How to organize a retreat for a large, remote team

If you’re in the planning stages of a retreat, you know handling all the logistical hurdles around the event can feel like a decathlon — especially if you’re putting together a retreat where folks are flying in from multiple cities. 

Last year, we organized a retreat for 34 employees. Since then, our 100% remote team size has nearly tripled, so we knew that planning this year’s retreat would be more challenging. As a team scales, so do the logistics around planning an international retreat. 

If you’re in the same position, we thought we’d let you in on our lessons and learnings from planning this year’s trip.

Timeline for planning the retreat

We started planning long before our company retreat occurred in September 2022. Our Office Manager Tiffany Olsen and I began the process in December 2021 by chatting with the leadership team to get feedback on the last retreat and potential locations. OpenPhone’s Co-Founder, Mahyar Raissi, shared with us that the retreat is our one time to meet most of our growing team for the first time and really create that bond so we can do great things together.

Ten months may seem like ages to plan a retreat, but we ended up needing every minute of that time. We’ll get into the details of our decision-making shortly, but for now, here’s how the timing shook out:

  • 10 months out: Brainstormed locations with leadership.
  • 7 months out: Had employees vote for their favorite of three country options.
  • 6 months out: Signed a contract with the resort.
  • 4 months out: Began booking flights and had employees organize any necessary visas.
  • 2 months out: Booked excursions and finalized our itinerary.
  • 1 month out: Confirmed headcount, submitted a final attendee list to the hotel, and finalized our itinerary.
  • 2 weeks out: Sent employees confirmation details and letters that explained the details of the retreat (in case they needed documentation during their travels).
  • 1 week out: Made a few minor tweaks to the itinerary.

If you’re planning your own corporate retreat, I’d recommend starting as early as possible, because issues will inevitably arise that will impact your planning. In our case, two significant events came up that stretched out our timelines somewhat:

  1. We’d originally been considering several European countries as potential retreat locations, but as the conflict in Ukraine escalated, we decided to consider a few more options outside of Europe.
  2. Due to the pandemic, a lot of visa documentation was delayed, requiring five to six months to process instead of the usual two to three.

If we had to go back and do anything differently, the biggest lesson for me here was to provide better communication with the team about potential visa requirements to be aware of, depending on what country they are traveling from. For example, a number of flights had a connecting stop in the US, which may have required a transit visa. 

Although having more time to plan for these things would have been helpful, we were still able to curate and execute a successful retreat for over 66 employees.

How we selected our dates and location

When it came to nailing down the “where” and “when” of our retreat, we started by brainstorming a few options with leadership.

Choosing a location might seem like a decision that boils down to price and convenience. However, when planning a trip for a global team, there are a number of factors you need to keep in mind. We looked at:

  • Safety
  • Accessibility
  • Potential travel visas our employees would need
  • Pricing, including taxes and exchange rates

Once we narrowed our options down to three countries, we opened up the decision to the entire company, allowing employees to vote on their preferred destination.

Letting employees vote for their country and date choices

Based on our chats with leadership, we had our retreat options down to Portugal, Brazil, and Greece. In late March, we sent out a Google Form survey company-wide, letting employees pick their top choice of retreat location and preferred retreat dates.

Google form asking for retreat data preferences for OpenPhone retreat

Unfortunately, just a few days after we’d sent out the survey, we decided we should include several more non-European options due to the growing uncertainty around the conflict in Ukraine. We sent out a second survey to employees, this time adding in the options of Mexico and the Dominican Republic.

How to organize a retreat: OpenPhone retreat survey in Google Forms

Once the votes were in, Mexico in September emerged as the clear winner — which meant we could get down to planning the finer details.

Working with a destination management company

Once we knew we’d be visiting Mexico, we connected with Destination Mexico, a destination management company (DMC). As a local organization, they were able to help us plan, find, and book services across Mexico. They also had helpful connections to local transportation, event companies, and hotels across the country.

DMCs use several different pricing structures. Some will charge a per-person fee for airport transfers and excursions. Some will charge a flat fee per event. Others will simply add on a percentage of the total cost they’re given by suppliers.

In our case, working with Destination Mexico didn’t cost anything extra. Destination Mexico paired us with a dedicated staff member early on who helped us book local transportation, hotel rooms, and excursions at no additional cost. We were also able to ship team swag to their office to hold before the retreat instead of having to use the resort, which saved us from paying any holding fees.

Working with Destination Mexico DMC turned out to be a godsend throughout the entire planning process. Their response times and level of support were amazing throughout. A DMC staff member even joined us at the retreat to ensure everything ran smoothly.

Deciding on a hotel

Originally, we planned to look for resorts in Tulum. However, Destination Mexico warned us there was major construction in the city, which would significantly impact traffic and our schedule. So, instead, we started looking for resorts in Riviera Maya.

Some criteria we looked at included:

  • Could the hotel’s restaurants accommodate employees’ allergies and dietary restrictions?
  • Was the property accessible?
  • Was the resort kid-friendly? (Our team members’ families were welcome to join them on the retreat, so this was a must.)
  • Were service dogs allowed on the property?
  • Was there a fee for booking fewer rooms than we’d originally negotiated in our contract?

When you’re coordinating travel for a large group, there are tons of details that you need to keep in mind. As new questions and requirements came up during the process, I jotted them down.

How to organize a retreat: Retreat checklist in Notion

These can be a checklist I can use for any future retreats (you’re welcome, future Rossel).

How to organize a retreat: Site of the Paradisus Playa Del Carmen for OpenPhone's retreat

After connecting with a few hotels, we found Paradisus Playa del Carmen fit our needs perfectly. Booking our hotel and knowing our final cost of accommodation also meant we could start to finalize our budget.

How we created a budget for the retreat

We had begun our budget planning with a rough idea of how much we could expect to pay for this year’s trip based on our San Diego retreat the year before. Factoring in last year’s costs and 111 people attending our Playa del Carmen retreat (including 66 OpenPholks and 46 family members that RSVPed), we set an initial target of $160,000.

In the end, our costs ran a little higher. There were a few reasons for that:

  • We needed audio-video (AV) setups in the hotel conference rooms we used since we wanted to stream our organization-wide meeting to OpenPholks who couldn’t make it to the retreat. 
  • We hired a photographer to join us on the retreat.
  • Booking international flights for 66 employees is simply expensive, and that’s hard to get around.

In the end, we paid close to $250,000 for the seven-day retreat. That included:

  • All-inclusive hotel bookings
  • Airfare
  • Covering the one-day excursion and food throughout the trip for OpenPholks’ spouses and children that attended
  • Ground transportation
  • Retreat swag
  • A company-wide, team-building activity hosted by a third party
  • AV setups in hotel conference rooms
  • Hiring a photographer

Where we saved on costs

When you’re organizing a trip at scale, small savings per person add up quickly. We knew there were a few opportunities to decrease our budget.

Booking an all-inclusive hotel

For our retreat last year in San Diego, we booked a hotel, restaurants, multiple excursions, and shuttles all separately. For a 34-person team, that was doable. With 66 employees RSVPing to this year’s retreat, however, every separate item we booked increased our budget significantly.

With that in mind, we decided to opt for an all-inclusive hotel. That meant all drinks and meals were included. We didn’t need to worry about shuttling our teams somewhere else for dinner. This cut down our meal, drinks, and transportation costs quite a bit.

Booking a single company-wide excursion

Initially, we planned to let team members choose two excursions from a menu of six à la carte options.

How to organize a retreat: Asking for activity preferences in Typeform

However, this approach drove our projected costs up significantly since it required us to book multiple excursions, each with their own transportation.

How to organize a retreat: Team photo of OpenPhone at Chichen Itza.

In the end, we decided to host one epic day excursion to Chichen Itza and a cenote, which reduced our costs significantly. We also made sure to leave plenty of free time in our itinerary so teams or individuals could organize their own activities if they wanted to.

Using points to save on flights

We used Brex as our spend management company. We had over a million Brex points — which we promptly used to book team members’ flights. 

Using our Brex points helped bring down our airfare costs significantly. After moving to Ramp, we’ll instead earn cashback we can reinvest next year. 

Flying a photographer down with us 

The final line item on our budget was organizing a production team to film the retreat.

We did this for our last retreat, and the results were phenomenal. A photographer and videography team captured several genuine, organic moments that took place among our team, and having that footage has been really helpful in recruiting and hiring.

Rather than trying to describe what OpenPhone’s culture is like to candidates, I can just send them a video from a previous retreat:

For this trip, we originally looked into hiring a local photographer and videographer in Mexico, but that would have ended up costing us over $10,000. 

In the end, we ended up contacting the photographer we hired for last year’s retreat to come down to Mexico with us. He snapped everyone’s headshots and took a ton of great photos throughout the trip. Our in-house video lead and social team also filmed throughout the retreat to help us cut down costs and capture all the memorable moments from our retreat. 

Price per person

Of course, many companies that organize a company retreat won’t opt to use a photographer or require additional AV support like we did. All in all, if we exclude those costs, our total would be closer to $230,000 — leaving the total cost per person at $2,072.

How we organized the retreat itinerary

Based on Mahyar and the rest of the leadership team’s vision for the trip, we wanted to ensure that the retreat was streamlined, relaxed, and the perfect balance of work and play for everyone involved.


Booking team members’ flights to and from Mexico took up a significant chunk of our time. There were only two of us doing it, and we worked hard to balance both convenience and cost. 

Next time, we’ll get an entire team to help out with this task or outsource it to an external company.

Ground transportation

We equipped everyone with a virtual corporate card from Ramp ahead of time with a pre-approved travel budget of $200. This covered travel to and from their own local airports along with meals on travel days. 

Destination Mexico organized several shuttles between the Cancun airport and our hotel on both our arrival and departure dates. When OpenPholks arrived in Cancun, they simply looked for a shuttle driver holding up an OpenPhone sign. All we had to do was send them everyone’s flight details. It was great to be able to outsource that task.

Balancing work and fun

Our retreat was a week long, and we wanted to be intentional about balancing work and fun during that time. 

This was the first time many OpenPholks would meet their coworkers, so our primary goal was to let team members bond. We knew if we provided a relaxing, fun environment that encouraged connection and spontaneous activities (like our board game nights which are always a huge hit), we’d all end up doing stronger, more collaborative work for the rest of the year.

Of course, we also carved out some time for high-impact, energizing work. This included an in-person All Hands (our company-wide meeting), a couple of team meetings, and a creative pitch competition. But we left plenty of room in the schedule for activities, dinners, and flexible plans.

Here’s how our schedule broke down:

  • Day 1: Arrival + private buffet dinner.
  • Day 2: 2 hours booked for team meetings + free time in the afternoon/evening.
  • Day 3: Half-day dedicated to the Pitch Competition + free time in the afternoon/evening.
  • Day 4: Company-wide excursion to Chichen Itza.
  • Day 5: Headshots, company-wide team activity, + free afternoon/evening.
  • Day 6: Team activities in the morning, All Hands meeting, + private buffet dinner.
  • Day 7: Departure.

In the end, we found this was the perfect blend of work and relaxation. Everyone left feeling far more connected to their coworkers. We’ve also received feedback that people feel a stronger sense of belonging with their team and our company. 

Organizing a pitch competition for cross-functional collaboration

One of our teams’ favorite activities during our San Diego retreat last year was our hackathon, where we brought teams together cross-functionally to solve unique OpenPhone problems.

How to organize a retreat: OpenPhone pitchathon

This year, we changed things up slightly and instead ran a pitch competition, where teams would come together to brainstorm and present potential solutions to improve OpenPhone. Teams could cook up ideas for potential features, bug fixes, marketing initiatives, or processes — nothing was off the table.

Ahead of the retreat, employees started coming up with ideas and organizing into teams, so they had a group to join during the retreat’s pitch competition.

How to organize a retreat: OpenPhone pitchathon projects

Teams had a day to perfect their pitches and then presented to the wider company during the company All Hands.

How we communicated around the retreat

As the size of a group grows, so does the potential for miscommunication. We kept information accessible and free-flowing for this retreat through four main channels.

1. Gathering information through Typeform

To book flights and ensure everyone’s needs were met, we needed to collect plenty of details from our guests. We did so by sharing a Typeform form with everyone at the company, in which we collected:

  • Guests’ names as shown on their passports
  • Passport details
  • Window, aisle, and middle seat preferences for flights
  • Known traveler and frequent flyer numbers
  • Preferred flight information
  • How many family members they planned to bring along (if any)
  • Any allergies or dietary restrictions we should be aware of
  • Any health conditions we should know about
  • All guests’ T-shirt sizes (for swag)
  • RSVPs to group outings
  • Emergency contacts
How to organize a retreat: OpenPhone RSVP Typeform for the retreat

This made it super easy for us to pull up everyone’s information as we booked accommodation, transportation, and excursions. We were able to send details to Destination Mexico at the click of a button.

2. Sharing updates during our All Hands meetings

At OpenPhone, we have a company-wide All Hands meeting every two weeks, where we connect and catch up on updates from across the company. Leading up to the retreat, we made sure to share retreat updates and reminders at every All Hands.

3. Creating a wiki in Notion

To centralize information on the retreat, we created a page in Notion, which acts as our company knowledge hub. Teams could find all the info they needed about the retreat on the page, including the schedule, transportation and visa information, and more. 

How to organize a retreat: retreat wiki providing vital information for attendants

We erred on the side of overcommunication in Notion. We also had:

  • links to any Typeform forms we needed the team to complete
  • our retreat expense policy
  •  suggestions on what to pack
  •  helpful information on the Cancun airport and hotel
How to organize a retreat: OpenPhone retreat itinerary in Mexico

Plus we included a PDF of the resort map and retreat schedule our team could download and access when they weren’t on WiFi.

4. Communicating updates in Slack

Finally, we shared live updates and answered questions in our #retreat channel in Slack. Providing folks with an open forum meant if someone asked a question once, everyone else could see the answer to it — helping us cut back on the number of repeated questions or requests.

It also let us keep OpenPholks in the loop throughout our trip, whether they were in team meetings, lounging by the pool, or off on an excursion. For instance, after we heard that several people wanted more time to complete their pitches for the competition, we altered our schedule on-site:

Communicating an update to the retreat itinerary in Slack

The pitchathon was a huge enough hit that we’ll be building new processes and features from every presentation. Stay tuned!

Organize your first retreat

Clearly organizing a corporate retreat for a large group isn’t an easy (or quick!) task. It took our People team the better part of a year to plan, and it’s the largest project we worked on in 2022.

However, having the right processes in place can make the journey more affordable and far less stressful. Next year, if our team doubles or triples in size, we’ll be able to use the same checklists, forms, and tools to make our planning easier.

If you have any questions about our planning process, leave a comment below. And if you’d like to join us on our next trip — check out our Careers page!

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