Tuesday, May 19

8:00 AM - 9:00 AM Arrivals

7:00 PM - 10:00 PM Welcome Reception + Dinner

Kick things off by getting to know the other senior AI transformation leaders in the room. We’ll have food, drinks, and plenty of space to mingle. Come as you are and start making connections before the main event begins.

Wednesday, May 20

7:30 AM - 8:30 AM Breakfast

Breakfast and casual conversation to start the day.

8:30 AM - 9:30 AM Welcome Address + Attendee Intros

Kick off the day with a welcome from Zapier’s Director of AI Transformation, Phil. We’ll ground ourselves in the goals of the retreat, introduce the group you’ll be learning alongside, and walk through how the day is designed to spark honest, high-impact conversation and hands on learning.

9:30 AM - 10:00 AM An Inside Look at AI at Zapier

A behind-the-scenes look from Zapier's Director of AI Transformation at how AI is transforming our work internally, from individual workflows to broader organizational change. You’ll hear real examples, practical use cases, and a clear framework for moving from experimenting with AI to using it more strategically.

10:00 AM - 10:30 AM AI Transformation Framework Workshop

You’ll work through a guided, team-level AI fluency reflection, mapping where your group honestly stands across the dimensions that drive real adoption, so you leave with a clearer picture of what’s working, what’s not, and where to focus next to move the outcomes you own.

10:30 AM - 10:45 AM Break

10:45 AM - 12:00 PM AI Transformation Framework Roundtables

Break out into small groups to discuss themes that have emerged from the AI Transformation Framework Workshop.

12:00 PM - 1:30 PM. Lunch + Activity

Enjoy a relaxed lunch with your fellow attendees. Chat, recharge, and connect in a different setting. We encourage you to sit with someone new and keep the conversations going from the morning sessions.

Before lunch, Sea State Farms will lead us in an (optional) oyster shucking experience.

1:30 PM - 3:00 PM Build-a-long with the Director of AI Transformation at Zapier

Before you start building, we’ll walk through the concepts, use cases, and approach behind the hands-on session. This is the bridge between inspiration and action, designed to help you see what’s possible and feel ready to build something relevant to your own work. Then, you’ll work through a practical use case with support from the Zapier team, building an AI-powered workflow you can learn from, adapt, and bring back to your team.

3:00 PM - 3:45 PM Build-a-long Roundtables

Next up, you’ll join one of five roundtable discussions based on themes that emerged from the build-a-long.

3:45 PM - 4:00 PM Recap

We’ll take a few minutes to reflect on what surprised you and what themes stuck with you, sharing any “aha” moments with the peers around you.

4:00 PM - 5:00 PM Break & Refresh

Time to freshen up, check email, or decompress before dinner.

5:00 PM - 5:30 PM Travel to Offsite Dinner

Meet at 5:00 PM  to board the shuttles for our offsite dinner. We’ll depart shortly after, so be sure to arrive on time. If you’re not sure where to go, just ask a member of the Zapier team.

5:30 PM - 9:30 PM Offsite Dinner + Experience at Atlantic Fish & Chophouse in Edgartown

Enjoy Cape Cod from the water on a charter boat on the way to a private dinner dockside in Edgartown

Thursday, May 21

8:00 AM - 9:00 AM Breakfast + Wrap Up

Start your morning with breakfast and casual conversation. At 8:15 AM, we’ll reflect on what stuck with you and what you’re taking home.

9:00 AM - 9:30 AM Send Off

As we close out the retreat, we’ll share a few final takeaways and parting thoughts. You’ll have time to connect with anyone you haven’t yet, exchange contact info, and ease into the rest of your day. Whether you’re wrapping up a conversation or taking a quiet moment to reflect, we’re so glad you were here.

9:30 AM - 11:30 AM Bike the Shining Sea Bikeway

Experience the wonderful coastal views, restaurants, and ice cream shops of Cape Cod along the Shining Sea Bikeway! Starting on the AutoCamp property and winding along this incredible path that leads you through some of the best sights on the Cape!

11:30 AM - 12:30 PM Grab and Go Lunch

Grab-and-go lunches will be available ahead of departures.

12:00 PM Departures