Keith Cowing
Executive Coach for CEOs and CPOs
Building a great company is hard.
You don't have to do it alone.
I've been a founder building from scratch and an executive scaling through a multi-billion dollar exit. Now I combine operating experience with a coach's empathy to help you build, lead and win.
It's messier, harder and lonelier than anyone admits.
You need more than a sounding board. You need to sharpen your strategy, hire the right team, build scalable systems, and protect your energy, all at once.
I've worked with 100+ founders and execs and I'm sharing what I learn. Take the insights and playbooks and run with them.
When you hit a critical juncture and need someone in your corner, I’ll jump in the trenches with you.
Clarity · Team · Systems · Energy
Ways we can work together
Executive Coaching for
CEOs and CPOs
FOCUS
Find Clarity in the Chaos: Refine your vision, strategy and operating plan. Navigate high-stakes decisions with conviction.
Build a World-Class Team: Hire, align, and unleash A+ players who deliver results even when you’re not in the room.
Drive Results: Move faster by removing bottlenecks, scaling your leadership, and protecting your energy.
INCLUDES
Unlimited access: Weekly or bi-weekly cadence plus on-demand calls. Unlimited async (email/text/docs). I’m in your corner.
Onboarding: Assessment & action plan. We define success, find blockers, and unlock immediate progress.
INVESTMENT
CPOs & Pre-Series A Founders: $2K/month
CEOs: $5K/month
Advisory Support for
Early Stage Founders
FOCUS
Prove Product-Market-Fit: Perform an objective assessment, iterate rapidly, and demonstrate meaningful proof points.
Build the Core Team: Identify, vet, and onboard key team members who thrive in an early-stage environment.
Raise Funding: Sharpen your narrative, prepare the pitch deck, and convert investor meetings into $.
INCLUDES
Live sessions: 60 mins bi-weekly.
Async support: Hands-on help with product, decks, and pitch practice.
Flexible terms: Flexible cash + equity options for pre-seed and seed-stage companies. Invest in your future while preserving runway.
Strategic offsites: Clarify strategy, lock in goals and plans, and help leaders gel as a unified team.
Skill-building workshops: The Founder to CEO Shift, Product Strategy for Executives, Strategic Narrative & Influence, Building Trust in the Face of Rapid Change, and a variety of topics that can be tailored to your needs.
INCLUDES: End-to-end agenda design, materials, facilitation, post-event action plan, custom pricing based on needs.
Workshops & Offsites
Executives Unplugged
Coaching, Open Sourced
Featured Episodes
Trusted by leading CEOs, builders, and teams
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"Working with Keith is wonderful. He is responsive, thoughtful, insightful, and solutions-oriented. He brings a blend of executive coaching coupled with domain expertise across product, technology, and company building. I value the foundational relationship and the actionable frameworks and tools. Keith's coaching has helped me navigate specific circumstances, adopt a leadership approach that is productive for the company, and achieve better emotional stability because I had a confidential space to problem-solve and discuss important matters.
-Michelle Zimmerman
CEO of Previvor Edge
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“Keith has been instrumental in helping me elevate my leadership as a CEO. As a founder himself, he brings a unique empathy and depth of understanding to every conversation… His coaching sharpened my ability to communicate with clarity and conviction, especially in high-stakes conversations with investors. He’s also been an invaluable connector, facilitating introductions that expanded Clinch’s investor network and accelerated our fundraising journey. I’d strongly recommend Keith to any CEO or founder looking to strengthen their leadership and executive communication.”
-Uday Chakravarthi
CEO of Clinch AGI
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"It was clear from our first meeting that Keith wasn’t an armchair coach. He’s been in the arena. As a seasoned product leader, he understood the realities of operating in fast-growing environments and the mix of ambition, accountability, and burnout that often comes with it. What I valued most was his ability to bring clarity and perspective. He helped me recalibrate expectations of myself and of the company, set healthy boundaries, and reconnect with what I actually wanted from my career. That work had a lasting impact."
-Anu Ram
Founder of Crux Partners, Previously CPO @ Certify
Join the Inner Circle
Frameworks, playbooks, unfiltered takes, and personal video replies — my open source version of executive coaching.
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