Go-to-market is where most AI companies stall. On one side, enterprise AI is broken — founders build features no one asked for, and corporates burn millions on pilots that never ship. On the other, pricing is the #1 unsolved question, most technical founders openly don't know how to sell, and every category is saturated. Two distinct problems — selling into corporates, and the founder-side of GTM — with one outcome: commercial traction.
From first meeting to signed contract.
Enterprise AI is broken on both sides, and most pilots die before production. These sessions are about how corporates actually buy — and how to be the vendor that makes it through procurement, security, and into production.
Why 95% of enterprise AI pilots fail
The patterns that kill pilots before production — and the questions to ask a corporate before you sign, so you don't spend six months building toward a deal that was never going to close.
Procurement, decoded
How corporates actually buy — security review, legal, budget owners, and the internal politics that decide deals. Map the real buying process, not the org chart.
Reverse pitches
We flip the room: corporates state what they actually want to buy, and founders respond. Demand, said out loud — no cold outreach required.
Inside a real corporate AI transformation
A CxO walks through an actual enterprise rollout — what shipped, what stalled, and what they wish vendors had understood going in.
Vendor risk, handled
SOC 2, ISO 27001, GDPR and the EU AI Act — what enterprise buyers require, what's worth doing early, and how to clear security review without an enterprise-sized team.
From first price to first ten customers.
The founder-side problem, whoever you're selling to: pricing, positioning, founder-led sales, the first ten customers, and US market entry.
Pricing AI products
Usage, subscription, or hybrid — pricing is the #1 unsolved question in AI, where token costs and margins shift under you. Frameworks and real numbers from founders who've repriced and lived to tell it.
Founder-led sales
Technical founders openly don't know how to sell — and no one can close the first deals but you. The motions, scripts and habits that turn engineers into closers.
Positioning in a saturated category
Every AI category is crowded, so positioning matters more than the demo. How to carve a slice you can own — and a story buyers repeat for you.
The first 10 customers
The unscalable, hand-to-hand playbook for landing the first ten — who to target, how to get the meeting, and how to turn design partners into references.
Your first sales hire
When to hire, who to hire (and who not to), and how to onboard them — without handing over a sales motion you haven't proven yourself first.
US market entry
Most founders in the Netherlands and Europe need US customers before US capital. Landing the first US logos and building a beachhead — anchored on the Rise San Francisco trip: Salesforce, OpenAI, Anthropic, and the operators doing it now.
The product is the easy part.
Now go to market
like you mean it.
Selling into corporates, or stuck on pricing and your first US customers? Let's talk.
Get in touch · bob@techleap.community →