Decagon was moving up-market fast, selling into some of the world's largest regulated enterprises. A major prospect gave us a month to prove a young AI company could meet enterprise expectations — and rescue a launch after an incumbent vendor stumbled.
I wrote the technical roadmap, persuaded leadership to stand up an eight-person engineering team, and started an AI red-teaming program. I coached the customer on how to threat-model AI, ran product pentesting, negotiated the DPAs and enterprise contracts, shaped legal strategy, prepped GTM leaders, and led the external audit.
We won the account. It opened a regulated market that's since become a major part of the business. I slept, eventually.