Startup Sales Consulting Tips & Tricks from 8 High-Performing Consultants

Consulting is hard. Startup sales consulting is an entirely different ballgame.

When consulting with startups, you need to help and train leaders, getting them into the right mindset for sales and revenue growth for their startup.

Your help and advice can have a direct impact on the success of the company.

Are you wondering what it takes to be a successful startup sales consultant? We talked to 8 top-tier sales consultants who regularly work with startups at different stages. They shared 14 top pieces of advice on sales consulting for startups.

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1. Balance Your Inbound and Outbound Efforts

Getting new consulting clients is a constant battle. Josh O’Brien of RevShoppe explains how consultants must balance their efforts between inbound and outbound sales. First, regarding inbound, he says:

“We’ve seen a lot of success from other sales consultants on LinkedIn, giving away free information.”

But you might be thinking, hold up. People pay me for my advice. Why would I give that away for free? Josh continues:

“Think about: How do you continue to drive value? What are the results I’m going to give? What kind of outcomes do I want to give my clients.

“Once you have those things, it’s easier to start demonstrating your intelligence and expertise to a point where people will start coming to you.”

That said, outbound sales is also essential.

"I think that if you’re young and hungry and have that outbound-hunter mentality, you’ll have a huge advantage. Go out there and find the customers you know you can help.”

2. Stay Focused on What You’re World-Class at

“Sometimes a consulting firm thinks: if it’s revenue related, we can do that,” says Jake Dunlap of Skaled.

But he learned from experience that trying to do everything doesn’t help a startup sales consulting business—in fact, quite the opposite.

“We’ve gotten a lot better at this over the years,” explains Jake. “Sure, there are a million things we could do. But what are the things we want to be world-class at?

“The more focused you get, the more focused your business and your message will be. And your people can focus because they know what they’re supposed to be doing.”

3. Learn to Stay on Top of a Fast-Moving Business

We asked Mark Colgan of Yellow O what is the biggest challenge for startup sales consultants. He said:

“If you’re working with a client who has raised a considerable amount of funding, they have pressures from VCs and the board. Things are moving very quickly—they’re hiring, adding new tech to their stack, etc. As an external consultant working a few days per work or per month, it can be hard to keep on top of all that because you’re not inside their business.”

Changes happen quickly in fast-growing startups, especially those with VC funding. So, how does Mark stay on track with his clients?

“Good communication with your client is essential,” he says.

“If you don’t have that, you could end up behind with everything within a week. I do my best to manage that expectation of communication before the engagement starts.”

While communication will differ from consultant to consultant (and even from project to project), you need to find the best way for you and your client to communicate clearly and effectively without wasting time.

Tools for asynchronous collaboration, such as Slack, Loom, Miro, Google Docs, or Asana, are all great options to consider as part of your tech stack.

4. To Get Consistent Business, Do Good Work

This may seem simple in theory, but the reality involves aligning your offer with your most effective way to achieve results.

For Alberto Nodale, this is time-related:

“The minimum timeframe I offer is two months because that’s when you can really start seeing results.”

But how does a two-month engagement help him get consistent work? Alberto explains:

“Most of my customers don’t stop after two months because they see the results, the team gets better, and as they do, the company grows, and they hire more sales reps. At that point, it becomes an interesting cycle because they need training programs for these people, and when they think of someone who specializes in remote SaaS sales, they come back to me.

“It’s really a cycle that feeds itself—if I do good work, the companies can grow and they will usually keep me on for much longer than two months.”

5. Overcome Pushback with Clarity

Many times, getting your clients the best results involves overcoming their previously held beliefs. How can you overcome resistance to your work within a startup?

Kevin Ramani has worked with many founders in the B2B tech startup world and has faced this problem himself. Here’s how he explains his mindset when facing this issue:

“If it was very easy to convince people to change and course-correct, then anybody could do it. I most certainly get people pushing back, and I think that if people believed in the path they’ve taken so far, naturally, they’re going to have some resistance in changing it.”

How can you overcome this kind of pushback?

“Part of my role as a sales consultant is to help people see the other path and how that is significantly more beneficial. I find that when people have more clarity on where things are going, they will naturally take the path of more clarity. So I have to be the one to light that way.”

6. Learn How to Easily Convey What You Do

Startup founders and leaders don’t have time to mess around. And with so much change happening, the POC you convinced initially may not be the person you’re dealing with down the road.

If you want to get (and keep) the attention of busy startup leaders, you need to be able to briefly and consistently explain what you do for your clients.

“We’ve tried to grow up and have continuity across our company,” says Josh. “We really thought about: what does RevShoppe do? What do we do for our clients? And how do we convey that easily? That way, it doesn’t matter who’s coming in and out of the organization.”

7. Do In-Depth Qualification, Just Like a Normal Sales Process

How do you qualify new startup sales consulting clients? Mor Assouline explains:

“The questions I would ask a prospect on a demo are typically the same questions I would ask a founder or CEO. So first, what’s their why? Essentially, I’m looking at their challenges and pain points. What does success look like to you in the first 90 days of implementation? Here, I’m looking for their expectations.”

After that, Mor explained to us how he digs deeper into the business and sales process with questions like:

• Do you have a product-market fit?
• What’s the biggest challenge you’ve seen since the launch?
• What’s your average sales cycle?
• What’s your average contract value?
• How many demos are you doing on average per month?
• What’s your demo-to-win rate?

“I also like to discuss business infrastructure, buyer scenario, ideal customer profile, and those types of questions.”

8. Adapt Your Offering to What Your Target Audience is Looking for

Mark's insight, drawn from his experience as a sales consultant, underscores a vital lesson about aligning your approach with your customers' needs. This lesson gains further significance when fused with strategic outbound sales tools, enabling you to craft a more effective engagement strategy.

“I used to run a service for outbound sales done for you. But that’s not what people wanted: they wanted revenue. So I changed the way I described and packaged the service.

“This change came simply because I spoke to a few of the founders and CEOs that I wanted to work with, got a better understanding of the language they were using and changed to use that language myself.”

The point: if you don’t know how your customers talk and what exactly they’re looking for, it’ll be more difficult to get their attention. Have conversations with your ideal customers and adapt to the way they describe their main pain points.

9. Avoid Being Prescriptive

Kevin Ramani started his engineering career at NASA, so it’s no surprise that he advises consultants:

“Take an experimental approach.”

This is important because many startup sales consultants push an exact formula on every business they work with. This cookie-cutter approach doesn’t allow space for the individuality of each new startup.

Here’s Kevin’s advice:

“Don’t be prescriptive. Remember that everything you know can fail with a new client. Instead, help the client approach this by setting up experiments and hypotheses to test. Improve, measure, iterate.

“Your job is not necessarily to give them results. Your job is to help them put the right frameworks in place to test and evaluate the results correctly.”

“Here’s a simple way to think about it: we all learn in science class that when you run an experiment, you’re looking to validate a certain hypothesis. But the results are invalid if your experiment is run with bad processes.

“As a startup sales consultant, your job is to help them set up the right experiments and run them the right way. Then, you can evaluate and interpret the results correctly. And even if the experiment fails, there’s valuable information there for the company.”

10. Act Like You’re Part of Their Team

Jake’s advice to new sales consultants is: Act as if.

“You need to act as if you are part of their team,”

says Jake.

“Keep an objective lens, but don’t play from the sidelines. Nobody hires a consultant to sit back and dictate. They’re hiring a consultant to help them solve things and get things done. That means you have to go out and play. To me, that’s one of the most important pieces of being a startup sales consultant.”

While it’s essential to keep that high-level view of what’s happening, you should also feel invested in the results the company gets. Effective startup sales consulting comes from a genuine motivation to help.

11. Remember You Can’t Scale Yourself Indefinitely

Scott Leese has helped multiple companies from $0 to $25M in ARR. But as he grew his consultancy, he hit a challenge:

“You can’t scale yourself infinitely,” says Scott. “At some point, I run out of bandwidth. I ran into this challenge myself, realizing that I could run a million-dollar-plus business alone, but if I wanted to do more, I had to grow. I was capped out.”

Here’s how Scott approached this challenge:

“The key is to find someone who can add value and supplement you in areas where you’re weak or deficient.”

Understandably, taking on more people in your solo consultancy is a big change. And this can be scary. Scott says:

“A big challenge was getting comfortable with the idea of having an employee. I’m responsible for somebody, their family, and their livelihood. Do I really want to deal with that? It’s something I wrestled with for a while, but I finally bit the bullet. And I’m very happy with the friend that I hired, but it’s a big change.”

The best kind of growth often happens outside your comfort zone. So, while you should approach this step with the level of seriousness it deserves, don’t let fear hold you back.

12. Genuinely Love Learning

We asked Mark Colgan what his favorite part of consulting is, and his answer was:

“I get to learn so much.

“I’m so curious about how businesses run, what their business model is, what success means to them, what it means for the founder to achieve those goals. For me, as a consultant, I get to speak to hundreds of people a year, which I can then refer and recommend to other people as well.

“One of my mantras is to always be connecting. So, even if I can’t help, I always want to introduce them to someone who can. That way, I’ve paid it forward without expecting anything in return, and these things typically do come back, there’s just no expectation of when or how.”

13. Don’t Evaluate Success in Dollars

Okay, this may sound a bit counterintuitive. After all, isn’t money the whole purpose of going into business? How do you evaluate the success of your work if it’s not in profit earned or revenue increased?

Kevin explains it here:

“For me, evaluating success for my clients is not in dollars. This may sound controversial, but for me, it’s fulfillment. I want to see people more fulfilled in the work they do.”

“I believe that when people are more fulfilled, they do better work. In fact, they do their best work. And if a founder is doing their best work, the company is doing its best work, and the results are speaking for themselves. That’s been my experience.”

14. Know When to Challenge a Client’s Vision

Iain Swanston of Klozers has seen the benefits of challenging a client’s original vision. And this is true of any type of sales.

“Typically,” explains Iain, “a buyer has a mental picture of what the solution looks like and how much they’re going to pay. And that mental picture is not always correct.”

“In sales, there is no one size fits all. You have to evaluate every conversation, company, and individual. If you decide to challenge them, it can absolutely work. But you also run the risk of them leaving to find what they originally envisioned. So try to understand them and see: how hard can I push this?”

As a sales consultant, you must discern when to stand your ground and when to bend and adapt to a client’s wishes. It’s not always easy, but taking the time to understand the individual and the context surrounding their original vision can help you create a clear path forward.

Build Your Startup Sales Consulting Business and Help Others Grow

As a startup sales consultant, you’re in the unique position of being an entrepreneur yourself as you guide other entrepreneurs and their teams.

You are an expert they turn to for advice and practical help. When you genuinely care about the results they get and are invested in helping them succeed, you’ll not only help your clients grow their businesses—you’ll be on your way to increasing your consultancy.