The path to $1B is being written right now.
AI companies are scaling faster than the old playbooks can keep up. The next ones are being written in real time by this generation of operators.
We're bringing together 50 of NYC's most ambitious leaders across Product, Engineering, Sales, and Growth from the fastest-growing B2B AI companies for a one-day retreat at Cedar Lakes Estate in upstate New York to connect, learn, and share.
Off-the-record stories and lessons from operators turned founders
Peer-led, unconference- style tactical talks. Candid conversations about what’s working, what’s breaking, and what they're trying next
Enjoy a beautiful day at Cedar Lakes Estate and make memories with some of the brightest minds in B2B AI
Featuring operators from
Co-Founder
Founded and scaled BetterCloud to over 2500 customers and a $750M exit to Vista Equity Partners
Co-Founder & CTO
Grew ARR from $10M to $50M in 6 months, recently raised Series B at $550M valuation
Bus pick up from Union Square to Cedar Lakes Estate
Arrival, breakfast, & welcome from Work-Bench
Keynote from David Politis, Co-Founder of BetterCloud
Fireside Chat with Aayush Shah, Co-Founder & CTO of Blacksmith
Lunch
Scavenger Hunt
Unconference Breakout Session 1
Cool Ass Marketing
Alex Lindahl (Clay) & Billy Gallagher (Crosby)
Wrangling the Slop Cannon: Technical Excellence Through Chaos
Chet Mancini (Norm) & Harry Ledley (Ramp)
Pricing: Usage-Based or Outcome-Based?
Rodrigo Alves Vieira (Cogent) & Danny Chesley (Work-Bench)
Talent Wars: Hiring, Firing and Everything in Between
Evan Lee (EliseAI) & Jeffrey Xu (Fleet)
Investing off the Clock: Angel Checks & Other Bets
Kevin Wong (Fleet) & Dylan Reider (Qualitate)
Unconference Breakout Session 2
Commitment Issues: Getting Enterprise to Sign
Tejas Sathian (Rogo) & Shane Ogunnaike (SpaceXAI)
Moat vs. Model: Place Your Bets
Zach Fry (Arthur) & Danny Chesley (Work-Bench)
Thinking about Thinking: The Mental Models that are Key in the Startup Journey
Proby Shandilya (Work-Bench) & Jon Lehr (Work-Bench)
"Asking for a Friend": I Want to Start a Company :)
Jess Lin (Work-Bench) & Earl Lee (Hightouch)
Equity 101 with Cooley
Unconference Breakout Session 3
Growth Playbooks: Let's Jam
Arjun Naskar (Baseten) & Stan Rymkiewicz (Default)
Agent Engineer / GTM Engineer / FDE: New Role, Who Dis?
Rohan Sinha (Profound) & Daniel Johnson (Clay)
Well, That Didn't Work: Lessons from the Flops
Rez Khan (Abridge) & Deepanker Saxena (Socure)
Managing Teams & Life in the Age of 996
Laura Vang (Decagon) & Rose Kozar (Courier Health)
AWS Marketplace
Cushman & Wakefield Office Hours
Happy Hour + Dinner
Bus back to Union Square
Tuesday, October 13th, 2026 · Cedar Lakes Estate
Presented with support from
