
Step away, think bigger, and connect deeper.
The CEO role is a high-stakes, high-pressure game. It’s easy to get stuck in the day-to-day grind, making decisions in isolation. That’s why we created the Pavilion CEO Retreat—an intimate, high-trust gathering designed for proven B2B tech leaders who want to level up, unplug, and connect with peers who actually get it.
This isn’t a conference. It’s a mastermind, a recharge, and a catalyst.
When & Where: July 31 – August 3 at Baron’s Cove, Sag Harbor, NY
Who's invited: Open to ten B2B tech Founders & CEOs doing $5M-$50M in revenue on a first come, first serve basis.
Mastermind sessions with Sam Jacobs & top operators.
No fluff, just real solutions to real CEO challenges.
Create connections through a curated experience.
Join high-performing B2B tech CEOs who have similar challenges, experiences, and goals.
Exclusive, high-end experiences.
A private yacht sail, sunset beach picnic, and salon-style dinner designed for deep conversations and real relationships.

What to expect from this retreat.
- Exclusive insights from CEOs who have raised capital, exited, and scaled profitably.
- A curated peer network—the kind you call when you’re making a make-or-break decision.
- A clearer mind and sharper strategy by taking a step back and building connections.
This experience is valued at $5,000 per attendee, but all you have to do is: book your flight, hotel, and a few meals. We take care of the rest.
Our agenda
Day 1 |
Guests Arrival 5:00 PM - 6:00 PM: Optional Welcome Happy Hour at Baron’s Cove Lounge |
Day 2 |
10:00 AM - 2:00 PM: Masterminds on CEO Challenges (Lunch will be served) Evening: Dinner (Location TBD) |
Day 3 |
10:00 AM - 2:00 PM: Yacht Excursion (Lunch will be served) 5:00 PM - 7:00 PM: Beach Picnic (More details to come) Times subject to change. |
Day 4 |
Closing remarks and reflections Departure Day |

Logistics
Hotel: Baron’s Cove, Sag Harbor, NY
Closest Airport: East Hampton Airport
You're responsible for:
- Airfare, hotel, transportation, and meals outside of scheduled events.
- We’ve secured a room block at Baron’s Cove at a rate of $1,279++ per night. Hotel rooms are limited — once our block sells out, you’ll need to book independently at prevailing rates.
After registration, our team will reach out to confirm room details with you.
Cancellations after June 30, 2025, will result in full charges, including room and tax.
Special lodging opportunity for Women Founders.
In partnership with Wednesday Women, we’re offering a limited, sponsored lodging option for a small group of high-growth women founders attending the retreat.
If you're a woman founder with $5M+ ARR, you may qualify to stay at the stunning beach house of Alina Vandenberghe, CEO of Chili Piper. Her house is located just minutes from the retreat hotel.
Note: Availability is limited to only 4 spots.
Register for our retreat today.
There are a limited amount of spots available for this Hampton's Retreat. If you are interested in attending, please register below.
Are you a woman founder leading a tech company that meets the requirements above? If so, click the button above to learn more about our off-site accommodation opportunity with CEO of ChiliPiper, Alina Vandenberghe.