I Took My Team on an All-Expenses-Paid Retreat: Here’s Why You Should Do the Same
Shocker! Offsite used offsite.com to plan our own offsite :). My thoughts as a CEO on why bringing our team on an all-expenses-paid trip is one of the highest ROI things we can do.
Jared here, founder/CEO of Offsite.
I’m writing this from the airport, en route to our company retreat in Mexico!
By the time you read this, we’ll already be deep into Day 2 of our quarterly team retreat—connecting, collaborating, and soaking in the sun, as well as everything our action-packed agenda has to offer.
But don’t let the headline fool you. This isn’t a vacation; it’s a strategic investment in our team, our company, and our future.
Honestly, these next few days may be the most important time spent by everyone on our team in Q1 2025.
For Chiefs of Staff, EAs, and other People Leaders reading this, I know that planning a corporate retreat can feel daunting—with all the necessary budget approvals, logistics, aligning schedules.
But if done right, the ROI far outweighs the cost. That’s why we’re here, and why, if you’re not already thinking about your next retreat, you should be.
Balancing Working “On” The Business, Working “On” Our Relationships, and Working “On” Our Tans
At Offsite, we know that the most effective retreats strike a balance between structured strategy and meaningful team bonding. That’s exactly how we’ve designed our own retreat, ensuring that every moment is intentional and impactful.
Here’s what’s on our schedule:
Strategy Sessions: Focused discussions on hitting our Q1 OKRs as well as thinking 1, 3, and 10+ years out about our department-level and company-wide strategy.
Site Visits with Hotel Partners and other Vendors: Meeting with boutique hospitality partners like the Santa Fe Hospitality Group (which operates 25 boutique hotels in Mexico, including some of the most popular venues in our curated marketplace).
Afternoon Team-Building Activities: Local experiences, from delicious meals and (definitely) time on the beach to surprise activities planned for us by some of our local DMC partners (DMC means Destination Management Company) are important for deepening trust and intimacy among the team through unique shared experiences, as well as a breath of fresh air after a record-breaking January.
Department-Level Breakouts: Time spent with our day-to-day working teams to unlock any issues that might keep us from hitting our Q1 OKRs and think through business process automations.
There’s something different about these discussions when they happen face-to-face, without the distractions of day-to-day tasks and Zoom fatigue, that lead to increased productivity for months and years following each offsite.
Basically, if you can do something via email or Zoom, you should NOT do that during an offsite.
For us, we have the unique ability to check in with vendors during our retreats as well, so we’re doing that in order to strengthen the “supply side” of our marketplace (which is part of why we can secure up to 50% off room blocks, meeting space, F&B, and more at 1000+ offsite venues globally on your behalf).
Why Invest in a Retreat?
It may seem counterintuitive—pulling the entire team away from their daily responsibilities for several days. But the benefits of an in-person retreat are undeniable.
Just some of what we expect to gain from this experience includes:
Face-to-Face Collaboration: Virtual meetings can’t replicate the energy of being in the same room.
Accelerated Onboarding: A retreat is an invaluable way for new hires to integrate into the team faster.
Strengthening Relationships: Stronger bonds lead to better communication, trust, and cross-functional collaboration.
Higher Employee Engagement & Retention: Employees who feel connected to their peers and company mission are more likely to stay.
Greater Alignment on Company Strategy: It’s easier to get everyone on the same page when distractions are removed.
Branding & Recruiting Benefits: Showcasing a strong culture and investment in people helps attract top talent.
One of the biggest takeaways?
A company retreat isn’t a luxury—it’s a high-leverage activity for scaling remote-first teams and ensuring that everyone feels deeply invested in the company’s success.
Why You Should Start Planning Your Own Retreat
By the time you’re reading this, we’ll already be well into our second full day of Offsite’s offsite. I’ll write again in the near future about how the retreat went, but I didn’t want to wait in encouraging you to plan your company’s 2025 offsites.
For those of you responsible for People Ops, executive alignment, or team cohesion—ask yourself:
When was the last time your team gathered in person to think bigger, solve challenges, and find greater alignment in your day-to-day work?
If it’s been too long, now is the time to start planning.
And if you’re not sure where to begin, or you want to save yourself 50-100+ hours of planning time per offsite (in addition to 20-50% of your overall budget, so finance approves your offsite plans without issue), that’s exactly why we built Offsite..
We take the logistical burden off your plate so you can focus on what really matters—making your next retreat a transformational experience for your team.
I’ll share more takeaways once we’re back, but for now, I’m looking forward to seeing my team in person soon, giving everyone big hugs, and celebrating our recent successes while game-planning for greater growth.
If you're considering planning your own retreat, let’s talk.
Ready To Plan Your Next Offsite?
Planning a corporate retreat involves juggling countless details, but you don’t have to do it alone.
At Offsite, we simplify the process by connecting you with a curated network of trusted venues, helping you secure the best rates, and handling the logistics so you can focus on what matters most—your team’s experience.
Offsite not only has a free-to-use, Airbnb-style marketplace where you can save up to 40% on 1000+ premier offsite venues globally, but we also provide “done for you” team retreat planning services.
Thanks for reading!
-Jared