The Offsite “Cadence" (or How to Maximize Budget, Buy-In, and ROI)
We've saved our clients over $5,000,000 as well as thousands of hours they otherwise would have spent planning retreats themselves. Here's how...
Since 2021, our team at Offsite has helped plan over 300 retreats across 25+ countries. We've saved companies millions of dollars, thousands of hours, and—maybe most importantly…a ton of stress.
And this week, we’re hitting a new milestone:
We planned multiple retreats happening right now across the U.S. for over 1,100 collective attendees—our biggest week ever for total offsite attendance!
And we’re still actively planning another ~50 offsites globally taking place between May 2025 and early 2026 for a wide range of leading tech companies, nonprofits, and Fortune 500s.
As the founder of Offsite, I want to thank you from the bottom of my heart, because none of this would be possible without you.
To every Chief of Staff, People leader, EA, founder, and executive who has trusted us with your team’s time and energy—thank you. You’ve helped shape Offsite into the partner it is today.
If you're new here and wondering how we’ve saved so many companies time, money, and logistical chaos, here’s a look inside the “cadence” plan for offsites that we’ve developed, optimizing for true business value and positive impact for the people on your team…not just “party planning” or logistics.
More importantly, this process can scale from a small offsite to a “cadence” or ongoing plan of strategic gatherings across your entire organization for many years to come.
Let’s jump into it!!!
1. Want to Save Money? Start Planning Sooner.
The best way to cut 20% or more off your offsite budget is simple: start planning early.
3–6 months out for 50–100 attendees
6–12 months out for 100+ attendees
The more lead time, the better your venue options, travel rates, and leverage in negotiations
When you commit to a cadence of retreats instead of a one-off, you can even structure multi-event partnerships with venues and vendors…unlocking deeper discounts and simplifying logistics for future retreats.
For example, we’re working with a Series-C backed defense tech startup who is working with Offsite for 20+ retreats with 500+ collective attendees (each event ranging from 10 to 250 attendees).
Because we’re planning so far out for them on their biggest events in particular, we've saved them over $500,000 in hard costs already (not to mention how much time we’ll save them), more than 5x our total fees and the ROI is only growing bigger as we still have 6+ months to plan various retreats for them on their current contract).
2. Want to Save Time? Run a Repeatable Planning Process.
If you’ve ever tried to DIY an offsite, you know how quickly the details pile up.
Venue sourcing, travel coordination, dietary logistics, last-minute speaker swaps, AV snafus…it is truly a full-time job.
The most efficient teams we work with follow a repeatable planning process:
Set clear objectives
Map your budget and stakeholders
Gather pre-offsite feedback from attendees
Plan your agenda hour by hour, and your budget line item by line item
Plan for logistical contingencies, but ultimately focus on “why” you’re meeting in the first place, and ensure you are meeting your business and people objectives.
Doing this once is great. But the real benefit comes when you build muscle memory around offsite planning across your company.
A cadence of retreats means each one gets easier, faster, and more effective.
3. Want to Increase ROI? Be Strategic About Your Team Retreats.
An offsite shouldn’t just be a feel-good event or party. It should be part of your rhythm of business, leveraged to help your team(s) increase focus, speed, engagement, trust, and momentum.
Start with the right strategic intent.
Are you kicking off a new fiscal year for sales/marketing?
Are you planning your upcoming quarter’s OKRs or making strategic decisions?
Do you need to create cross-functional trust between Ops and Customer Success?
Each of these requires different agenda design, prep, and facilitation.
We’re currently running the All-Hands Meeting for a ~$5B company in Denver, CO for over 900 employees.
We’ve also helped this same company with a Sales Kickoff, Product Kickoff (SKO for product and engineering), various marketing team retreats, and smaller “onsites” for training cohorts of new employees.
While we have helped them standardize budgets, pre and post-offsite feedback forms, internal communications, vendor searching, negotiating, and contracting, and much more...
At the end of the day, each retreat calls for different intention, and how you generate ROI will come from different programming decisions that must be made with the business and people goals in mind for each individual offsite, contextualized by the bigger vision of the company’s overarching mission, vision, and values.
The Takeaway: Build a Cadence of Retreats
Here’s where the best companies pull ahead: they don’t stop at one offsite.
They build a company-wide cadence of retreats across different functions, layers, and audiences.
When done right, an offsite becomes less of an “event” and more of a drumbeat for how your company communicates, plans, and builds effective culture.
Here’s what that might look like for a 100 to 1000 employee company, depending on the make-up of various departments and their needs to gather IRL:
January: Sales Kickoff (SKO)
March/June/Sept/Dec: Quarterly Executive Retreats
Spring: President’s Club or top-performer incentive trip
Summer/Fall: Company-wide All-Hands Meeting
Ongoing: Department-level offsites (Product, Marketing, CX, etc.)
Customer-Facing: Annual user conference, partner summit, or customer advisory board gathering
Other: Board retreats, mini-offsites around trade shows
Each of these retreats serves a different purpose, but together they form a system that increases employee engagement, retention, and alignment consistently over time.
When your team knows that these moments are built into the rhythm of the company, participation goes up. So does trust. So does follow-through.
TL;DR
If you want offsites that actually move the needle:
Start early to maximize budget
Run a process to streamline logistics and reduce burnout
Tie every retreat to strategic initiatives to drive real ROI
Build a cadence, not just one-off events, for greater connection and alignment.
At Offsite, we’ve helped hundreds of teams move from scattered retreat planning to a unified, high-impact rhythm across their entire org.
Thanks
Jared
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When you are ready to plan your next offsite, make a free account at offsite.com to search our curated marketplace with thousands of amazing offsite venues, up to 50% savings on room blocks, meeting space, and more.
Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why companies like Remote, Buffer, 15Five, Metabase, Hampton, and others trust Offsite for their team retreats.