There comes a moment in every growing business when the wheels start to wobble.
You feel it in the meetings that go nowhere. You see it in the KPIs that don’t exist or aren’t trusted. You sense it in your team—talented, committed, but constantly stuck reacting instead of executing.
If you’re a founder or CEO who's hit that inflection point, chances are, you’re in what I call Stage 3.
I’m Tim, the CFO at Ninety and a Certified Exit Planning Advisor (CEPA®) with six exits totaling over $10 billion. I don’t know everything, but I do know how to help business leaders break through this exact kind of plateau.
And I come with urgent news: What got you here won’t get you there.
If you want to scale and eventually exit, you must stop managing the business and start building the machine that runs it.
Most businesses I have worked with find themselves stuck at Stage 3, when things get complicated.
You’re no longer a scrappy startup relying on founder instinct and hustle. You’ve got a team. You’ve built a product or service that works. But now, complexity multiplies. The systems and people that served you well in early growth can start to become bottlenecks. Progress slows. Frustration builds. And while it might feel like a temporary dip, many companies get stuck here for years.
The antidote lies in operational maturity. Specifically, it lies in mastering three foundational elements: People, Meetings, and Data. These aren’t revolutionary ideas. But applying discipline to them in a structured way is what separates scalable companies from those that stall.
In Stages 1 and 2, you’re focused on survival. But at Stage 3, leadership must evolve. You can’t have executives who are still doing the work. You need leaders who drive accountability. That might mean transitioning some team members into new seats, or in some cases, out of the company altogether.
I’ll give you a common example. When a company comes to me stuck in Stage 2 or 3, it’s not a hire they need, but a termination. Almost always, someone probably started out as an executive assistant and has since become the founder’s go-to person for delegation. They’ve got a fancy title with the word “strategic” in it—director of strategy, operational strategy—even though they’re not very strategic.
It isn’t necessarily their fault that they were over-promoted. Over time, too many people delegated their responsibilities to them, and they became the Jake/Jane of all trades, master of none. And to get beyond Stage 2 or 3, all your leadership needs to be specialized. Unfortunately, that second-in-command needs to transition to a different seat, or no seat at all.
Moving beyond Stage 3 also means introducing consistent, objective performance reviews that look at more than just outcomes. Competency, commitment, capacity, and cultural fit all matter.
A Quarterly Conversation cadence ensures regular assessment, coaching, and alignment. According to Gallup, organizations that conduct regular employee feedback and performance reviews see 14.9% lower turnover rates.1
Many Stage 3 companies suffer from reactive, unproductive meetings. There is a lot of talk, a lot of updates, and very little decision-making. The goal is to shift from ad hoc disruption to structured rhythm. That means setting annual goals, holding quarterly planning sessions, and running weekly meetings focusing on solving the most urgent and important issues.
Meetings should ladder up from team actions to company goals and be the heartbeat of your execution engine. A Harvard Business Review study found that 71% of senior managers said meetings are unproductive and inefficient—evidence that more structure is not only helpful, it's necessary.2
Ninety has a tool that facilitates the prioritization of meeting topics. Because what I’ve observed over 20+ years of working with small businesses is that more money is wasted on the inappropriate use of meeting time than any other financial leak within a company.
Let me give you an example.
I was consulting for an organization squarely in the Stage 3 category. There was a team member I’ll refer to as “Office Mom.” Office Mom is a member of the “overpromoted” group I mentioned in the previous section, and most decisions filtered through her advisement. Office Mom had been put in charge of a partnership the founders didn’t have time to deal with.
The organization had a goal of $30 million in revenue for the year, and the deal Office Mom was heading up was worth $120,000—not negligible, but also not a heavy hitting contract.
One Monday morning Office Mom rushed into the office, interrupting an in-meeting office. “There’s a problem with the deal. We really need to address it right now.”
Everyone in the room pivoted toward Office Mom, and the meeting's goals were both derailed and unmet. In my mind, I said, This contract isn’t even material. But I watched and observed as the founders gave Office Mom the floor and the permission to direct their IT department to spend $400,000 on a two-week sprint to build out a solution for the $120,000 client.
And the founders were baffled as to why they couldn’t scale beyond Stage 3.
Their meeting cadence and content needed to align with their overall goals. In addition, they need to be vigilantly guarded. When you allow short-term execution to dictate relevance and order, you’ll run from one dumpster fire to the next without satisfying long-term benchmarks, treading water, and wasting time and money.
In early stages, gut instinct and hustle can drive results. But at scale, you need clarity. Can your team answer the question: “Are we winning or losing?” If not, you need measurable KPIs that track not just financials, but progress across goals, people, and customers. Simplicity is key. The best scorecards aren’t bloated spreadsheets but focused tools that quickly surface issues.
And they shouldn’t just sit with the senior leadership team—eventually, every team and individual should have their own indicators of success. A McKinsey report notes that companies that regularly track key performance indicators (KPIs) are twice as likely to hit their goals.3
What ties all this together is the concept of a Unifying Operating System. Think of it as the software of your business—a set of shared frameworks, tools, and cadences that align your people and processes. It’s not about rigid rules; it’s about repeatable excellence. A good OS combines time-tested best practices with custom-fit execution. It includes structured planning, disciplined meeting rhythms, and tools that track real progress. More importantly, it creates a culture of accountability and clarity.
Most companies don’t fail because they lack ambition or talent. They plateau because they haven’t installed the infrastructure that allows the founder to get out of the weeds. Until you do that, you can’t scale—and you certainly can’t exit.
At minimum, leadership should step back every 90 days to ask: Where are we stuck? What’s working? What’s not? Are we focused on the right rocks? That regular reflection, coupled with a clear operating rhythm, helps prevent the all-too-common cycle of one year of growth followed by one year of stall.
Beyond internal rhythm, there’s also a mindset shift that must occur at this stage. Founders often conflate effort with impact. But scaling requires letting go. It’s about building something that can grow without your constant presence. That’s not just good for business—it’s essential if you ever hope to sell or step back. Buyers and investors aren’t looking to acquire your sweat equity. They want systems, processes, and a team that can execute predictably. In his book Built to Sell, author John Warrillow says a company that depends too heavily on its founder is far less attractive—and far less valuable—to buyers.4
Another consideration is how Stage 3 maturity sets the stage for future automation and process scalability. By establishing clear KPIs, robust leadership accountability, and disciplined meetings, you’re laying the groundwork for more advanced systems and technologies to take root in Stage 4. That might mean implementing enterprise tools like Salesforce or EOS software platforms, or it might mean streamlining customer onboarding through CRM automation. Either way, Stage 3 is where the foundation gets poured.
Everything is a risk. Companies that break through Stage 3 accelerate toward meaningful exits. Those that don’t often plateau indefinitely—or worse, regress. And the difference isn’t vision or hustle. It’s systems.
If you recognize yourself in this cycle, the good news is that you're not alone, and you're not doomed. Stage 3 is tough, but it’s also a launching pad. It’s the first real test of whether you’re building a business that can thrive without you. The founders who make it through don’t do it by pushing harder. They do it by building better systems.
So, if you’re a business owner ready to scale and exit, ask yourself:
If the answer is no, it’s time to evolve. It’s time to get serious about your people, your cadence, and your data. It’s time to stop being the engine of your business and start being the architect of its growth.
Because the true value of your business, to investors, to acquirers, and even to yourself, won’t be measured by how hard you work. It will be measured by how well it runs without you.