50+ Scaleups: 15 GTM Lessons Learned

Over the last three years, I've had the pleasure of advising more than 50 scale-ups, conducting over 10 due diligence projects, and coaching and working with CEOs and chairs across the UK and 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 face that I've worked with is often not centered on the root causes, and I'll explain 15 of these specific learnings below with some actions that can reframe your thinking on how to solve root cause issues. 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 all the 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 50+ scale-ups is it's good to reframe into the context of the root causes. These root causes are what I observed below in the 15 challenges and observations of go-to-market and the things I've learned over the last two 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 things I get asked to look at is whether this business has a top-of-funnel problem or a lead generation problem. The sales leader says there are not 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 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 performance of the business is a big problem of credibility 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 on constantly trying to dig into where the real problem lies and try 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 have indexed on strategy and planning and have realized from the last two years that it's all important and crucial to get right. Still, 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 strategy of the business. Marketing is everything because marketing includes selling, content, communications, messaging, and enablement. When scaling, many companies need to remember to recognize that the root cause of many of the business problems is marketing issues. 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 more than short-term activities that the chief revenue officer drives, and if the pipeline isn't in the right place, there shouldn't be an excuse to look at marketing. It's across the whole team and the entire strategy, and people sometimes need to pay attention to this perspective. Marketing doesn't need to measure every single metric. Ensure that the metrics you're measuring align with the whole go-to-market function and what needs to happen in terms of KPIs.

Action: Review the role of marketing in the business and make sure that marketing is driving the entire 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 typically are skeptical of your differentiation and worry about differentiation and your message to the market. What's true right now is every market is fiercely competitive. Within SaaS and professional services, every vendor says they do the same thing or perceive themselves 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, make sure you include some of that narrative because that's what the investors often lack and want to know.

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 that I see being successful are the ones where the 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 that they understand, and then they're looking to deliver against.

Action: The action here is 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 the same as CEOs, who want to avoid high turnover and churn of people in a business. But you must be constantly aware that the biggest lever to your success as a CRO, CMO, or CEO is the people within the company—having good people, having the right plan, focusing on the right priorities, and having 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 the 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: The action here is trying to highlight the funnel conversion problem and make sure you solve it in the right way and take action on it. At most board meetings, people come to me and say, "There's a funnel conversion problem." I try to solve that question through one of the above "Use Cases" and figure out if it's a process problem or a specific issue within the funnel. I often see GTM failing to execute well against this challenge; keep that from happening.

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, you want to scale something, and you want to be successful. But often, what happens is that when people think about scale, they start to dig 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 using tools and automation and only use numbers in a sheet; they need to remember the most important thing is 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 do things that scale—in product, in engineering, in marketing, in sales—when they haven't been in the correct order of steps to set up the scaling process to be successful. 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: The action for this one is to 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.

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 six months, 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 create demand, and more CEOs, chairs, and investors are starting to realize that this is the way forward rather than relying on salespeople because salespeople 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 to create demand 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 either need a plan for an effective content strategy or a plan for evangelizing the pains and gains of 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 think if you are because, in most due diligence projects I do, the company focuses messaging on its product and how great it is. They still need to tap into the key psychological factor of selling, which is 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 that solves that problem.

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 on your website, on your sales collateral, and on your 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 that you have either as the CEO or as the business overall to 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: The action here is to go and review or go back and think about whether you have a differentiated point of view at the moment. If not, go away and work on creating one. Once you have a confident, differentiated point of view, you have the foundations for creating a solid marketing messaging and 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.

Learning number eleven: Companies still need to leverage customers better. In nine out of ten GTM plans I review, there's always minimal detail on the customers and the use cases with the customers and the markets in which they play. It's all predominantly based on strategy, tactics around demand gen, sales process, or sales plans, but the content does not include use cases; the content does not include 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, 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 is a thing that is happening in forums and communities all over the world, where people are recommending products and services all the time to their peers. The reason it's called modern word of mouth is because this was more manual before. 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: The action here is to stop using the excuse of, "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 the use case, and then you should be embedding all your marketing and storytelling around the customer story or the use case. It's much simpler doing that than creating stories from scratch or content from no basis of 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 apply 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 levers are also the levers that the investors or the CEO are interested in because they know they link clearly to how the company can scale and build. 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 seen over the last few years is that many service companies think about pivoting to products and, in most cases, fail because of the divergence or focus 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 who have tried to pivot, been unsuccessful, either gone out of business, or returned to being a services company.

Action: If you're thinking about doing this pivot, recognize it will take a long time and plan ahead for that. Or just recognize that you can potentially build a great services business if you're doing the right thing, and it might not be the best thing to do to build a product business.

Learning number fourteen: Prioritization and initiatives. When I do a mid-cycle review—and by mid-cycle review, what I mean is 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 fundamental that comes out of that 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, 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 prop 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 and 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 who 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 how they get on with 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 sales wants, needs, and demands of that role.

Conversely, there still needs to be more awareness of what marketing is from the sales side. And it's on both sides to educate each other and help each other understand how that problem can be fixed and solved. 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, having accountability for each other's respective areas, respecting each other's areas, and each team trying to help each other solve problems together, not solve problems in different ways.

Action: The action here is to reflect on your current sales and marketing alignment and try to be, first principles, thinking about what good looks like, how we work well together, and getting people together. Don't just say you're in alignment; I'll give you a use case on this. Recently, I did an audit, and both sales and marketing leaders said they were in alignment, but ultimately, this was just for face value. When you dig in, you find out the sales leader was saying there was alignment, but fundamentally, there wasn't, and the marketing leader struggled to create that alignment.

Unfortunately, the marketing leader sometimes can feel second-rate to the CRO or the salesperson, so they can be subservient and accept that position. As the marketing leader, you've got to be the one. It shouldn't just be on you to push 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.