weird that makes you happy?
• What’s something you’ve always wanted to do but haven’t? Why haven’t you done it?
• If you could be a superhero, what would you be and why?
• Which one of our “core values” would be most difficult for you to uphold?
• What is your favorite curse word? Use it in a sentence about your last job.
• If you were given $500 to plan a company event what would it be and why?
• If you were a dessert, what would you be?
• Describe a time when you had to break the rule to get the job done.
• What question were you expecting us to ask that we didn’t?
• On a scale of 1 to 10, how weird are you?

“It’s not so much the number; it’s more seeing how candidates react to a question”, explains Tony Hsieh, Zappo’s CEO. It brings out the personality of a job candidate.

Hsieh also used to ask the limo driver who brought a job applicant to the office how he was treated.

Now that I’ve shared all this advice on conducting hiring interviews with you, it’s important that you ...

Don’t weigh interviews too heavily!

The interview shouldn’t be the deciding factor in your hiring decision.

In a startup, it’s all about performance. What can each team member contribute to the company?

I like to bring up the example of a basketball team, because in sports, it’s all about performing. A coach who wants to bring a new player into the team would first and foremost want to see how they perform on the field. What they actually do matters more than what they say they do.

This is why you want to place them in a situation where they demonstrate their abilities as quickly as possible. If you’re hiring a salesperson, make them pick up the phone and pitch!

If you think hiring is hard, try firing ...

Hiring is largely hard because mistakes are painful to fix. But mistakes will happen. It’s unavoidable. The important thing is to fix your mistakes quickly.

Address a hiring mismatch promptly, with clear feedback and a documented assessment of the work. Do not let an unresolved performance problem drift.

Be respectful when firing someone, and try to help them transition into a position at another company that suits them better. After all, it was you who made the mistake of hiring them! But by all means, do not delay the decision because you feel bad about it.

“The way to be a great at hiring is to be unafraid of firing.” , Gary Vaynerchuck

In the last three chapters, I talked about the types of questions you can ask in interviews, how to get real answers from candidates, and why you shouldn’t rely too much on interview questions.

In this chapter, we’ll look at three work samples that can help you assess how a candidate approaches tasks relevant to your sales process.

You can only get so much information out of questions. Putting potential sales hires in practical situations to see how they act (and not what they say) is when you’ll learn the most about their talents and truly discover what they’re capable of.

Here are three simple yet powerful and practical tests that you can give your potential sales hires to uncover whether they’ll be a good addition to your sales team.

Let’s take a look.

1. Ask them to sell you something

When people show up to interviews, they’re dressed perfectly. They smile perfectly. Every strand of hair is perfectly in place. They walk and talk like a salesperson.

By the first look, you’re probably impressed and you might think, “If I feel like this, then our prospects and customers will be impressed, too.”

Often, this could not be further from the truth.

I’ve seen a lot of people who’ve sailed through the interview process. They’ve nailed every single question. Charmed the entire room. Said all the right things. But the moment you put them in a realistic sales situation? Complete meltdown.

That’s why asking them to pitch you something will help you find out if they’re more than just talk.

What should they pitch you?

• The previous product they were selling. See how they act selling something they’re experienced in and have extensive knowledge about.
• Your product. They might not have a full understanding of your product, but you want to see how they navigate the conversation when they don’t know everything about what they’re selling.

Ask the candidate to role-play a sales conversation that reflects your actual process. Explain the scenario and evaluation criteria, and give them a reasonable amount of preparation time.

Use a realistic mock call with a small, consistent interview panel. Explain the scenario and evaluation criteria in advance, then assess how the candidate listens, responds, and applies feedback.

This is a test to see what they’re made of, right on the sales floor. Do they like the challenge and rise to the occasion? Or do they crash and burn?

Create a realistic sales scenario

Make the exercise realistic and consistent across candidates. Evaluate listening, discovery, clarity, judgment, and next steps rather than performance polish alone.

Things to take into consideration:

• What’s their energy like?
• What’s their body language like?
• How do they talk?
• How do they structure the conversation?
• What kind of questions do they ask?

At the end, give them one thing you want them to improve or change. Then do the whole thing again. Be the same person and say almost the same things. All you want to see is if they took your feedback and made those changes. You want to know if this person is coachable.

You can start off easy and increase the level of difficulty throughout the conversation to get a sense of how experienced this person is and how they deal under pressure. Be really tough just to see what their natural reaction is. Will they have a nervous breakdown or pass with flying colors?

At the end of the exercise, will they ask you for feedback? Did they see this as a learning experience or are they not happy with you? You can tell a lot about a person based on their energy and you’ll get a good sense of their character once the exercise is over.

2. Write a cold email to a potential prospect

Even if cold emails are not a part of your sales process, it’s a great exercise for potential sales hires.

Explain who your ideal customer is, explain your product, and then tell your candidate they’ve got 30 minutes to do the following:

• Research a company that fits the ideal customer profile
• Find a person within that company to contact
• Write an email to that person
• Provide an analysis of why they chose that company, that person and why the wrote the email the way they did
• Send the email to you as if you were the prospect

This is a great exercise to uncover a few things:

• Do they understand who your customer is?
• Do they understand your market?
• Are they strategic in the way they communicate?
• Are they able to analyze themselves?

This simple exercise will tell you a lot about what type of person they are, what kind of experience they have and what their ability and talent for this job is.

Even if you don’t do cold emails, your salespeople will have to communicate with your prospects and customers in a written format. If they’re really good at it, it will be a huge plus.

3. Review public competitor information

Ask the candidate to review publicly available information about a few competitors, or provide the same materials to everyone. Ask what they learned and how they would use it in a customer conversation.

Ask the candidate to review public product pages, pricing, help articles, and customer stories. Do not ask them to pose as a buyer or obtain information through a misleading call.

Have them note what the public materials say about the product, likely customers, and pricing, and clearly label what they could not verify.

This exercise can show how the candidate researches a market, separates evidence from assumptions, and summarizes implications for a sales conversation.

A candidate can demonstrate discovery skills in a role-play based on your own product. There is no need to misrepresent themselves to a competitor.

As they review public materials, ask them to consider questions such as:

• What customer problem does this product appear to address?
• What evidence do the materials provide about the intended customer?
• What does the published roadmap or announcement say, if anything, about timing?
• What remains unclear from the public materials?
• What problem or use case does the feature seem designed to address?
• What pricing or packaging details are published, and what is not clear?
• What can you infer about the user experience from public demos or screenshots, and what cannot be assessed?

Ask the candidate to explain the evidence behind their summary, distinguish facts from hypotheses, and describe how they would validate open questions ethically.

If they’re not in the habit of asking follow-up questions and going as far as they possibly can in their quest for information, they’re not going to be great at sales.

When they present you with all this data, ask them, “How do you think we relate to all these companies?”

Because if they talk to a prospect and that prospect asks, “How do you compare to company X?” They need to be able to present this information to them in a way that puts you ahead of the competition. You want to see how they think about the entire market.

These are three exercises that’ll help you uncover a ton of information about potential sales hires.

There are other things you can do that are less explicit, but still action-based tests that’ll help you evaluate your sales candidates.

Here are a few things:

• Give them feedback throughout the day and see if they change and adjust based on your advice. Are they capable of learning and are they capable of learning fast?
• How much are they driving the interview process versus relying on you to drive it? Will they ask for next steps? Will they ask for feedback? Will they ask questions or just say thank you and be on their way? This is a great way to see if someone will proactively ask for the next step instead of waiting for you to tell them. If they’re not going for the close for their own job, it’s unlikely they will close deals for your business. The follow-up is the most important thing in sales. If they don’t have the follow-up hustle, then things don’t look good.

Try these three simple exercises during your sales hiring process and you’ll have a better assessment of a sales candidate’s skills than any interview could provide.

When we ran our outsourced sales business, one kind of prospect made us especially cautious.

These were the customers who wanted us to fix their business with the magic of sales. Some of them were willing to throw a lot of money at us to make it happen for them. Most of the time, we were strong enough to say NO.

Often times, these are the entrepreneurs who build a beautiful product and are in love with their idea, and think the only thing missing is some marketing/sales/biz dev guy to come in and “do the business stuff.” They usually misunderstand what the business side of business is about, and have very little appreciation for it.

Sales are either slow or non-existent. They’re not generating enough revenue. They don’t know how to make their business work ... and want “others” to figure it out for them.

Here’s an ugly truth that outsourced sales companies don’t want you to know:

If you can’t sell your own product, no one else will be able to sell it for you either.

And that’s a bitter pill to swallow, especially if you are an entrepreneur struggling to keep your business alive. You’ll become so desperate that you clutch at any straw you can find. You’ll think, “Hey, these guys know sales, I’ll just bring them in and they’ll do it for me.”

But that’s just wishful thinking, born from the seed of desperation.

The truth is, if you have zero (or next to zero) sales, then ...

It’s not the sales part that’s at fault. It’s your product

If you truly have a great product, you will be able to close at least some deals.

Even if you’re not a salesperson.

Even if you suck at sales.

Even if your pitch is flawed.

Even if your hustle is lame.

If your product is solid, you’ll be able to close your uncle, or your ex-boss, or your buddy’s dad, someone ...

Figure it out before you source it out

It’s ok to outsource sales because others are better at doing it. But first, you yourself need to have figured out the basic sales model. Don’t just outsource something to somebody else that you don’t understand yourself.

Don’t expect some professional sales team to bring you from 0 to 1.

That step from 0 to 1 is always the step you need to make.

Taking it from 1 to 5? From 5 to 12? From 12 to 23? From 23 to a 100? Yes, bring in outside experts. But 0 to 1? That’s your job!

But what if you really do need help?

What if you really can’t get from 0 to 1 by yourself? Well, it’s ok if you are looking for help on how to figure it out. It’s ok if you’re willing to do what it takes, and need someone to coach you through the process.

But don’t look for someone who will figure it out for you. If you’re looking for somebody who will do all the steps for you that are necessary to figure it out, you’re fucked.

Figuring out the basics is your job. You don’t need to figure it out until the very last detail, but at least you should have mastered the sales exploration phase and be ready to transition into the sales execution phase.

I wrote about the four stages of startup sales in “The ultimate sales hiring guide for founders and managers” and the transition point between sales exploration to sales execution is between stage #2 to stage #3. You want to have something that the outsourced sales company can build upon and optimize.

If you have nothing, that’s not enough.

When startup founders decide to hire their first salesperson, they try to assess the risks involved in changing their engineering-focused culture by bringing in someone for sales.

They know what the upside could be, but wonder what the downside of making their first sales hire might look like.

Before you do any sales recruiting, you need to make sure you understand the top risks involved in order to be able to proactively manage them and maximize your chances of successfully building your startup sales team.

Risk #1: Losing touch with your customers

If you put sales into a silo you’re not involved in anymore, you miss out on a lot of market intel. Engaging with prospects and listening to their objections is indispensable for you.

That means talking to them one-on-one, observing their body language, and having real conversations. You, as a founder, need the first-hand experience.

It will help you to gain a much deeper understanding of your customers and with that achieve product/market fit faster.

Risk #2: Not being able to judge sales performance

Before a sales motion is repeatable, rep results may vary as you learn which customers, messages, and channels work. Set expectations for experimentation and measure learning as well as outcomes.

If the motion is still unproven, give the salesperson a clear learning agenda, bounded experiments, and access to customer feedback. Avoid judging exploration against a mature team’s forecast.

Risk #3: Hiring a salesperson can screw up your culture

Sales and engineering may have different responsibilities and incentives. Make those differences explicit, build shared customer context, and give both teams a clear way to resolve disagreements.

Hire for the capabilities your sales motion needs, and define the behaviors that help people work well across the company. Support integration with clear communication norms and shared customer context.

Risk #4: Hiring without testing the sales behaviors you need

High-pressure selling

A rep can close deals and still harm customer trust through pressure, misleading claims, or poor qualification. Assess these behaviors alongside bookings.

They’ll try to close deals that shouldn’t be closed, and they’ll stretch the truth or lie to customers just to earn a commission. They don’t care about long-term viability; they just care about bringing in cash today.

They can hurt your brand and reputation and destroy any trust you have in the marketplace.

Low-assertiveness selling

A rep may avoid clear recommendations or next steps. Coach those behaviors directly instead of assuming a gentle style means low ambition.

Look for whether the candidate can recommend a next step, follow through, and set expectations. Use an exercise to separate a skill gap from assumptions about personality.

A great salesperson has to be both competitive and compassionate!

Risk #5: Hiring sales leadership too soon

Experience helps when it matches the work, but years alone do not tell you whether someone can build an early sales motion. Ask candidates to explain their role, customer, process, and results, then test how they would learn from your market.

• Figuring out how to sell your product/crafting your first pitch
• Building a sales funnel from scratch
• Developing sales materials
• Creating a sales objection document
• Making referrals part of your lead generation process
• Writing and testing cold email templates to generate more leads

So when is the right time to bring in sales leadership?

When your sales motion is repeatable enough to support execution, hire for the capabilities you need next, such as coaching, forecasting, or process improvement. Confirm the motion is documented well enough for a new leader to assess.

A polished interview can hide gaps, and an awkward one can hide useful skills. You need more than a first impression.

So how do you weed out bad candidates?

It’s not easy to uncover who’ll be the right sales hire for your company. The work and criteria will differ, but these lessons from our hiring experience can help you decide what evidence to look for.

Here are questions to investigate during the hiring process. Treat them as prompts for follow-up, not automatic disqualifiers.

1. They can’t get the basics right

Check accuracy and follow-through in work that resembles the job. Clarify a missed deadline or mistake before drawing conclusions, and keep profile photos or personal presentation out of the scorecard.

2. They haven’t done their homework

If a candidate has not researched the role or company, ask what information they had and how they evaluate an opportunity. Preparation is one signal; assess prospecting and qualification skills directly in a work sample.

3. They can’t pitch

Use a realistic pitch exercise to assess communication. Being good at selling oneself in an interview is not the same as understanding and helping a customer.

A good elevator pitch goes a long way. It’s not more difficult than answering these questions:

• Where are you coming from?
• Where are you right now?
• Where are you going?

Ask for examples that help you assess the skills and behaviors required for the role. Personal background is not a substitute for a structured evaluation.

4. They’ve been switching jobs

Short tenures can have many explanations, including role changes, layoffs, or a mismatch in expectations. Ask neutrally what the candidate was responsible for, why they moved, and what they learned.

It might not be a bad thing necessarily, but pay attention to how they answer the questions about why they left their previous positions after a short amount of time.

5. Their title or tenure seems unchanged

A stable role can reflect many things, including deep expertise or limited advancement opportunities. Ask what responsibilities grew, what they learned, and what kind of work they want next.

6. They’re bad mouthing ex-employers

If a candidate describes a past conflict, ask what happened, what they could have done differently, and what they learned. Consider the answer alongside other evidence rather than disqualifying them for criticizing a former manager.

If you’ve had an issue with someone in the company, there’s a respectful way of saying that. “It wasn’t a good cultural fit so I decided to move on” would be the appropriate way to say, “My boss was an asshole.”

Let’s leave it at that.

7. They share sensitive information from past employers

If a potential sales hire starts sharing data and company secrets, they’re out. This means they’ll be doing it at your company, too.

8. They don’t have any questions

Questions can show curiosity and thoughtful evaluation, but candidates may have different interview styles or need more context. Give them time to ask questions and assess sales discovery skills separately.

9. They don’t have a reason for applying for the job

Ask what interests the candidate about this role and what they need to learn to decide whether it fits.

Applying to several companies is normal. Evaluate their understanding of this job and their ability to do it, not whether your company is their only option.

Give candidates enough information to ask useful questions and make a thoughtful decision.

10. They have weak references

This red flag comes in three parts:

• Reference lists vary for many reasons. Ask for a mix of people who can speak to the candidate’s work, and use a consistent reference process rather than inferring poor performance from one employer’s references.
• They didn’t think about what makes for a good reference. If the office manager says someone can make a mean pasta carbonara, it’s not going to mean much. Doesn’t matter if the person makes for a great lunch partner if they can’t close a deal.
• They didn’t prepare their references. When you call up a reference, they should expect your call and be prepared for it. If someone picks up the phone and has no idea who you are or why you’re calling, that’s just sloppy work.

11. Their account contains unresolved inconsistencies

If something in a candidate’s account does not add up, identify the specific inconsistency and ask a neutral follow-up. Record the evidence and compare it with references or work samples; a gut feeling alone is not a reliable decision rule.

Trust matters. Build the decision on specific, checked evidence rather than how familiar or comfortable a candidate feels.

12. They are too aggressive

Confidence helps when it comes with listening and respect. In a role-play, observe whether the candidate can ask useful questions, respond to cues, and make a clear recommendation without talking over the buyer.

Watch what they actually do: interrupt, ignore a stated need, or continue applying pressure after a clear no. Those behaviors are more informative than a personality label.

Repeated disrespect or disregard for feedback in the process is worth exploring with specific examples and follow-up questions.

13. They avoid recommendations or next steps

Warmth and consideration are strengths. Assess whether the candidate can also set expectations, handle objections, and ask for a clear next step.

14. Their interest in the work is unclear

People express interest differently. Ask what work engages them and observe preparation, curiosity, and follow-through. Do not confuse a quiet style with a lack of motivation.

After hiring, use appropriate call reviews to coach observable behaviors such as discovery, listening, and clear next steps.

Choose examples together, give specific feedback, and agree on what to practice next. Judge the substance of the conversation, not whether the rep sounds like you.

15. They lack self-awareness

I often test people’s level of self-awareness. If a person is very far removed from the reality of a situation, that’s likely to be an issue. People need to be able to assess themselves in order to make progress and improve.

Often, I weigh the importance of this based on level of seniority. If a sales candidate is really junior, it’s not as big of an issue. But if someone is really senior and doesn’t have the level of self-awareness that one would expect at that stage, I’d be concerned.

16. They don’t seem coachable

Test coachability directly rather than inferring it from confidence or interview style.

Give clear, specific feedback on a work sample, allow time to apply it, and compare the next attempt. Look for learning and useful questions, not instant agreement.

17. They’re defensive

If a candidate challenges feedback, ask how they see the situation. Distinguish a useful explanation or disagreement from a repeated refusal to consider evidence.

18. They don’t have any drive

What motivates them as a salesperson? Is it the money? The thrill of the close? The idea of bringing value to someone else’s life? The chance of changing the world?

Whatever it may be, there’s a reason why we all get out of bed in the morning. Having drive and motivation is key to doing anything well, let alone selling.

19. Their examples only describe wins

Ask for a difficult decision, lost opportunity, or piece of feedback that changed their approach.

Probe their contribution to the result and what they would do differently with the same information today.

A successful track record is not a red flag. You are checking judgment and reflection, not requiring a particular failure story.

20. Their examples do not show learning

Difficult outcomes can reflect the market, company, role, or individual choices. Ask what changed in the candidate’s approach and look for evidence of improvement.

Use these prompts only when they connect to the role, and apply the same criteria to every candidate. Replace a vague red flag with a follow-up question or a work sample.

I don’t use a fixed number of red flags as an automatic rejection rule. Investigate each concern, weigh it against the role criteria, and document the evidence behind your decision.

Are you guaranteed to make the right hiring decisions based on this? Of course not. But I hope they’ll help you in the process of weeding out bad sales candidates.

Ten years ago, I hired a salesperson with incredible drive. He had recently lost everything, his job, his house, all his money. But he was hungry to get back in the game and work his ass off. He was underqualified, but what he lacked in experience, he made up for in energy. So I took a chance on him.

I spent too much time trying to make the hire work. I coached the pitch and outbound process, but after a year we still had not seen progress against clear expectations. The lesson was to define the skills, support, and review points up front, then act on evidence rather than hoping for a breakthrough.

I ended up wasting my own time and my new employee’s time, just trying to get him to be good enough. By the time I let him go, not only was he out of a job, but he had just wasted a year trying to fit a role that wasn’t right for him.

He was one of many hiring mistakes I’ve made. And while I still believe in hiring based on attitude and not just experience, I’ve realized that risky hires need to be carefully managed to ensure they become successful.

How to evaluate a developing candidate

A less experienced candidate may bring curiosity and strong learning habits, but neither experience nor enthusiasm alone predicts success. Assess relevant strengths, coachability, and the support the role requires.

A candidate who is still developing may need more coaching and ramp time. Set clear expectations, offer support, and review progress against the same role criteria you use for other reps.

How to work with underdogs

Candidates may value the chance to grow, but do not assume a less experienced hire will stay longer or show greater loyalty. Set clear expectations, offer meaningful development, and evaluate the skills they demonstrate.

They’re also my personal kryptonite because I’ve been an underdog for most of my career.

A candidate’s career stage does not tell you whether they have the skills for the role. Define what can be learned on the job, provide a realistic ramp, and base decisions on observed progress.

By setting up a bulletproof system for evaluating the performance of a new hire, you’ll accomplish three things:

1. Weed out underperformers by setting your expectations in stone.
2. Enable those who have what it takes to succeed by holding them to high standards.
3. Set the same expectations for all your sales reps.

Gauging your expectations will help your underdog achieve top results and succeed within your company. Here are four questions to ask yourself when preparing to hire them.

1. Can they show examples of learning a new skill or applying feedback?

Self-assessments are imperfect. Ask for concrete examples, then use a realistic work sample to understand the candidate’s current skills.

Ask for specific examples of how the candidate approaches work and follows through. Then compare those examples with a realistic exercise; do not label someone a “misfit” based on an impression of their work ethic.

While a new hire is learning, review work that is relevant to the role: preparation, customer conversations, follow-up quality, and how they apply coaching. Do not treat hours worked or visible busyness as proof of commitment.

• Check to see if they are eagerly taking notes and learning the processes
• Get feedback from their peers to see how well they’re absorbing new information
• Ask for concerns from the hires themselves to get a sense of how motivated they are to improve

If progress is below expectations, identify the specific skill gap, check whether training and tools are adequate, and agree on a review date. Make staffing decisions based on documented performance and support, not a guess about future effort.

1. How long are you prepared to wait for them to catch up?

A new hire who lacks role clarity or training can struggle for reasons beyond individual effort. Set clear outcomes, provide support, and review progress early so you can address gaps before they compound.

Ramp time varies with the product, sales cycle, prior experience, and quality of enablement. Set milestones based on your own motion and review early signals before drawing conclusions.

Agree on a realistic ramp period before hiring, based on the role and sales cycle. Use that period to provide coaching and evaluate progress; do not double an arbitrary estimate as a universal rule.

1. How will you onboard this hire?

Training takes time, so plan it deliberately. Give new reps guided practice and timely feedback. Do not expect someone to teach themselves an unfamiliar product and sales motion while carrying a full quota.

A developing rep may need more structured coaching, but the manager is not the only possible trainer. Share enablement responsibilities while ensuring someone owns the plan and feedback.

You can do this by having a metrics-based training program set in stone:

• Measure performance through things like time to close a sale, or amount of emails that resulted in a qualified lead.
• Use these metrics to pinpoint their strengths and weaknesses, and work with them on improving them.
• Delegate some training responsibilities to more experienced staff members to improve team dynamic.

To see whether your training program is working, have a weekly 1:1 with the new hire yourself. This way you can see first-hand whether any progress has been made.

1. How will you measure success?

Use both quantitative results and qualitative evidence, such as conversation quality, learning, judgment, and follow-through. Interpret early metrics in context of lead quality, territory, and ramp stage.

Too many managers set expectations either unreasonably high (equivalent to their top performers), or unreasonably low (because they’re newbies). The ultimate benchmark should be equal to the average performance among your sales reps.

This benchmark is the minimum performance expectation, anything below, will indicate that the employee wasn’t worth the investment. You are not hiring an underdog because you want an employee with a free pass, you’re hiring an underdog because their hunger and energy gave you the impression they were capable of not just catching up, but excelling.

So, if doubling the amount of time you anticipated isn’t enough for the underdogs to meet your standards, then you’ll know that it’s time to let them go.

Turn your underdogs into rock stars

Keep in mind that every rock star employee once started out as an underdog. While an underdog requires more training and work than other applicants do, should they persevere, their allegiance and passion will make them some of the best employees you’ve ever worked with.

Motivation can help, but it is not a substitute for role skills, sound judgment, and support. Look for learning behavior and consistent follow-through, then build the product and sales knowledge through training.

If you catch these gems early, you’ll find that the underdogs can have a spectacular, long-lasting impact, both on overall sales performance and on the team dynamic, making them well-worth the risk and the investment.

Consider a hypothetical candidate, Charlie, who brings deep industry experience and a valuable network. The scenario below illustrates what can go wrong when a company hires on promises without checking how that experience fits the work. It is not a prediction about senior candidates.

Charlie says he wants to join because he believes in your vision and likes the pace of a startup. Take that interest seriously, then ask how he would work with your actual customers, resources, and constraints.

A senior hire is especially tempting when growth is difficult. Before hiring, define the problem to solve and check whether it calls for sales leadership, a different motion, or more customer learning.

These are the kinds of thoughts you’ll be pondering in your mind:

• Why is sales so difficult?
• Why don’t we have more customers?
• We need someone who can close more and bigger deals.

There he is, Charlie, your knight in shining armor, ready to slay the monster that’s holding you back from explosive growth.

If it sounds like a cheap fairy tale ... that’s because it is!

Here’s what will happen

Charlie will join your team, and he’ll negotiate as much money and equity out of you as you’re willing to give up. (But hey, that just shows what a great salesperson he is, right?)

Charlie will start calling, reaching out into his network, building a stellar pipeline. You’ll hear him talk much about prospects, leads and opportunities.

All that’s needed to turn these opportunities into customers is ...

• More and higher quality sales materials
• Expensive steak dinners
• A “slight” tweak to your product, an added feature, a different UX (Charlie knows what will make prospects buy because of all the conversations he’s having, so of course you should listen to him.)
• A redesigned website
• A better drip campaign
• A new piece of sales or marketing software (“Yes, $15,000 looks like a lot, but that’s just the price of doing business, trust me on this.”)
• Hiring an outsourced lead generation company
• Spending $60,000 on AdWords
• Feeding a unicorn with magic barley on full moon nights

Charlie will initially make little asks, reasonable requests, but they’ll increasingly turn into bigger and bolder demands. After everything you’ll have invested already, you’re not going to suddenly pull out. All of it would have been wasted.

All those hot deals he’s working on take forever, and never materialize. “It takes time to close those massive deals,” he’ll tell you. Which isn’t wrong, but you need to be involved, to have a read on the temperature of the deals yourself and not just trust someone else’s judgment at the super early stage.

At one point, most likely when it’s already too late, you’ll realize it: Inside that shining armor is not a knight, but a black hole that devours all your startup’s resources, until there’s nothing left of it. Charlie will be on to the next startup, peddling his counterfeit sales expertise.

Why do so many smart founders fall for Charlie Charlatan?

For the same reason smart people have fallen for con men’s schemes since hundreds of years: they want to believe them! The shysters’ promises sound so good; we desperately want it to be true. That desire overrides all the sophisticated processing going on in our neocortex.

Even Charlie often believes his own bullshit. From his point of view, it’s always forces outside of his control (the founders, the market, the VCs, the other reps, the incompetent VPs, the CEO) that prevent him from the breakthrough success he’s chasing.

A senior salesperson may choose an established company, a startup, or something else. Do not assume compensation or risk tolerance from their title. Be direct about your resources, the role, and what success would require.

But shouldn’t you hire people above your own weight class?

Common hiring advice: Recruit someone who’s better than you are at _____ (sales/product/management/marketing/etc).

Look for someone who brings strengths the role needs and can work effectively with your team. Be clear about the areas where you expect them to lead and the support you can provide.

Hiring people below your own skill level is fairly easy.

Hiring people in the same level as you is hard.

Hiring people who are a level above you, a bit more experienced, a bit more skillful, a bit better at what they do than the things that you are doing, that’s crazy hard.

The more the role differs from your current experience, the more important it is to clarify scope, decision rights, and mutual expectations.

A very senior candidate may be out of reach for some early companies, but do not rule someone out based on company size alone. Discuss scope, compensation, equity, risk, and evidence of fit openly.

The one exception

If that VP of Sales rock star is someone you’ve known all your life. Your brother, your mother, your cousin, your childhood friend from school? Different story.

But anything other than that? Almost certainly a pipedream. You’ve got better chances of success driving to Vegas and betting all that equity and money on red.

Reality check

If you ever find yourself in a situation like this and you’re still tempted after reading this because you’re too scared to lose the great opportunity to bring that sales rock star on board, put your Charlie to the test.

Before either side makes a major commitment, agree on a job-related way to test the candidate’s claims. For example, review a realistic account plan or customer scenario together, with clear scope and compensation if the work produces value.

That’s it. If they are really that excited about joining your startup, it’s not too big an ask. In fact, it’s in their own interest. Have them close a deal for you.

Evaluate evidence of execution, not promises or pipeline alone. A structured work sample can test how they qualify, plan, and advance an opportunity without asking them to perform real unpaid work.

If the evidence is strong, check references and align on the role, resources, and success measures before making an offer.

Build a sales process your new hires can follow ↗

If you’re faced with the challenge of developing a commission structure for your first sales hire as a startup, there are two very different ways you can go about it.

The collaborative way

You’re looking for someone with whom you can collaboratively create a sales commission structure.

“I don’t know the right way to do this, but I want to find out together with you.

I will pay you a base salary for the first couple of months while we develop the commission plan.

If you want maximum money, go to a more established company that has everything in place already. If you want maximum learning and growth, join us because you’ll work directly with me (one of the founders or senior hires at the startup).

We’ll have to create this sales commission plan not just for you, but for every future sales rep as well. So this won’t be an easy job.”

Find someone truly excited about tackling this challenge, and then get to work together. Or go in the opposite direction.

The provisional-plan approach

You can start with a provisional commission plan based on explicit assumptions. Explain what is known, what is still being tested, and how you will review the plan with the rep.

What if they don’t deliver these numbers?

If the plan produces unintended behavior or unrealistic earnings, diagnose why. Discuss changes transparently and honor the terms already agreed to; do not treat replacing reps as the fix for a flawed plan.

Changing the plan after a rep has relied on it can damage trust and may conflict with the agreement. Set a review cadence and change process up front, and get appropriate internal review before changing terms.

If the plan needs to change, explain why, review the impact with the current reps, and follow the change process you agreed on. A flawed plan is a reason to improve the plan, not automatically to replace the team.

Don’t wait

Choose the approach that matches your information and capacity. Either way, document the assumptions, explain the plan clearly, and review it with the rep after you have enough evidence.

One of the biggest mistakes I’ve seen founders make is waiting way too long to figure out “the perfect commission structure” before hiring salespeople.

You will not know how a compensation plan works until it meets your actual sales motion. Start with a clear, explainable design, define what you will monitor, and revise it carefully as you learn.

We know founders that have been waiting for over two years before hiring much-needed salespeople because they had analysis paralysis about the “right compensation structure.” Don’t be one of those startups!

Crunching the numbers

Once you have decided which way to go, you’ll need to think about the actual numbers. How do you best incentivize sales reps? How do you align their interests with your business’ interests?

The plan should reward productive selling while discouraging poor-fit deals. Consider margin, retention, discounting, customer outcomes, and the parts of the process the rep can control.

Real-life case study

A friend of mine got hired as the head of sales and business development at a cool startup.

He was about to hire the first salesperson, and needed to come up with a commission structure.

Their product costs several hundred dollars a month. His idea was to pay out $100 every month for the sales rep who brought in the deal for the first 12 months.

He asked, “What do you think? Is that a good idea?”

I told him to not spread things out so much. Instead, pay upfront, but pay a little less.

For example, the manager considered paying a smaller commission after a defined period instead of spreading payments across a full year. The right timing depends on the sales cycle, retention pattern, cash flow, and the behavior the plan should reward.

What’s the advantage in structuring things like this?

Do not assume recurring commissions make reps complacent. Tie incentives to behaviors and outcomes that matter, such as durable revenue and customer fit, and ask reps how the plan shapes their decisions.

Is this the perfect commission structure for his business? I doubt so. But it’s a decent way to get started.

Compensation/sales fit

But what about churn? Expansion revenue? I know there are a lot of details that need to be fine-tuned to design a compensation plan that will fuel and scale your sales efforts. I don’t want to suggest that it’s easy at all.

Run the plan long enough to observe how it affects selling behavior, deal quality, and customer outcomes. Review the evidence with the team and adjust the design transparently.

For more advice on this topic, you can also read Aaron Ross’s excellent book Predictable Revenue for some examples of how to develop your compensation structure with your sales team.

Salespeople need initiative, but talent alone does not replace a clear process. Choose a team structure that makes ownership, handoffs, coaching, and customer experience explicit.

Adding headcount without a clear sales process makes it harder to coach people or understand results. Document the work, the handoffs, and the outcomes you expect before expanding the team.

Choose a structure based on your sales motion, team size, customer needs, and available management capacity. Revisit it when those conditions change.

Here are the three basic sales team structures that you can use to ramp up your sales game and start off on the right foot.

Don’t forget the culture

There’s two simple goals you want to meet when it comes to organizing your sales team:

1. Drive maximum results.
2. Define team behaviors that support the customer and the work.

Competitor structures can suggest questions, but they do not prove what will work for you. If a competitor appears successful with a model, investigate the customer, economics, team design, and operating conditions behind it.

Choose the structure that supports the outcomes you need, then measure customer experience, productivity, and collaboration to see whether it is working.

Team structure shapes how work gets done, so revisit it as your sales motion and customer needs change. Name the behaviors you want to reinforce and make them part of coaching and operating routines.

Don’t leave it up to chance. Choose the sales model and team that works for your business and you’ll build a sales machine capable of sustaining long-term growth.

Explore the three sales team structures ↗

Guest chapter by Nick Persico. The original account describes onboarding at Smart Host; adapt the sequence to your own product and sales motion.

I was hired by Sysco, the largest foodservice distributor in North America, to be an outside sales rep at 21 years old. My first day was in the beginning of February, and they had me in a training program until the middle of May.

That’s right; three months went by before I actually got to speak to my first prospect.

The beauty of being a startup is that you get to skip all of that nonsense. Forget long training sessions filled with hypothetical bullshit.

Here is one four-week onboarding example. Treat the timing as a starting point: adapt it to product complexity, customer risk, and the rep’s prior experience.

Before their first day

Prepare a schedule with learning goals, practice, and check-ins. Set milestones for product knowledge, discovery, and safe customer conversations, then adjust the pace based on evidence of readiness.

At the end of two weeks, what milestones should each new hire have under their belt? Should they already have a pipeline? Closed a deal? That’s up to you, but set a benchmark and make it clear that everyone should be on pace to hit the milestones.

Choose a first day that works for the team and new hire. A Saturday may suit some teams, but it is not necessary for effective onboarding.

Give new hires focused time with teammates, access to the tools they need, and a clear plan for their first week. Schedule this during normal working hours that respect the team’s availability.

Most importantly, they know what’s expected of them when they come in Monday morning.

Week 1: Learn, practice, and begin supported conversations

Begin with product basics, customer context, observation, and role-play. Once a rep can explain the product accurately and knows when to get help, introduce supervised customer conversations. Review the work together each day:

Stop fucking around with training sessions and put them in front of prospects as soon as possible. Let them learn the hard and fast way like you did.

Use the first week to let them learn the ropes on their own. Schedule a stand up at the end of each day where they can ask you questions. A daily stand up is very important for a number of reasons:

• The team asks questions about direct feedback they are hearing out in the market. You can help them get better at managing objections or improve their pitch.
• You’ll be able to figure out if the leads they’re calling are any good. Look at daily reach rates to see if you can add or improve on the lead list overnight.
• They are part of the improvement process. The discussion is there to help everyone improve, as well as improve the sales process.

New hires need guided practice as well as clear explanations. Let them observe, try realistic scenarios, receive feedback, and gradually take on customer conversations when they are ready.

Teach the sales process as reps prepare for each step

Sequence training around what the rep needs next. Teach core workflows before asking someone to use them, then reinforce the lesson with a realistic task.

Practice proposals and account setup with examples before using them on a live opportunity.

Teach each part of the sales process before the rep is expected to handle it with a customer. Where appropriate, pair instruction with practice on live opportunities and coach in the moment.

Reps may progress at different rates. Use shared readiness criteria and individual coaching so each person gets the support they need before taking on the next step.

Coach one skill at a time

Use the third week to identify specific development needs from the work you have observed. Compare progress with the learning plan, not with a vague impression of who is hustling hardest.

One person may be weak at organizing their day. Another may be using the wrong terminology to describe something. Identify those weaknesses and communicate them, and have each person focus on improving on that single aspect of their sales game.

Use the single focus to see if they are capable of prioritizing things. Did they improve on that metric or trait? Did they take the feedback?

If so, you’re starting to build a great sales team.

Week 4: Review readiness for greater ownership

Review whether reps can identify mistakes, use feedback, and manage the tasks they have practiced. Expand ownership where the evidence supports it and keep coaching the gaps.

Set clear expectations for responsibilities, goals, and support. Adjust ramp targets to the sales cycle and evidence of readiness.

A shared training guide can speed up learning without skipping practice or coaching.

A new hire can begin learning the product on day one, but they should only make customer calls once they can represent it accurately and handle common questions or know how to get help.

A reusable training guide can make onboarding more consistent. Pair it with practice, coaching, and updates from real customer questions.

Practice alongside instruction

Practice helps people apply what they have learned. Start with realistic scenarios, then add customer-facing responsibility as the rep demonstrates readiness.

It’s like learning to swim - you can’t learn it by reading about swimming. You need to actually get in the water.

The documentation you give them is just a life jacket to keep them afloat, not a boat that prepares them for getting in the water.

Create a new sales rep training manual

What are the 20% of questions that prospects ask 80% of the time? What are the 10 to 20 most common things they want to know?

Write down these questions.

Then write down the short and concise answers.

(Involve the most successful members of your sales team in creating this training guide for new sales hires.) You’re basically creating an objection management document.

Have your new sales hires study this document, so that they can confidently answer the majority of questions prospects ask.

Don’t know the answer?

What if a prospect asks the new sales rep a question they haven’t been trained on?

Train your new sales reps to say this:

1. That’s a great question.
2. I don’t know the answer for this.
3. But I will find it out for you. I will go to a person in the company that’s the best person to answer this and I will make sure to come back to you with an honest and accurate answer today. Is that ok with you?”

This accomplishes two important things:

• It enables your sale reps to get the right answer to the prospect, and learn more about your product.
• It creates trust, because it’s authentic and truthful.

We called hundreds of thousands of people when we were still running our outsourced sales force, and nobody ever was upset about this. People often appreciate getting such an unexpectedly candid answer from a salesperson. They’d rather have honest answers later over bullshit answers now.

But what if it’s a super simple question?

Some questions are so basic that it can be almost embarrassing if a sales rep doesn’t know the answer. Things like, “How long has your company been in business?”

How should a new sales rep respond if they can’t answer such a simple question?

Same formula, just add these words after “I don’t know the answer”: “Because this is my first week. I just got started here.”

Nobody is mad at people who are new at a business. Everybody has been in that position and knows what it’s like.

What’s your company culture?

Don’t expect your salespeople to be perfect and know all the answers. It’s going to create pressure for them to bullshit when they don’t know the answer.

They will just say things like, “Oh we have been around for three years.” - “Why did you say that?” - “Well, I didn’t want them to know that I don’t know and embarrass us.”

You know what’s embarrassing? Having to make up lies instead of giving forthright replies.

Just be honest. It’s an opportunity to stand out from the crowd, and it starts with the way you onboard new sales reps.

Don’t require them to have all the right answers, require them to have the right attitude.

Flip it, and reverse it

Here’s how you take this to the next level. Have your sales reps respond to questions they can’t answer as follows:

1. Great question.
2. I don’t know the answer (because I’m new here).
3. But I’ll find it out for you.
4. In the meanwhile, let me ask you, “What would you want the answer to be in a perfect scenario?”
5. Why?

That fourth and fifth step is where the magic happens.

Prospects have a chance to say what they want and then explain why they want it.

Your sales reps can flip the question around, and turn it into an opportunity to learn more about the prospects, to understand them better, to qualify them.

Here are some questions that will be helpful for this step:

• What would be your ideal answer?
• How are you going to use this? / What’s the use case?
• What is the workflow when this is relevant and important?
• What do you want the answer to be and why is that important to you?
• Tell me a little bit more about your company/team, and by the end of the conversation I will make sure to come back with any missing information.
• Why do you want that to be that way? Why is this important to you?

Typically, what happens with new sales hires who don’t ask these questions is that they don’t provide enough context.

They’ll go to the engineer and say, “Somebody asked me, how do you configure this on the API level?”

Engineer: “What’s the use case for this question? Why is this relevant?”

New sales rep: “I don’t know, I just put down the question. I didn’t ask them anything about it.”

And then an engineer can’t provide them with a good answer, because they lack context.

Most sales leaders teach new reps to give the right answers. Great sales leaders teach new reps to ask the right questions.

You’re ready to start hiring.

I covered everything from when you should start hiring sales reps to how to quickly yet efficiently onboard them, as well as my unconventional interviewing hacks.

And if I’ve done my job right, you should be feeling more knowledgeable and motivated to hire some great sales reps.

There’s only one thing possibly holding you back from jumpstarting your own sales hiring process: you.

Too many people put off doing what could be done today for tomorrow.

While you may be feeling pumped now, if you don’t immediately get the ball rolling on sales hiring, you’re going to keep putting it off until the lack of salespeople goes from being an inconvenience to a full-blown pain.

That’s why I want to show you the power of right the fuck now and challenge you to apply it to your own sales hiring process.

How I got Paul Graham from Y Combinator to introduce me ... right then and there

Years ago, we had a meeting with Paul Graham and I asked him if he’d email an investor. “Sure”, said Paul.

When you ask for something, always be prepared for a yes!

I already had my laptop open, with an incognito browser window on the Gmail login screen. I turned my laptop towards him and said, “Can you do it right now?”

PG laughed, logged in and sent the email right then and there.

Could I have emailed him about it later? Yup. Would he still have done it? Probably. But this was important for us and “probably” wasn’t good enough.

“Probably” shouldn’t be good enough for you either, otherwise whatever it is probably isn’t worth doing in the first place.

The power of right the fuck now challenge

At this point, you should know if you’re ready to hire sales reps and what type of traits to look for.

Now, it’s time to take that knowledge and start searching for those great sales reps.

That’s why I want you to take the right the fuck now challenge.

It’s only three steps, the exact steps you need to take to start finding sales reps.

1. Make a list of 10 people who you think are great and killing it.
2. Write them an email asking if they know anyone else who is killing it.
3. Contact the people they refer and start recruiting them, using the advice from the chapter “Hire above your talent class: How to recruit the un-recruitable.”

To make it a little easier, I’m going to give you an email template to use when asking for referrals.

Start with a clear role brief, a consistent interview scorecard, and an onboarding plan. Put an owner and a date against each step so your hiring process moves forward.

Finding great sales reps won’t be easy, that’s why you have to start now, instead of tomorrow.

What are you waiting for?