Webinar: Why You Should Build a Team Offsite into Your Budget

April 6, 2022
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Webinar: Why You Should Build a Team Offsite into Your Budget
OfficeTogether Team
April 6, 2022

We've noticed an emerging trend in workplace culture: CEOs are choosing travel to get their teams together for in-person collaboration and camaraderie.

First, there was our company's commitment to offsites every year. It's such a unique part of our culture, that we planned a webinar months in advance to share about it. Our CEO has posted on LinkedIn multiple times about the uncommon tradition she started the first year of the company.

Then, as we were boarding our flight to Offsite #1 of 2022, an article appeared on Protocol: "Why one tech CEO paid to fly his employees out to Mexico City for a week." (See Source 1)

When we arrived in Playa Del Carmen, the rental house behind ours was also occupied by another company hosting their team.

The rental's staff shared that the two bookings after ours were also, indeed, company retreats.


How and why is this trend happening for business? We shared the insider's perspective of the thought process and planning for an offsite. Read below for a recap of the webinar recording.

Founder/CEO Amy Yin, Head of Sales & Operations Jacquelyn Wong, and Executive Assistant to the CEO Sash Campbell spoke about why companies should host offsites and how offsites can fit into a budget. They specifically discussed planning OfficeTogether's 2022 offsite to Playa Del Carmen, Mexico.


Some highlights from their conversation include…


The Why


Why are offsites so vital?


OfficeTogether is a hybrid company with employees scattered across the country. Offsites let us come together and spend time together on a personal level. They help bring back that in-person office feel we remember from before covid.


OfficeTogether leadership prioritizes the team, making sure they are engaged and happy. Employee engagement goes beyond employee satisfaction. It affects the company's bottom line. According to a Google study, engaged sales employees produce four times as much revenue as less engaged employees.


CEO/Founder Amy says offices need to be mixed with offsites to really connect with people. Because our team is scattered across the country, bringing everyone to our office in New York for a week is actually more expensive than all meeting in Mexico for a week. 


You get so many valuable experiences on an offsite that you don't get in an office or when everyone is dispersed. Everyone staying at one property gives a sense of unity and personal conversations come naturally from the environment. It's a way to strengthen interpersonal relationships. Additionally, Amy has noticed our team is able to have longer, focused conversations at the offsite in a way we wouldn't if we were on Zoom. Read more on the data supporting in-person collaboration in our blog post here.


Most companies are spending less on office catering and events in this era of hybrid work. That money can be allocated other places, such as offsites.




Flexibility is key. Know the cancellation policies on any hotels, properties, flights, rental cars, and activities. You never know when you might need to reschedule, especially with covid.


Keep in mind your team members' personalities and life situations. Some are parents, some are introverts versus extroverts. Having a range of options can be best, where some people can relax and others can do something adventurous like snorkel or surf.


Not overscheduling is important. We learned people need time between activities to have snacks, go to bathroom, etc. Scheduling back-to-back will make employees stressed. Ideally, there should be time for people to do "thinking intensive" activities, adventurous activities, and also relax.


Remember communication through the planning process. Send team members reminders of the property, if they need current passports, etc. Help your team plan ahead. Also communicate any final details. For example, remember to bring board games, chargers, and extra outlets. You want everyone to feel prepared. 


Keep in mind team members' dietary preferences and allergies. Make any arrangements or special accommodations beforehand.




We started more than 3 months out planning for the Playa Del Rey offsite. As soon as one offsite happens, we begin brainstorming for the next one.


The earlier you start, the better the rates are and the less stressful the planning is. There's ample time to handle it when curveballs pop up.


In addition to using Air BNB and Vrbo, consider going directly to the property. You might be able to negotiate a better price and also will have a direct line of communication.

The OfficeTogether team broke down their budget into three categories: flights, accommodations, and meals/entertainment. The team started with accommodations first, using a budget of $10,000. Some retreat spaces will offer a chef staffed with accommodations. This was a selling factor of the rental for our retreat. It eliminated expensive restaurant dinners and transport to and from different venues, a major convenience and savings.


Tips and Tricks


Be transparent with your team. Get team member input and participation. Ask where they would be excited to go. Ask their opinion on properties under consideration. Make team members feel like they have an input.


Spreadsheets are your best friend. On these you can map out everything: flight prices, rental car prices, activities, etc.


Thank you Amy, Jacquelyn, and Sash for sharing all your insights! And thank you to everyone who was able to attend or watch at a later time.

Source 1: https://www.protocol.com/newsletters/protocol-workplace/business-travel-andrew-hoag-teampay

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