UpSellit × Allaway
The Client
UpSellit is a managed conversion optimization partner for ecommerce — the team brands bring in when a site is getting traffic but losing sales. Founded in 2005, with offices in Los Angeles and London, they build behavioral marketing programs that recover abandoned carts, personalize the on-site experience and bring shoppers back by email, SMS and push — for clients ranging from emerging retailers to FedEx, Whirlpool and Kay Jewelers.
Every program is run by people rather than software: strategists, designers, developers and account managers working as an extension of the client’s own team. Which is why the annual company retreat matters more here than most. UpSellit’s people are spread across two continents and spend the year inside other companies’ funnels. The trip is the one week they are all in the same place — and 2025 was the company’s twentieth year, so it had to be the best one yet.
Allaway planned and produced it. Five days in Mexico at The Fives Oceanfront, 75+ people, March 2025. We wrote the program end to end — arrival transfers through to staggered departures — and we were on site for all of it. Hotel requirements, every meal and dietary need, every vendor, every excursion and every company ask were confirmed before the first guest landed, so nothing on the ground needed a decision. UpSellit came back the following year.
The Program
The Fives Oceanfront, Mexico
March 18 – 22, 2025
UpSellit 20th Anniversary
Every line above was confirmed before anyone landed — rooms and room drops, meals and dietary requirements, vendors, excursions, transfers and every company ask. Allaway wrote the program and stayed on site for all five days to run it.
Daily Excursions
An incentive trip earns its name when nobody feels scheduled. So every day carried more than one thing to do, running at the same time, and people picked on the morning. A full-day catamaran with lunch on the water. Tulum and a cenote swim. Ziplining. A cooking class. Snorkeling off the beach, paint and sip, spa treatments, a volleyball tournament, and early riser pilates on the roof for anyone up before the rest of the company.
Every one of them was booked, confirmed and paid ahead of the trip, with transfers timed to the group and packed lunches for the dietary requirements that needed them. Allaway was on site for all five days, so the only decision anyone had to make was which one they fancied.
Team Building
The centerpiece of the week was a private dinner on Isla Mujeres. On the Friday the group left the pier by boat, crossed to the island, and sat down together at Travelers Table — one long table, a set menu, no departments and no seating plan. For a company whose people work across two continents and mostly meet through a screen, it was the only evening all seventy-five were in the same place doing the same thing.
It was not the only one that worked. The rooftop lip sync battle, the beach volleyball tournament, the fiesta dinner with folklore dancers, the group photo before dessert — the program was built so that none of the team building ever announced itself as team building. Nobody was put in a breakout room. They just kept ending up together.
The Venue
The Fives Oceanfront carried the whole week. The welcome dinner on the beach, cocktail hours and the lip sync battle on the rooftop, the Mexican fiesta at Al Mare, lunches at Ro Marley, the spa, four beach cabanas held daily, the pool, the volleyball court on the sand, and a lobby bar open to midnight every night. Seventy-five people, five days, one address — nobody needed a taxi to get to dinner, and every excursion left from the same lobby.
That matters more than it sounds. A venue that can absorb a full group, a private dinner, six concurrent activities and a late bar without anything feeling borrowed is rare. Every employee came back with positive feedback — on the property and on the week.
























The Aftermovie
From the Client
Ambar
B.
Chief Financial Officer
UpSellit
Best. Trip. Ever!! The Allaway team is simply amazing! Hannah, Boo, Massi, and the rest of the crew are top-tier professionals — truly world-class organizers. Couldn’t have asked for a better experience!
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