Keith Cowing

1:1 Executive coaching

An Operator in Your Corner

I coach founders and CEOs through the hardest parts of building and scaling. Coaching with me is a confidential, ongoing partnership. You bring the real stuff: the decisions keeping you up at night, the team dynamics nobody else sees, the questions you can't ask in a board meeting. I bring operating experience, an outside perspective from working with 100+ founders and executives, and empathy and support to help you think clearly and move with conviction.

The Four Unlocks

These four areas help me understand where you are and where we should focus to have the fastest impact on you and your business.

🧭 01 - CLarity

  • Getting so clear on strategy that everybody in the company can repeat it
  • Creating differentiation and defensibility
  • Allocating resources to fund the highest impact bets
  • Getting clear on what success looks like for you personally, not just for the company

♟️ 02 - TEAM

  • Sourcing, assessing, and selling candidates who are in high demand
  • Onboarding and grafting new leaders so they stick
  • Building and managing your board
  • Getting the team operating as a high speed unit
  • Building accountability structures and making the hard personnel calls

⚙️ 03 - SYSTEMS

  • Customers: assessing the end-to-end journey, removing friction and earning trust
  • Cash: managing burn, margins, revenue growth, and fundraising
  • Technology: investing in your technology to generate a sustainable edge
  • People: designing an org with efficient communication and excellent decision-making

☀️ 04 - energy

  • Sleep, nutrition, and exercise
  • Mental state and emotional resilience
  • Managing your calendar and attention as strategic assets
  • Knowing when to sprint and when to rest
  • Preparing for high-stakes moments: board meetings, fundraises, M&A, difficult conversations

Trusted by Founders and Executives

"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, Previvor Edge

“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, Clinch AGI

“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, Crux Partners

Work with Me

for ceos and product executives

1:1 Executive Coaching

WHAT WE WORK ON
We focus on the four levers that drive scaling: clarity, team, systems, and energy. Every engagement is different. We diagnose what's causing you stress and where there is opportunity. Then we make small, sustainable, changes that drive results.

WHAT’S INCLUDED
Unlimited access, anchored by weekly or bi-weekly Zoom sessions plus on-demand calls and async support when you need it. Starts with an onboarding assessment to define success, find blockers, and unlock immediate progress. I'm in your corner. We can meet in person if you're in NYC.

INVESTMENT
CPOs & Pre-Series A Founders: $2K/month
CEOs: $5K/month

Book a Free Session

for early stage founders

Early-Stage Advisory

WHAT WE WORK ON
We focus on three things: validating your product with real proof points, building the core team that thrives in early-stage chaos, and sharpening your fundraising narrative to convert investor meetings into dollars.

WHAT’S INCLUDED
Bi-weekly sessions plus async support — hands-on help with product, decks, and pitch practice. I'm in your corner.

INVESTMENT
Flexible cash + equity options designed to invest in your future while preserving runway.

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