CTO coaching with Eric Weiss
I’m Eric Weiss, a CTO coach for Series A and B SaaS and AI companies. I’m a former founder and CTO who built the PlayStation Network, I coached OpenAI’s platform engineering leaders from 2019 to 2022, and I’ve coached 75+ technical leaders over 15 years.
What CTOs bring me
You were promoted for technical judgment. Now the job is hiring, delegating, and earning a seat at the exec table.
Roadmap fights, unclear decision rights, and a board that hears two different stories.
Teams doubling, managers who’ve never managed, and delivery slowing as headcount grows.
VPs who don’t work out, senior engineers who leave, and a hiring pipeline that still depends on you.
Explaining technical strategy in business terms, and owning the technology story in the next raise.
Making the tradeoffs explicit, so the business stops treating engineering as a black box.
What CTOs say
“Eric has a unique combination of having first-hand experience as a product and technology leader. His perspective and advice were very valuable as we worked to take our product and tech organizations to the next level.”
Alexis SmirnovCo-Founder and CTO, Dialogue“Eric is an exceptional executive coach. It was a perfect fit for me because he has extensive experience as a CTO. We worked on a vast range of problems, from recruiting and team motivation to goal setting and coaching engineering leaders within the company.”
Evgeny BelorusetsCTO, Archive“Working with Eric has been a game changer. Eric has an uncanny ability to cut through the noise, clarify priorities, and create structure that actually drives momentum.”
Ira HayesCo-Founder and CTO, DojoAir“Eric consistently provided great insights and ideas and was relentless in his pursuit to continuously improve the way we worked. I would unequivocally recommend Eric to any technology executive.”
Larry XuVP of Software Development, TealiumRead the OpenAI case study · More client stories
CTOs I’ve coached are backed by General Catalyst, Andreessen Horowitz, Sequoia, GV, Bessemer, Battery, Menlo, Founders Fund, Y Combinator, and Lux.
How it works
90-minute sessions every two weeks, calls in between, a CTO Scorecard at kickoff, and a 90-day plan. Three-month minimum.
From $5,000 a month
Co-founder and CEO-CTO coaching is scoped on the Clarity Call. Some partner funds support coaching for their portfolio CTOs.
FAQ
A CTO coach helps a technical leader make the jump from best engineer in the room to executive: hiring and developing leaders, delegating, aligning with the CEO and board, and running engineering as a business function.
Look for a coach who has held the CTO seat at a scaling company, coaches CTOs specifically, and can show results. That’s the bar I hold myself to.
My 1:1 CTO coaching starts at $5,000 a month, with a three-month minimum.
Yes. I coach co-founders and C-suite pairs together, with joint and individual sessions to settle roles, decision rights, and conflict.
Yes. I coach over video with CTOs across the US, Canada, and Europe, and I’m based in San Diego.