Outschool 2025 Retreat
We’re so excited for this year’s offsite!
LOCATION: LUMA Hotel, San Francisco, CA
OFFSITE DATES:
Monday, May 12: Team Arrivals & Welcome Party
Tuesday, May 13: Team Sessions & Dinner
Wednesday, May 14: Team Sessions, Group Outing & Bonding
Thursday, May 15: Team Departures
More information and full itinerary provided below!
Location 🏨
Homebase: Luma Hotel San Francisco
ITINERARY
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8:30 AM – 6:30 PM: ✈️ Travel
3:00 PM: 🏨 Check-In Starts @ Luma Hotel (100 Channel St, San Francisco, CA 94158)
When you check-in at Luma Hotel, be sure to find our Happied representatives in the lobby for your shirt and name tag.
If you are driving to the retreat, please plan to park with the hotel valet. The cost will be billed to Outschool.
6:30 PM – 9:30 PM: 🎉 Welcome Party @ Cavaña (Hotel Rooftop)
Join fellow Outschoolers and our board members at the Luma Hotel rooftop restaurant, Cavaña, for an evening of food, drinks, and fun.
Enjoy a meal and beverages on this lovely rooftop overlooking SF. Tasty bites include:
SPANISH RICE CROQUETTES
BEEF EMPANADAS
QUESADILLAS
CRISPY SHRIMP
AND MORE!
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8:30 AM – 9:30 AM: 🍽️ Breakfast @ Gather Space
Coffee and food will be provided in the main area Gather. Feel free to bring the food into Willet Ballroom. Notecards will be scattered at the tables to spark discussion on our current education system.
9:30 AM – 9:45 AM: 👋 Welcome & Kick-Off with Amir @ Willet Ballroom
A welcome message from Amir.
9:45 AM – 10:45 AM: 🌟 Product Vision with Francesco @ Willet Ballroom
Francesco will lead a discussion on where our product stands today, the key trends shaping our space, and the strategic direction we’re heading toward.
10:45 AM – 11:00 AM: ☕ Social Time with fellow Outschoolers
Delphina will introduce our social challenge to help bring even more fun into spending time getting to know each other.
**Egret is also reserved first come first serve for 1-1 coffee chats!
11:00 AM – 12:00 PM: 🧠 Alternative Education Panel with Outschool Users @ Willet Ballroom
We've invited some local users that are focused on homeschooling, microschooling, unschooling, and everything in between and use Outschool as part of that journey. Cassie will host the conversation and Q&A. Come prepared with questions!
12:00 PM – 12:30 PM: ☕ Break
Free time - grab a coffee, take a break, chat with co-workers.
**Egret is also reserved first come first serve for 1-1 coffee chats!
12:30 PM – 1:30 PM: 🍽️Lunch @ Gather Space
Enjoy a Greek Island Buffet (greek salad, lemon chicken, gyro, eggplant, spanikopita) that will be servied in Gather. You can eat in Gather or back in Willet.
1:30 PM – 3:00 PM: 💡 Design Sprint Session with Shu + Outschool Users @ Willet Ballroom
Join the Design Team for a real-time collaboration session with Outschool customers! We will break up into groups and have a blue sky ideation session drafting off of our 2 year product strategy. Bring your knowledge and sharpie skills to help create the future. No drawing skill required. Bonus: Our Outschool Users will be joining us!
3:00 PM – 3:30 PM: ☕ Snacks & Fireside Chat with Amir @ Willet Ballroom
Grab a snack from Gather, then join us for a fireside chat with Amir as he shares reflections, insights, and a look ahead. Bring your curiosity and questions for an open conversation.
3:30 PM – 5:00 PM: 🧭 Eliad Group Session with Aaron Eden & Eric Vallone @ Willet Ballroom
Explore the values and practices that define alternative and self-directed education in a hands-on session with Eliad Group co-founders Aaron Eden and Eric Vallone. As longtime friends of Outschool and global leaders in building transformative learning environments, Aaron and Eric will guide us through a series of activities that connect personal learning experiences to system-level possibilities. Together, we’ll surface insights to inform how we work, the products we build, and how we support the families we serve.
5:00 PM – 5:15 PM: 🙌 Daily Values OUTshouts @ Willet Ballroom
Wrap up the day by giving a shoutout to the teammates who brought our values and leadership principles to life during today’s sessions. Come ready to celebrate the impact you saw and be recognized for the role you played in making today a success.
5:15 PM – 6:30 PM: 🧘 Break/Team time
Unwind from the day, sneak in a quick nap, call home to family members, and re-charge for the evening's festivities!
6:30 PM – 9:30 PM: ⛳ Dinner & Fun @ SPARK Social SF (8min walk from LUMA - 601 Mission Bay Boulevard North, San Francisco, CA 94158)
Meet in the hotel lobby at 6:20pm if you want to walk as a group to the venue.
SPARK Social SF is a food truck park, beer & sangria garden located in the heart of San Francisco’s Mission Bay neighborhood.
Outschool will have a reserved outdoor covered lounge area. Each employee will receive a $36 meal card to be used on an appetizer, meal and dessert. We will also have access to unlimited beer, wine, sangria and soft drinks. Mini golf is reserved - let’s par-tee!
Top rated food trucks include:
Domingo's International Kitchen Fusion (Mexican-International Fusion)
Los Kuyas (Mexican-Filipino Fusion)
Atlas Bites (Mediterranean)
Burger Littles (American)
Gyros on Wheels (Greek)
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*Plan to wear your Outschool shirt or bring it along for group photos later in the day!
8:00 AM - 8:30 AM: ✨ Womxn ERG Coffee Walk & Talk @ Twyne Coffee Bar
Meet at Twyne Coffee Bar in the lobby at 8am to grab a coffee. The the group will head over to Mission Creek Park for a walk along the water. Check out the #womxn slack channel for more details!
8:30 AM – 9:30 AM: 🍽️ Breakfast @ Gather Space
Coffee and food will be provided in the Gather Space. Today's discussion activity will be channeling your inner educator and creating your own Outschool class - rise & DESIGN!
9:30 AM – 9:45 AM: 👋 Welcome to Day 2 with Amir and Xueyan @ Willet Ballroom
Reflections and kick-off with Amir and Xueyan
9:45 AM – 11:15 AM: 📲 Persona Spotlight Challenge with Erica @ Willet Ballroom
Competition time! We'll break into teams to internalize updated personas and messaging through quick, creative, social media-style video ads that capture audience attention, highlight empathy, and integrate new messaging seamlessly. Prizes will be awarded for Best Aligned to Persona, Most Creative, and People's Choice.
11:15 AM – 11:45 PM: ☕ Break
Enjoy some free time to answer emails, mingle with co-workers, sneak in a walk or grab a coffee. The time is yours!
**Egret is also reserved first come first serve for 1-1 coffee chats!
11:45 AM – 12:30 PM: 💭 OutThink - Brains Welcome with Daniel @ Willet Ballroom
Daniel will lead us through a brainstorm on topics such as: Value adds for Memberships, AI Features to add to Outschool, Moonshots, and more!
12:30 PM – 1:30 PM: 🍽️ Lunch @ Gather Space
Enjoy a Pacific Rim Feast (Thai salad, chicken teriyaki, citrus salmon, spring rolls, chow mein) to either enjoy in Gather or take back into Willet.
1:30 PM – 2:30 PM: 🌱 Outschool.org with Alex, Zach, Kris, Justin @ Willet Ballroom
Get to know the mission behind Outschool.org! The team will share a brief history, highlight key initiatives from the past year, and showcase how they're expanding access to learning through community-driven impact.
2:30PM: Grab a quick snack to-go @ Gather before the team scavenger hunt!
2:30 PM – 5:00 PM: 🔍 Team Scavenger Hunt
Ready to hit the streets? Join us for a fast-paced, fun-filled scavenger hunt through San Francisco’s SOMA neighborhood, led by The Hunt. You’ll team up, solve clues, and race to uncover hidden gems.
**We'll meet back in the Willet Ballroom to celebrate our winners with a champagne toast!5:00 PM – 5:30 PM: ✨ Wrap-Up & Wins
We’ll cap off the day by announcing challenge winners, celebrating standout moments, and sharing a few closing thoughts before heading to our final dinner together.
5:30 PM – 6:30 PM: 🧘 Break/Team Time
Unwind from the day, sneak in a quick nap, call home to family members, and re-charge for the evening's festivities!
6:30 PM – 9:30 PM: 🍽️ Farewell Dinner & Retreat Recap @ ATwater Tavern (7 min walk from LUMA - 295 Terry A Francois Blvd, San Francisco, CA 94158)
Meet in the hotel lobby at 6:20pm if you want to walk as a group to the restuarant.
Located along the historic SF waterfront, ATwater Tavern offers panoramic views of the San Francisco Bay, Oracle Park, Bay Bridge and more.
Outschool will have a reserved party room. A buffet style dinner will be served including a salad, entrees and sides. We'll say our goodbyes and have one last chance to give praise to our fellow Outschoolers.
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8:30 AM – 9:30 AM: 🍽️ Breakfast To-Go @ Gather
There will be an easy breakfast to-go provided in the Gather space. Coffee included!
9:30 AM – 7:30 PM: ✈️ Travel
Hotel check-out is at 12pm. A space will be available for you to store your luggage if you have a later flight.
Important Contacts ☎️
Primary On-site Coordinator: Dana Frund
dana@happied.co
+1-724-433-7398
On-site Coordinator: Jennifer Lopez-Roper
+1-305-494-3493
Outschool Contact: SJ Kwapien
+1-610-235-9998
Slack Group 💬
Be on the lookout for #outschool-on-the-bay-2025 for updates throughout the offsite, and feel free to ask any questions in there as well.
Dress Code 🧦
Monday, May 12 – Travel Casual
Whether you're catching a flight, hopping in a rideshare, or rolling in from across town - come in whatever makes you feel relaxed and ready to start the week.Tuesday, May 13 – Come As You Are
No dress code today! Just come comfy, casual, and authentically you.Wednesday, May 14 – Team Spirit + Fancy(ish) Night
During the day: Plan to wear your Outschool shirt or bring it along for group photos later in the day! (you’ll receive your shirt at check-in!). Please also wear comfy shoes for our team scavenger hunt in the afternoon.
In the evening: Go big, go casual, or land somewhere in between. If dressing up sounds fun, this is your moment! If not, jeans and a tee are equally welcome. Just show up feeling like yourself.
Photos 📸
Add your retreat photos to the communal Google folder!