My Story
After engineering school I moved to Silicon Valley and caught the startup bug. I went to back to business school just as cloud, mobile, and social were reshaping the tech world. Everything was changing and I wanted to build.
Into the Arena
I started Seamless Receipts, raised venture capital, and led the company through an acquisition by Sailthru. It was trial by fire: building product, making payroll, hiring and firing, selling, and learning hard leadership lessons in real time.
The Operator in my Corner
After my startup, I joined the product teams at LinkedIn and Twitter, then became VP of Product at Flatiron Health, where we scaled from startup through hyper-growth and a $2B acquisition by Roche. Along the way I was coached by Ken Norton (GV, ex-Google Docs/Calendar/Maps), which showed me how powerful the right operator in your corner can be.
The New Playbook
Those experiences shaped my philosophy. Real growth comes from a cycle of action, feedback, and reflection. That cycle is the foundation of my coaching today, where I fuse structured playbooks and operational expertise with empathetic coaching to help leaders scale faster. I also teach at Cornell Tech and host Executives Unplugged, sharing these playbooks and unfiltered conversations with founders, CEOs, and operators.
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).
