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🏞️ Retreats

Quarterly in-person retreats are crucial for Flexpa. Every three months, the entire team meets together in person for a three-day retreat that serves as a cornerstone of our company culture. During these retreats, we engage in various activities, including team-building exercises, strategic discussions on our go-to-market and product strategies, and retroing past OKRs (Objectives and Key Results) while finalizing the OKRs for the upcoming quarter. These retreats are instrumental in fostering collaboration, aligning our goals, and propelling our mission forward.

First and foremost, the retreats provide us with team-building opportunities that we otherwise miss out on as a remote team. Being able to connect with each other on a personal level in the same room is invaluable in building stronger ties. We strengthen our relationships, enhance collaboration skills, provide critical process feedback, and build camaraderie. These activities create a cohesive and motivated workforce, which is vital for achieving our mission of refactoring healthcare.

Additionally, the retreats offer us a dedicated space for strategic discussions. With our entire team present, we can tap into the wealth of diverse perspectives from different departments. During Flexpa retreats, we engage in brainstorming sessions, workshops, and in-depth conversations to refine our go-to-market and product strategies. By collectively reviewing our past performance, analyzing market trends, and leveraging our collective intelligence, we can make informed decisions and adapt our approaches. This collaborative approach ensures that our strategies are robust and aligned with our mission.

Lastly, the retreats are a great way to finalize our OKRs for the next quarter. Through comprehensive discussions and input from the entire team, we define ambitious objectives and key results that propel us forward. These goals guide our efforts, helping us measure progress and stay focused on our mission to refactor healthcare. We also vote as a team on the location of the next retreat.

As a remote-first organization, our quarterly in-person retreats are the heartbeat of our operational and cultural framework. Through these retreats, we cultivate a strong sense of camaraderie, nurture collaboration, provide the space for strategic discussions, and align on ambitious objectives to drive our mission of refactoring healthcare. The retreats play an integral role in propelling our company forward, ensuring that we remain focused, motivated, and united in transforming the healthcare landscape forever.


Preparation for a Flexpa Retreat happens at the start of each quarter. As soon as the location for the next retreat is known, we start searching for a place to stay and host the retreat.

Logistics planning

Timeline Housing accommodations must have:

  • 1 room per person (utilizing Airbnb, Vrbo, or other short-term rental platform)
  • Multiple bathrooms
  • A large dining table that seats 10+ people
  • Decent reviews, no red flags
  • Fast wifi speed and reliability
  • Proximity to activities and resources (grocery stores, etc)

By mid-quarter (6 weeks in), we aim to have the following completed:

  1. T minus 9 weeks
    • Housing accommodations booked
    • Team has flights purchased
    • List of attendees finalized
  2. T minus 6 weeks
    • Meals / catering orders submitted and confirmed

Housing accommodations must have:

  • 1 room per person (utilizing Airbnb, Vrbo, or other short-term rental platform)
  • Multiple bathrooms
  • A large dining table that seats 10+ people
  • Decent reviews, no red flags
  • Fast wifi speed and reliability
  • Proximity to activities and resources (grocery stores, etc)

Agenda planning

We want the future leaders at Flexpa to have the opportunity to practice leading and running a quarterly retreat. Quarterly retreats are a high value time for the team to reflect on the past quarter and plan ahead. They are also of high value in building rapport, spending time with each other, and having fun!


You are responsible for:

  1. Planning the retreat activities and their sequence.
  2. Planning conversations should bias towards being in public channels (#quarterly)
  3. Meetings regarding planning should have Fred from Fireflies invited so that others on the team can review if interested, and it can be a resource for future planners.
  4. Planning the social activities and dinner reservations
  5. research + ask the team for ideas too!

You are not responsible for:

  1. Booking lodging or travel
  2. Planning / ordering lunches
  3. Running every single activity - though you should each run at least one


  1. T minus 5 weeks
    • Handoff meeting from previous retreat planning owners
    • Review previous retreat formats from retreat folder
    • Review retreat feedback from latest retreat
    • Begin brainstorming agenda and evening activities
    • Kick off OKR planning with founders
  2. T minus 3 weeks
    • Have drafted an agenda based on product priorities
    • Begin getting feedback on agenda and finding interested activity leaders
    • Gather buy-in from the team for extra curricular activities
  3. T minus 2 weeks
    • Ensure activity owners feel prepared, understand the activity they are running, and its details
    • Review retreat agenda with AA & CC for feedback, logistics, and any expenses
    • Make bookings/reservations for extra curricular activities
    • Have rough draft of the following quarter’s OKRs
  4. T minus 1 week
    • Post retreat agenda for team in #quarterly to review and ask questions.
    • Ensure any pre-work is outlined so team has the time to digest and complete them before the retreat
    • Do you need any supplies to be ordered before the retreat?

Agenda considerations

  • Overall itinerary

    • Retreat activities fit into Tuesday, Wednesday, and Thursday days
    • Monday is mostly a travel day, but organizing a team dinner for those who arrive before dinner is important for Day 1 camaraderie
    • Friday is a travel/personal day for everyone
    • Game time itinerary management will always be the case. People need breaks, things go longer, shorter, etc
  • What activities should be included?

    • What are the highest leverage things for us to do in person?
    • What are the biggest priorities for next quarter?
    • What was the feedback from the last quarter?
    • What will set us up for the next quarter or further the best?
    • What products/problems/opportunities can we brainstorm to get the juices flowing early?
  • Activities that need to be present in some form:

    • Tuesday
    • Kickoff as retreat opening (Owner: Co-founders)
    • Start/Stop/Continue style retro [soon after kickoff]
    • (Optional) JD updates if new Flexpals have joined, or roles have changed, (Team/ Andrew Arruda)
    • Any day
    • Product roadmap presentation (Owner: Brendan Keeler)
    • Review and score previous quarter OKRs (Owner: Andrew Arruda)
    • Discuss upcoming quarter’s OKRs (Owner: Andrew Arruda)
    • Thursday
    • Discuss upcoming quarter’s OKRs (Owner: Andrew Arruda)
    • Update Flexpa GPS (Owner: Team / Andrew Arruda)
    • Pick next retreat organizers
    • Vote for next quarter’s retreat location
    • Retreat closing (Owner: Founders)

Remember, throughtout agenda planning, the previous planners and the co-founders are always at your disposal to bounce ideas around!

The week following the retreat, we aim to have the following completed: * The decision as to which Flexpal/s will be leading the next retreat * Feedback on each Flexpal has been shared around how they showed up to the retreat


Be sure to book your travel as soon as possible. We recommend booking flights at least 6 weeks in advance to get the best rates.

When booking your flights, please keep the following in mind:

  • Arrival: Please plan to arrive on Monday evening before the retreat starts on Tuesday morning.
  • Departure: Please plan to depart after Thursday evening when the retreat ends. Many Flexpals choose to leave Friday morning but sometimes a Thursday evening departure is necessary and the team will understand.
  • Expensing: Please book economy class flights book economy class flights to an airport close to the retreat. You will be reimbursed for your flights after you submit your receipt on your next pay cycle.