Ion Feldman, CTO at Rightway, has learned to love one thing about scaling a company from a kitchen table to nearly 1,000 employees: his job completely changes every six months. In this episode, Ion shares what it means to lead engineering when the role refuses to stay still—from writing code in the early days to building product, security, and data teams, and now shaping AI infrastructure. He explains how to stay hands-on without micromanaging, why he deliberately works himself out of roles by hiring people better than him, and how to preserve startup urgency inside a heavily regulated industry. If you’ve ever wondered how CTOs balance technical depth with business strategy while keeping their team fast and focused, this conversation delivers.

Key Takeaways

Treat change as part of the job.

Ion’s leadership mindset centers on adapting to wherever the company needs him most—product, security, data, or AI. He views change as an opportunity to grow, not a disruption to avoid.

Hire yourself out of the role.

He dives deep into an area, builds it from scratch, then brings in experts who can take it to the next level. Once the right leadership is in place, he steps back completely and lets them own it.

Hands-on time creates credibility.

Ion makes sure every leader spends time building. Each quarter, his team takes a week off from meetings and Slack to focus on creating something new. It keeps them close to the work and sharp as technical leaders.

AI adoption needs clarity and focus.

Rightway avoids vague “use AI” goals by targeting clear use cases like unit test generation and onboarding to codebases. Sharing examples and results drives faster adoption than leaving teams to figure it out alone.

Fail fast and move forward.

Ion builds space for experimentation but expects quick recognition of failure. The goal is not to avoid mistakes but to learn, pivot, and evolve faster.

Timestamped Highlights

[02:10 ] The zero to one mindset – Why Ion thrives on constant reinvention and the satisfaction of building new functions from the ground up.

[06:41 ] Three pillars of AI strategy – How Rightway is transforming work through AI enablement, applied projects, and bold experiments.

[08:26 ] Delegating by design – How going deep before handing off creates clarity and trust across teams.

[15:42 ] Skills that matter later – Ion reflects on learning public speaking and business fluency after years of technical focus.

[17:48 ] Creating space for risk – How to give your team agency to take on big challenges and fail fast without fear.

[21:22 ] Preparing successors – Why the best leaders hire people who will replace them and rethink everything they built.

What Stuck With Us

"I don't know, maybe I just get bored easily. I think a lot of people could view it as a burden and they want to stay in their lane of expertise, but I see it as an opportunity to learn and change things up."

Pro Tips for Tech Leaders

Take a week each quarter to build something with zero meetings or Slack. It reconnects you and your team with what you actually love about engineering.

Wait to hire senior leadership until the need is undeniable. The role becomes meaningful, and you’ll attract higher caliber talent.

Give your engineers specific AI examples and let them experiment from there. Adoption follows clarity, not mandates.