Past the Pilot
Heads of AI on what it took to move a model from demo to production.
ep_05 · The eval that caught what the demo hid
Heads of AI and CTOs get a dozen AI pitches a week. Almost nobody asks them what works in production. Host that conversation. We book the technical buyers you want as design partners, run the show and hand you 30 minutes of product signal from each.
AI startup lead generation works differently when buyers are pitched daily. We invite CTOs, heads of AI and technical buyers to talk about what they have shipped, and the conversation surfaces what they need next.
At seed and Series A, the guest list doubles as your design partner list: people with the problem now and the authority to say yes to a pilot.
Question two, "Where does that plan feel fragile?", shows where current models break for this buyer. Question three names the pilots that died last year. Your roadmap and your pipeline come out of the same 30 minutes.
How the program runs →Technical buyers have seen every AI demo. Few have had a peer ask how they evaluate, ship and govern models.
Engineers trade eval setups and failure stories with other builders. An invitation to talk shop gets a yes a demo never would.
Each interview maps a use case, a failure mode and a budget line. Eighteen of them is a roadmap review with the people who would pay for it.
A 12-person startup is a risky vendor. A founder who has hosted 20 heads of AI is a known name before procurement asks.
| the host asks | what an AI founder learns |
|---|---|
| "Walk me through the next 12 months. What has to go right?" | Which AI use cases are funded, and by when |
| "Where does that plan feel fragile?" | Where current models or data break for them |
| "What did you try last year that you wouldn't try again?" | Dead pilots, incumbent vendors, spend appetite |
| "If you could fix one thing before Q4, which would it be?" | Your wedge: the first paid pilot |
| "When a decision like that comes up, whose phone rings first?" | Who from security, legal and procurement joins the deal |
Fictional. Each gives a technical buyer a reason to talk: a hard problem solved, or one still open.
Heads of AI on what it took to move a model from demo to production.
ep_05 · The eval that caught what the demo hid
Support leaders on putting AI agents in front of real customers.
ep_09 · Handing a third of the queue to an agent
Security, legal and IT leaders on how an AI tool gets cleared to buy.
ep_02 · What a CISO reads first in an AI vendor questionnaire
Have 20 names you'd want as design partners? List their titles in the application and bring the names to the fit call. A producer checks guest supply in your market before the call.
A seed-stage devtools company on Pilot, hosting CTOs. Six weeks to the first paid pilot.
seed · devtools · pilot
design partners signed from 18 episodes.
I got 30 minutes with CTOs who'd ignored six of our sales emails.
Same engine, different guest list: host investors instead of pitching them. A pre-seed AI founder hosted 27 investors in 7 weeks and filled the round.
"We're pre-product. What would we even talk about?"
Their work, not your product. The show covers how teams evaluate, ship and govern AI. Nothing gets demoed on the record.
"Our buyers are too technical for a podcast."
Technical buyers turn down pitches, not peers. The brief goes deep on architecture and evals, and your technical co-founder can host.
"We can't spare founder time before the round."
About two hours a week: 30 minutes per guest. Research, invitations, pre-interviews, editing and CRM notes run without you. Raising now? Point the same hours at investors.
At seed you have one ICP and one question: will these buyers pay. Pilot runs a single segment at 4–6 recorded guests a month.
Proving the channel with one ICP.
+ $1,500 setup, credited on upgrade within 90 days
Bring the people you'd most want as design partners to the fit call. You get guest supply, expected acceptances and a pipeline range before you commit.