Keith Cowing

Coach for Founders, CEOs and Product Executives,
Host of Executives Unplugged

Building a great company is messy, hard, and lonely.

You need to sharpen your strategy, hire the right team, build scalable systems, and protect your energy, all at once. I know what the pressure feels like.

I've been a founder and an executive and experienced both failures and multi-billion dollar exits. Now I combine operating experience with a coach's empathy to help you build, lead and win.

Clarity · Team · Systems · Energy

Ways we can work together

1:1 Executive Coaching

A confidential, ongoing partnership for founders, CEOs, and product executives. Unlimited access: weekly or bi-weekly sessions, ad hoc calls when the world moves fast, and async support whenever you need it. Your priorities drive everything. We figure out what will have the biggest impact on your company and your leadership. Then I jump in the trenches with you. This isn’t a sounding board to help you find minor improvements. This is a holistic approach to transform your experience as a leader, with a coach and an operator in your corner every step of the way.

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Workshops & Offsites

I design and facilitate workshops and offsites for executive teams and founder cohorts. Topics include:

  • The Founder to CEO Shift

  • Product Strategy for Executives

  • Strategic Narrative & Influence

  • Leveraging AI and Human Connection to Lead Through Rapid Change

  • Building Trust in the Face of Uncertainty

Every engagement is custom: end-to-end agenda design, materials, facilitation, and a post-event action plan. These can be standalone sessions or part of an ongoing coaching relationship.

Discuss a Workshop

Executives Unplugged

Coaching, Open Sourced

Featured Episodes

Executives Unplugged
Field Notes from 20 Years of NYC Startups

What if AI made you more present, not more addicted?

Why 50% of Startup Executive Hires Fail (and How to Fix It)

In this episode, Meghan Oliver reveals her framework for how to wildly reduce the risk of a mis-hire and either close your next great executive or land your next great gig.

250 Board Meetings Later: This CEO’s playbook will change your board meetings forever

Matt Blumberg reveals why he bans slides, forces independent directors to "audition" for a seat, and uses AI to simulate Steve Jobs in the boardroom.

See all Episodes

Join the Inner Circle

Frameworks, playbooks, unfiltered takes, and personal video replies — my open source version of executive coaching.