The most advanced AI operating model in this episode wasn't built from a strategy deck. It was built from desperation — and that turns out to be the best design constraint available.Miloš Djurdjevic is co-CEO and co-founder of heyData, a Berlin-based compliance platform that scaled to several thousand customers, closed a $16.5M Series A, and kept the team at 60 people — on purpose — while running more than 14 AI agents in marketing, near-fully automated customer support, and more agents than headco...
The most advanced AI operating model in this episode wasn't built from a strategy deck. It was built from desperation — and that turns out to be the best design constraint available.
Miloš Djurdjevic is co-CEO and co-founder of heyData, a Berlin-based compliance platform that scaled to several thousand customers, closed a $16.5M Series A, and kept the team at 60 people — on purpose — while running more than 14 AI agents in marketing, near-fully automated customer support, and more agents than headcount in revenue operations.
When heyData was growing fastest before its Series A, the team didn't have a choice. There weren't enough people to handle the customer volume, the compliance questions, or the marketing load. So they started automating — not because it was fashionable, but because the alternative was falling behind. Customer success built a knowledge base from years of accumulated compliance Q&A, then layered AI agents on top until response times dropped from several days to under an hour. Marketing restructured an entire role around managing and iterating on agents rather than producing output directly. Revenue ops rebuilt itself around agents first, humans second. The thread running through all of it: the team was too stretched to be afraid of AI. Every person saw it as capacity relief, not a threat.
The secondary conversation in this episode is one Roland flags as increasingly important: whether BI as a function becomes obsolete in an AI-first company. Miloš's answer is direct — at heyData, they depend on it more than ever, not less. As AI takes on more of the analytical work, the job of the BI team shifts from producing reports to ensuring the data underneath those reports is structured, clean, and trustworthy. AI is only as useful as the data that feeds it, and that data hygiene work still requires dedicated human judgment. It's not a disappearing role — it's a fundamentally different one.
Roland observes that the heyData story confirms something he sees consistently in his advisory work: durable AI adoption almost never starts with a mandate. It starts with a constraint. The founders who have the most sophisticated AI operations today are, disproportionately, the ones who had no other option a year or two ago. Understanding that dynamic — and what it takes to replicate the results without the underlying pressure — is the open question this episode raises.
Key Moments:
00:00 — Why a compliance company became an AI operations lab before AI was fashionable
01:57 — The deliberate case for staying at 60 people after a $16.5M raise — and what every new hire actually costs
05:10 — How heyData built its first AI system in customer success: from a knowledge base of compliance Q&A to sub-hour response times
08:10 — Top-down vs. bottom-up AI adoption — and the cross-functional task force model that made both work together
10:31 — Why heyData's team never feared AI would cost them their jobs — and the specific context that made that true
14:16 — Is BI becoming obsolete in an AI-first company? Miloš's honest answer, and what the role actually becomes
17:21 — Raising a $16.5M Series A in a market that demands AI nativeness — what was harder than expected, and what wasn't
19:31 — 14 AI agents in a 6-person marketing team: how the role of "AI lead" got created and what that person actually does
22:52 — The personal backstory: growing up between Bavaria and Serbia, two doctors for parents, and what persistence looks like when it's inherited
If building an AI-augmented operating model — rather than just adopting AI tools — is the challenge in front of your team right now, a Breakthrough Workshop with Midstage is the fastest way to find the right leverage point. Book at breakthrough.midstage.ac
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