My Story
I started my career as a Silicon Valley tech geek and in fall of 2008 I went to business school at Cornell with ambitions to become an entrepreneur, admidst a rapidly changing world. Bear Stearns collapsed, Lehman vanished, and GM and Chrysler took government bailouts. Meanwhile, Amazon ushered in the cloud era and Apple changed the game with the iPhone. Business school gave me space for reflection and analysis. That was valuable, but the case studies lagged behind reality and I was hungry for action. Change was afoot and I was ready to build.
Into the Arena
I started a company while in school, raised venture capital and ran it for three years through its acquisition by Sailthru. That’s where I learned to build, sell, and lead. I was building a product, building a team, making payroll, dealing with tricky leadership issues, and doing lots of selling. Selling to customers, selling to investors, selling to partners, and selling to prospective team members. This was trial by fire. I had the opposite problem now: nonstop action but little structured feedback. I was learning many lessons the hard way.
Me talking about the future (and pitching my startup) at an industry conference in Orlando. Sounds like a boondoggle, but I was working day and night without rest.
The Operator in My Corner
After my startup, I joined LinkedIn and then Twitter, learning from people who previously built products like Gmail and YouTube. My real breakthrough came at Flatiron Health, where I was VP of Product as we scaled the company from startup days through hypergrowth and a $2.1B acquisition by Roche. I got coaching from Ken Norton, a GV partner and former product leader behind products like Google Docs, Calendar, and Maps.
The three pieces finally came together: high-stakes action, immediate expert feedback, and structured reflection. My growth accelerated exponentially.
Me presenting on-stage in Nashville to 500+ Flatiron customers. I don’t usually wear suits, but there were a lot of doctors in the room.
The New Playbook
That experience shaped my philosophy: the best learning and growth comes from a rapid cycle of action, feedback, and reflection.
It’s the foundation of my coaching today. My work isn’t about slow, passive discovery. It’s an operator’s structured playbooks and real-time feedback fused with empathetic coaching, so leaders can find their way and make better decisions faster.
This also shapes my teaching as an adjunct at Cornell Tech, where I’m proud to help bridge classroom and real-world practice. My courses have reached 6,000+ students globally and I also share playbooks, insights and unfiltered conversations through my podcast, Executives Unplugged. I’m actively creating the fresh, open-source content I wished existed back in 2008.
Me faciliating a workshop for senior leaders in Florida.
Outside the Arena
I grew up in NH and still love driving pickup trucks. I earned an MBA and a BS in Electrical and Computer Engineering from Cornell. Outside work, you might find me traveling with my family, practicing to become a BBQ pitmaster, going for a bike ride, or cheering for the New England Patriots. I also have a dog that’s largely Belgian Malinois and needs 4-5 miles of exercise per day. I get plenty of steps.
Lia enjoying a 3 mile walk in the woods.
Let's Connect
You can explore my free content on Executives Unplugged, connect with me on LinkedIn or reach out directly via email (kc@keithcowing.com).