Enterprise Sales for Startups

Many startup founders daydream about enterprise sales.

One minute, you’re developing software in a studio apartment. The next, you’re on a beach with Bill Gates.

Bill: “I’m so glad you created the perfect product for every single Fortune 500 business.”

You: “Me too, Bill. I can’t believe how easy it was.”

Bill: “Want the last sip of this piña colada?”

For a short time, I thought enterprise sales was really easy. Until it wasn’t.

I made my fair share of mistakes (and learned a lot of tough lessons) along the way. And that’s why I created Enterprise Sales for Startups. I want to help you make smart decisions for your business, especially if you’re considering enterprise sales.

Founders ask me enterprise questions all the time:

When should we think about enterprise? How do we get started? Isn’t selling to large organizations risky? Why were you and Bill sharing a piña colada? Aren’t you both billionaires in your dream?

I put together this guide to answer (most of) these questions. And I often use my own history with enterprise sales as a reference.

As for how to read Enterprise Sales for Startups, feel free to jump around. The ideal order really depends on your situation: are you just getting started or do you simply need a refresher?

Either way, it’s a quick read. Perfect for the beach.

Go get ’em!

Steli

Enterprise sales can be treacherous, especially if you’re an inexperienced startup founder.

It’s just too easy to make mistakes. You fail to provide adequate support during a pilot. Or you don’t get buy-in from key stakeholders. By the time you’ve learned from your mistakes, it’s often too late; you’ve missed your window for success.

That’s exactly what happened when my first startup went belly-up a few years ago.

It was mid-2007. We were a tiny team: just me and one engineer. Our open education Facebook app wasn’t getting any real traction, and it seemed like we were slowly losing momentum.

One day, out of the blue, we got a message from a senior executive at Google: “This is EXACTLY what I want to do internally at Google. I want to have engineers around the world teach each other.”

As a tiny startup, we were excited and terrified at the same time. We’d been struggling for so long in the end-consumer space. Maybe enterprise sales was the way to finally grow the business.

We set up meetings with Google and more high-level executives got involved. They loved our product and vision, but we still had our doubts. We were too small. Our product wasn’t ready yet. We didn’t know about enterprise sales. But the opportunity was too tempting to resist. So we decided to go the B2B and enterprise sales route.

This shit is easy

We set up meetings with several other tech companies through our investors. We hustled hard and pitched perfectly. The product concept was great and high-level leadership loved it, not just at Google, but Intuit and Oracle, too. They all agree to do a pilot.

At that point, we were high-fiving ourselves. I still remember thinking, “Everybody says enterprise sales is so hard. This isn’t hard. This shit is easy!”

But 12 months later…

The Google deal fell flat. Intuit was a dud. Oracle broke our heart.

So what happened?

The senior director at Google was so excited that she ended up joining our advisory board. That’s a great start.

Unfortunately, we assumed that paying for the pilot (and having a senior director on our advisory board) would guarantee our software’s success. We assumed they would know how to implement the solution into their organization.

We obviously had no fucking clue about enterprise sales.

What we failed to recognize was that management pushed the execution down to a project manager. And that project manager wasn’t excited about our software. She had little interest in promoting our platform as an internal tool within Google. So she went through the motions just enough to be able to say, “We tried, but it wasn’t a good fit.”

You have to sell to ALL the stakeholders

That project manager was not a bad person. We just never made an effort to establish a relationship with her. We never sold her on our vision. We didn’t ask her what we could do to support the pilot.

• We didn’t provide her with any training materials
• We didn’t offer a roadmap for the pilot
• We didn’t share any KPIs
• We didn’t supply internal marketing and promotional materials
• We didn’t help her understand how this could be an opportunity for her career

We weren’t aware of the other projects she could pursue, or the other vendors who wanted Google’s business. We failed to manage the whole thing. And it fell apart.

We felt crushed. But we still had Intuit in the pipeline…

They probably know better than us

Intuit had an idea for how they wanted to use our platform, but we didn’t think it would work. We figured they knew better than us (and we were afraid to bring it up) so we kept our mouths shut. They’d probably come up with a way to make it work and, in the process, teach us a thing or two.

Their “pilot” ended up being nothing more than a poorly written email to their internal user base. There wasn’t any follow up or follow through. As you can imagine, the response to their pilot was weak, so they filed the whole thing away.

What mistake did we make here? We didn’t raise attention to obvious red flags, we never suggested alternatives, and we failed to manage the entire process.

But the most painful experience was Oracle

We worked almost nine months on closing that deal. We built relationships with a senior vice president, director, and managers on different levels.

We had a huge pilot in mind. We worked out a detailed plan of action, identified metrics to measure success, and agreed on a budget. They’d be spending tens of thousands of dollars on the pilot.

After nine months of schmoozing, hustling, and planning, the senior vice president left Oracle to become the CEO at another company. He took all the people we built relationships with at Oracle with him. We were left with nothing.

It was soul-crushing. We felt like enterprise sales had chewed us up and spit us out. My partner left. I was totally burned out. We didn’t accomplish anything. All that work and we had nothing to show for it.

If you want to fix weak spots in your enterprise sales approach, ask yourself these questions:

• Who are the key stakeholders involved in this deal?
• On a scale of 1 to 10, how much does each stakeholder want this deal to happen?
• Does each stakeholder see an opportunity in their career for this?
• Is each stakeholder excited and passionate about your solution? Have you sold the vision to each person?
• What are the major objections each stakeholder has?
• Do you manage the onboarding process and pilot yourself?
• Are you actively involved in making the pilot work for your prospect?
• Do you have clear metrics to determine how the prospect defines success?

You’ll need to answer all of these questions (and a bunch more) if you want to avoid the costly mistakes I made with my first startup.

Be sure to keep this list close as you plan your own enterprise sales approach. And frequently revisit your answers to ensure that you’re set up for success.

Not too long ago, a founder told me an enterprise sales story that speaks to a problem many startups have.

The company had a highly technical product and zero customers. They’d focused on enterprise sales for months when (finally!) they recruited an internal champion at a large organization. He was an IT manager who loved their product, and he sent tons of buying signals.

Eventually, he said, “You guys should fly out here for a meeting with the purchasing department to make this deal happen!”

So the whole team got on a plane, ready to crush the meeting.

Ten minutes after entering the conference room, however, they realized that only one person was enthusiastic about the deal: the IT Manager. The other executives talked about maybe doing a pilot at some point, but a deal was miles and miles away.

This was more of a “getting to know each other” meeting. The IT Manager wanted the deal to happen, but he didn’t wield the power to push things forward.

Disappointed, the founders flew home.

The IT Manager felt horrible

He wanted to somehow make it up to the founder, so he said, “I still have a bit of budget left over for this fiscal year, and I have to spend it before the end of the month. If you can build a mini-product for me, I can pay you $25k.”

While this wasn’t a project the founder wanted to pursue (and it wasn’t on their core product roadmap) it seemed easy enough to execute and would give them their first customer.

So the founder asked me, “Should we close this deal or not?”

What was my answer?

I said, “Do you still believe in this IT Manager? Do you trust in his ability to communicate well within his own organization and get the deal done?” He said no.

“Then find someone who can manage this process better.”

And forget about that tiny project in the meantime. Don’t worry about a small win that could maybe lead to a larger deal later on. It’s a profitable distraction trap.

There are 3 reasons why it’s dangerous to fall for the profitable distraction trap:

1. It distracts from your core product. Even if you estimate that the project would only take three weeks of work, it’s notoriously hard to predict these things accurately. This could easily escalate into a three-month project and throw off the timeline for your core product.
2. It weakens your follow-up negotiations. You’re currently in a position of strength. Your internal champion feels obligated to you because your team flew all that way for nothing. Taking on a small project shifts that dynamic. Demonstrate confidence in your product and your company. You won’t change your entire product roadmap for one customer.
3. Calling this organization your first customer would be unwise. Most prospects and investors want to talk to your first customer, especially if you bring them up in conversation. If this first customer is totally unrelated to your core product, the reference is worthless. It’d actually make you look really bad.

How do you decline a deal like this while still maintaining a good relationship with your internal champion?

Try saying something like:

“We would love to help you, but this is not part of our product roadmap in the short-term. Let’s keep in touch, and when your organization is ready, let’s make the original deal happen.

We appreciate that you want to support us in the short-term, and we think there’s something you can do to help.

Who do you know in other organizations that might benefit from our solution? Who in your circle of friends and peers should know we exist?

Connecting us to these people would be the most valuable thing you could do for us right now!”

This response shows that you want to focus on your core product, while still allowing the relationship to grow. By asking for referrals, you’re also making sure to feed your funnel with warm leads and build up your enterprise pipeline.

If you’ve got a solution that you think can benefit enterprise customers, there’s plenty to consider.

Let’s cover some of the benefits and drawbacks of enterprise sales:

Should you focus on enterprise sales first?

That depends on how well you know your target audience. Look for things that give you a competitive advantage:

• Do you have a personal or professional network you can tap into?
• Do you possess insider knowledge?
• Do you have experience working in or with enterprise organizations?
• Do you have some recognizable branding within enterprise markets?

If you don’t have any of these competitive advantages...

If you lack a clear advantage in this market, consider starting with smaller organizations where you can test the use case and buying process with less exposure. Choose a segment you can serve well, then use actual conversion, retention, and delivery evidence to decide whether to move upmarket.

Smaller deals can produce more frequent learning, but deal volume is not the only useful signal. Track whether customers reach the intended outcome, renew, and can be served sustainably before moving upstream.

Example: Close

When we began selling Close, we focused on startups and small sales teams. That gave us a starting point for deciding which opportunities fit our product and which would require a different approach.

As adoption grew, we began seeing medium-sized businesses and larger organizations sign up, often through customer referrals. In that period, many did not move beyond the free trial.

Over time, product improvements coincided with stronger results among some larger customers. Treat that as a signal to investigate: compare qualified demand, conversion, retention, and the cost of supporting those accounts before committing more resources.

This is one possible path, not a universal rule. Compare it with your own customer evidence, runway, product readiness, and ability to deliver before choosing where to focus.

Define your ideal customer profile ↗

What’s one of the most common mistakes startups make when they commit to enterprise sales?

They assume that selling to businesses literally means selling to businesses. But enterprise sales is multi-dimensional. In reality, you’re selling to:

1. The company
2. The department
3. The individual person

In an ideal world, you need to focus on selling on all three levels. Unfortunately, in the real world, you often have to prioritize.

When you’re qualifying (and selling to) prospects, whose needs should you consider? Let’s look at all three in more detail.

The company

Business outcomes and priorities, which include:

• Big strategic initiatives
• Product and feature launches
• Total revenue numbers
• Cost savings
• Large-scale marketing and brand campaigns
• Competitive gameplans

The department

Departmental needs can include:

• Specific KPIs
• Department-specific projects
• Department-specific initiatives
• Company politics (e.g. wars with other departments, competition for budgets and resources, etc.)
• Potential changes in management
• Department-specific solutions for company problems
• Circumnavigation of externally-imposed constraints

The individual

Ask the people evaluating and using your product what success would mean for them. Relevant concerns may include:

• Career goals (e.g. promotion, raise, job security, etc.)
• Credit for key deliverables
• Workload and responsibilities
• Time available for implementation and ongoing use
• Confidence in the decision and support for the change

There’s a great story about the importance of individual buyer needs when selling to large organizations in Ben Horowitz’s book, The Hard Thing About Hard Things:

An early lesson I learned in my career was that whenever a large organization attempts to do anything, it always comes down to a single person who can delay the entire project. An engineer might get stuck waiting for a decision or a manager may think she doesn’t have authority to make a critical purchase. These small, seemingly minor hesitations can cause fatal delays. I could not afford any hesitation, so I scheduled a daily meeting with Anthony, Jason, and the team, though they were now based in Plano. The purpose was to remove all roadblocks. If anyone was stuck on anything for any reason, it could not last more than twenty-four hours, the time between meetings.

Meanwhile, Anthony worked furiously to find the exciting value we could offer EDS. We started with little things that did not change our fate, but revealed important clues. We flew our main EDS executive, Frank, out to meet with our top engineers and architects. In booking the trip, Anthony reported that Frank requested the longest layover possible in the connecting airport. I thought that I misheard him. “What, he wants a long layover?”

Anthony: “Yep.”

Ben: “Why would anybody want a long layover in an airport?”

Anthony: “Apparently, he likes to hang out in the airport bar between flights.”

Ben: “Why does he like to do that?”

Anthony: “I asked him the same question. Frank said: ‘Because I hate my job and I hate my family.’”

In this case, they ended up buying a whole company just to meet one of Frank’s needs. If you haven’t read this book yet, I recommend you do so.

How to deal with conflicting needs

A person’s priorities may differ from their team’s priorities. When that happens, find out where the conflict lies before proposing a solution.

Help your contact make a sound case. Connect their practical needs with the organization’s goals, and be clear about trade-offs you cannot resolve.

A useful champion understands the problem and can help others evaluate your solution. Support that person with evidence and answers, while continuing to build relationships across the buying group.

Selling to larger organizations can require more coordination than a self-serve sale, particularly when several teams evaluate the purchase.

There is no standard time to close an enterprise deal. The path can include reaching the right people, building internal support, evaluating the solution, and completing procurement. Map the stages with each buyer and plan for delays as well as a no-decision outcome.

A larger organization may evaluate a SaaS product differently from an individual self-serve buyer. Questions to investigate include:

• Does the buying group want a guided evaluation, or can users assess the product through self-service?
• Can the standard product meet the use case, or are configuration or product changes required?
• What hosting, deployment, data-residency, or security requirements apply to this buyer? Some organizations ask about on-premise deployment; establish whether that is a requirement before treating it as representative.

Security, user administration, data handling, contracting, and procurement may all matter, but the requirements differ by organization. Ask what applies to this purchase and confirm what your product and team can support.

If the opportunity fits your product and capacity...

Know what you can and cannot promise

Be clear about current capabilities, limits, and timing. Record open questions, validate requests with the people who own delivery, and avoid committing until you know what the work would require.

If the buyer proposes a pilot, agree on the participants, owner, duration, success measures, support, and decision date. Check that the team can deliver it and that the result will answer a real purchase question.

Know what to charge for enterprise deals

Set pricing from the value, scope, support burden, and economics of the account. If you expect negotiation, define in advance what flexibility you can offer and what would make the deal unsustainable. Avoid adding an arbitrary markup just to create discount room.

Price training and support according to the work required and the value delivered. Offer the level of help the customer needs and your team can consistently provide.

Choose contract length and payment timing based on customer value, implementation effort, cash needs, and the buyer’s procurement rules. Annual or longer terms can make sense when both sides benefit, but monthly, phased, or pilot arrangements may be appropriate. Do not require prepayment by default; explain any commitment and trade-offs clearly.

If you put in the effort, and you make smart choices along the way, even one enterprise customer can drive massive growth for your business.

Enterprise sales is a unique game with its own playbook, so it’s important to know the rules before you get started.

Here are seven considerations that can help a startup plan for a complex sale:

Rule #1: Plan for a buying process that may take time

The time from first contact to a decision depends on the buyer, use case, stakeholders, budget, and procurement steps. Estimate from the actual process you uncover, then revisit the forecast as evidence changes.

Rule #2: Deals can change or stop, even after strong progress

A purchase can stall or end for reasons inside or outside your influence. For example:

• A champion or key contact changes roles or leaves
• Changes in corporate strategy
• Changes in the economy
• Other changes in priorities, resources, timing, or fit can also affect a decision.

Rule #3: Sell to multiple stakeholders

Map the people and teams involved, then learn what each needs to evaluate, approve, implement, and use the solution.

Different groups may have different requirements. An executive sponsor can support a purchase while IT, security, finance, or end users raise questions that affect implementation or timing. Surface those needs early and agree on how to resolve them.

Rule #4: Price for value and viable delivery

A discount, freemium entry point, or paid pilot can each be useful in the right context. Evaluate whether the offer attracts a qualified buyer, supports a clear evaluation, and leaves enough margin to deliver the promised value.

Price alone does not determine perceived value. A low-cost or free offer can help a buyer evaluate a product, but it should have a clear scope, audience, and next step. Match price to the value, risk, and support involved.

Rule #5: Understand the people making and carrying out the decision

People weigh organizational goals alongside their responsibilities, incentives, workload, and risk. Learn what each participant is accountable for and connect the product to outcomes they value without assuming personal motives.

Rule #6: Learn before the product is fully built

You can discuss a problem and test demand before the product is complete, provided you are clear about what exists and what remains uncertain. Use those conversations to learn, not to imply that an unfinished capability is available.

You might say that you are exploring a problem and ask how the organization handles it today, what outcome matters, and what evidence would make a solution worth evaluating.

Keep interested prospects informed only when you have a useful update. Treat their feedback as input, not as evidence that they will buy when the product launches.

Rule #7: Move upmarket when the evidence supports it

A company may move upstream as product fit, demand, delivery capacity, and economics support it. It may also choose to serve smaller customers or multiple segments. Reassess the trade-offs with evidence rather than treating one path as inevitable.

In a multi-person sale, an encouraging response from one decision-maker is not the same as a completed purchase. Confirm who else must evaluate, approve, implement, or use the solution before forecasting the deal as closed.

I’ve committed this mistake many times. An influential person in the organization buys into my value proposition and commits to a purchase. Deal won! I sit back and relax. There’s other people I’ll have to talk with, but the deal is done.

Then some engineer wants to talk with me about integrations. Sure, I’ll help him out. I’m a nice guy, and I want them to be successful.

I get on the call, assuming it’s going to be a pleasant conversation where an enthusiastic engineer asks me for some expert advice.

From surefire win to lost opportunity

But instead, the engineer asks a lot of tough questions. He seems disengaged and critical, and eventually starts pushing me around, saying things like, “If you can’t figure out X, Y and Z, you can forget about this deal I’m not going to sign off on this!”

Wait a minute. What just happened here? I thought the deal was won, and now this guy is giving me a hard time?

Believe me when I tell you: seeing a done deal fall apart hurts badly.

Here’s how you can prevent this from happening:

Learn about different stakeholders

When you meet someone involved in a purchase, ask what they need to evaluate, how the change may affect their work, and what concerns or requirements their team has. Do not assume their agenda or personal incentives; let them describe them.

Sell each stakeholder individually

Once you understand a stakeholder’s goals and concerns, explain the parts of the solution that are relevant to them. Invite questions and be candid about limitations rather than manufacturing a personal reason to buy.

“Deals close when everyone involved, every stakeholder, influencer and decision maker feels the impact of going with your product or service will change their world for the better and that your solution is key in reaching the goals and objectives they’re trying to accomplish.”

• Jim Keenan, How to Know When a Deal is Ready to Close

Complex sales often require explaining the solution to several people, each with different questions and responsibilities.

This takes work, so prioritize the stakeholders and questions that can change fit, approval, implementation, or adoption. A thoughtful process can reduce avoidable gaps, though it cannot guarantee a win.

Every participant deserves a respectful, relevant conversation

A concern may come from someone outside the expected decision-making group. Ask people how they are involved and what they need; avoid ranking their importance before you understand the process.

You should treat people with respect just because it’s the right thing to do, but it also makes a lot of business sense.

Build your army of internal champions

Building support across the relevant stakeholders can help surface concerns and clarify what needs to happen next. It does not remove the possibility of objections or a changed decision.

Treat each interaction as an opportunity to understand the buyer’s needs and share relevant information. Keep the conversation useful rather than turning every contact into a sales pitch.

For a complex purchase, identify the people and teams involved and understand their roles, requirements, and decision rights.

As a founder, you might find yourself faced with a new challenge: breaking into enterprise sales. Few people come into this game with a playbook in hand. I sure as hell didn’t, and I learned my lessons the hard way.

What’s one of the most painful (and expensive) learning experiences a startup can go through? Investing months of work into a deal only to see it fall apart in front of your eyes.

The CEO is the beginning (not the end) of the deal

A positive conversation with a CEO or senior executive may open a door, but it rarely explains the whole buying process. Ask who will assess the solution, own implementation, and approve the purchase.

An executive sponsor may delegate evaluation or implementation to colleagues. The sponsor can remain influential, but the project owner and other stakeholders may shape whether the solution is workable.

A productive executive meeting may lead to introductions to the people responsible for evaluation, implementation, or approval. Confirm the next step and why each person should be involved.

The next steps depend on the buyer. They may include:

1. Selling all other stakeholders involved in the deal
2. Selling the person that’s going to manage the project internally

Step #1: Close all the stakeholders

Purchasing processes differ. Ask the buyer what approvals, reviews, and implementation decisions apply to this purchase.

Ask: “If you decide this is a fit, what typically needs to happen before the purchase can move forward?” Then map the named steps, owners, dependencies, and timing with the buyer.

A complex purchase can take weeks or months, and some take longer. Use the buyer’s stated process and your own stage history to create a realistic forecast rather than relying on a fixed range.

Spend effort in proportion to the opportunity and evidence. Revisit the fit, access to stakeholders, business case, and likely delivery work as the process develops; no checklist can guarantee a result.

Ask the relevant groups, such as legal, procurement, security, IT, or finance, what review is required for this purchase and when they can engage. Requirements vary, so confirm them with the buyer.

You can help the buyer coordinate next steps by documenting owners, open questions, and dependencies. Keep responsibility shared and respect the customer’s process.

Step #2: Close your internal champion

The person responsible for implementation may have different questions from the executive sponsor. Involve them early enough to assess workload, readiness, and likely adoption risks.

Explain the organizational outcomes and practical impact for the people doing the work. Ask what support would help them evaluate and implement the change; do not frame the decision around career benefits by default.

Use questions such as:

• What goals do they have and how can your product help them?
• Which objections and fears do they have with regard to your project?
• Which objections will they encounter when implementing your solution in the organization?
• What is the best way for you to empower them to succeed with this new project?

Invest appropriate time in the relationship with the implementation owner. An executive may open the door, while day-to-day success depends on many factors, including fit, resources, and the customer’s operating context.

In a past example from Close’s sales experience, a rep was selling the company’s inside sales CRM to a large organization.

The company had sales teams all over the world, and their U.S. team manager loved our product, and wanted to champion it within the company.

But the ultimate decision-makers (VP of Sales & CEO) were both located at their headquarters in Italy. Our sales rep had never spoken with them. Instead, he coached the U.S. team manager on how to handle common questions and objections.

Here’s what the sales rep told me at one point: “Now I’m just waiting until the end of the month, because that’s when she’s going to be able to get buy-in from the VP of Sales and the CEO.”

The rep saw a risk: the decision-makers had not yet heard the product story directly.

An internal champion can be valuable, but ask whether decision-makers need a direct conversation and whether the champion has the time and information to represent the solution. Offer to join when it would help.

Stay in control of moving the deal forward

Agree with the buyer and champion on who owns each next step. You can coordinate and follow up, while leaving internal decisions and responsibilities with the customer.

Internal champions can’t sell your product as well as you can

A champion may not have the product detail or context to answer every question. Make it easy to bring the right subject-matter expert into the conversation when useful.

If a question needs a detailed answer, help the champion get an accurate response. That protects their credibility and gives the buying group reliable information.

The decision-maker will think: “Well, if they don’t even know the answer to these obvious questions, should I trust their judgment on this? That product is probably not a good fit for us.”

Avoid ineffective communication

The internal champion will have to go back to you (the actual sales person) to ask these questions, and forward your answers to the decision-maker.

Relaying information through several people can add delay or lose context. When a question affects the decision, offer a direct conversation with the relevant stakeholders and share a concise written answer they can circulate.

Get access to the decision-makers

If an internal champion wants to make the deal happen for you, here’s what you should tell them:

“I’m glad you love the product. Thank you so much for championing this. Let’s do this together. I want to be of service to you and support you as much as possible in this process so that it’ll be a success for all of us.

I know that [the decision-makers] will have questions about our product and company that you couldn’t possibly know the answers to.

Let’s schedule a quick 30-minute call with you, me, and [the decision-makers]. We’ll be able to answer all the questions and I can be there as an expert supporting you in making your case.”

What if a gatekeeper wants to shield the decision-maker?

Sometimes the decision-makers have instructed their gatekeepers to keep you away from them. They don’t want to deal with sales reps.

Typically a gatekeeper will tell you something like:

“Our VP of Sales wanted me to do all the research and come back with all the information for them, so that they can make a decision, without having to interact with account managers from different vendors.”

Two ways to offer useful support:

• Offer expertise: “Would it help to have someone available for technical questions? We can join a short session or send answers your team can review in its own time.”
• Bring in a relevant leader: “If your team wants to discuss our roadmap or delivery commitment, I can arrange a conversation with the person responsible.”

Match the conversation to the questions the buyer needs answered. A senior title is useful only when that person brings relevant knowledge or authority.

Ask your contact how decision-makers prefer to evaluate vendors. If direct access is unavailable, agree on what information they need and how questions will reach you.

Keep the decision process visible. Help your champion, confirm next steps, and revisit qualification when you cannot learn enough to assess the opportunity.

The software is approaching renewal, and the administrator responsible for day-to-day use seems disengaged. Before reaching a conclusion, look at adoption, support history, ownership, workload, and any concerns they have raised.

Slow or missing replies and limited product use are signals to investigate, not proof that someone does not care. Ask what is getting in the way and whether the product still fits their needs.

It can be frustrating when engagement drops, but avoid speculating about the administrator or escalating with a list of complaints. First gather the facts and offer a constructive conversation about what would help.

Pause before escalating. Review the account history, clarify what outcome is at risk, and decide with the customer on an appropriate next step.

If an administrator is struggling at renewal, the underlying issue may have developed earlier. Raise adoption or support concerns when they appear, and agree on an owner and next step rather than waiting until renewal.

Low engagement can have many causes, including unclear ownership, workload, fit, or unresolved product concerns. Ask what is getting in the way before deciding how to respond.

A strong product does not guarantee renewal. Check whether the customer is achieving value, whether unresolved issues remain, and how renewal decisions are made in this account.

Nurture these 3 relationships to foster long-term success

It feels great to close deals and get checks in the mail; these are easy indicators of success. But SaaS sales are built on more than just closing. They require an iron bedrock of solid relationships and good communication that’s built over time.

For subscription software, an executive’s approval may be one step in a broader decision. Learn who else evaluates, administers, pays for, or uses the product in this account.

To succeed at SaaS sales, there are three other critical relationships you have to nurture. Let’s run through the key players:

• The administrator: the person at the company responsible for the implementation of your software
• The boss: the person with the budget, the ultimate decision-maker
• Everyone else: all the other stakeholders involved in the deal

You + admin

The day-to-day application of your product will almost certainly be delegated down in the organization to an administrator or project manager, and it’s critical that you secure this person’s backing.

You want to turn them into an internal champion by doing the following:

• Provide the admin with training materials
• Present KPIs to evaluate your product
• Allow them to understand how this can advance their career
• Take a genuine interest in them as a person

When it comes to deciding whether or not to renew, the administrator of your software is the first one approached, and you need to take the time to sell them on your product.

Admin + boss

The most powerful way to get the admin on your side is to make them look good in front of their boss. You can achieve this by aligning their success with the success of your product. Find out what their needs and motivations are.

From the start of the relationship, ask the boss about the administrator:

• “What’s your relationship like with the admin?”
• “What are their responsibilities in relation to mine?”
• “What’s the best way for me to work with them?”
• “What are their deliverables?”

The Law of Reciprocity in sales applies. Make the administrator look good in front of their boss, and they’ll make you look good when it comes time for renewal.

You + everyone else

A complex purchase may involve legal, procurement, technical, security, or other teams. Ask the buyer which groups are relevant, what each needs to review, and when to involve them.

Influence and responsibility can sit in unexpected places. Treat each person respectfully, learn their role, and involve them when their input affects evaluation, approval, implementation, or use.

How to navigate interpersonal issues

Going the extra mile to build relationships with all stakeholders preempts a lot of problems. You develop a base of internal support within the company that’s actively enthusiastic about your product.

If you’ve taken the time to invest in the administrator and they remain uncooperative, reach out to their boss.

Here’s how you should proceed based upon this response.

Test the waters

Start with the facts.

“Hey, we’ve been working together for a month or two. This is what’s been working.” Slip in a nice promotional detail on how well your product works for the company.

Then, tread into grayer territory, doing your best to remain objective.

• “Here are some questions I have on how to proceed going forward, due to issues X, Y and Z.”
• “Here are my internal communications with the administrator.”
• “What do we need to do to make sure this issue gets resolved? Should I take on more responsibility? How can we reconfigure expectations to everyone’s benefit?”

Instead of assigning blame, describe the situation, and outline the problem as factually as possible. Demarcate the parameters within which you’re working.

And close the renewal

The response you receive from the boss will likely fall along two lines, which will determine how you proceed.

1. The administrator is acknowledged as a weak-link

You find someone else in the company who is aligned with you. In this scenario, it’s appropriate to be more open about the issue and your problems with the administrator.

You’ve put in the time and built relationships with stakeholders; try to get them and the boss towards renewal.

1. Your concerns about the administrator are brushed off, and you’re told to resolve the problem on your own

You can let the matter lie with your fingers crossed, and hope for the best come renewal time, or take your issues more directly to the stakeholder and confront them; it’s a coin toss.

You’ve tried your best to invest in the administrator, demonstrated interest in their success, and you’ve reached out to other stakeholders as well.

Even if the deal collapses, you’ve done everything you can. Investing in people is just good business practice, and will facilitate your future success.

Stack the deck

Sales outcomes are uncertain, especially when several people and priorities are involved. A clear process can reveal risks and improve coordination, but it cannot guarantee the outcome.

A relationship-led approach can help you understand the buyer’s context and support a better decision. Balance that work with clear qualification, product fit, and sustainable economics.

For a subscription business, durable growth depends on customers receiving enough value to continue. Measure that value and the cost of delivering it instead of assuming unlimited upside.

How often are your deals derailed by the unexpected?

A prospect says, “We need to run this by legal” or “Technically, procurement has the final sign-off.”

If legal or procurement appears late, revisit what was asked and what the buyer shared. The process may have been unclear, or new information may have emerged. Update your qualification and forecast without assigning blame.

After you’ve qualified a prospect, this should be one of the first questions you ask:

“What will it take for you to become a customer?”

You’re doing two things with this question:

1. Exploring the prospect’s buying process
2. Encouraging them to imagine a scenario in which they buy your product

Here’s what a typical conversation might look like using the virtual close:

You: “I definitely think we’re a good fit. What will it take for you to become a customer?”

Prospect: “We’ll probably have to take this information back to the team.”

If the answer is broad, ask a respectful follow-up such as: “What usually happens after the team reviews it?” The goal is to understand the process, not to pressure the buyer or eliminate every uncertainty.

You: “Once your team reviews this information, what typically happens next?”

Prospect: “We’ll schedule another call and get our stakeholders together. I’m sure they’ll have more questions.”

You: “Okay, and let’s say I answer those questions to their satisfaction. What happens next?”

Prospect: “We’ll probably want to get a pilot proposal from you.”

This is where you can ask more specific questions, like:

• What’s the average length of a proposal?
• Is there any specific information the proposal should include?
• What’s the average length of a pilot?
• How do you measure success?

Even after you find out the necessary information (they want a 5-page proposal that includes a high-level breakdown of the onboarding process, the pilot will last 1-3 months, and their main KPIs are sales growth and customer acquisition cost) you’re still not done.

You: “Once we send over the proposal, what typically happens next?”

Customer: “Well, then it would have to go through legal.”

At this point, most salespeople might stop asking questions

A reference to legal may leave important questions open. Ask what the review covers, who owns it, and what steps may follow, while recognizing the buyer may not know every detail yet.

You need to keep pushing:

You: “After legal gives the go-ahead, are we ready to move forward?”

Customer: “Yes, we’d only need to run this past a few higher-ups, then the ethics committee and procurement.”

You: “Interesting. What can you tell me about this part of the process?”

Customer: “Well, the ethics committee usually takes a couple weeks to review agreements, and if everything looks good, they’ll send it to procurement, who has the final sign-off.”

You: “Great. And then we’re in business, right?”

Customer: “Yes. At that point, we’d purchase your product.”

You now have a working view of the steps the buyer described. Confirm the owners and timing, and keep the forecast provisional until the required approvals and decision are complete.

What are the benefits of the virtual close?

• You understand all the necessary steps to close a deal
• You guide the prospect through these same steps to avoid confusion
• You explore opportunities to shorten the time it takes to close (eg. running the proposal by the ethics committee and procurement at the same time)
• You help the prospect visualize a future where they become a customer
• You discover major red flags that could slow down the deal or prevent it from happening

This can reveal whether the opportunity fits your business. For example, if the approval burden is high relative to the expected value, or the budget does not cover the proposed scope, clarify the trade-offs before investing more time.

A buyer may have interest but no budget available in the current planning period. Ask when funding could be reconsidered and whether a pilot is useful, affordable, and connected to a real decision.

That’s pretty good to know, right? You want to discover these red flags in the first conversation, not three months into the proposal process.

When you ask for the virtual close, you gain clarity

Some late-stage surprises can be reduced by asking how the buyer evaluates and approves a purchase. New stakeholders or constraints may still emerge, so treat qualification as ongoing rather than assuming every issue was foreseeable.

A useful opening question is: “If this proves to be a fit, what would need to happen for you to move forward?”

Follow up to understand the steps, decision criteria, and unresolved questions. A clear process is useful even when it leads to a no or a later decision.

If a buyer is moving slowly, first understand why. Is the value unclear, is a requirement unresolved, has priority changed, or is a decision not due yet? Choose a next step that addresses the reason rather than manufacturing urgency.

There are several responsible ways to help a buyer make progress: clarify value, resolve open questions, and agree on a realistic next step. Use deadlines or limited availability only when they are real and relevant.

A time-bounded evaluation, when it is genuinely limited

If a new product or plan has genuinely limited evaluation capacity, explain the reason, eligibility, timeline, and support available. Set a seat or company limit only when it reflects actual capacity and can be honored.

You could explain the program this way:

• “We are evaluating a small group because our team can support only [verified number] participants during [period]. Here is what the evaluation includes, what it does not include, and how we will decide whether to expand it. If the timing does not work for you, we can discuss a later evaluation.”
• “We plan to begin on [confirmed date]. To take part in this evaluation, we need your decision by [necessary date] so we can plan access and support. If that timing is not feasible, let’s discuss another option.”
• “We will confirm availability based on the support capacity described above. I can share the current status and update you if it changes.”
• “At the moment, [verified capacity] places remain. You can take the time needed to assess fit; I can answer questions or discuss a later start if capacity changes.”

A real capacity limit can help both sides plan an evaluation. Do not invent scarcity or use it to imply value; explain the constraint and let the buyer decide whether the timing works.

A confirmed pricing change

If you have approved a price change, explain the affected plans, effective date, and who it applies to. Give buyers accurate time to assess the offer; do not imply a coming increase merely to accelerate a decision.

When communicating a price change, state the current and new price, who is affected, and when the change takes effect. A concrete explanation helps a buyer assess the offer without pressure.

Offer a clear incentive when it supports a real business objective

A promotion can be considered when the terms are approved, the economics work, and the buyer can evaluate them without undue pressure. Possible structures include:

1. A clearly scoped discount
   “For an order signed by [valid date], the price would be [specific amount] for [defined scope and term]. Here are the standard terms and the total cost.”
2. Additional access or capabilities, if available
   “For [defined term], we can include [specific capability] at [specific price], subject to these terms.”
   Describe any added capability, limits, and duration explicitly so the buyer can compare the total value and cost.
3. Additional seats, if useful to the buyer
   “We can include [number] additional seats for [defined period] at no extra charge, if that matches your rollout plan.”
   Seat incentives should have a clear duration and fit the buyer’s expected usage.
4. A defined service
   “We can include [specific onboarding or training service] for [defined scope and period]. Here is what is included and what would be separately scoped.”
   Support, consulting, training, and onboarding can be part of an offer when the service is available, clearly scoped, and sustainable for your team.
   If you include or discount a service, define its scope, duration, and any ongoing cost. Compare the total offer with the buyer’s needs and your delivery capacity.

Plan stronger discovery conversations ↗

Buying timelines vary. Rather than assume that six months is typical, ask the buyer to map the steps, owners, dependencies, and likely timing for this purchase.

A clear process can help the parties avoid preventable waiting, though it cannot guarantee a faster decision.

Deal size and buying speed vary by organization and use case. Once you understand the buyer’s process, you can look for reasonable ways to reduce avoidable handoffs or waiting. Two practices may help:

1. Understand the enterprise’s buying cycle

Map the buyer’s actual decision path: who evaluates, what approvals or reviews apply, what information is needed, and who owns each step. Record dependencies and timing as estimates, then confirm them with the buyer.

How do you do that?

You ask the prospect: “What’s it going to take for you guys to buy? What are all the steps involved?”

The prospect will likely say something like, “Well, we’ll have to get approval from this department and get buy-in from this stakeholder.”

Avoid treating the first answer as a complete map. Thank them, then ask whether there are other reviews, approvals, or dependencies to include.

Why is that a mistake?

The buyer may still be learning the process, or additional steps may not be known yet. Keep the map open and update it as new information appears.

A useful follow-up is: “After those steps, what else might need to happen before a decision?”

Let the buyer describe what they know about the path to a decision. Confirm open items, owners, and dependencies; the map is a working plan, not a guarantee of approval or payment.

Once you’ve mapped out their buying cycle, you move on to the next step.

2. Parallelize processes

Find out which of these steps you can go through in parallel. Rather than doing Step 1, then 2, 3, and 4, try to find opportunities to take multiple steps at once. Maybe you can already get started on Step 5, while you’re still working with them on Step 2.

Where the buyer agrees and dependencies allow it, some reviews can proceed in parallel. Confirm with each owner before starting overlapping work.

For illustration, a purchase might include some of these workstreams:

1. You work on getting the green light from the various stakeholders
2. You talk with their procurement department, which specializes in purchasing from outside vendors
3. You often have to go through legal to finalize contract language

Ask whether any of these conversations can begin in parallel without creating rework or bypassing the buyer’s approval process.

Here’s what you can say

When the buyer agrees that the solution may fit, you could say:

“From what we have discussed, there may be a fit. What should we learn or confirm next?”

“It sounds like several people or teams may need to weigh in. Who should be involved, and what would each need to evaluate?”

“We can help with the steps that are useful to you. Let’s agree on owners and timing as we learn more.”

“Would it be useful to ask procurement or legal what they need and when they can review? If so, we can coordinate that with you. We can begin early where it avoids rework, while respecting your internal process.”

Does that sound fair?”

Some buyers may choose to involve procurement or legal early; others may prefer to wait. Ask what works in their process and do not assume a particular response.

Starting a review early may reduce waiting when the buyer agrees and the materials are ready. The amount of time saved depends on the process and cannot be promised in advance.

Whenever you’re able to save time, it makes your life (and your customer’s life) easier, and it helps you become a more profitable, faster-growing company.

When a large prospect shows interest in your startup, it’s easy to jump on the bandwagon. But there’s one thing you should consider before exploring a future in enterprise sales.

For example, suppose a company selling direct to consumers is asked by one prospect to integrate with a particular enterprise platform. How should the team evaluate that request?

Many founders, especially those with limited enterprise sales experience, might say, “Let’s try a pilot and see if companies who use SAP also have a need for our product.”

Here’s the problem:

Before changing the roadmap, investigate the buyer’s problem, the number of likely customers with the same need, the cost of integration, and whether the resulting product still fits your strategy.

A small discovery step can test assumptions sooner than a full product or go-to-market shift. A representative pilot, repeated customer interviews, or a scoped integration test may still take time, so define what you need to learn and the smallest useful evidence in advance.

If you choose to pursue enterprise sales, resource the work deliberately

Consider whether your team can support enterprise work alongside other routes to market. A dedicated focus may be warranted when evidence supports it, but a startup need not abandon other segments by default. Map the investment and learning required to evaluate the choice:

• Agree on a demo or pilot only if it answers a defined question and the scope is deliverable
• Assess willingness to pay and likely contract terms without requiring a long-term contract as a test
• Implement your product
• Generate recurring value for the customer
• Document evidence that the solution addresses a problem shared by the target segment

Repeat the research with other likely buyers. One company’s workflow may not generalize, and platform-specific development should follow evidence of broader demand.

The time required depends on the question, access to buyers, and size of the product change. Set a review point and decision criteria so the team can stop, continue, or revise the investment as evidence arrives.

Validate the request from more than one perspective

If a prospect requests a platform integration, verify the need and feasibility with people who understand the buyer, implementation, and product context. For example:

Talk with people at the platform provider, where appropriate

Explain the use case and ask what they can share about fit, constraints, and likely customer needs. Treat their views as input, not market proof.

Talk with implementation partners or consultants, where relevant

Ask about implementation work, integrations, maintenance, and common customer requirements. Validate claims with additional sources where possible.

Talk with teams that have built similar integrations

Include different outcomes and ask about unexpected work, customer demand, maintenance, and what they would change. Look for patterns rather than relying on one company’s experience.

Review adjacent products and alternatives

Use public materials, customer interviews, and product evaluations to understand alternatives. Competitors may not share information, so do not make the research plan depend on their cooperation.

Are you ready to make the commitment?

If you are unsure, gather more evidence before making a large product or go-to-market commitment. Interest from one or two executives is a useful lead, not proof of repeatable demand.

In an earlier startup, companies including Google, Intuit, and Oracle expressed interest. I mistook that attention and early pilot activity for an easy path into enterprise sales. The work proved much harder, and by the time we understood the fit, we had spent substantial time and energy.

We made mistakes on a path we did not yet understand. The experience cost time, energy, and money, which is why I would now validate the assumptions and delivery burden earlier.

If the evidence supports a larger commitment, define the next investment and review point

Commit resources in stages against explicit learning and delivery milestones. Set review points where the team can assess demand, product fit, and the work required to serve customers, then continue, adjust, or stop based on what you learn.

Are you nearing agreement with a buyer and preparing the purchase documents?

A document based on language the buyer has reviewed before may help clarify expectations. Ask whether the buyer can share a suitable template, then have the appropriate people review any proposed terms. The process and document type vary by purchase.

A contract process can take time, especially when each side reviews a new document from scratch

One possible sequence is:

1. You download a template online and tweak it with the help of a lawyer
2. You send the draft agreement to your buyer
3. Your buyer sends the draft agreement to their legal department
4. The buyer’s legal team reviews the document and may request changes based on its process and risk requirements
5. Legal makes edits and sends them back to your buyer
6. The buyer sends the edits to you
7. You adjust the wording according to their requests (with the help of your lawyer)
8. You send the revised draft agreement back to the buyer
9. The buyer sends it to legal again
10. The process continues for several rounds

Several rounds of review can add time and cost for both sides.

Keep track of open contract questions and who owns each response. The timeline can change for reasons on either side, so coordinate early and forecast with appropriate uncertainty.

A clear owner and next step for each open item can keep the process organized.

How to start from a buyer’s template

If the buyer has a standard template for a comparable purchase, ask whether it is appropriate to use as a starting point. It may still require review and changes.

Call up your buyer and say:

“If you have a template or agreement from a comparable purchase that your team is comfortable sharing, could we use it as a starting point? We would still review the terms on our side.”

If you have something like that, let’s try to use that as our template for this deal.”

A familiar template may make the buyer’s process easier to navigate, but it is not necessarily pre-approved for this purchase. Confirm that it is suitable and allow each side to review the terms.

A buyer’s existing template may reduce drafting work, but it does not guarantee faster review, signature, or a completed deal. Keep the process moving through clear owners and timely responses.

Enterprise sales can open substantial opportunities, but the deal has to work for your customer and your business. Revenue is only part of the calculation; delivery, support, and focus matter too.

If enterprise sales is not right for you, keep building in the segment you can serve well. Revisit the decision when customer evidence and your ability to deliver change. Moving upmarket is an option, not a graduation requirement.

But if you’re ready for the challenge, I have one last piece of advice:

Start today.

You’ve got long sales cycles ahead of you. And internal champions to recruit. And multiple stakeholders to sell.

Seriously, there’s tons to do.

If the evidence supports pursuing enterprise sales, choose one bounded next step: map a buyer’s process, test a specific product requirement, or assess the capacity needed to serve the account. Then review what you learned before committing further.