Woflow Executive Offsite Case Study: Corporate Retreat in Bend, Oregon
A remote-first tech company brought 50 team members together in Bend, Oregon for a four-and-a-half-day executive offsite designed to rebuild trust, strengthen alignment, and create the kind of shared experiences that simply don’t happen on Zoom.
Project Overview
- Client: Woflow
- Industry: Remote-first technology company
- Event Type: Executive offsite & corporate retreat
- Location: Brasada Ranch, Bend, Oregon
- Duration: 4.5 days
- Team Size: 50 people
This executive offsite was designed to bring a distributed remote team together in person, reset company culture, and build trust that simply can’t happen over video calls.
The Challenge
Woflow operates as a remote-first tech company with team members spread across multiple time zones. While productivity remained strong, leadership recognized a deeper challenge:
- Limited organic trust-building
- Fragmented collaboration
- Few shared experiences beyond Zoom meetings
- Manage full service logistics including venue, activities, food and beverage, and run of show
They didn’t want a typical corporate retreat.
They needed a strategic offsite experience that would rebuild alignment and strengthen relationships at a human level.
The Goal
The goal of this corporate offsite was to:
- Strengthen trust across teams
- Accelerate collaboration and decision-making
- Create shared memories that translate into better teamwork
- Design an experience that felt intentional, inclusive, and energizing
Our Strategic Approach
Location Selection
Brasada Ranch in Bend, Oregon was selected for its natural setting, privacy, and ability to support both structured programming and informal connection.
The environment allowed participants to step away from daily routines and engage fully with one another.
Experience-First Event Design
Rather than building the offsite around schedules and sessions, we designed it around side-by-side experiences.
Every meal, activity, and transition was intentionally crafted to create moments where trust could form naturally.
The Offsite Experience
Day 1 – Arrivals & Welcome
- Leadership-hosted happy hour at a private cabin
- BBQ dinner by the fire with s’mores
- Live solo musician setting a relaxed tone
Day 2 – Team Challenge & Strategy
- Regatta Challenge led by a professional facilitator (all 50 participants)
- Facilitated debrief and strategy discussion
- Optional wellness programming (yoga and guided walks)
- Family-style dinner using locally sourced ingredients
Day 3 – Split Activities & Evening Experience
Morning Split Groups:
- Group A: Wrangler immersion (roping, grooming, arena riding games)
- Group B: Archery, axe throwing, and lawn games
Afternoon & Evening:
- High Desert BBQ lunch
- Wood-fired dinner featuring flat iron steak and Columbia River steelhead
- Glow-in-the-dark pickleball party with DJ
Day 4 – Full Participation & Downtown Bend
- Groups swapped activities to ensure full participation
- Boxed picnic lunch
- Off-property dinner at a local Bend brewery and restaurant
Day 5 – Departures
- Grab-and-go breakfast for seamless departures
Food & Hospitality Philosophy
Food was treated as a core part of the experience, not a logistical detail.
- Thoughtfully designed vegetarian and vegan options
- Elevated, plant-forward cuisine
- Meals designed to encourage conversation and connection
This approach ensured every guest felt included and considered.
The Outcome
Client Feedback
Jordan Nemrow, Co-Founder & CTO, Woflow
“There is no substitute for being together in person.
When people spend time side by side sharing meals, participating in challenges, and laughing about moments that never show up on Zoom, everything about how they work together changes.
Conversations get clearer. Collaboration gets faster. Teams feel more connected and aligned.
Even one intentional offsite a year can have an outsized impact on company culture.”
What Made This Executive Offsite Successful
Strategic Programming
No long presentations. No forced activities.
Every experience was designed to support natural connection.
Inclusive Design
Split activities, flexible programming, and thoughtful meal planning ensured full participation across the team.
Trust Acceleration
Activities like the Regatta Challenge and shared evening experiences created shared stories that strengthened team bonds.
Hospitality as Strategy
Every decision was guided by one question:
What experience will create the best outcome for the people in this room?
Key Takeaway
This was not traditional event planning.
This was strategic hospitality.
One intentionally designed corporate offsite can reset energy, rebuild alignment, and strengthen culture more effectively than dozens of virtual meetings.
FAQ
What was the purpose of this executive offsite?
The goal was to bring Woflow’s distributed team together in person to strengthen trust, improve collaboration, and reset company culture through shared experiences rather than traditional meetings.
How long was the Woflow offsite?
The offsite ran for four and a half days, with Sunday arrivals and Thursday departures, allowing enough time for meaningful connection without feeling rushed.
Why was Bend, Oregon chosen for this corporate retreat?
Bend offered a balance of privacy, natural surroundings, and flexible venues that supported both structured programming and informal, side-by-side experiences.
What made this offsite different from a typical corporate retreat?
This offsite was designed around connection, not coordination. Instead of packed schedules and presentations, the focus was on activities, meals, and transitions that naturally built trust.
Can Clandestine Events design similar executive offsites for other companies?
Yes. Every offsite we design is customized around company size, culture, and goals, whether it’s a leadership retreat, company-wide offsite, or multi-day executive gathering.
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