8 Takeaways From Skift’s First Retreat as a Fully Dispersed Company

Skift's worldwide team gathers in Puerto Rico

Skift Take

Skift gathered its worldwide team together for a retreat in Puerto Rico and discovered that traveling in a post-pandemic world can be challenging.

The world sputtered shut during the pandemic, but for those with the ability to work remote — it was all systems go. That was the case for Skift. Ultimately, the decision was made in the summer of 2020 to close the last remaining Skift office, its headquarters in Manhattan, and make the company fully dispersed.

There have been occasional gatherings since, in co-working spaces — Skifters working together at long tables, laptop to laptop — and some interactions at in-person events. But the entire global team has not gathered in two years. That is until last week. 

From as far away as California, India, Denmark, and Scotland, the team traveled to Puerto Rico, and this is what happened. It was the chance to experience all we had been reporting on ourselves about travel, company retreats and remote work, and the new ways to enhance company culture.

Live Your Brand

Skift focuses on the transformative power of travel. Puerto Rico, Cuba, Colombia, Montreal, Long Island — Skifters excitedly share details from past retreats with each other, their enthusiasm saying it all. 

Since its first year, the Skift retreat has been a cherished activity. In 2014, a company of only 10 traveled to Iceland. The accommodations were far from luxurious, eight in one room and two in the other, but the trip was invaluable. “We were celebrating getting a round of financing and figuring out how to create our independent path and make money doing it,” recalls Rafat Ali, Skift’s founder and CEO. “It was in Iceland where we formulated our long-term vision for the company.” 

Embrace the Destination

Bonding intensifies when immersed in a new culture. In Puerto Rico, the local spirit is called Boricua, and it was alive during the retreat. 

The sights, smells, and sounds of the island were celebrated at Jajome Terrace, a magnificent stone guesthouse set high atop a mountain. Dinner was served on a sprawling verandah surrounded by mountains and lush vegetation. A full moon, sparkling stars, and a symphony of serenading coqui, Puerto Rico’s beloved tree frogs, made the experience complete. 

Crystal Diaz, the creator of El Pretexto, a culinary farm and lodge minutes from Jajome, also tucked away in the lush mountains, an area she is helping promote, interacted with the group, sharing her passion for Puerto Rican food. Cubanelle peppers, garlic, cilantro, and culantro — she gathered them all in a basket and explained each, passing them around for a better look and smell as the sun dipped behind the clouds in the mountain range below. Later in the evening, Diaz walked around with a cast iron pot, all the ingredients now lightly sauteed into an aromatic sofrito. 

The Skift team at Jajome Terrace in Cayey, Puerto Rico

Skift retreats focus on unique experiences like this and an insider’s look at a destination. That is what Brad Dean, CEO of Discover Puerto Rico, offered as he joined Ali to chat about the island at a morning beachfront meeting. The Zika virus in 2017, Hurricane Maria in 2019, two powerful earthquakes followed by the Covid pandemic — “The people of Puerto Rico have earned their PhDs in resiliency,” said Dean. 

Free Time Often Equates to Bonding Time 

Meal functions, walking tours, zip-lining, and snorkeling — were all highlights of the retreat as was free time when team members made their own plans. From grabbing a drink in a beachfront restaurant, crashing waves in the distance; dancing salsa at a local dance club; to enjoying a cup of delectable gelato in Old San Juan; the bonding and memories created will last long after suitcases are unpacked.

Engaged Employees Are More Productive

A company that rewards its team and values its employees reaps the benefits. A soft blue t-shirt awaited each team member. The logo created by Skift designer Beatrice Tagliaferri featured an adorable Puerto Rican coqui. Team spirit soared as the group assembled for a photo, all wearing these t-shirts. 

An all-expense trip to an exotic locale like Puerto Rico, accommodations in the San Juan Marriott Resort & Stellaris Casino, a beachfront resort, is an attractive perk. It is also used as a lure to attract new employees. 

“Company retreats are expensive, but the benefits they reap offer dividends many times over,” said Ali. 

Give Them Something to Talk About 

Adrenaline-inducing activities create excitement. Zip-lining high above the tree line, snorkeling in aqua blue water, colorful fish and eel dancing below, navigating the cobblestone streets of Old San Juan during a walking and food tour as the sky opens up and rain pours down will soon not be forgotten. When things don’t go exactly how planned is when many memories are created. 

The Skift team at Cuartel de Ballajá-Interior Old San Juan, Puerto Rico

Group Think

Working in silos often results in siloed ideas. So there is nothing better than coming together as a group to bounce ideas off each other. This Puerto Rico retreat was the first time many who collaborate daily met in person.  

Spending time together creates connection that a Zoom call cannot do. And deeper relationships often equate to products with much more depth. 

Covid Must Still Be Considered

The reality is Covid is still with us, will probably always exist, and eradication seems unlikely. New variants are highly transmissible but cause less severe illness. Travel and testing now go hand-in-hand. A European-based employee tested positive for Covid a few days before departing for Puerto Rico and had to miss the retreat. For the group on-site, each morning started with a rapid test before gathering. Although precautions like this help prevent the spread of Covid, new variants are highly contagious. 

Travel Delays Are a Reality

Airlines are struggling to keep up with the surge of travel. It took one Skift employee 48 hours to travel from San Juan to Montreal due to canceled flights. Delays, cancellations, and packed planes await travelers, but most are willing to be inconvenienced to satiate the thirst for travel.