Unknown. Inspiring. Unforgettable: The Group 8A Digital Nomad Program

Unknown. Inspiring. Unforgettable: The Group 8A Digital Nomad Program
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Caleb Siegel

“When you’re doing something you enjoy, it doesn’t feel like work.”

For those of us at Group 8A, a New York City-based digital marketing agency, this is our workplace mantra. From group work-outs to team dinners, and company retreats, we always have something cool to look forward to and be excited about. 

Don’t get me wrong, we work hard—really hard—but, for my part, I was ready to see just how far I could take this mantra. 

2020 was an unprecedented year for everyone and the Group 8A team was no exception. We found it was particularly challenging to abruptly switch from working in our New York City offices to working from home.

As someone who loves traveling, I was beginning to feel cooped up in my cramped New York apartment. There were only so many Echelon spin bike classes I could take!

Then, as the world started to open up, I had an idea: if we can work from anywhere in the world, why not start a “digital nomad program” to both expand my personal horizons and my professional abilities to positively impact my company?

So, I approached our CEO, Eric, with my idea.

“I’m thinking somewhere in the US for a week,” I said.

Eric responded immediately: “Why are you thinking so small?” 🤯

I pitched the idea to four of my fellow coworkers from diverse professional backgrounds: 


Ariel Benichou, Affiliate Marketing Analyst

Caleb Siegel (Me), Account Manager,

Joshua Deutsch, Paid Search Operator,

Max Kops, Influencer Outreach Liaison


And, just a few months later, the four of us found ourselves soaring over volcanos, waterfalls, rainbows, pristine beaches, and crystal-clear water to spend an entire month in the most beautiful place we ever laid eyes on: Hawaii.

Greeted by leis, hula dancers and the Aloha spirit, the inaugural class of the Group 8A Digital Nomad program was officially born.

 Digital Nomad Program_Hawaii_Montage

For our trip, we worked during the day and kept our New York City hours even though we were on Island Time. A usual work day for us was from 3am to 3pm though this gave us plenty of free time during the evenings and weekends to explore the islands.

When we landed on Thursday night, we set up our office in an Airbnb and then began exploring.

Our first order of business: Shark Diving

(We’d insert the most amazing video of us with the sharks, but we lost the GoPro, so you’ll need to use your imagination).

Our first Saturday together, we went to the gorgeous island of Kaui, where we sailed the world-renown Na Pali coast (and caught some Ono on the way), found a natural pool, Queen’s Bath, to swim in, and hiked the Grand Canyon of the Pacific, Waimea Canyon.

Grand Canyon of the Pacific, Waimea Canyon

During the work week, being a good Digital Nomad, Josh woke up at 2:30am every day for his morning marketing meetings. But, being a good Digital Nomad also meant sitting on our Lanai (Balcony) so he didn’t wake up the rest of us. I had client calls throughout the day from 5am – noon, which allowed me some peace and quiet for work while everyone else was winding down.

Of course, it wasn’t all work during the week. As soon as the day was done, we went on hikes to the iconic Diamond Head Crater, ATV’d through a ranch made famous by the Jurassic Park franchise, and ultimately hosted a virtual happy hour event with our coworkers to bring some Hawaiian spirit to New York.

Jurassic Park franchise

Our second weekend, we flew to the island of Maui to feast our eyes on the otherworldly craters, waterfalls, red sand beaches, and marine life—dolphins, whales, sea turtles, and Humuhumunukunukuapuaa. While we were hiking through a bamboo forest in Haleakala National Park, we met a couple who’d founded an e-commerce company and all jumped at the opportunity to learn more about their work and marketing needs. Later, we reflected on how this moment allowed us the opportunity to collectively help Group 8A in unique and inspiring ways. 

For me, the most memorable excursion was during our final weekend on the Big Island of Hawai’i. We took sailboats onto the pitch-black sea and then paddled out on surfboards that illuminated the midnight ocean waters. This light attracted plankton, which is a delicacy for Manta Rays, and attracted these gentle giants to swim within mere inches of us to feast. The small amount of fear we might have had being out on the still ocean with these 10-foot-long creatures beneath us was erased by the breathtaking feeling the experience created. It was then that I realized what the Digital Nomad program was all about—doing something that was a little bit unknown, a little bit scary but, ultimately, one that was inspiring and unforgettable.

Digital Nomad Program_Hawaii

As the trip was ending, we huddled together on the couch around one computer for a meeting with Eric to debrief about the trip. As Digital Nomads, we expected to discuss how much we appreciated the opportunity to have these awe-inspiring, once-in-a-lifetime experiences, but were shocked to find a large portion of the call being dedicated to the more mundane things we enjoyed doing together like going grocery shopping, making dinner, and, yes, even getting COVID tests. The conversation solidified the idea that working together in Hawaii and being able to again meet in-person allowed us a greater opportunity to come up with innovative, outside-of-the-box ideas we otherwise wouldn’t have been able to achieve if we were solely interacting over Zoom. For a month, we bonded as a team and formed relationships that would benefit us personally and professionally even after returning home.

Clearly, the Digital Nomad pilot program was a success and we remain grateful for Group 8A’s support in an endeavor that would have been otherwise impossible. We are incredibly excited for what the future holds for Group 8A as the company continues to develop new ways of forging professional and personal relationships, encouraging creativity, and embracing the lifestyle of the digital nomad.

Mahalo! 🤙