Offsites are an integral part of Tremendous culture. Twice per year, we spend a week in a fun location to celebrate, bond, and work (a bit).

Attendance is highly encouraged. Offsites are a good time, and the bonds you build in person have a lasting impact on how you collaborate with your teammates.

Note: we also do subteam offsites focused on work. This doc is just about our semiannual all-company offsites.


  • Held in the second halves of Q1 and Q3
  • 4-5 nights, Mon through Fri/Sat


  • We stay in a boutique hotel
  • Everyone has their own room
  • Tremendous folks only, no +1s


  • It’s a mix of socializing, activities, presentations & work
  • Presentations happen on Tuesday & Wednesday
  • Team-specific work happens on Thursday
  • Work-related activities are mandatory; everything else is optional


Team bonding

The primary purpose is to get to know your teammates on a personal level. Remote work is great, but there’s no substitute for in-person socializing. Offsites are our chance to connect in a way that we can’t online.

Many teammates will tell you how they felt much closer to their coworkers after their first offsite. Offsites transform your working relationships by building increased levels of connection and trust, and that carries over to the virtual world when we all return home.

Team bonding happens in a few ways:

  • Organically. Folks will hang out in common spaces, go for coffee, play games, etc. None of this is preplanned. We think this is the best way to get to know each other because it’s most natural.
  • Company events. These include happy hours, meals, and team bonding activities. It’s assumed you’ll attend these, but if you need to drop out for work or personal reasons, that’s okay.
  • Group tourist activities. Walking tours, cooking classes, etc. These are optional and require advance signup.


Offsites are a great opportunity to align on important company initiatives. There are two hours of presentations during each of the first two full days of the offsite. Everyone is expected to show up bright-eyed and bushy-tailed so don’t party too hard the nights before.

The presentations will typically cover whatever we think is most pertinent for everyone to know. Depending on your role, some information may already be familiar, but for many, it will be new. We try to get a variety of presenters from many departments to give a flavor of what’s happening across the company.

Team-specific work

On Thursday morning, we split into subteams to do work. Team leaders decide how to best use the time, and are responsible for planning the agenda.


Offsites are the time to celebrate our wins. Let’s enjoy the ride.

Working at offsites

It’s expected you’ll work less during the week to accommodate group activities and socializing. With your manager’s input, you’re responsible for determining what the appropriate workload is. Make sure to communicate with teammates and external parties if they will be impacted.

Depending on your role, there may be certain responsibilities that you can’t or shouldn’t delay. For example, external-facing teams like Sales, Success, and Support need to take calls and respond to inquiries. That might mean you’ll be unable to attend certain activities, unfortunately.

What’s the vibe?

If you’ve already been to an offsite, you know. For new folks, here’s what to expect:

  • People are friendly and welcoming. We’ve done a darn good job of recruiting smart and personable folks.
  • Mornings and evenings are usually busy with company stuff. Afternoons are free for work, chilling, and exploring the city.
  • Random groups will do ad hoc activities like coffee, museums, etc. You’re free and encouraged to join any group or activity that interests you. They often get announced on Slack.
  • Those who party, party responsibly. We’ve yet to have a problem unless you count the time Kapil spent 4k on bottle service.
  • When it’s work time, it’s work time. Show up ready to contribute and ask questions.
  • It’s chill but is a work event at all times. Read our code of conduct.


How do we choose where to hold the offsite?

We look at a few cities in parallel with specific venues in mind. We consider convenience, weather, price, walkability, neighborhood, vibe, event space, and more.

Then, via a highly scientific method, we choose the one with the highest awesomeness-to-suffering ratio, where suffering measures travel times, jet lag, costs, etc. We’re willing to endure more pain for better locations.

The best way to influence the selection of future destinations is to provide thoughtful feedback after each offsite. We review feedback closely and consider it in future planning.

When will we announce the next offsite?

Immediately after we have a signed contract with the hotel. Our goal is to provide at least 6 months advance notice.

Can you travel around the offsite?

A number of folks have traveled immediately before or after offsites to visit nearby cities and countries. We want to continue allowing this, but we have to be mindful of the total number of people doing it. We’re unwilling to sacrifice multiple weeks of productivity for a single offsite.

If you’d like to take time off, you should submit a request to your manager well in advance. Your manager may say no, especially if other teammates also request time off. It’s best not to book additional travel until you’ve received permission.

Managers – it is your responsibility to make sure that your team is appropriately staffed around the offsite. You will likely have to decline some vacation requests.

You can also, of course, travel if you maintain your normal work schedule. Like, actually though – you will be held to this.

As for expensing, Tremendous will cover the cost up to what the route without additional travel would have been. Any incremental cost is yours.

If I can’t attend, is there a way to participate remotely?

We want to make offsites inclusive even for folks who can’t attend. That means we’ll record or live broadcast all presentations and loop you in via Zoom for team-specific meetings.

The social events are tougher, unfortunately. To protect our reputations, we won’t be streaming karaoke.

Why no +1s?

They’re lovely. We know. But they’re not invited for a few reasons:

  • We don’t see each other in person often
  • +1s change the social dynamic to be less Tremendous-centric
  • +1s make offsites more intimidating for new folks


If you’re traveling with a +1 immediately after the offsite, they can stay in your room on the last night. Company events like meals are exclusively for Tremendous folks, but your +1 is welcome to mingle with the team otherwise.

If personal circumstances make your attendance challenging without a +1 (e.g. you have a very young child), please let us know.

How can you contribute?

We love that folks are eager to contribute to offsites and Tremendous culture. We’re thinking of ways to formalize this, but for now, here are the best ways to have an impact:

  • Make an effort to socialize with folks you don’t know
  • Ask good questions at presentations
  • Help out in little ways when you see an opportunity (e.g. coordinating Ubers)
  • Exhibit your natural charm and enthusiasm
  • Respond to the post-offsite survey