What Scaling Coupa Taught Me About Building Before You're Ready
I joined Coupa when annual recurring revenue was under $1 million. When I left, we were at $100 million ARR and had completed a successful IPO. The sales organization grew from three people to 100 during that stretch. I've spent a lot of time since then thinking about what I actually believed in those early days versus what I understand now, because the gap between those two things is where the real lessons live.
Back then, I thought the job was to close deals. That sounds obvious, even embarrassing to admit. But when you're in a small, scrappy software company trying to prove the model works, every quarter feels like survival mode. You measure yourself by the number on the board at the end of the month. I was good at selling, good at finding the next customer, and I assumed that if we just kept doing that, everything else would work itself out. It didn't. Not automatically, anyway.
Here's what I didn't fully appreciate at the time: the systems you build in year two follow you into year five. The way you structure territories, how you define a qualified opportunity, whether you hold the line on forecast discipline when a rep is two days from quarter end, all of that gets baked into the culture. At Coupa, we were lucky. We had leadership that cared about building things the right way, not just moving fast. But I've watched other companies skip those foundations and pay for it later when they're trying to layer process onto chaos.
The specific moment that shifted my thinking came during a period when we were scaling the sales team faster than our onboarding and enablement could keep up. We were hiring talented people and then dropping them into a system that wasn't ready for them. Ramp times stretched. Win rates dipped. The instinct, especially from the outside, was to hire more. My instinct at the time was similar. But the real problem wasn't headcount. It was that we hadn't built the infrastructure to make each new person successful before we added the next one. Adding people to a broken system doesn't fix the system. It scales the problem.
That lesson stayed with me through my time at Tipalti, where I led revenue growth from $2 million to $70 million ARR while building the go-to-market team globally from three to 85 people. I came in with a different mindset. I was more deliberate about sequencing. Before we added headcount, I asked whether the person we were about to hire had a clear territory, a defined motion, the tools and content they needed to ramp, and a manager with enough bandwidth to develop them. Not every answer was yes. But asking the question early changed the decisions we made.
What I think now is that the best revenue leaders aren't just closers or people managers. They're architects. The job is to design a system that produces consistent, predictable output and then staff it with great people who can operate within that system and, eventually, improve it. That takes longer than hiring fast and hoping. It requires saying no to shortcuts that feel urgent but create compounding problems later.
I also think about the Oracle years, earlier in my career, where I led global CRM SaaS sales and closed major Fortune 100 accounts. That experience gave me a deep appreciation for enterprise complexity, long sales cycles, and the discipline required to manage a large deal from first meeting to signed contract. But it also reinforced something I had to relearn in startup environments: process that works at scale can suffocate a company that isn't there yet. The translation isn't direct. You have to adapt what you know to the stage you're actually in, not the stage you're aspiring to reach.
The shift in my thinking still matters because I see early-stage and growth-stage companies repeat the same mistakes constantly. They either under-invest in infrastructure and burn through good talent, or they over-engineer process and lose the speed that makes startups competitive. The answer is somewhere in between, and finding it requires leaders who are honest about what stage they're in and what the business actually needs right now. That's the work I care most about, and it's the perspective I bring every time I walk into a new company trying to build something that lasts.