#53: Find Your Next $10M with Metrics-Backed Go-To-Market

Chip Royce, Flywheel Advisors

Reaching your first meaningful market milestone is supposed to mean that you’ve “arrived.” You have a working demand generation engine in a defined niche, a go-to-market playbook the team can run, and a revenue line that no longer looks like a random walk.

Then the board asks a different question: “Where does the next $10M come from?”

That is where many successful B2B technology CEOs drift into what I call the Success Trap. The very focus that helped you build Act One becomes a liability in Act Two. You assume the way forward is a bigger version of what you are already doing: the same playbook, aimed at a slightly larger ICP, in a somewhat flashier segment, with the same engine underneath.

On a slide, that story is neat and comforting. In practice, it is how working engines get stretched into markets they are not built to win, and how good companies end up making Second Act bets that quietly damage the business that brought them this far.

The alternative is to treat your Second Act as a metrics question, not a TAM question, and to design a metrics-backed go-to-market for your next $10M using the data you already have. Instead of chasing the biggest category, you use a deliberately structured process to choose and pilot your next market before you commit the company to it.

This article lays out that approach:

• Why the Success Trap is so common,
• How to use your existing metrics to identify true adjacencies,
• How to score those options with an Adjacency Matrix, and
• Why a disciplined “pilot, not launch” go-to-market motion is the safest way to enter your next market.

The “Success Trap”: When Act One Biases Act Two

Most of the CEOs I work with did not stumble into their first working market. They fought for it.

They selected (or eventually discovered) a narrow use case where their technology was a strong fit. They refined messaging until their best customers could repeat it back to them. They experimented with channels until they found a handful that consistently produced credible opportunities. Over time, that focus turned into a recognizable playbook that could be handed to new sellers without collapsing.

That focus is an asset. It forced trade-offs. It protected the company from chasing every shiny object. It created a shared understanding internally of “who we are for and how we win.”

The challenge is that once this first playbook is successful, it becomes the default lens through which every new opportunity is evaluated. Act Two is quietly framed as:

• “The same type of buyer, but in a bigger logo or a larger company.”
• “The same use case, but in a new vertical that looks promising on a slide.”
• “The same product and motion, extended to geographies where the TAM line is large.”

This is the Success Trap. The story in the board deck is that you are “scaling what works.” What is often happening under the surface is that you are copy-pasting a playbook into contexts where its underlying assumptions do not hold.

You see this in a few predictable patterns:

• Expansion decisions justified by large, abstract market size rather than by evidence that your current engine already works there.
• Sales teams asked to sell into industries they do not understand, using language and proof points designed for a different buyer.
• Marketing pushed to generate interest in segments where your awareness, credibility, and existing customer base are thin.

The risk is not that the new market is uninteresting. Many of these adjacencies are genuinely attractive in the abstract. The risk is that the company confuses “big TAM” with “our engine will win here,” and makes a large, irreversible bet based on that confusion.

The way out of the Success Trap is to stop treating Second Act decisions as a search for the biggest or hottest market, and to start treating them as a search for the market where your current engine already gives you an advantage—and where you can credibly build a go-to-market strategy for the next \$10M of revenue.

That requires looking down at your own numbers before you look up at the TAM slide.

Why Expansion Is a Metrics Question, Not a TAM Question

Most Second Act conversations begin with some version of a classic market sizing slide.

Someone draws three concentric circles: Total Addressable Market, Serviceable Market, and a small wedge that represents the “modest share” you only need to capture to hit ambitious targets.

This is useful as context. It is dangerous as a decision tool.

TAM tells you how much money is spent in a category. It does not tell you where your particular engine is likely to win. It does not know:

• which types of customers renew and expand on schedule and which quietly slip away;
• which segments move through your pipeline with minimal friction and which ones stall out in legal, security, or “no decision”;
• which acquisition motions you can run profitably and which ones only look good until you do a full CAC:LTV calculation by channel and segment.

If your Second Act plan is driven by where the circles on that slide are largest, you are making a bet about global demand, not about your actual strengths.

A more honest starting point is to anchor your metrics-backed market expansion thinking in three families of metrics you already have:

Retention and “good churn” by segment

Look at who stays and grows with you, not just who buys once.

• Which cohorts have the cleanest renewal and expansion patterns?
• Where are gross and net retention strongest?
• In which segments do you quietly celebrate when a customer leaves because they were the wrong fit from the start?

This gives you a view of which types of customers are truly aligned with your value, not just your pipeline.

Pipeline velocity and quality

Map how deals move in different segments.

• Where does the time from first meaningful interaction to closed-won resemble the kind of cycle your business is designed to support?
• In which use cases do your sellers report, “These people understand what we do almost immediately”?
• Where is your forecast accuracy highest?

This shows you where your current playbook is intuitive to the buyer and to your team, versus where you are forcing it.

CAC:LTV and payback by channel and segment

Don’t treat CAC and LTV as company-level numbers. Segment them.

• Which combinations of segment and channel produce acceptable payback periods and strong lifetime value?
• Where does partner-sourced or community-sourced demand land with larger average contract value and better retention than performance marketing?
• Where are you “winning” logos at economics that degrade your margin profile?

Together, these three lenses give you an internal map of where your engine already works. Your metrics-backed go-to-market for your next \$10M should live on that map.

A useful question for the leadership team is:

“Looking only at our own metrics, where do we already behave as if we belong in that segment?”

To see how powerful that shift can be, it helps to look at a concrete example.

A Tax Prep Company’s Second Act: From Consumer TAM to B2B2C Engine

Several years ago, I worked with an online tax preparation company that, on paper, had a strong consumer proposition. The product was designed for US taxpayers filing personal returns. It competed directly with incumbents such as TurboTax, TaxAct, and H&R Block. The interface was modern, the user experience was smoother, and the price points were lower.

When you looked at the consumer tax filing base, the TAM line was enormous. Tens of millions of filers, with an unavoidable annual trigger to use a product in the category. It was easy to build a model where capturing a modest percentage of that market drove impressive revenue growth.

In that framing, the Second Act was simple: spend aggressively to acquire more consumers, take share from incumbents, and let the sheer size of the market do the rest.

In reality, two issues surfaced quickly.

First, brand equity mattered more than expected. Tax filing is a high-anxiety category. Many consumers are extremely reluctant to change providers as long as their current process “works well enough.” A modest improvement in user experience and a lower price were not always strong enough reasons to override that inertia and risk.

Second, customer acquisition costs were structurally unfriendly. To gain visibility in such a crowded space, the company needed a heavy, sustained investment in paid media. Incumbents were willing to endure high acquisition costs because they were playing a long game, using tax as an entry point into a larger financial relationship. As a pure-play tax preparation service, our client did not have that same set of levers.

The metrics reflected this reality. CAC for consumer acquisition was high. Payback periods stretched. Retention at the individual filer level was reasonable, but the economics of acquiring each new customer at scale were difficult to make truly compelling.

The turning point did not come from a new consumer insight. It came from revisiting the company’s own data and customer behavior with fresh eyes.

Three patterns stood out.

First, usage data and inbound requests revealed a cluster of small tax firms and online preparers using the product in an unanticipated way. They were stretching a consumer-oriented tool to support professional workflows. They were more vocal about feature needs, more engaged with support, and far more sensitive to changes in throughput and reliability than the average consumer.

Second, sales and support conversations with these firms moved differently. These buyers were less focused on brand and more focused on throughput, cost per filing, and ease of managing large numbers of client returns. The company’s team noticed that these conversations felt closer to a B2B sale than to a consumer conversion.

Third, pricing and value perception were fundamentally different. These firms were willing to pay more per filing than individual consumers. They could pass the cost through to their own clients, and they were comparing the software to legacy professional tools that were more expensive and often more cumbersome.

Taken together, these signals suggested a different Second Act. Instead of treating every US taxpayer as the target, the company could focus on the businesses that served those taxpayers.

That insight led to a deliberate pivot:

• The core tax engine remained the same.
• On top of it, the company built a B2B2C offer: co-branded and white-label solutions for accountants and online tax preparers.
• The product evolved to support bulk management, firm-level controls, and co-branding capabilities that mattered to those partners.
• The go-to-market engine shifted away from consumer marketing and toward a partnership-driven model, informed by the company’s existing strength in building and supporting these relationships.

The economics changed dramatically. The company unlocked a new, serviceable market where customers paid more, churn was lower, and acquisition was built on relationships and reputation rather than on a continuous paid media arms race. That Second Act ultimately produced a roughly twenty-fold increase in revenue and positioned the company for acquisition by a fintech unicorn.

The critical point is that this Second Act was not obvious on a consumer TAM slide. It was obvious once the company took its own metrics seriously: retention behavior, usage patterns, and the implicit adjacencies they had already begun to serve.

Your business likely has similar signals.

The challenge is to turn those signals into a structured decision framework rather than a collection of anecdotes.

The Adjacency Matrix: A Structured Way to Choose Your Second Market

Once you accept that expansion decisions should be grounded in your own data, you face a more practical question: How do we compare the next-market options in front of us in a disciplined way?

This is where an Adjacency Matrix is useful. It provides a simple but rigorous way to score and compare potential markets based on how “adjacent” they really are to your current engine.

A straightforward version uses four dimensions:

Problem Overlap

• How similar is the core problem in the new market to the one you already solve today?
• If you stripped away industry jargon, would your existing customer stories still make sense to this audience?
• Do they wake up with the same underlying pain, even if it shows up in different workflows or regulations?

Audience Proximity

• How close is this new audience to the people you already know how to reach and influence?
• Do they attend the same events, read the same publications, and participate in the same communities?
• Can your current channels (both digital and offline) reliably put you in front of them?

Sales Process Reuse

• How much of your existing sales motion can you carry over into this market?
• Are deal sizes, stakeholders, approval processes, and typical objections broadly similar?
• Can your current team plausibly sell into this segment without essentially learning an entirely new profession?

Strategic Value

• If you win in this adjacency, what does it do for the long-term story and resilience of your business?
• Does it deepen your moat?
• Does it open a path to additional segments or expand your platform’s relevance?
• Does it enhance, rather than dilute, your positioning with investors and acquirers?

For each candidate market, you score these four dimensions using the data you already have: retention by segment, pipeline behavior, CAC:LTV, and qualitative feedback from the field. This becomes a practical, metrics-backed market expansion tool, not a theoretical exercise.

In the tax preparation example, when you apply this lens, the difference between the consumer market and the preparer market becomes clear.

The consumer market scored something like:

• Problem Overlap: medium. The need to file taxes is universal, but the day-to-day pain is episodic and heavily influenced by brand trust.
• Audience Proximity: broad, but expensive. Reaching consumers at scale required costly, competitive channels.
• Sales Process Reuse: low. The self-serve, brand-driven consumer motion was not where the company’s relational strengths lay.
• Strategic Value: mixed. The company was one of many in a crowded field with limited leverage beyond tax season.

The professional preparer market scored differently:

• Problem Overlap: high. The underlying tax engine addressed the same core function, but now in a context where throughput, efficiency, and workflow integration were critical.
• Audience Proximity: narrower, but more reachable. The audience was smaller and more defined, reachable through professional networks, industry events, and targeted outreach.
• Sales Process Reuse: high. Sales and support were already handling these conversations informally; formalizing them played to the existing team’s strengths.
• Strategic Value: high. Winning here created a scalable B2B2C engine with strong retention and a defensible position as the preferred platform for a critical part of partners’ service delivery.

The Adjacency Matrix did not “choose” the market automatically. What it did was make the trade-offs explicit, grounded in how the existing engine behaved. It turned a conversation about abstract opportunity into a conversation about where the company had earned the right to win next—and where a go-to-market strategy for the next \$10M is most realistic.

You can run the same exercise with your own options: new verticals, regions, or buyer types that are already showing up at the edge of your current motion.

Once a promising adjacency emerges from that analysis, the temptation is to “launch” it. That is usually the wrong first move.

“Pilot, Not Launch”: Testing Your Second Act Without Breaking Your First

Even with a disciplined adjacency choice, many teams fall into another predictable trap: treating the Second Act as a foregone conclusion instead of an experiment.

The pattern looks familiar:

• A new market is chosen.
• Brand, product, sales, and marketing are all tasked with supporting it.
• Campaigns are launched, targets are set, and dashboards are re-engineered to blend the old and new motion.

The organization’s focus is split before any real proof exists that the new market will behave the way the model assumes.

If the assumptions prove wrong, the impact goes beyond a failed expansion. The core engine is disrupted. Teams are left with half-built motions in two directions. Morale suffers as “the big strategic bet” turns into a series of ad hoc adjustments.

The alternative is to adopt a “pilot not launch” go-to-market mindset for your Second Act.

In practice, that means four things.

First, you assemble a small, cross-functional Second Act team. This is not an all-hands pivot. It is a dedicated group—usually one senior product owner, one marketer, and one experienced seller or partnership lead—whose mandate is to validate the adjacency with minimal disruption to the core business. Second, you define clear, metrics-based hypotheses for this new market, based on your Adjacency Matrix scores.

For example:

• “We believe that the problem overlap is high enough that our existing value proposition will resonate with modest industry language changes.”
• “We believe that our primary acquisition channel for this market will be partner-led or sales-led, not paid media.”
• “We believe we can close the first three customers in this segment with a sales cycle length within 20 percent of our core segment.”

Third, you design a contained experiment. You pick a narrow slice of the new market and commit to winning a small number of real customers there. You build only the product functionality and collateral required to support those early relationships. You route those opportunities through the channels where your metrics tell you you are already strongest. Fourth, you let the results determine the next move.

Once you have those first three to five customers, you examine:

• How expensive were they to acquire, in time and capital, compared to your core?
• Did the deals move through the pipeline in the way you expected?
• Are early usage and retention signals consistent with the “good customer” profiles in your existing base?

Based on that evidence, you make an explicit choice:

• Scale the adjacency and progressively integrate it into the main engine.
• Refine your view of the segment or your approach based on what you learned.
• Or walk away and re-focus, knowing you protected the core and bought clarity at a controlled cost.

Treating your Second Act as a pilot, not launch go-to-market motion does not reduce ambition. It reduces the probability that ambition will pull you into a market you do not deserve to win.

What a Metrics-Backed Second Act Changes Inside the Company

When you handle your Second Act as a metrics-backed go-to-market playbook for the next $10M, the experience inside the business is different.

Your core strengths remain protected. The teams serving your existing market do not wake up to find their priorities subordinated overnight to an unproven bet. Instead, they see a disciplined extension from strength, with clear guardrails about how far the company will go until evidence is in hand.

Strategic conversations at the board level become more concrete. Instead of arguing over which market story sounds most compelling, you can walk through retention cohorts, pipeline behavior, CAC:LTV by segment, and a visible Adjacency Matrix. You can explain not only where you are going next, but why you are not going elsewhere this year.

Internally, you reduce the sense of whiplash. Teams are not asked to pivot from one “next big thing” to another every planning cycle. They see a consistent pattern: diagnose, select adjacencies with a structured lens, pilot not launch, then scale with confidence.

Most importantly, the Second Act narrative itself becomes investable. Investors and acquirers are not simply buying into a theoretical TAM story. They are buying into a company that knows where its engine is strong, has a repeatable approach to finding and validating new markets, and is willing to stop or redirect when the data says so.

That is the real promise of a metrics-backed Second Act: growth that is ambitious without being reckless.

Putting This to Work in Your Context

If you are facing the “what’s our next $10M?” question today, you can start applying this approach with a few practical steps. Think of this as your metrics-backed go-to-market playbook for the next $10M:

1. List three to five plausible next markets you are already discussing internally. These might be new verticals, regions, or buyer types where you see some early activity or interest.
2. For each, score them informally on the four Adjacency Matrix dimensions: problem overlap, audience proximity, sales process reuse, and strategic value. Use your existing metrics and frontline observations, not just your aspirations.
3. Identify the one adjacency where your engine appears most advantaged today, even if the TAM slide for that segment looks less glamorous than others.
4. Design a “pilot, not launch” approach to that market. Define what winning the first three to five customers would mean, what hypotheses you are testing, and what thresholds would cause you to either scale or stop.

If, as you work through that process, you want an external, data-driven stress test of your Second Act and your current-year revenue plan, that is exactly the function of a Revenue Plan Audit: treating your growth narrative and your expansion bets with the same rigor you apply to your financials.

Whether you involve a partner or not, the core shift is the same:

Stop asking, “Which market is biggest?”

Start asking, “Where do our metrics already say we deserve to win next. And how do we build a metrics-backed go-to-market for our next $10M there?”

Are You in the 10%?

This message is for the 10% of B2B leaders who already see this shift. If you are ready to move from persuasion to trust and build the operating system for your future sales organization, then we should speak.

FAQ: Building a Metrics-Backed Go-To-Market for Your Next $10M