100+ Scaleups: 15 GTM Lessons Learned

Over the last six years, I’ve had the pleasure of advising more than 100+ scale-ups, conducting numerous due diligence projects, and coaching and working with CEOs and chairs across the UK and the US. Through this experience, I’ve gained valuable insights into the acute go-to-market challenges that most scale-ups face, typically those with revenues between $2 million and $25 million. While the challenges may follow similar patterns, the key to effective advising lies in understanding the unique context of each business.

No one piece of generic advice is relevant for every company. Many things are in play, like market dynamics, competition, category creation, product, people, positioning, messaging, and value proposition; there’s a lot in that mix.

The big problem most scale-ups I’ve worked with face is often not centered on the root causes. I’ll explain 15 specific learnings below, with actions that can reframe your thinking about how to solve these challenges. Most scale-ups try to solve the problems in the same way. They have a top-of-funnel problem; they try to get more leads. They have a sales performance problem; they remove the entire sales team and hire new salespeople. They have a marketing problem; they hire a marketing leader and invest in channels, paid advertising, and tactics.

These are all the common ways people try to solve scaling problems. And what I’ve observed while working with 100+ scale-ups is that it’s good to reframe into the context of the root causes. These root causes are reflected in the 15 go-to-market challenges and observations below, as well as in the things I’ve learned over the last six years.

Learning number one:

You don’t have a lead flow or top-of-funnel problem; you have a messaging problem. One of the most common questions I get asked is whether this business has a top-of-funnel problem or a lead-generation problem. The sales leader says there aren't enough leads, and the assumption is that if they get a load of leads, the product is good, the service is so good, and the conversion rates are reasonable, they’ll convert to revenue. I hear this repeatedly, “Our conversion rates are 40%; we just need more leads.” And a specific story on this one: one due diligence program I worked on, they said their problem was too many leads. Now, once it got into the details, three months post-completion, that wasn’t the problem. The team assumed this was the problem, so why are deals not closing? However, once you got into the details, the problem was that 80% of the leads were lower quality, not the right ICP.

At the same time, there was no sales process for how you segmented leads. So, the sales team could have been more efficient in working on those, and that’s an example of what you commonly see as a lack of awareness of trying to find the real problem. And it’s often the case that you don’t have a lead problem. You have a messaging problem. Write that down. You won’t fix your sales problem with more leads. The only way you’ll fix it is with better messaging. 99 times out of 100, the problem isn’t leads; it’s in your messaging.

Action: Reflect on your current messaging. How powerful is it? Because if you have the right messaging and clearly describe what you do, those words move people to action. With the right messaging, your marketing becomes effortless. So don’t think about the problem statement of “more leads.” Think about how you can improve your messaging.

Learning number two:

Execution is what matters. Execution is an undeniable point, which won’t surprise anyone. Still, in every single due diligence review I’ve done, it’s prevalent that the go-to-market plan seems logical, or there’s a situation where you’re mid-cycle in the plan. You’re doing an audit, and everything in that audit seems logical. It’s got a good plan, sales strategy, and marketing strategy, but there’s a massive tension that’s not filtering through to results. When you talk to operating leaders, the fact that everything’s logical doesn’t match the business’s performance is a big credibility problem for those leaders. There’s one thing you don’t want to be: someone confident and poor at execution, or confident with a lack of results.

Action: The action here is to be clear about constantly digging into where the real problem lies and trying to solve those problems. Don’t rely on a plan or a strategy being logical. If there are poor results, scrap your thinking in many ways, go back to square one, and think about how you can make things simpler and narrowly improve results or get better at execution. Looking back on my career, perhaps I over-indexed on strategy and planning - I have realized from the last six years that it’s all-important and crucial to get right. But, you have to ensure things are getting done and you’re solving root-cause issues, not the wrong problems that don’t make a difference.

Learning number three:

Marketing bears the brunt of poor pipeline development. Although this is relevant in some capacity, the narrative must ensure marketing is seen as more than just a lead-generation entity within a business. Marketing powers the whole company in many ways. The marketing strategy is the business’s strategy. Marketing is everything because marketing includes selling, content, communications, messaging, and enablement. When scaling, many companies need to recognize that the root cause of many business problems is marketing. Still, people sometimes need a different idea of what marketing can be and what marketing is.

Marketing is the entire strategy and should be tightly linked to the go-to-market (GTM) plan. It should be driven less through short-term activities that the chief revenue officer drives, and if the pipeline isn’t in the right place, look at the strategic plan behind marketing. It’s across the whole team and the entire strategy, and people sometimes need to pay attention to this perspective.

Action: Review the role of marketing in the business and ensure it is driving the overall strategy. And remember this: your funnel conversion problems and your top of funnel or your middle funnel may differ from what you think they might be. It could be down to poor marketing, sales execution, conversion, or customer experience driven by the marketing strategy. Ensure the broader scope of marketing is well-defined and embedded across your GTM strategy.

Learning number four:

Investors are typically skeptical of your differentiation and worry about your differentiation and your message to the market. What’s true right now is that every market is fiercely competitive. In SaaS (now AI), every vendor says they do the same thing, or claims to be different when they’re not. The presentation to boards typically shows value prop statements and messaging statements, but far too often, there needs to be more clarity on the state of the market, how you win, what makes you different, and how you message that to prospects. The “how you win " narrative must be improved in many instances, especially for investors.

Action: You may think you have everything figured out here, but go back and reflect on whether we are clear on differentiation. Do we know how we’ll win? Are we specific enough to carve a wedge within our market for our differentiated product? That’s the action to take away. Make sure that you have that really well defined, and then, at your next board meeting, include some of that narrative, because that’s what investors often lack and want to know. They want to know the market context, how you’ll win in the category, and what makes you truly differentiated. Do you understand your customer's three visceralpains and how they map to your value?

Learning number five:

Everything is about people. You can have the best strategy in the world, the best plan, the best MarTech, and the best process, but the go-to-market teams I see succeed are the ones where people drive results. They’re digging into clear challenges, and they’re solving problems. So it’s a combination of being great problem solvers, getting work done, and having a plan they understand and can deliver against.

Action: The action here is that if things aren’t going to plan, it doesn’t necessarily mean you’ve got the wrong strategy. It could mean the wrong people in the context of that business. That means you fail to get the execution that you need to hit the plan, and people’s decisions are always hard. And believe me, investors are just like CEOs, who want to avoid high turnover and employee churn in a business. But you must be constantly aware that the biggest lever for your success as a CRO, CMO, or CEO is the people within the company—having good people, the right plan, the right priorities, the right performance, and a great culture. If you combine those, you’re more likely to be on how to win.

Learning number six:

Everyone has a funnel conversion problem. As I mentioned in learning one, perhaps the funnel conversion problem is down to messaging, positioning, value proposition, and the root causes of your go-to-market, not the data market. How to solve a funnel conversion? There are different ways to do it. You can either do it from a process standpoint, which means reviewing your processes, ensuring everything is good from a data perspective, and ensuring that the insights you’re presenting show an accurate representation of your funnel, which should highlight where the funnel conversion problem is. The conversation at the board can be much more pointed towards solving problems.

So, from a table-stakes perspective, ensure your process is clean and clear. The other problem with funnel conversion can be the capabilities of sales or marketing. Another problem is poor execution against the customer experience in the customer journey, driven through marketing. These are the typical three issues.

Action: Stop assuming a funnel conversion problem is a sales effort problem, and diagnose the root cause before you throw resources at it. Work through it in order. First, clean up the process and the data so the funnel you’re looking at is accurate, because you can't fix what you can't see clearly, and a clean funnel makes the board conversation more pointed rather than vague. Then check the two real culprits: whether sales and marketing can actually convert, and whether the customer experience and journey are being executed well. And before any of that, sense-check the obvious one at the top of the funnel: weak messaging, positioning, or value proposition often shows up as a conversion problem further down the funnel. Name which of these it is first, then fix that, rather than guessing.

Learning number seven:

People need to think about what works to scale. Let me explain. The overall goal of a business is to scale. That’s why investors put money into the company, and that’s why you, the CEO, have ambitions to have a good exit. Or you want to change a market, scale something, and be successful. But often, when people think about scale, they start digging into the wrong things. I mean by that to take outbound marketing, for example, as a tactical use case. When you’re looking to scale, people over-index on tools and automation, using only numbers in a sheet; they need to remember that the most important things are targeting the right people, having good messaging, and doing human things that don’t scale to improve conversions. And it can be a scary situation when the business across the board is looking to scale—in product, engineering, marketing, and sales, without taking the right steps in the right order to set up the scaling process for success. In that last example, you can scale outbound successfully once you feel confident you’ve got the right messaging. You can scale the sales team once you think you have a process for creating demand in your funnel.

Action: Ensure you don’t get too far ahead of yourself. Scaling is the overall goal, but think about the order of steps you need to take to pull the trigger on scaling at the right point. You’re far more likely to be successful with the scaling process because you have the fundamental things in place. Sequence actions in the right order. An old CEO I worked alongside always had a great system for each area of the business - he would look at what is the sequence of the next five moves for each challenge / functional area. He’d write them down, then get people to execute against them in the right order. Sounds simple, but hard to do in practice.

Learning number eight:

The mindset is shifting from sales-led growth. Four or five years ago, people only considered how to hit their plan by hiring more sales reps. Unfortunately, that still happens in some cases. Over the last two years, I’ve heard numerous narratives of people coming out of the board meeting saying, “Oh, we didn’t hit plan because the VP of sales didn’t work out. We didn’t hit the plan because the two salespeople didn’t work out.”

This is still happening, but people are starting to realize that you need to create demand before you hire salespeople. And how do you create demand? You do that through marketing. You do that through the founder, CEO, thought leadership, and content. You do that by creating a lean marketing process and infrastructure to scale or generate demand, and more CEOs, chairs, and investors are realizing this is the way forward rather than relying on salespeople, who are not good at creating demand. They are good at converting demand into revenue.

Action: So the action here is, what’s your demand creation process? Do you have one? Do you have a marketing infrastructure for demand? If you don’t, you’ll be reliant on hiring salespeople, which doesn’t work, and this is a lesson for me. It will work if you have the right salespeople and develop the process or structure around demand creation and audience building for your proposition or the problem you solve.

Learning number nine:

It’s incredible that people still default to mainly talking about their product or service. People know, across the board, in many cases, that the key is tapping into the pains and the gains of an audience or who they sell to and creating valuable content that either focuses on those pains or those gains and is distributed in front of them regularly. However, it’s still commonplace for many companies to need either an effective content strategy or a plan to evangelize the pains and gains for their prospects. They don’t have a content plan at all. Their website, or what they talk about, is all about their product and themselves. You may think you’re talking about the challenge, but take a step back and ask yourself if you are, because in most due diligence projects I do, the company focuses its messaging on its product and how great it is. They still need to tap into the key psychological factor of selling: how to reframe a problem in someone’s head, how to sell against it, and how to tap into that problem and be the one who solves it.

Action: Please go and review how you’re talking about your proposition. Are you too product-led? Are you talking about the customer’s problems? Review that across your website, sales collateral, and marketing messaging. Nobody cares about your product. People care about their problems being solved. Write that down.

Learning number ten:

Most people need help with a differentiated point of view. Most companies, whether service companies or product companies, again struggle with being clear on their differentiation, and if you struggle with being clear on your differentiation, that causes so many problems —from what your marketing messaging will be to how well your sales team talk to prospects, convert prospects and convert into revenue, and it makes the competitive market that you’re in and the category battle super tough because you’re not precise.

Most people feel that their differentiation is in their product. But although that’s true at one level, I believe it all starts with the differentiated point of view you have, either as the CEO or as the business overall, toward the market. Suppose you figure out your differentiated point of view to start with, based on how you want to reframe the conversation in your market, and you have a clear and firm position with that differentiated point of view. That’s the starting point of thought leadership, which leads to a straightforward sales story. Most people don’t think of it this way.

Still, I’ve seen those who have a differentiated point of view at the start are much more confident and clear about threading differentiation into that point of view and having a powerful narrative from your thought leadership at the top of the differentiated point of view, right into your marketing messaging and how you angle your differentiation, and then right into your sales story, where you can be much more explicit about where you fit in the market and your differentiation.

Action: In the AI-driven world, STRATEGIC DIFFERENTIATION IS MORE IMPORTANT THAN EVER. Review whether you currently have a differentiated point of view. If not, go away and work on creating one. Once you have a confident, differentiated point of view, you have the foundations for creating solid marketing messaging and a strong sales story that will help you sell more, resonate better with the market, and also help you build an audience because the people who build an audience are the ones who have a differentiated point of view. Examples in the current world - Sam Altman sells AI like electricity on ameter, a consumer view. Dario Amodei says AI will write 90% of code, a B2B view aimed at developers. Satya Nadella calls the models acommodity and puts business context, the docs, decks, and emails inside Microsoft, at the center. Three bets, three GTM motions. Buyerswant to know which one we think wins.

Learning number eleven:

Companies still need to better leverage their customers. In nine out of ten GTM plans I review, there’s minimal detail on the customers, their use cases, and the markets in which they play. It’s predominantly based on strategy and tactics around demand gen, sales process, or sales plans, but the content does not include use cases or customers. The strategy and the plan are not based on the customer. And although this seems unbelievable, it’s true. It’s a significant lesson I pass on every time —your number one strategy should be selling and serving customers and creating a great experience once they’ve bought from you.

Once you’ve figured out that flywheel, you can do everything off the back of it, and many people struggle with go-to-market, top-of-funnel, and middle-of-the-funnel. The only way you solve getting more business and selling more and being more effective at converting deals is through an obsession with landing new customers and turning those new customers into advocates and doing an excellent job for them, because there’s a real trend these days within the go-to-market strategy, which is called modern word of mouth. Modern word of mouth happens in forums and communities all over the world, where people recommend products and services to their peers. The reason it’s called modern word of mouth is that it used to be more manual. Now, it can be leveraged on a larger scale because it’s on digital platforms, with access to more people who see that information. But the only way you’re going to drive modern word of mouth is through delivering excellent success outcomes for your customers.

Action: Stop using the excuse, “Oh, we can’t get any customer stories.” Go and rethink how you engage with a customer; go and replan your entire strategy around your customer’s success. If you do that right, you can use that customer story or use case, and then you should embed all your marketing and storytelling around it. It’s much simpler to do that than to create stories from scratch or content with no basis for a use case.

Learning number twelve:

People have tons of metrics but don’t often pick the right ones. Marketing can sometimes be very guilty of this; not to pick on marketing, but because they’re pressured to show every metric, they overload CEOs or boards with too many metrics. And you compound the problem by having too many metrics with a lack of results, which hurts credibility. The wrong metrics can be applied within the sales team and other functional areas.

Action: The action here is to assess what metrics you’re reporting, especially marketing and sales, and make sure they align with the levers that really make a difference within the business. These are also the levers that investors and the CEO are interested in because they clearly link to how the company can scale and grow. Learn what metrics are important and what people want to know, and keep the rest to yourselves.

Learning number thirteen:

The services-to-product pivot. Many companies want to go with the product because the multiple on exit can be better, or because of the perception that a product business is more valuable. However, one lesson I’ve learned over the last few years is that many service companies consider pivoting to products and, in most cases, fail due to a lack of focus or prioritization. You’re providing a different outcome and service to your customers. It presents a go-to-market challenge as well because selling a product versus selling a service is different, and you’ve got to recognize that because the way you angle the problem you’re solving is different. And there’s a litany in a graveyard of companies that have tried to pivot, been unsuccessful, either gone out of business, or returned to being a services company. The interesting context right now is that product companies are considering “services as software” because of AI, so the pivot has been turned on its head. But the opposite principles still apply - services and products are two different business models.

Action: Services to product: Don’t half-pivot. Treat it as a new business, because that’s what it is. Before you commit, ringfence a product team so client work can’t pull them off it, fund a runway long enough to find traction without leaning on services revenue, and confirm you know the new buyer, the new outcome you’re selling, and the new way you sell it. If you can’t name one outcome a customer will pay for without you in the room, you’re not ready. Commit fully or don’t start.

Product to services (AI / services-as-software): Add a delivery layer that sells outcomes, not just access to the tool. Use forward-deployed people to get customers live and to hold the AI to a result the customer would pay for. Price on the outcome, not the seat. Staff and account for this separately so the product team keeps shipping, and feed everything the delivery team learns straight back into the product.

Hybrid like Palantir: Run both on purpose and make them feed each other. Use services to win customers and learn their real problems, then turn that learning into a product. Services fund the business and de-risk the roadmap; product makes the services repeatable and scalable. Fund and staff the two sides separately so neither starves the other; keep a tight loop so delivery insights flow into the product; and report services and product revenue clearly, because they scale and are valued differently.

Learning number fourteen:

Prioritization and initiatives. When I do a mid-cycle review—and by mid-cycle review, I mean you may not be operating to plan, and you’re looking to dive into inefficiencies in your go-to-market program—the leading root cause that comes out of it every single time is that there’s too much going on. There’s a lack of prioritization for suitable go-to-market activities.

There may be too many channels spread too thin with a not big enough team, a lack of execution against one or two channels, i.e., doing content or events well from a sales standpoint, trying to sell to 10 different markets with an unclear value proposition in each market, and also a lack of ability to say no to new initiatives at every time. And so every quarter, there’s a new initiative. Every few months, there’s a new initiative. At the same time, there’s a lack of execution against what’s happening in the present. Part of my process is to help the marketing leader, CRO, or CEO be honest about what is to be clear on and work through those priorities.

Action: If you are feeling overwhelmed and there are many priorities happening, there are 66 OKRs, so take a step back. Perhaps, you know, go and do a strategy day with the leadership team and try to pick out the core three levers that you need to focus on right now that will be the things that can help you focus and keep things more uncomplicated to make sure that you’re more likely to hit plan. Slim down the marketing. Think of lean marketing, lean selling, and focused strategy. The companies I’ve worked with that have gone away and done that have gone on to do great things and have been much more precise in building and scaling their businesses.

Learning number fifteen:

The classic sales and marketing alignment. Most have discussed an excellent alignment game in every situation I’ve covered. They’ve talked well about how they get on with the CRO and the CMO. But then, once you get into the details of an audit or something else, you see a disconnect between what sales are doing and what marketing is doing, and there’s still, albeit the narrative is now about go-to-market being one team. A part of it is education because there’s sometimes still a lack of awareness on the marketing side for salespeople or the salespeople’s wants, needs, and demands of that role.

Conversely, there still needs to be greater marketing awareness on the sales side. And it’s on both sides to educate each other and help each other understand how to fix the problem. The companies that are doing well, and this is super obvious, are the companies with strong, strong, and decent sales and marketing alignment. Strong alignment means working on the same page, holding each other accountable for our respective areas, respecting each other’s areas, and each team trying to help the other solve problems together, not solve them in different ways.

Action: Reflect on your current sales and marketing alignment and, using first-principles thinking, consider what good looks like, how we work well together, and how to bring people together. Don’t just say you’re aligned; I’ll give you a use case for this. Recently, I conducted an audit, and both sales and marketing leaders said they were aligned, but ultimately, this was just at face value. When you dig in, you find that the sales leader said there was alignment, but fundamentally, there wasn’t, and the marketing leader struggled to create it.

Unfortunately, the marketing leader can sometimes feel second-rate to the CRO or the salesperson, so they may be subservient and accept that position. As the marketing leader, you’ve got to be the one. It shouldn’t be just on you to drive alignment. So, you know, if you’re the investor or at the board level, make sure that whoever is in charge in terms of the CRO or CEO has an appreciation for marketing and that they understand that the activities and actions they should be doing should be thoroughly integrated and focused on the same things.

BONUS Learning number sixteen:

Buyers aren’t doing your homework anymore. AI is.

For twenty years, the sales game had a built-in delay. A buyer would Google around, maybe read a few blog posts, ask a peer in a Slack group, and slowly form an opinion before they ever pick up the phone. That delay was where sales reps used to do their work. You had time to shape the narrative, build trust, and educate them on the category. That delay is gone.

Buyers now go to an LLM, describe their problem, and get a shortlist in response. Three, four, six vendors in a category, side by side, with a summary of what each one supposedly does differently. By the time they get on a call with you, they’ve already had what feels like a peer review of your entire market. And here’s the part that should worry you: they’re often booking calls with all six vendors back to back, same week, sometimes same day. You’re not the first conversation anymore. You’re the third call before lunch.

I’ve started seeing this show up in due diligence reviews as a pattern nobody on the leadership team has clocked yet. Sales cycles that used to have natural breathing room between stages are compressing, because the buyer arrived pre-informed and is now speed-running a comparison they built themselves, with an AI’s help, before any rep got involved. The sales team thinks they’re losing deals to a competitor. Half the time, they’re losing deals to a worse five minutes on a call that an LLM had already set the buyer up to judge harshly.

This changes two things at once, and most companies are only working on one of them, if that.

First, your differentiation has to be sharp enough to survive being summarized by a machine that’s never met you. If your positioning is vague, an LLM will flatten you into “another vendor in the space” right alongside four competitors who all said the same thing in their last blog post. The companies winning right now are the ones whose differentiation is so specific and repeatable that it survives translation. Not a tagline. An actual point of view that holds up even when a third party is doing the explaining on your behalf, without you in the room. You also have to become experts at pitching your differentiation to humans, so if you’re vendor six in terms of when they speak to you, how will you clarify your difference in the human-to-human setting?

Second, your sales process has to perform under a completely different kind of pressure. The buyer isn’t blank slate curious anymore. They’re already holding a comparison chart in their head, half of which your company didn’t write and can’t fully see. Your rep walks in, assuming they’re starting the conversation. They’re actually walking into round three of a contest they didn’t get to referee. If your sales team is still running a discovery-first script built for a buyer who knows nothing, they’re going to keep losing to companies whose reps know they’re now being benchmarked from the first minute, not the fifth call.

Action: Go look at how your category gets described when someone asks an LLM to compare vendors in your space. Actually do this today. Then ask whether your differentiation, the thing you say makes you different, survives that comparison or disappears into the pile. If it disappears, that’s not a marketing problem to fix next quarter. That’s the most urgent root cause on this list, because it’s compressing your sales cycle whether you’ve noticed it or not. And retrain your sales team on the assumption that every buyer walking in has already done a version of the diligence that used to take them weeks, in an afternoon, with a tool that may have gotten your differentiation wrong, and nobody corrected it.

In conclusion

In conclusion, these are the things I’ve learned over the last five years. They’re things which I’m sure wouldn’t surprise you. There are things that may have surprised you. But the key takeaway is, in all the situations with the 15 that I’ve come across, this crucial perspective of reframing where the problem lies. Because at times, the problem often seems obvious, but because it’s obvious, you forget to take a step back and reframe your thinking to solve that problem.

In many of these cases, across the 15 go-to-market issues, it’s because they’re following the same playbook or generic advice for resolving them rather than reframing how they think they should solve them. My advice is that what I work with everyone I coach, or I’ve done due diligence on, is to try and help reframe, to provide a different context, to get into the root cause, and solve the thing or obstacle in a different way that helps get to the next step and action quicker.

And I think if you adopt this mindset and approach and understand the reality of the go-to-market challenges you will face, you’re far more likely to pick them off, solve them better and quicker, scale the business, and move on to the next problem.

Good luck, and take action on all the points above.

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