Hi, I’m Keith.
Coach to CEOs, CPOs and CTOs. Host of Executives Unplugged.
Leaders at VC and PE-backed companies face relentless demands: tight timelines, limited resources, complex stakeholder dynamics, and intense pressure to deliver. I’ve guided teams through these hurdles as both a CPO and a CEO, and I work with executives every day who face similar challenges. I have seen what works (and what doesn’t) and through my podcast, newsletter, and coaching, I share real-world successes, pitfalls, playbooks, and tailored questions to help you gain clarity and drive results.
Who I work with
CEOs
As a CEO in a VC or PE-backed environment, you face pressure to deliver results fast. I help you clarify your vision and strategy, align stakeholders, build trust, make hard decisions, adapt quickly, tackle organizational challenges, and execute - even when resources are tight.
CPOs and CTOs
As a builder, you juggle product roadmaps, cross-functional teams, technical debt, AI shifts, and evolving customer needs. I help you refine your strategy, foster executive buy-in, and drive innovation and progress without burning out.
Free Coaching Content
Executives Unplugged Podcast
Welcome to Executives Unplugged, the show for leaders navigating rapid change with limited resources and relentless expectations.
Join operator and executive coach Keith Cowing as he sits down with world-class leaders to decode their playbooks. Drawing on experience leading teams through both failures and multi-billion dollar exits, he skips the idealistic frameworks for battle-tested tactics that will help you make high-stakes decisions with confidence, align your team and drive rapid results, and find clarity in the chaos.
Leadership is messy, but you don’t have to face it alone. Executives Unplugged puts the best operators and insights in your corner to help you win and enjoy the ride.Listen on your favorite platform
Recent episodes