Geanne Weaver-Hepler (Director of EX, Charlie Health), Allison Vendt (VP, People Ops & Head of EX at Dropbox), Nick Freeman (Co-CEO, Marco), and Brian Elliott (CEO, Work Forward) joined us to talk about what’s broken with employee connection—and how to fix it.
We explored practical frameworks for offsites, hybrid team building, and creating meaningful connection moments across distributed workforces.
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(06:00) Why we stopped talking about connection—and why that’s a mistake
(08:00) Gallup data: engagement is falling, especially for managers
(10:00) Geanne on building connection at scale at Charlie Health
(13:00) From Airbnb bonding to 400-person team offsites
(14:00) Dropbox’s shift from office-first to virtual-first with intentional team gatherings
(16:00) The importance of milestone-based anchor weeks
(17:00) Nick: What makes an offsite successful? Frequency, location, and shared space
(19:00) Using AI to plan team retreats faster and smarter
(20:00) Lessons learned: The pendulum swings of remote, RTO, and hybrid
(22:00) Brian: Airbnb’s team cadence model and the importance of rhythm
(25:00) Dropbox’s “gathering matrix” and designing for outcomes
(27:30) Virtual connection challenges & async collaboration tips
(30:00) Why structured rituals help sustain remote trust
(32:00) Peer learning over presentations: How Charlie Health restructured their offsites
(33:30) Role-playing, competition, and fun as part of sales team development
(36:00) Common offsite pitfalls: over-indexing on logistics, under-indexing on experience
(37:00) How to save 20–30% on offsites by avoiding weekends & bundling bookings
(39:00) Q&A: What to say to executives who don’t see the value in connection
(41:00) Q&A: How Dropbox uses Slack, swag, and planning to drive pre-event excitement
(43:00) Q&A: Aligning in-office vs. remote culture differences
(45:00) Q&A: Measuring success with post-event surveys and engagement impact
(48:00) Q&A: Designing experiences for introverts and overstimulated employees
(50:00) Playbooks: Charlie Health’s tiered gathering strategy & Founders Trip
(51:00) Dropbox’s Offsite-in-a-Box and Virtual First Toolkit
(53:00) Why group travel is the fastest-growing segment of corporate spend
(54:00) Tips for booking better hotels, avoiding weekend rates, and maximizing ROI
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