Keith Cowing

Executive coaching for CEOs and leadership teams

Decision-making is the new bottleneck. Your team can execute faster than ever, but so can everybody else. I help leadership teams sharpen their point of view, make better decisions faster, and build the trust it takes to win.

Get my field notesBuild conviction in your decisions and alignment on your team.

An operator in your corner

As founder and CEO of Seamless Receipts and Ruby, I led each company through an acquisition and learned to build from scratch. As VP of Product at Flatiron Health (acquired for $2.1B), I learned to scale. I also worked on the product teams at Goldman Sachs, Twitter, and LinkedIn. Along the way, I got some things right and made a lot of mistakes. I’m here to share what I’ve learned.

As a coach, I’ve worked with 100+ founders and executives and trained 10K+ professionals worldwide. I bring an operator’s mindset, the empathy of someone who’s had to make the hard calls, and a front-row seat to how ambitious leaders are redesigning the way their teams work.

Keith Cowing leading a workshop for a room of leaders

1:1 Executive Coaching

A confidential partnership for CEOs and executives working through high-stakes decisions, board and team dynamics, leaders who aren’t scaling, and the hard stuff you can’t discuss openly with your team. Weekly or bi-weekly sessions, async support, and calls whenever you need them. The first session is free and doubles as a chemistry check: bring your hardest problem and we’ll go to work.

How coaching works

Offsites and Workshops

From a single workshop to a multi-day offsite, I design and facilitate sessions around the biggest challenge your leadership team is facing. That might be decision-making, trust, alignment, cadence, strategy, or shaping your own AI-native operating model. It starts with a simple question: What would you like your team to walk away with?

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Executives Unplugged

Candid conversations with founders and execs about making critical decisions, building and aligning your team, and showing up at your best.

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