My Story
I’m an executive coach for CEOs and CPOs. I started my career as an engineer. But over the next two decades of building products and companies, from scrappy founding days to scaling through a $2B exit, I learned something. The most complex systems aren’t circuits, they’re human. I’ve lived the transformation from tech geek to founder to executive. I know the intense, isolating pressure of each stage. Today, I help founders and executives navigate that chaos so they don’t have to do it alone.
Into the Arena: Founder
Founding a company is a masterclass in humility. I lived the full arc as the founder of Seamless Receipts (acquired by Sailthru): building the first product, raising venture capital, hiring and firing, selling, making payroll, and dealing with tricky management issues. I learned many leadership lessons the hard way. When I work with founders today, I’m not coaching from a textbook. I’m coaching with a deep understanding of what it feels like to be the one everybody looks to when times are uncertain.
Scaling Companies: Operator
After my startup was acquired, my world shifted from being gritty and scrappy to scaling and operating. At companies like LinkedIn, Twitter, and Flatiron Health, I learned how to design the organizations and systems that enable multi-billion dollar outcomes. I’ve navigated the high-stakes complexity of major acquisitions and rapid scaling, and I use that experience to help leaders move from just grinding harder to true, sustainable executive leadership.
In Your Corner: Coach
I had an aha moment when I started working with Ken Norton, a legendary coach and former Google executive. I experienced how powerful it is to have somebody in your corner who is both an experienced operator and an empathetic coach. It changed the trajectory of my leadership at Flatiron Health and inspired me to become a coach myself. I now have the privilege of working with ambitious founders and executives every day to help them become the best leaders and operators they can be.
Outside the Arena
I grew up in NH and still love driving pickup trucks. I earned a BS in Electrical and Computer Engineering and an MBA 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 a Belgian Malinois mix 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). If you’re in the arena and could use a partner in your corner, I’d love to hear your story.
