My Story
From Founder to Executive to Coach
I started my career as an engineer. Then over two decades of building products and companies, I learned something. The most complex systems aren’t circuits; they’re human. I’ve lived the transformation from builder to founder to executive. I know the intense, isolating pressure of each stage. Now I help founders and executives navigate that chaos so they can own their own journey.
Into the Arena: Founder
Founding a company is a masterclass in humility. I lived the full arc as 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 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 times are uncertain.
Scaling: Operator
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 the organizations and systems that change industries. I’ve navigated multi-billion dollars acquisitions and rapid scaling, and I use that experience to help leaders move from grinding harder to leading like an executive.
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 and inspired me to become a coach myself. Now I work with ambitious founders and executives every day to help them become the best leaders they can be.
Outside the Arena
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.
Let's Connect
Explore my free content on Executives Unplugged, connect with me on LinkedIn, or reach out directly at kc@keithcowing.com. If you’re in the arena and could use a partner in your corner, I’d love to hear your story.
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