What I Thought I Knew
You know what surprised me most about moving into senior sales leadership? It wasn't the strategy. It wasn't the customers. It was realizing that everything I thought made me successful had to be rebuilt from the ground up.
I had spent over a decade excelling in enterprise sales. I could walk into a utility company navigating $30 billion in wildfire liabilities and orchestrate sixty people across engineering, customer teams, and regulatory bodies. I could sustain an eighteen-month negotiation with a semiconductor customer when every quarter brought fresh pressure to close faster. I knew how to hold ground, how to read a room, how to make the complex look effortless.
That muscle memory served me well until it didn't.
When I stepped into my first leadership role, those same instincts — the ones I'd spent a decade sharpening — almost destroyed my effectiveness. Not because the instincts were wrong. Because I was applying them in the wrong direction.
Sitting on My Hands
Around month four, I still hadn't figured it out. I kept jumping in to save deals. I kept orchestrating the complex engagements myself. I kept being the hero. And I kept wondering why the team wasn't developing the capabilities they needed.
My executive coach said something that stopped me cold. She told me that every time I solved a problem for my team, I was teaching them that they weren't capable of solving it themselves.
That hit different.
So I learned the 70% Rule. If someone on my team could do something 70% as well as I could, I delegated it to them. The 30 % gap between their capability and mine wasn't a problem to fix. It was the space where learning happened. Filling that gap for them didn't close it. It preserved it.
Early on, watching a team member struggle through account planning I could have done faster in my sleep felt almost physically painful. Every instinct I had said, take it back. Take it back and do it right. But taking it back would have told them something they'd carry for months: that I didn't trust them to figure it out.
By month nine, the people who had been at 70% were running at 85 and 90. Some had developed approaches I hadn't thought of. They'd outgrown my version of the work because I hadn't done it for them.
I learned that my job wasn't to be the best seller in the room anymore. My job was to build people who could sell better than I ever did.
The Breakpoint
The second lesson came from nearly quitting.
Around month four, I entered what I now call the Breakpoint. I woke up every day questioning whether I belonged in this role. The operational complexity was relentless. Fire drills cascaded. My calendar was filled with meetings I hadn't scheduled. The work felt like wading through wet concrete.
I wanted to quit. Not abstractly. I genuinely considered asking to return to an individual contributor role where I knew I could succeed.
That's when I pulled out a whiteboard and drew something I had been thinking about: the Gartner Hype Cycle. The five phases that technologies experience as they move from novelty to mainstream adoption are the peak of inflated expectations, the crash into disillusionment, and the gradual climb toward productivity. I marked where I was. Deep in phase three – Trough of Disillusionment. Exactly where the framework predicted I would be.
I wasn't failing. I was on schedule.
I kept that whiteboard visible for months. On the days when I questioned everything, I looked at it: Still in the trough. Still normal. Still temporary. Keep going.
And I learned to create that same safety for my team. In our weekly meetings, I made space for admitting what we didn't know. For calling the hard weeks hard. For celebrating the small wins that looked insignificant from the outside. People needed to know it was okay to struggle. Building something from zero is supposed to be difficult. Pretending otherwise doesn't make it easier. It just makes people feel alone in it.
The CIO Who Answered
January 15, 2019. The email arrived at 7:13 PM: a utility company's notice to file bankruptcy on or about January 29th—over $30 billion in wildfire liabilities. Eighty-five people are dead. Equipment failures have been traced back to nearly two decades ago.
I called the newly appointed CIO. She answered.
I told her I was calling to express my commitment to standing by the company and to assure her that she could rely on my teammates and me. That we weren't walking away.
She said she had been fielding calls from vendors all day — asking about invoices, suspending contracts, protecting their exposure. Then she said: 'You were not one of them. And that was refreshing.'
Nine months later, the largest public safety power shutoff California had ever seen knocked out service to 5.4 million customers across 38 counties. The utility's website crashed. Secondary systems we had built together became inaccessible. We mobilized — war room protocols, architecture redesigned in real time, state regulators watching. We got the systems working. Then we rebuilt them right.
What I learned from those months was this: customer obsession isn't about showing up for the wins. It's about showing up when it's hard. The relationships that matter most are forged in adversity, not convenience.
As a leader, I carry that into how I think about developing people. Staying committed to someone's growth when it's slower and harder than doing the work yourself — especially then — is what customer obsession looks like when your customer is your team.
What You Can Control
My executive coach warned me early on: I would have to communicate many things to my team that I had no control over. This would frustrate me.
She was right.
Quota changes. Organizational restructures. Compensation adjustments. Policy shifts. None of it is mine to decide. All of it is mine to navigate. The framework she gave me became my anchor: control what you can control, influence everything else.
What I could control: how I communicated hard news. I showed up for the team regardless of what came down from above. How consistently I protected the environment we had built, even as the environment above us shifted.
What I could influence: how decisions landed, through relationships and advocacy. How the team felt about circumstances they didn't choose. Whether they experienced leadership as someone who absorbed the turbulence or someone who passed it straight through.
Most leadership frustration, I've come to believe, comes from fighting to control what you can only influence while neglecting what you actually have. The distinction sounds simple. Living it is not.
The Flywheel
I used to think culture was about inspiration. Get people fired up in the meeting. Send the right message at the right moment. Lead with energy. And yes, that matters. But inspiration fades. Mechanisms endure.
So I built them. Weekly meetings with a standing structure — wins, blockers, learning. Monthly reviews where we examined what losses had taught us, not just what wins had proven. Qualification frameworks. Executive engagement rhythms. Partnership development cadences. Not because I didn't trust my team. Because I wanted to make their results more predictable and their work less chaotic.
The first few meetings felt forced. People weren't sure how to engage. I questioned whether the time investment was worth it.
By rotation five, the pattern had settled. By rotation twelve, the team was driving it. By rotation twenty-five, I was largely a participant in something the team had made their own.
That's how flywheels work. Early rotations are expensive. Later rotations are nearly free. And what you get from a mature flywheel isn't just efficiency, it's something you've built that keeps turning after you leave the room. That's the whole point.
The Builder
Halfway through my first year, I stopped and worked through something I'd been circling for months: Why do I lead? Not what do I do, or what are my results? Why.
The answer I arrived at: I build people and teams through trust, challenge, and example so they reach their full potential.
That became the filter for every decision I made after that. Not, am I getting this done? But am I building capability, or just getting things done? They look the same in the short term. They produce completely different teams over the course of a year.
The best customers I ever served didn't make themselves the hero of their own organizations. The CIO navigating bankruptcy stayed committed to her people as everything around her was restructured. The executives who earned the deepest loyalty were the ones who mobilized resources, told the truth about what they didn't know, and then got out of the way.
Leadership is service. I work for my team, not the other way around.
I'm still on what the hype cycle calls the slope of enlightenment. I expect to be there for years. That's the point. Leadership isn't something you master and finish. It's something you build, and rebuild, and refine.
The journey from seller to leader wasn't about learning to manage. It was about learning to multiply. One great seller closes great deals. One great builder builds sellers who close deals you'll never have to touch.
That's what I carry forward. And I'm just getting started.