CTO Network: Inside Helloprint's Rebuild

​You've added agents around the edges. A workflow here, a function there. Now you're looking at your team and asking the question nobody wants to say out loud: how many of these jobs is AI actually going to do?

​At Helloprint, the answer was most of them.

​They went from 300+ people to roughly 40% of that. Not through restructuring, not through a hiring freeze, not because of the market. Because AI is doing the work. Agents in the core flows. Legacy systems retired, not refactored. The org chart collapsed inward.

​This is a working session, not a story. 30+ CTOs and founding engineers in a room with the person who ran the rebuild. No slides. No demo. Bring your hardest question.

​Back in Rotterdam, during Upstream Festival

​We're taking CTO Network back to Rotterdam, hosted in Helloprint's home city during Upstream Festival week. One of the most ambitious AI rebuilds in Dutch tech, in the city that's quietly becoming the country's most interesting scale-up ecosystem. We're proud to be there, and proud to do it with Up!Rotterdam in the room.

​Opening deep dive with Michael Heerkens, CIO at Helloprint (and former CTO)

​Michael led the technical rebuild from the CTO seat and now runs it as CIO, meaning he's lived both sides: the architecture decisions and the operating reality on the other end of them. He'll walk through what was actually built, what broke, and what it cost.

​Format

​Breakfast. Caffeine. Open Q&A from the start. Michael answers what the room asks, including the questions a vendor wouldn't.

​Why it matters

​Most CTOs are still framing AI as productivity. Helloprint reframed it as substitution and ran the experiment to its end state. If you're trying to figure out what an AI-first org actually looks like under the hood (architecture, evals, on-call, cost, the org chart on the other side), this is the room.

​RSVP to join. Limited seats. Invitation only.

​Hosted in partnership with Helloprint and Up!Rotterdam, during Upstream Festival.