Most companies treat offsites like a silver bullet; a few days of bonding and strategy to carry them through 12 months of execution.
That doesn’t scale. Strategy fades. Priorities shift. People forget faster than you’d like to admit.
After 17 quarters of iteration at Partly, we landed on something simple: connection and alignment aren’t events. They’re rhythms.
This post focuses on the part of our operating cadence that created the biggest step-change in clarity, accountability, and energy: our Quarterly Season Openers.
The Problem with the Annual Offsite Model
Most companies treat offsites like a magical reset button:
Bring the team together once a year
Set the strategy
Hope it holds for the next 12 months
It rarely does.
Annual alignment is a myth. Strategy shifts. People forget. Startups (especially early-stage ones) are supposed to move fast, learn, and adjust. Your operating model should support that, not fight it.
Most offsites lack a clear objective. If you don’t know the "why," you won’t design the right agenda. You’ll get good vibes but not much else.
Good vibes ≠ Great execution. Team bonding matters. But not everyone wants a full week of socialising. And connection without clarity burns out quickly.
What We Do Instead
We run Quarterly Season Openers: in-person weeks for the entire company, once per quarter.
The goal is simple: reset, realign, and refocus.
In these weeks, every team aligns on quarterly goals. Every person walks away with one single-threaded priority for the next 90 days: their One Thing.
It’s not a to-do list. It’s an outcome. It clarifies what matters and kills busywork.
We host Season Openers in our hubs: Christchurch, London, and Manila. They complement (not replace) our Annual Offsite. Together, they form the cadence we call Peak Moments.
Each Season Opener runs Monday to Friday. The highlight is Launch Day on Thursday, when we share company priorities and celebrate team wins.
The rest of the week is designed to build context, accelerate learning, and deepen connection:
Coffee delivered to HQ, team lunches, and shared dinners
Workshops (customer deep dives, finance 101, equity overviews)
Fireside chats with external leaders (e.g. Figma, Sharesies, Crimson)
Optional evening events (board games, bowling, pub quiz, etc)
Local meetups and community events
What We Learned (The Hard Way)
1. More is not better. We used to pack Season Opener Weeks with sessions and activities. It was too much. People left exhausted and scattered.
Now we optimise for balance: structured sessions, space for deep work, and optional social time.
2. Structure matters. Too many small breaks = no focus. We now batch sessions and anchor them around meals. People reset properly and engage more fully.
3. Don’t force everything. We make strategic sessions mandatory. Social events are opt-in. Some people recharge solo, not at karaoke night. That’s fine.
4. Start and end strong. We used to just drift in and out of the week. Now we open with a kickoff lunch and close with a Friday wrap-up. Clear bookends create momentum.
5. Measure everything. After each Season Opener, we run a short team survey:
NPS: How impactful was the week?
What should we start, stop, continue?
Which sessions were most useful?
Are you clear on your One Thing?
The feedback loops are short, honest, and drive real improvements.
And Once a Year: The Annual Offsite
Our Annual Offsite is different by design.
It’s not about quarterly execution. It’s about zooming out. Big-picture strategy, long-term planning, and deep team connection.
We bring the entire global team together for 3 days and 2 nights. We rent out a dedicated space; no hotels, no outsiders, no distractions.
Each offsite is anchored by a single theme. Last year’s: The Road to Series B. It helped demystify our funding journey and aligned the team on what we need to achieve.
We go deep. We connect. We leave clear.
The Payoff
Quarterly Season Openers helped us stay as aligned at 85 people across 9 countries as we were at 5.
They keep us agile. They make space for deep connection and deep focus. And they reinforce the idea that execution is a rhythm, not a single event.
You can steal this. Tweak it. Adapt it to your team. Just don’t rely on one offsite a year to hold your company together.
Rhythm beats intensity.
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. See a screenshot of our “Launch Day” on the Thursday below.
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?
Final Thoughts
Offsites are moments. But performance comes from momentum.
The best teams don’t align once a year. They reset, refocus, and recommit every quarter.
This model made it real for us. Take what’s useful. Leave the rest. Then build a rhythm that works for you.
I write about scaling ops, talent, culture, performance, accountability, and anything else that’s keeping you up at night as a startup founder, CEO, COO, or CPO. Subscribe below to receive the monthly newsletter.
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Cheers,
Harry
I enjoyed this and looking forward to your next article
Great read, thanks Harry!