I started as an engineer. Then I became a venture-backed CEO, VP of Product at Flatiron Health from Series B through $2.1B acquisition, and eventually a coach. I've failed too, and have the scar tissue to prove it. Every role taught me something different about what it takes to build and lead under pressure.
20 years of building and scaling
Founding a company is a masterclass in humility. I lived the full arc as a venture-backed founder: building the first product, raising capital, hiring and firing, selling, making payroll, and eventually navigating an acquisition. I learned most leadership lessons the hard way. When I work with founders today, I’m not coaching from a textbook. I’m coaching from a deep understanding of what it feels like to be the one everybody looks to when the future is uncertain.
After my startup was acquired, my world shifted from gritty and scrappy to scaling and operating. At LinkedIn, Twitter, and Flatiron Health, I learned how to design organizations, build scalable systems, and lead through rapid change. I've navigated board dynamics, executive hiring, and the kind of complexity that only comes with scale. I bring that operating experience to every coaching engagement.
As VP of Product at Flatiron, I worked with Ken Norton—a legendary coach and former Google executive who led teams at Docs, Calendar, and Maps. Having an operator in my corner who combined deep experience with empathetic coaching was a career-defining shift. It taught me that coaching can be more than passive discovery; it can be a high-velocity cycle of action, targeted feedback, and structured reflection. Ken didn't just coach—he also understood the context and moved at startup speed. Today, I bring that same operating rigor and pace to my own clients.
I grew up in New Hampshire and still love driving pickup trucks. I earned a BS in Electrical and Computer Engineering and an MBA from Cornell. Outside work, you’ll 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 (Belgian Malinois mix) who needs 4-5 miles of exercise per day. I get plenty of steps.
I’d love to hear your story. You can connect with me on LinkedIn, reach out directly at kc@keithcowing.com or join the inner circle for weekly lessons from the field.
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