The problem wasn't strategy. It was that nobody agreed what the strategy was.

The Situation

The vacation rentals business was losing ground — and the team didn't have a shared view of why.

Wanderly's Vacation Rentals business was under real pressure. Site traffic was down 13% year-over-year. Bookings had declined 33–37% YoY across every booking type. Only 18% of available listings had received a booking that year — despite nearly one million properties on platform. Competitors were pulling ahead.

The harder problem wasn't the numbers. It was that a newly restructured, cross-functional product team — spanning product management, engineering, design, analytics, SEO, supply, and customer success — had never had dedicated time to align on the business, the customer, or a shared direction for the year ahead. They were executing, but not toward a common vision.

There was no shortage of smart people with opinions about what to fix. What was missing was a structured process to get those opinions into the room, surface the real blockers, and turn a list of problems into a strategy the whole team could own.

The Intervention

Three days in Oxford. One goal: leave with a strategy the team actually built together.

The off-site was designed and led as a structured facilitation — not a leadership presentation with Q&A, but a genuine working session in which the cross-functional team would diagnose the business, explore the opportunity space, and converge on priorities together. The design choices were deliberate:

• Commissioned and compiled a comprehensive pre-read — a current state assessment covering KPIs, competitive landscape, customer research, and brand health — distributed in advance so the team arrived informed, not catching up
• Built a 3-day agenda sequenced from current-state reflection → opportunity exploration → prioritization and ownership, so the team moved through divergence to convergence rather than generating ideas without resolution
• Designed break-out sessions around specific customer and business questions — traffic acquisition, loyalty, supply utilization, platform ecosystem integration, data science — each grounded in a clear problem statement with a designated owner
• Facilitated a brand exploration session to surface and challenge assumptions about the VR value proposition and whether the existing multi-brand architecture was serving or undermining the business

The Outcome

A team that arrived with questions left with a shared strategy and the ownership to execute it.

The post-event survey told a clear story: 100% of the 18 attendees agreed the off-site met its objectives. Not a single person was dissatisfied — with the structure, the session topics, the facilitation, or the event overall. 61% were "very satisfied" overall; 55% "strongly agreed" the event was well-structured.

More importantly, the team left with what they came for: a shared diagnosis of the business, a prioritized set of opportunity areas with clear owners, and the cross-functional relationships needed to execute faster. The open strategic questions — who is our customer, what is our value proposition, where should we invest — moved from unspoken assumptions to explicit choices the team had made together.

The format itself became a model. 83% of attendees said they wanted sessions like this at least every six months — and the structured approach to pre-reads, facilitated divergence, and ownership mapping carried forward into how the vacation rentals product team ran strategy work going forward.