I Helped Grow a Startup to a $1.8 Billion Acquisition by Adobe — Here’s the Secret to Scaling Successfully

Growing a company is a challenge that scales quickly in difficulty. Building from zero to $25 million in revenue is not easy, but many companies and leaders manage it. Scaling from $50 million to $200 million is substantially harder. And crossing the next thresholds — growing from $200 million toward $1 billion, for example — is so hard to do that of the roughly 225,000 companies founded in the last 20 years, fewer than 15 crossed the $1 billion revenue threshold.

However, there is one thing in common that each new step requires, and it’s something many founders and CEOs resist, especially as their companies really begin to thrive: To reach the next level, you have to tear up the playbook that got you there in the first place.

In my career, I’ve led through this evolution at every stage of growth, joining a team to take Omniture from startup to $1.8 billion acquisition by Adobe, then scaling the revenue from hundreds of millions to $3.5 billion at Adobe, and now driving the same trajectory at BambooHR. Sustained growth at scale doesn’t come from optimizing what’s working now. It comes from rebuilding the company for the future, not once, but multiple times. It means transforming go-to-market motions, rebuilding executive teams, re-architecting organizational structures and evolving product vision.

The companies that succeed at scale are those that can evolve their systems and people as fast as they evolve their product. Here’s what I’ve learned about when and how to rebuild to get to the next stage.

Recognize the plateau before your KPIs turn red

Making changes isn’t the hardest part of leading through transformation. It’s recognizing when you need to make them. Things that used to be your core competency suddenly stop working like they did in the past. You inspect your KPIs, and nothing is screaming red, but a bunch of metrics are misbehaving. That’s your signal that it’s time for a teardown.

I think about this through an S-curve framework. Every business model, every go-to-market motion, every organizational structure has a natural growth curve. The challenge is being self-critical enough to recognize when your curve is starting to flatten out. If you wait until your dashboard goes red, then you’ve likely missed your window to get ahead.

The truth is, most executives wait for perfect information before they are willing to make the necessary changes. As a leader, you rationalize, you justify and you think you can optimize your way through a bad stretch. But if you’re only considering changes once your S-curve is clearly dropping, then it’s already too late. The price of waiting far outweighs the short-term pain of rebuilding.

I often look back at decisions I made in the past and think, “Who made that decision?” The catch, of course, is that it was me — and the real challenge isn’t just spotting outdated decisions, but separating yourself from them. You have to accept that the past you and the current you are essentially different leaders operating at different scales.

Transform your go-to-market motion for the market you’re not reaching

Six years ago, BambooHR had one of the best inbound B2B selling models on the planet. A prospect would fill out a form on our website, we would call them in under five minutes, and they would buy. It was that good. And that’s exactly why we hadn’t needed to transform — until suddenly we did.

We were putting more into our inbound engine and getting less out. Our “aha moment” was recognizing very clearly that 90% of the market wasn’t actively in-market at any given time, and our model only captured those raising their hand.

Our transformation meant expanding from pure inbound to a multi-channel engine: outbound sales, brand advertising, international expansion and what we call “create” motions. If you’re a go-to-market expert, nothing about this is novel. It’s 101-level stuff. But transformation doesn’t mean inventing strategies that have never existed. It means deploying well-worn strategies in your specific context at the right time.

The playbook exists. The hard part is admitting that what worked brilliantly at your previous scale won’t carry you to the next one.

Rebuild your executive team — again and again

I recently had lunch with one of the co-founders of a large public software company. I asked him what version of their executive team he thought they were on. He said, “Probably the fifth generation.”

If you’re early in your journey, thinking about having to rebuild your leadership team five times can be daunting. At BambooHR, we’ve brought in six new executives over the past few years, including leaders of our revenue, finance, marketing, technology and product teams.

It’s exhausting work, but here’s what I’ve learned: Team renewal is invigorating. New voices bring fresh energy and new perspectives.

Like AI, humans need context: Communicate with boring consistency

Once you recognize the need to rebuild and start making changes, your next challenge is bringing your organization along with you. If people don’t understand the “why” behind the transformation, you’ll lose them.

I spent an entire leadership summit with our top leaders explaining the S-curve concept, and how we have to find our next growth curve as a company — and as individuals — or we will plateau. I thought I had communicated my vision clearly. Two weeks later, I heard through various channels that one of my leaders had told someone outside the company that they didn’t understand our goals or why so many changes were happening.

You have to be boringly consistent in describing the “why.” Humans have context windows, just like AI. If I described the strategy once in October, is a human’s context window long enough to hold onto it? The answer is probably not. You have to communicate the same message over and over, finding new ways to bring energy to it so it actually lands.

Be bold when you don’t know

My advice to CEOs going through transformation — and the advice I continue to give myself — is this: Be bold. Activity equals learning. If you don’t know, ship something and learn from it.

The competitive advantage belongs to companies that iterate faster than anyone else. If my learning cycle is twice as fast as my competitor’s, I like my chances. And in a world where every playbook is being rewritten, the willingness to rebuild as often and as quickly as necessary is what separates the companies that scale from those that plateau and even disappear.