Removing Obstacles Is the Real Job of Leadership
After more than 25 years building go-to-market organizations, I've held a lot of titles. CRO. VP of Sales. Senior executive. Board member. But the belief that has shaped how I actually do the work, day in and day out, is quieter than any of those titles suggest. It's this: my job as a leader is to clear the path so talented people can run. Not to direct every step. Not to carry the ball myself. To remove whatever is standing between good people and great results.
This isn't a passive philosophy. It's one of the most active things a leader can do. At Coupa, when I joined, there were three people on the sales team and the company had less than $1 million in annual recurring revenue. The goal was to scale that team to 100 people and grow ARR past $100 million on a path to IPO. That kind of growth doesn't happen because a leader is making every call. It happens because you build a system, hire people who are better than you in their specific roles, and then spend your energy eliminating the friction that slows them down.
Friction takes many forms. Sometimes it's a broken forecast process that forces reps to spend hours on administrative work instead of selling. Sometimes it's a misalignment between sales and marketing that creates conflicting messages in the market. Sometimes it's a compensation plan that accidentally punishes the behaviors you actually want. At Tipalti, where I led revenue growth from $2 million to $70 million ARR while scaling the team from three to 85 people globally, much of my focus was on building the operational infrastructure that let the team move fast without losing discipline. Forecasting models. Hiring frameworks. Cross-functional alignment with marketing, product, and finance. These aren't glamorous things, but they are what make consistent, repeatable growth possible.
There's a version of leadership that looks impressive from the outside because the leader is constantly visible, constantly solving problems, constantly in the room. I've seen that style up close, and it tends to create dependency. People stop making decisions because they've learned to wait for the leader to decide. They stop taking ownership because ownership has never really been theirs. The team gets good at executing instructions, not at thinking and adapting. That works fine when markets are stable and the playbook is clear. It breaks down fast when conditions change, and conditions always change.
The leaders I've respected most over my career, including the best CEOs I've partnered with, share a common trait. They hire people they trust, give them real accountability, and then protect their ability to do the work. They ask good questions more than they give answers. They create environments where honest feedback flows both ways. They're willing to hold everyone, including themselves, to a high standard. And when someone on the team is struggling, their first question isn't "why aren't you performing?" but "what's in your way?"
That last question changed how I manage. Early in my career at Oracle, I was focused almost entirely on outcomes. Hit the number, close the deal, grow the territory. Those things matter. But I learned over time that outcomes are downstream of environment. If someone isn't performing, the honest answer is often that something in the system is working against them, not that the person is simply deficient. Maybe the territory is structured wrong. Maybe the product message isn't landing. Maybe the onboarding process didn't set them up. A leader who only manages outcomes misses all of that.
So the belief I'd put at the center of how I work is this: take care of your people and they will take care of the business. Not as a feel-good slogan, but as an operating principle with teeth. It means building real clarity around expectations. It means providing resources, feedback, and support without creating dependency. It means accountability and care existing in the same room at the same time. That combination, when it works, produces teams that don't need to be pushed. They're already running. My job is just to make sure the road is clear.
As I continue working with companies at various stages of growth, that principle is the one I keep coming back to. The specific tactics change. The markets shift. The technology evolves. But the organizations that build something durable are almost always the ones that figured out how to get out of their own people's way.