AI Native GTM : Design a winning pilot program

Su Belagodu

AI Governance Strategist

Turn AI Pilots into Signed, Adopted Contracts

Your AI pilot went well. The demo landed. The champion loved it. Then it went quiet.

Landing a pilot is the easy part now. Buyers have budgets to experiment and say yes to trials quickly. Turning that trial into a signed contract, and then into a product people actually use, is where AI founders lose. Nobody agreed on what success looked like. The person who ran the pilot can’t sign. Security shows up in month three. Legal starts redlining after the pilot ends. And the first time the model gets something wrong, nobody has an answer.

Every one of these failures starts before kickoff. So does the fix.

In this live working session, you’ll design a pilot built to convert, map the seven people who can stop your deal, write the terms that turn day 60 into a signature, and build your answer to the question every AI review board asks: what happens when your AI is wrong? You’ll also see where AI speeds up the work once the judgment is made.

Bring a live deal. You’ll fill in a worksheet for it as we go, and leave with five tools and a plan you can use this week.

What you’ll learn

This session teaches the framework that separates teams shipping trustworthy AI from teams shipping AI that gets abandoned midway.

  • Use the seven-field Pilot Canvas to agree on the baseline, success metrics and production price before kickoff.

  • Map the seven stakeholders behind a production yes, know when to reach each one, and the question that finds them.

  • Write the seven terms that make day 60 a signature, and run proof and paperwork on one 90-day timeline

Workshop agenda

  • Why AI pilots stall after the demo

    We open with a real pilot that went quiet: free, unscoped, no baseline. Spot which of its red flags are already in your own deals.

  • Live exercise: Build your Pilot Canvas

    Open the worksheet and fill in the three fields that decide conversion for your live deal: the baseline, the success metrics and the decision.

Learn directly from Su

Su Belagodu

Su Belagodu

AI Native CPO, Creator of HITL proprietary model; Ethical AI advisor

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Who this workshop is for

  • Executive & Governance Teams Your AI is live. But is it defensible? Score your oversight maturity and close the gap

  • Product & Technical Teams You built the AI. Now lets build the guardrails. Use the HHI™ to measure if your human review loops are working.

  • AI Transformation Leaders Rolling out AI across the org? The HITL maturity model gives your transformation a governance backbone

What's included

Su Belagodu

Live sessions

Learn directly from Su Belagodu in a real-time, interactive format.

Community of peers

Stay accountable and share insights with like-minded professionals.

Post-Workshop Office Hours

A 30-minute group office hours session 3–4 weeks after the workshop to answer questions, review progress, and troubleshoot implementation challenges.

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Private cohort

Run a cohort for your org

A dedicated cohort with a custom schedule and curriculum, tailored to your team.

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$275

USD

Nov 16
·

12–1:30pm EST

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