Executive Coaching for Technical Founders
You built the technology and the company is growing. Now the job is the board, the executive team, the politics, and the next raise. I coach technical founders through that shift, because I’ve lived it.
I’m a former founder and CTO who built the PlayStation Network, and I spent nearly three years inside OpenAI as it went from research lab to production platform. I’ve coached more than 75 founders and technical leaders over 15 years, and Prismatic ranks me in the top 1% of executive coaches.
Coaching is built around the decisions actually on your plate this quarter: one-on-one, with your co-founders and executive team, or for your next raise. If you want a sense of how I think before we talk, start with my books, Above the Chaos on leading calmly under pressure and Growth by Design on earning product-market fit.
Who This Executive Coaching Is For
Stuck in the Weeds
Every decision comes back to you. The team can't ship without your sign-off. You're the most expensive bottleneck in the company and you know it. We build the systems that get you out.
Running the Executive Team
You hired experienced executives from bigger companies and you aren't sure how to lead them. Someone isn't working out and you've let it slide for a quarter. We build the system that lets you lead them.
Managing the Board and the Raise
Your board sees a technologist when you need them to see a CEO, and the next raise is coming. We work on your story, your deck, and how you show up in the room.
Ways to Work Together
1:1 Executive Coaching
For the founder or CTO facing a recurring leadership challenge. Sessions every two weeks for at least three months, starting with the CEO Scorecard. From $5,000 a month for venture-backed companies.
Co-Founder and C-Suite Coaching
For co-founders or an executive team that isn't running as one. Joint sessions on roles, decision rights, and conflict, alongside one-on-one work. Scoped on the Clarity Call.
Strategic Offsites
For a leadership team facing one big decision: strategy, a reorg, or annual planning. One facilitated day, designed with you beforehand. $5,000 day rate.
Fundraising Coaching
For founders preparing a raise. Story and deck prep, making the business fundable, and introductions to investors in my network. Scoped on the Clarity Call.
Testimonials
Swaraj Banerjee
From hiring the best engineering leaders, to building insightful product feedback loops, to building both company-wide and personal habits -- I could not be more grateful to have his help.
Brendan Keeler
Head of Product at Flexpa
Justin Wieland
Founder of Reach Tech
What We Work On
Evolve as a Leader
Most founders are running on instinct. What got you here won’t get you there.
- Build a leadership operating system that scales exponentially without you holding everything together
- Hire and inspire a winning team that ships quality products
- Manage the psychological weight of carrying the company without burning out
- Know exactly where your company needs you to grow and how to get there
- Show up to your board and your C-suite as the mature executive your company needs
Clarify Your Vision
Transform the complex future into a concrete plan of attack.
- Define a north star your engineering team can execute against
- Build OKRs that connect company strategy to daily engineering decisions
- Get product, design, and engineering aligned and pulling in the same direction
- Make prioritization calls you can defend to your CEO, your board, and your team
Execute Flawlessly
Teams don’t fail because engineers are bad. They fail because the system is broken.
- Hire the right people the first time, with a process that doesn't rely on your gut
- Stop shipping the wrong thing and build what your customers actually need
- Integrate product and engineering so they stop fighting and start collaborating
- Build the documentation, process, and team structure that scales exponentially
Build Connection
Design a culture that allows your team to thrive.
- Build an engineering culture that keeps senior talent happy and develops juniors
- Give your team a feedback and accountability system that helps them grow
- Develop the leaders below you so the company stops depending on your heroics
- Connect your team with your customers so they understand exactly what to build
More Testimonials
James Heath
JD Carter
Executive Coaching FAQ
Who is this coaching for?
CTOs and technical founders at venture-backed companies, mostly Series A and B, who are great at building technology and now have to build the human systems around it: the team, the leaders, how the work gets orchestrated, and the story. If everything in the company still routes through you, this is for you.
What does an engagement look like?
It starts with the CEO Scorecard, a self-assessment we review together at kickoff to pick the one leadership area that matters most for the next 90 days. We meet every two weeks for a minimum of three months. After each session you get a written recap of wins, challenges, and commitments. At 90 days you retake the scorecard so we can measure what changed.
What results do clients see?
Clients have raised more than $100M, and Sempre Health and Sendlane each raised more than $30M during their engagements. Heap made 300+ hires in six months with 90% retention, and Sendlane tripled retention. On average, clients see a 10 to 20x return on what they put into coaching.
What do we work on?
We work on whatever is slowing the company down at the top: hiring and keeping great people, getting your leadership team to run as an extension of you, delegating, co-founder dynamics, board and investor relationships, and the story you tell when you raise. We pick one priority at kickoff and work it until it moves.
Who is Eric Weiss?
Eric Weiss is a former founder and CTO who built the PlayStation Network and spent nearly three years inside OpenAI coaching the platform engineering leaders who took GPT-3 and ChatGPT to millions of users. He has coached more than 75 founders and technical leaders over 15 years, and Prismatic ranks him in the top 1% of executive coaches.
How do I know I'm ready for a coach?
You're ready when the company has outgrown you doing the work yourself. You're still in the weeds on technical decisions, you can't land or keep the talent you need, your leadership team waits on you, and the same problems keep coming back. Founders who do the homework between sessions get the most out of it.
Do you coach co-founders together?
Yes. Along with one-on-one coaching, I coach co-founder pairs and C-suite teams together, and I facilitate strategic offsites. Co-founder conflict and a leadership team that doesn't run as one are problems I work on often.
Do you coach remotely?
Yes. My clients are spread across the US, Canada, and Europe, so sessions run over video.
How do we get started?
Book a Clarity Call. We'll talk through where you're stuck and whether working together makes sense. If it does, you'll take the CEO Scorecard before kickoff, so our first session starts with real data on where you lead well and where you're stuck.
Let's Scale Together
Ready to work together?
Book a 30-minute Clarity Call. We talk through where you’re stuck, and you leave knowing whether coaching is the right lever. Or email eric@chaostoclarity.io.