

PickleTalk: Enterprise Operators × AI Founders (Seed to Series A)
12 Scrappy Founders - outdoor endurance community for founders, operators & investors in the Bay Area.
What is this?
Founders and enterprise operators usually meet in the worst possible setting: a cold email, a demo call, a pilot that dies in procurement.
We try to fix that.
Pickleball first (beginner friendly!), because it's hard to stay in sales mode with someone you just lost a game to.
Then dinner/drinks, 12 people, 1 topic: what makes a large company buy from an AI startup and what kills the deal.
Who is it for?
Execs and operators from mid-market and enterprise companies
Founders (seed to Series A) selling to mid-market/enterprises
12 seats total. Everyone vetted.
Where & When?
Thursday, Oct 1. Treasure Island, SF
4:00 to 5:30 | Pickleball
6:00 to 8:00 | Dinner
Partners:
Arceus is an AI-native legal service for venture-backed startups, backed by Greycroft, Craft Ventures, Conviction and South Park Commons.
From everyday NDAs to the MSA, Arceus reviews, negotiates and drafts contracts in hours with flat pricing agreed before work starts.