I've spent 15 years inside the inflection points I now help others navigate.

Every major success and every meaningful failure in my career took root at an inflection point — a moment when the trajectory of my career or the future of the company I worked for hinged on a single, big decision. These are the moments that separate the leaders who shape what happens next from those who react to it. They're not comfortable. They demand conviction, clarity, and a willingness to take calculated risk. But they also reward preparation — the best outcomes don't come from bold moves recklessly made, but from big bets supported by rigorous thinking and adaptable frameworks.

I chose to begin my career in government service when the majority of my classmates went to finance or consulting. I spent six years building my career in intelligence, leading teams across four continents and in forward deployed environments, and earning a master's degree from the premier institution for my field. When I realized I'd reached a ceiling on the impact I could expect to have, I made the harder choice: walking away from that investment and the safety of a government job to pursue private sector opportunities. It's a leap many government employees contemplate, but it's a notoriously hard pill to swallow for most. That decision changed the entire trajectory of my career.

Not long after, a good friend of mine connected me with a security startup called StackRox. They offered a rare opportunity but it implied a steep commitment. I exchanged a comfortable red teaming gig in sunny San Diego for a weekly flight to the Bay Area. At StackRox, I helped drive the decision to rebuild the product from the ground up — pivoting the value proposition from container detection and response to Kubernetes security at a time when the market hadn't yet keyed in on the security implications of container orchestration. It was a bet on where the industry was headed. We executed the rebuild, the market caught up, and the product value drove a 30× acquisition multiple.

Post acquisition, I made what most would call the financially questionable decision to leave my vesting behind so I could accept a role with GitLab. There I took on a product line with great early traction and turned it into a revenue growth engine for the company. My team scaled GitLab Ultimate from $40M to $450M run rate. Easily the largest portfolio I've managed and a rousing success.

But then the AI wave hit and everything changed. With a DevOps platform built around coding workflows for a product, the company found itself suddenly at the epicenter of a tidal change: software development was about to be reinvented from the ground up. Anxiety took hold, the organization churned, and the conditions for building a coherent AI strategy were far from ideal. Nonetheless, my team shipped the company's first suite of AI products. It was far from clean and left much to be desired, but it kept the company in the race at the time.

The juxtaposition of those two experiences at GitLab was stark. The first taught me invaluable skills about how to scale a product when you're starting from a good foundation. But of all the inflection points I've seen in my career, the pressure cooker of the early days of AI offered the most indisputable evidence that any deficiency in courage, clarity, or rigor at a true inflection point will quickly send you sideways.

Now I'm building a practice that leverages my experiences to help smart people navigate high-stakes decisions and equip their teams to walk with them through the fire. Whether it's a founder who can't yet see the path to PMF, a senior leader standing at a career crossroads, or a company betting its future on a strategic pivot, the work is the same. I help you see your situation clearly, make the hard call, and build the plan to execute it.