Keith Cowing

Building a great company has never been messier.

EXECUTIVE COACH

I’m Keith. I coach founders, CEOs, and leadership teams working to make better decisions, move faster, and build AI-native operating models.

WAYS TO WORK TOGETHER

An operator in your corner

I’ve been a founder, CEO, and product executive, building from zero to one and leading teams through hyper-growth and a multi-billion dollar acquisition. I bring an operator's experience, a coach's empathy, and a front-row view into how AI-native leaders are unlocking new levels of performance.

Clarity
Team
Systems
Energy

1:1 Executive COACHING

In the trenches with you

A confidential partnership for founders, CEOs, and executives navigating high-stakes decisions, team dynamics, AI transformation, and completely new ways of working. Weekly or bi-weekly sessions, async support, and ad hoc calls whenever you need them.

How I work with founders & executives

WORKSHOPS and OFFSITEs

For leadership teams redesigning how they work

Custom-designed workshops and offsites for leadership teams navigating AI, decision rights, team alignment, and operating cadence. Recent topics include The AI-Native Executive Team, Building Trust During Uncertain Times, and From Delivery to Strategic Product Leadership.

Discuss a workshop

EXECUTIVES UNPLUGGED

What I'm learning from founders, executives, and AI builders

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JOIN THE INNER CIRCLE

One email a week. No fluff, just lessons from the field.