Hello and welcome to another edition of Founder to Founder 👋

Earlier this month, we got the whole company together in San Diego for our annual OpenPhone offsite.

As we got back home I thought that it was the best offsite we’ve had, by far.

Of course, there’s always room for improvement, but we’ve come a long way.

As a remote-first company, spending time in-person as a team is critical. It’s one of the most high-ROI things we do as a team, in my opinion.

And considering we’ve recently crossed the 120-employee mark, lots of planning went into it this time around.

So I thought we’d share how we planned a 120+ person offsite with fellow founders (or anyone tasked with getting their remote team together).

I asked our VP of People Rachel Kleban, who led the planning process, to join me in sharing the behind-the-scenes.

Whether you’re hosting 10 teammates or 100, I hope learning about our process will help you make your offsites something everyone looks forward to (and leaves them excited for the next).

📒 DEEP DIVE

How we planned our company offsite for 120 people

An inside look at the OpenPhone 2025 offsite

A little history on company offsites at OpenPhone

This year was our 5th company offsite at OpenPhone. We did it by building on our experience from previous years. Here’s a little history to get you up to speed:

• 2019: Our first offsite in Lake Tahoe, CA. We were 8 people at the time. 6 attended. We rented an Airbnb and spent the time working on the roadmap + boating. Simpler times.

• 2020: COVID kept us home 😷

• 2021: 22/34 teammates joined us in San Diego, CA. Even though this technically was our second offsite, it felt like the first (2019 felt more like a team get-together), and it was epic. We even made a nice video to capture the memories.

• 2022: Cancun, Mexico, as a team of 67. We had 87 people at OpenPhone at the time, which means 77% attendance. We organized everything in-house, which sounds crazy in retrospect.

• 2023: Offsite was postponed from late 2023 to early 2024 for multiple reasons, but mainly our capacity to plan it.

• 2024: Bourne, TX (outside of San Antonio) as a team of 83 (123 people at OpenPhone at the time). Our first “grown up” offsite. Here’s a nice recap of it.

• 2025: San Marcos, CA (outside of San Diego) as a team of 99 (out of 127 total). It was a record-breaking 78% attendance and our best offsite yet, IMO.

Inside our best company offsite yet

While drafting this post, I really wanted to make sure I thought of everything we did to plan this offsite. So, I reached out to some of my founder friends to ask what they'd want to know.

So, let me take you step by step through how we planned our 2025 offsite.

Goals for the offsite

When we started planning our offsite in September (yes, that’s 6 months lead time), I remember talking to our VP of People, Rachel Kleban, about what we wanted to accomplish. Here are the goals that came up.

Connecting with our mission & vision

This year, we felt that our mission and vision set before weren’t representing our journey as a company and needed a refresh. So, we embarked on a journey that left us with a revised vision and mission. We wanted to use the company offsite as the opportunity to make sure everyone can connect with our mission & vision in a meaningful way.

Rachel put it very well:

Now, you might be thinking that this is all a fancy way of saying that we had a presentation on our new mission & vision.

And yes, we did :)

But we went a step further. Instead of reiterating what they are, we broke out into groups and had every group share:

• Their perspective on what makes our vision so exciting in 2025 & beyond

• Their ideas for how we might be able to help our customers make their customers feel valued through the product

What could’ve been just a regular presentation turned into an interactive session that would’ve not been the same if we were all on Zoom.

Connecting with our customers

At last year’s offsite, I shared several customer stories with the team. I wanted to get folks closer to our customers and to talk about the amazing businesses using OpenPhone. We even put together a nice video to go with it.

While it was great, I'd always dreamt of having our customers join us. And this year, that dream came true. 🙂

So as soon as we started thinking about our 2025 offsite, Rachel involved Peter Roessler, our Director of User Research, who already spends lots of time with our customers to help make sure we build the right products for them.

But instead of just having some of our customers there for a happy hour or a fireside chat, Peter put together a design thinking workshop so we could design solutions together with our customers.

It was incredible.

Not only the opportunity to interview and get candid feedback from customers on what we’re building IRL, but actually having a chance to brainstorm solutions to their problems as a group and present them something back was very special.

One table came up with a mockup that could get shipped soon. Just saying ;)

Helping folks connect with their team & company as a whole

Because we’re fully remote, our annual offsite is often the only chance that many folks have of meeting people from different teams, and we want to maximize the quantity and quality of those interactions.

People want help meeting folks they wouldn’t normally cross paths with. One of the most consistent pieces of feedback we got from our team: don’t leave it up to chance.

Actually assigning groups for dinners, activities, and discussions makes it way easier for people to mix in a meaningful way.

And structure matters. In big group Q&As, most people won’t talk. But in small groups, they usually do. The goal is to set everything up so that everyone feels comfortable participating.

Creating content together

One of the challenges of being fully-remote is that you can’t easily create content involving your team.

So, we thought of the company offsite as the ultimate content creation event.

We’ve recorded customer stories, internal interviews, product content and even did a teaser for a new feature over our Awards Ceremony/Dinner.

Being around our teammates and customers brought a level of excitement and openness that doesn’t exist when filming content not in person (through Zoom, Riverside, etc).

The customers were able to get to know everyone, understand how we operate, and really get excited about our product and the future of OpenPhone before they were interviewed.

Also, being in person means that we get more faces involved in content. What other companies can say they had Support/Sales/Engineering excited to be in a skit while playing flag football?

Logistics

Now, with goals and intentions out of the way, there were many key logistics decisions we made in putting the offsite together.

Planning team

We collaborated with The Offsite Co for the second year in a row.

Up until 2024, we planned offsites fully in-house. It worked, to a degree, but now I realize everything we were missing. Maybe not for a <50 event, but anything with 50+ attendees is a whole new level of complexity.

Here are the things they handled for us:

• Venue selection, negotiation, and communication

• Transportation planning

• Fun activities like golfing, go-kart racing, and painting classes

This allowed our internal team to focus on:

• Setting a vision for the agenda and flow

• Designing rich and meaningful content

• Being present with our colleagues

The logistics are a lot of work, and there are people who can do it in their sleep. Let them, so you can focus on the content and the experience from a culture and company perspective.

Location

This is perhaps one of the biggest factors in offsite planning—and the one you can’t walk back on.

Here are some things we based our decision on for 2025 in San Diego:

1. Proximity to a major international airport. With plenty of teammates traveling from outside of the US, it was important to be close to an airport with lots of connections. San Diego checked that box.

2. Ability to combine airport proximity with the ability to find a venue that’s nice and secluded enough from all the hustle & bustle. Interestingly, we've generally opted for places that (for lack of a better word) forced people to be together. But we have gotten some feedback that people travel really far and would like more proximity to be able to explore, which is something we will continue to try to find the right balance on.

3. Weather. Many Northern options got disqualified because of the weather. Our fiscal year starts in February, so we find March to be a good time for the offsite, so we aim to go to a place that’s warm.

4. Venue. Location can also depend on the kinds of venues you’re able to get in that location. Does it have good meeting spaces, plenty of places for people to gather, amenities, and activities?

5. Cost. Can we put together a great experience for our team within a reasonable budget? I’ll share more on the budget in a bit. 🙂

We shortlisted to 2 options and let the team vote. San Diego won ☀️

Duration

This year, we went for 2 full days + 2 half-days (for travel). This was similar to what we did last year.

Some of the feedback we got this year indicated that it was a little too short, so that’s something we’ll consider for 2026.

On the positive side, we made the most out of every hour we had together.

Budget

Our offsite cost ~$3k per person, and we had 99 people attend. You can do the math from there. 🙂

Unless your team is a lot more colocated, it would be hard to do something < $2k per person, considering the cost of flights/accommodation/food/activities.

For some of our offsites, we booked flights using Brex points to help offset the cost.

I also think there’s some thoughtfulness that can go into making sure the spend matches your size/stage and you’re not overdoing it.

Agenda

Putting together the agenda for the annual offsite is high stakes, but there’s a little more wiggle room and flexibility you can have with it.

Once we got some of the bigger blocks figured out—2 key company sessions (including one featuring our customers), 3 dinners, and 1 special “choose your own adventure” activity—there wasn’t that much time left to play with.

We knew teams wanted time to work together:

• Sales were making calls and following up with prospects

• Support was crushing tickets in the queue and talking about process improvement

• Marketing & Product worked on a launch (Stay tuned for that)😉

We also knew there was some downtime needed for people to recharge after activities and before dinner.

And we couldn’t skip our signature Company Awards ceremony recognizing winners of values awards, fun awards (eg - “the person most likely to be on mute”), and promotions.

OpenPhone is also known to have a very strong karaoke game...

Results & ROI

Team satisfaction for the 2025 offsite came in at 4.7/5, up from 4.6 in 2024—which, if you ask me, is pretty great.

But beyond the numbers, the real ROI is in the moments that stuck with me:

• Watching people from different teams get way too competitive during go-karting. 🏎️

• Hearing a childhood story from a teammate on the bus on the way to dinner. This story would never come up on Zoom.

• Seeing an Engineer light up while talking to a customer, realizing they’re working on something that actually matters.

• Watching people absolutely go for it on the karaoke stage—some crushing it, others (me) making up for it with enthusiasm.

You can’t really quantify these moments. But it’s why these offsites matter.

The wrap-up

If there’s one thing I’ve realized after 5 offsites, it’s that these things don’t magically “work” just because you booked a nice venue or brought everyone together.

It’s all in the details: the prep, the goals, the intention behind each session, the way you nudge people to connect. That’s what makes the difference between a “fun few days” and something that actually moves the company forward.

This year felt like the first time we got that balance right. Maybe not perfect, but better than ever.

So if you’re planning an offsite, no matter how big of a team you have, I hope this gave you a few ideas.

And if you’ve done something that worked well, I’d love to hear about it as we begin thinking about 2026.

Thanks for reading,

Daryna

ps - massive thanks and kudos to our People team (Rachel, Tiffany, Olivia) and the team at The Offsite Co for putting together this incredible event. Thanks to our customers who joined us in person. To OpenPholks - both those who joined and who couldn’t come - thank you 💜

pps - want to join us at the 2026 offsite? We’re hiring ;) openphone.com/careers