UpSellit × Allaway

UpSellit × Allaway — Best trip.
Ever.

75+ Attendees
2 Years Running
Cabo Cancún · Mexico
100% Rebooked

The Client

Who is UpSellit?

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.

Company
Managed conversion optimization for ecommerce
Founded
2005 · Los Angeles & London
Category
Company Retreat · Incentive Travel
Allaway Partnership
2025 — 2026
2025 Program
UpSellit 20th Anniversary · March 18–22
Venue
The Fives Oceanfront, Mexico
Attendees
75+ per trip
Allaway Scope
Program design · Hotel & F&B · Vendors · Excursions · On-site management

The Program

Five days. Nothing left to chance.

The Fives Oceanfront, Mexico
March 18 – 22, 2025
UpSellit 20th Anniversary

01 Tue 18 March
  • 11:00a – 5:00pAirport transfers from Cancún, grouped by flight
  • 3:00pCheck-in, welcome notes and room drops
  • 6:00pCocktail hour on the beach
  • 7:00pWelcome dinner on the beach
  • 8:00pBeachfront drinks, then the late-night bar
02 Wed 19 March
  • 9:00a – 6:00pCatamaran tour and lunch on the water
  • 6:30pRooftop cocktail hour
  • 7:30pRooftop dinner and the company group photo
  • 8:30pThe UpSellit Lip Sync Battle
  • 10:00pLate-night bar
03 Thu 20 March
  • 7:30aEarly riser pilates and stretch on the rooftop
  • 7:50a – 3:30pTulum tour and cenote swim
  • 9:00aSnorkeling, spa treatments and four beach cabanas
  • 2:00pPaint and sip
  • 4:30pBeach volleyball tournament
  • 7:00pMexican fiesta dinner with folklore dancers
  • 8:00pDance party, live entertainment and a churro station
04 Fri 21 March
  • 7:30aEarly riser pilates and stretch
  • 9:30a – 2:30pCooking class
  • 10:00a – 4:00pZipline
  • 9:00aSpa treatments and beach cabanas
  • 5:45pTravelers Table dinner experience, offsite
  • 10:00pLate-night bar
05 Sat 22 March
  • 7:00a – 11:00aFinal breakfast
  • 12:00pCheck-out and departures, staggered to flight times

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.

The Fives Oceanfront · Mexico · 2025
Catamaran day on the UpSellit retreat, Mexico, 19 March 2025
Excursion day on the UpSellit retreat, Mexico, 20 March 2025
Final full day of the UpSellit retreat, Mexico, 21 March 2025

Daily Excursions

Nothing compulsory. Everything optional.

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.

Catamaran & Lunch Tulum & Cenote Zipline Cooking Class Snorkeling Paint & Sip Spa & Cabanas

Team Building

The whole company. One table.

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.

Isla Mujeres Private Dinner Lip Sync Battle Beach Volleyball Mexican Fiesta Group Photo
Isla Mujeres · Mexico · 2025 The UpSellit team together on their 2025 retreat in Mexico, produced by Allaway
The Fives Oceanfront · Mexico
The Fives Oceanfront, Mexico, ahead of the UpSellit retreat
The Fives Oceanfront on the UpSellit arrival day, 18 March 2025
Grounds and facilities at The Fives Oceanfront
Beachfront at The Fives Oceanfront
Guest areas at The Fives Oceanfront

The Venue

One property. No complaints.

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.

Oceanfront Resort Rooftop Beach & Cabanas Two Restaurants Spa 75+ Rooms
Explore The Fives

Five days. In frames.

UpSellit · Mexico · March 2025
UpSellit retreat at The Fives Oceanfront, Mexico, 21 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 21 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 20 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 20 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 19 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 21 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 19 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 18 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 20 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 18 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 20 March 2025, produced by Allaway
UpSellit retreat at The Fives Oceanfront, Mexico, 21 March 2025, produced by Allaway

The Aftermovie

See it in motion.

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!

Work with us

Let’s build something.

A reply within two business days. No back and forth. Tell us what you’re building and we’ll tell you how we’d do it.