About Me
After engineering school I moved to Silicon Valley and completely caught the startup bug. I ended up at business school in 2008, amidst a financial crisis but also major platform shifts with cloud, mobile, and social all happening at once. Change was afoot and I was ready to build.
Into the Arena
I started a company (Seamless Receipts), raised venture capital and led it for through an acquisition by Sailthru. I was building a product, building a team, making payroll, dealing with tricky leadership issues, and doing lots of selling. This was trial by fire and I learned many lessons the hard way.
The Operator in my Corner
After my startup, I joined the product team at LinkedIn and then Twitter, learning from incredible product leaders. My real breakthrough came at Flatiron Health, where I was VP of Product as we scaled the company from a startup through hyper-growth and a $2B acquisition by Roche. I was fortunate to get coaching from Ken Norton, a GV partner and former product leader behind Google Docs, Calendar, and Maps.
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 professor at Cornell Tech, where I bridge the classroom with real-world practice. My courses have reached 6K+ students globally and I also share playbooks, insights and unfiltered conversations through Executives Unplugged.
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, cooking low and slow BBQ, riding my bike, 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.
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).
