Client:
A fast-growing EdTech company with a remote team of 60+
Objective:
Provide the right environment for the team to align on customer journey stages through detailed and nuanced conversations.
“Team retreats counter the isolation created by remote work. We need a retreat every so often to recharge our relationships and maintain our culture.” - Mae Rigby
The Story
Here’s the thing about corporate retreats. The goal can be well defined and the desired outcome in clear view from the beginning. Yet planning them can still be a logistical nightmare for your leadership’s bandwidth. Coordinating with multiple vendors, managing multiple proposals and rate sheets, and ensuring that no detail falls through the cracks can take up 100 hours in your schedule.
Mae Rigby, Head of People at 240 Tutoring, faced a fast approaching deadline for their retreat. As a team leader, her day-to-day schedule wasn’t conducive to creating a full scale retreat plan. Each passing day meant missed opportunities, and worse still, the likelihood of spending a lot of money for little result. Having been through retreat planning the year prior, Mae knew it was not something she wanted to have on her plate this year.
“It was stressful, causing us to work long hours, or our other main work would build up.”
Mae needed a partner on her team who could allow her to remain focused on her leadership duties while they handled the end-to-end plan for their company retreat.
The Ask
Create a premium experience that reflects the company’s values. A retreat that balanced the work agenda with valuable bonding experiences. The overarching goal was to leave with a team needing to get on the same page and return with a team that felt focused, rewarded, and motivated.
“As a remote team, we get a big bang for our buck being in person together. To all get on the same page would be very helpful.”
On this trip, leadership felt it was important to allow employees to bring their family, which has a measurable impact on morale, but can provide logistical challenges. The retreat had to include fun activities that appealed to different age groups and times for relaxing and recharging.
“To truly build trust and deepen a relationship, and make the effort to truly understand them: one powerful way is by meeting their family…..bringing children felt kinder than asking employees to find childcare for a few days.”
The Solution:
240 Tutoring chooses Pilot Retreats to plan their 5 day retreat to Orlando, Florida.Once Pilot understood the desired outcomes for this retreat, planning was in full motion. Reaching out through a network of partners, Pilot gathered the best locations with negotiated group rates. A curated set of options for these locations from family-friendly activities to overall themes were presented for review. Soon after travel logistics, meeting room reservations, and small delightful flourishes to enhance their experiences were being prepared.
“Not having to go back and forth with the hotel? That was so nice. Pilot was our representative and had our best interests at heart.”
Mae found herself free of the tangled web of logistics and in the plush seat of approving the vision. She was connected via a dedicated Slack channel to communicate directly with the Pilot team. This allowed information to be passed along immediately and quickly acted on.
“You turned probably a 40-hour-plus thing into something I only had to think about for an hour or two…They were super attentive on Slack. I hate sending emails and waiting hours. They made it easy."
To maximize the amount of time together for this remote team, travel plans were designed to have attendees arriving in a similar time frame. As they stepped on site, the adults found custom branded tote bags in their rooms. While kids were presented with stuffed alligators and oranges to welcome them to Florida. As they watched fireworks from their welcome dinner, 240 tutoring could feel that this retreat was going to be different.
For Pilot, the challenge of including activities and customizations that were fun for different age groups, while maintaining a balance of work and rest, allowed for more creative solutions. Mae and the other attendees didn’t have to worry about A/V equipment, lunch delivery, or refreshments for meeting periods. Rather they found themselves scoping out the best place in the pool to see the screen for movie night, picking the right teammate for the pickleball tournament, and discussing strategies for the all family photo scavenger hunt!
“We all had so much fun doing the photo scavenger hunt. Like, the kids were super into it. Everyone thought they were gonna win. Like, it was just hilarious.”Wherever they were sitting down for dinner, a meeting, or just to float in the lazy river, all details big and small were handled. This unlocked the real benefits of the retreat: everyone together in an environment that fostered conversation, boosted morale, and deepened the investment in the company’s mission. The results:
Through this partnership 240 Tutoring was able to benefit from:
Time Efficiency: Valuable executive hours redirected to strategic planning, team development, and leadership priorities.
Strategic Alignment: In-person collaboration achieved full team consensus on critical customer journey milestones, a breakthrough that wasn’t happening over Zoom.
Detail Oriented Planning: Flights, arrival gifts, activities, restaurants, meeting area reservations. Everything was right at leadership's fingertips.
“The app kept everyone on the same page at all times.”
Morale & Retention Impact: The inclusive retreat strengthened the foundations of their culture. Families enjoyed a premium, inclusive experience that built goodwill and loyalty.
A Memorable Experience:
“It was nice to step away from life and step into luxury.”
For 240 Tutoring, this retreat wasn’t just an escape, it was a strategic investment with measurable ROI. By outsourcing the complexity of planning to Pilot, leadership recovered over 100 hours of executive time and redirected it toward what mattered: aligning on customer journey milestones and strengthening team culture.
Pilot handled every detail so Mae and her team could stay focused on results:
“Working with Pilot made the event planning decision making process 10x easier than planning an event on our own.”
Seamless execution that turned five days into a high-impact conversation (and fun for the family!) The payoff? Sharper alignment. Higher morale. Stronger retention. And a team that came back recharged, reconnected, and ready to focus on their goals.
If you're a fast-moving team navigating the chaos of growth, Pilot isn’t a nice-to-have. It’s a strategic advantage.