Eric Weiss, The CTO Coach
I help CTOs scale up without burning out.
I built the PlayStation Network, ran defense systems for aircraft carriers at Raytheon, led an enterprise-scale data science and machine learning team at Qualcomm, and spent nearly three years inside OpenAI taking their AI models from the lab into production. I have coached more than 75 technical founders and executives over the past decade. I help CTOs overcome their biggest growing pain: Leading people.
Scaling tech is easy. Scaling people is hard.
The Work
I work with CTOs, CEOs, and CPOs at every stage of the company. From the first 10 engineers to the post-Series B org starting to crack under its own weight. The technical leaders who scale well are the ones who engineer the business as deliberately as they engineer the product.
Hiring frameworks, team structure, roadmap discipline, OKRs, executive presence, board dynamics, and more. That’s the CTO Operating System I provide.
Before Coaching
I spent two decades as the engineer, then the leader, before I was ever the coach.
At Sony I helped build and launch the PlayStation Network, which is where I learned what happens to an architecture and an organization when millions of people show up at once. At Raytheon I ran software for defense systems deployed on aircraft carriers, where a bad release is not something you roll back. At Qualcomm I led the data science and engineering team behind a $7.8 billion IP licensing business, and found out how much of a technical leader’s job is persuasion inside a company that does not speak your language.
Then I spent nearly three years inside OpenAI, where I helped operationalize GPT-3 as it went from a research artifact to a platform under real load. I watched an org double, and double again, and I saw exactly which parts of a company break first when the product outruns the team.
That is the sequence I coach from. I have filled nearly every seat myself, from software engineer to data scientist to CTO, so when you describe your quarter I am not translating it.
Over the past decade I have coached more than 75 technical founders and executives, including leaders at OpenAI, Heap, Sendlane, Tealium, Dialogue, Sempre Health, Reach Technologies, Pathpoint, ecoATM, and OneUp Sales. I am based in San Diego and coach leaders across the US, Canada, and Europe.
Beyond the Coaching Room
I am the President of the Design Forward Alliance and VP of Startup San Diego. I invest in early-stage companies, advise VC firms, and publish the Chaos to Clarity Podcast for technical founders navigating the hard parts of scale.
The Books
I wrote two books because I cannot sit across from every leader who needs the conversation.
Above the Chaos is a Stoic playbook for founders who became the bottleneck. Eight principles, nine exercises, and a Leadership Philosophy Canvas for holding your composure when everything routes through you.
Growth by Design is a founder’s operating system for earning product-market fit. Ten pillars and a PMF Scorecard, for teams that need fit to be a discipline instead of a wish.
Both come with a free eBook and a workbook, and both are the same material I run with leaders in executive coaching.
Why It Works
Most executive coaches have never run an engineering org. They’re therapists or HR people. They just don’t get what we’re going through.
I know what a 3am production incident feels like, what it costs to lose a senior engineer that kept your team together, and what it takes to earn the trust of a C-suite that doesn’t understand what your team does. The frameworks I’ve built come from 20 years of doing the work, not studying it.
Let's Scale Together
Book a free strategy call or email eric@chaostoclarity.io.