Beyond the Annual Offsite: The Cadence That Keeps Teams Aligned & Accountable
The Quarterly Rhythm That Fuels Growth and High-Performing Teams
I used to view company offsites as a fun perk. An opportunity for team bonding, free (VC-subsidised) travel, and perhaps a workshop and strategy session thrown in for good measure.
While working at various Series B/C-stage startups and pre-IPO companies like Airbnb, we did the obligatory annual retreat. We would:
✈️ Fly everyone out;
🎲 Play team-building games;
🍕 Enjoy lunch and dinners together; and
📊 Sit through a couple of (hastily produced) presentations.
… then we would head back to the grind — typically hungover, definitely exhausted — but with a glimmer of hope that the newfound camaraderie and focus would help guide us the rest of the year.
Sound familiar?
While enjoyable at the time, I now realise this approach was flawed. It’s analogous to building a house from a blueprint with no construction plan; you might get the start of a foundation, but you’ll have nothing solid to build on in the months ahead.
After 17 quarters of experimenting at Partly, I like to believe we've learned a few things. We’ve made several mistakes, but with tight feedback loops and a culture of constant experimentation, we landed on something that, at least, works for us.
The most simple and obvious discovery was that connection and alignment aren’t a one-time event; they are rhythms.
Our very simple framework aims to weave together strategy, focus, radical accountability, and connection into our operating rhythm and, as a result, our company’s DNA.
It’s not about one big offsite to base the year around; instead, it’s a continuous cycle. This post does not attempt to cover our end-to-end operating rhythm (that’s for another time), but rather, it will zoom in on one aspect that has had an outsized impact: our Quarterly Season Openers.
These have helped us to:
🎯 Remain as aligned and connected with 85 people spread across 9 countries as we were with 5;
📈 Ensure our team is radically accountable and extremely clear on their ‘one thing’ for the quarter ahead; and
🚀 Embrace change to move at the speed we need to (we see change as a super-strength, not something to hide behind or excuse as “startup chaos”).
Here’s how it works and why I believe most companies get it wrong.
The Problem with the “One-and-Done” Approach
Most companies treat company offsites like a magical band-aid, something that can fix multiple problems and prepare teams for the 12-month journey ahead.
I believe the hope is that a few days of novelty and fun will strengthen bonds and, thus, translate into a sustained period of high-quality work across teams.
Why does this fail?
❌ Annual alignment is a myth. Strategy fades. Priorities shift. People forget. By design, most startups (especially in the earlier stages) should be moving fast, learning, and adjusting their approach, i.e. they should be realigning and changing how the team operates throughout the year.
❌ Lack of deep thought and preparation. Most company retreats or offsites I’ve experienced lack a clear mission or “why”. Without a clear why, it’s very hard to prepare an end-to-end experience or agenda to match that objective.
❌ Good vibes ≠ great execution. Team bonding is fantastic, but not every individual or personality type is excited about a week (or multiple days) of socialising. The most effective offsites can and should solve for far more than just connection.
How Partly Drives Connection and Alignment
1️⃣ Quarterly Season Openers
💡 What They Are:
Quarterly in-person weeks for the entire company to align on quarterly goals, team priorities, and individual’s single-threaded goals (their “One Thing”).
We host these at our three main hubs: Christchurch (ANZ), London (UK and EU), and Manila (SEA).
They act as connection points throughout the year and complement rather than replace the annual offsite. The Quarterly Season Openers and Annual Offsite combine to form our “Peak Moments” spread throughout the year.
💡 How They Work:
A complete Season Opener Week runs from Monday to Friday, peaking on Thursday with our official Season Launch presentation.
The critical output of the week is clarity. For a significant part of the week, leadership and team leads are working together to discuss, poke holes in, and ultimately land on the key focus for the quarter ahead, resulting in:
Clear company strategy & priorities for the quarter;
Each team having measurable output and input metrics; and
Every individual having an extremely clear “One Thing", i.e. a single-threaded goal for the next 3 months.
The weeks contain a mixture of activities designed to share context, accelerate learning, and connect as a team. Some examples include:
Meals: coffee/breakfast delivered to HQ; team lunches; dinners out
Workshops: customer deep dives; equity/ESOP overviews; finance 101
Fireside chats: Dylan Feld (Figma); Brooke Shields (Sharesies); Jamie Beaton (Crimson)
Team events: pub quizzes; board game nights; disc golf; bowling, etc.
Other: Rust tech meetups; community events, etc.
💡 Where You Can See The Details:
At the bottom of this post, I’ve provided links to resources (duplicatable Notion templates) for the Season Opener Plan and Season Opener Creation Steps, which you can copy/edit/use as you see fit.
Below is a screenshot of Launch Day on Thursday
2️⃣ Annual Offsites
💡 What They Are:
A once-a-year retreat where the entire global team comes together.
Unlike Season Openers, it’s not about quarterly execution. It’s about big-picture strategy, long-term planning, and deep team bonding.
💡 How They Work:
Our annual offsite is typically 3 full days and 2 nights away (usually Wednesday to Friday). They are held in a unique, remote location (but not so remote that travel becomes a nightmare).
The core output for the offsite differs each year but is based on one high-level theme.
For example, our last offsite theme was "The Road to Series B”. For many, this helped demystify the startup journey and fundraising process. For everyone, it laid out precisely what we need to achieve as a company by when.
We rent out an entire space: no hotels, no shared spaces, no outside distractions. This allows us to completely step away from the day-to-day. Just space and time to go deep on strategy, team-building, and shared experiences.
Some Things We’ve Learned (And Mistakes You Can Avoid)
1️⃣ More Is Not Always More
In the early days, we kept adding more to Season Openers; more sessions, more activities, more team events.
It backfired. People soon found Season Opener Weeks overwhelming and exhausting. They struggled to recharge their batteries or get work done.
Now, we focus on balance, combining structured sessions, deep work, and optional social events.
2️⃣ Structure Matters
Too many small breaks create "limbo land", where people can’t focus or fully engage.
The fix? We now batch sessions together and, where possible, anchor them around meals so people can reset properly.
3️⃣ Mandatory vs. Optional
Not everything should be forced. Some people love social events, whereas others need downtime to recharge and reset.
We make our core strategic sessions and workshops mandatory, but people can opt out of evening social activities if they need to recharge.
4️⃣ Start and End Strong
One minor mistake we made early on: We didn’t design bookends for a meaningful “start” and “end” to the week. People drifted away, and the week ended with a whimper.
The fix? On Monday, we have a high-energy kickoff lunch to welcome travellers and start the week. We have a final wrap-up event on Friday, often leading into lunch or an afternoon happy hour.
The Importance of Feedback Loops
One of the most minor yet impactful decisions we made was to always measure and survey our team after each Season Opener week. While questions have changed over time, it would typically be a Typeform consisting of the following questions:
A Season Opener NPS (score from 1-10 for impact/effectiveness)
(Start) What 1-2 things should we start doing in Season Opener Weeks?
(Continue) What 1-2 things should we continue doing or do more of in Season Opener Weeks?
(Stop) What 1-2 things should we stop doing or do less of in Season Opener Weeks?
Which three sessions did you get the most value from and why?
After this week, I am clear on my 'ONE thing' needed to achieve our company goals (score from 1-10)
(Optional) Do you have any future workshop ideas or team activities? Bonus points for offers to help run or organise!
Resources (Things You Can Steal)
📌 Want to experiment with running your Season Openers?
I’ve compiled Notion templates you can duplicate/edit/adapt to your company’s needs as you see fit.
Season Opener Plan: end-to-end plan or agenda to design your week, and eventually, share with your team.
Season Opener Creation Steps: outlines the step-by-step prep work needed before the Season Opener Week.
Key links
📌 Want to receive templates and startup memos in future?
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Harry
I enjoyed this and looking forward to your next article
Great read, thanks Harry!