The Strength in Our Differences: Inside Caliber’s 2026 Chicago Off-site.

As a fully remote marketing and communications agency, we spend most of the year working together from across the country. Once a year, our off-site brings everyone into the same room. 

This year, that room was in Chicago.

Over a few days together, we had plenty of opportunities to learn more about what each of us brings to the team—and what happens when those different strengths, perspectives and personalities come together. We talked about collaboration, challenged ourselves to adapt when things didn’t go according to plan and made plenty of time to simply enjoy being in the same place.

The off-site actually started a day early for Caliber’s leadership team, who arrived in Chicago ahead of the full group for a day of in-person time together before everyone joined on Wednesday.

Beyond the screen

After arriving and settling into the Kimpton Gray in downtown Chicago, we kicked off the offsite with a welcome reception and dinner.

In true Caliber fashion, even the cocktail menu had a personalized touch, with signature drinks aptly named “Talking Point” and “On the Record.” (If you’ve joined us for Fin & Juice at Money20/20 — or one of our other conference happy hours — you know a themed menu is something of a Caliber staple.) Between dinner, catching up with familiar faces and meeting colleagues in person for the first time, there was plenty to talk about. 

CEO Grace Keith Rodriguez continued an offsite tradition with an original poem welcoming the team to Chicago. Her message invited us to look around the room at the team we’ve become since our Nashville offsite — and how easy it can be to miss that progress when we usually see one another through a screen.

She invited us to pay attention to the ways people have found their voices, stretched themselves and brought their individual strengths to the team. The paths to Caliber may have looked different, but everyone in the room has helped shape the team we are today.

That idea carried into Thursday morning, when our learning sessions turned the focus toward how we show up for one another and the different experiences, strengths and perspectives each person brings.

After an icebreaker, we broke into small groups to reflect on teamwork and collaboration. We considered questions like: When did you feel like a great teammate? When did you let your team down? What’s your biggest strength, and where do you still need support? What does being part of a team actually mean to you?

As we compared answers, we started to see another side of the strengths we rely on most: lean on them too heavily and they can just as easily get in the way. Independence can make it harder to ask for help. An eye for detail can turn into a pursuit of perfection. A go-getter mentality can lead to taking on too much.

Being a strong teammate means having enough self-awareness to recognize those tendencies and knowing when to lean into your strengths, when to adjust and when to rely on the people around you.

Building something new

That same morning, we got an early look at a new project the Caliber team has been developing behind the scenes.

Listening closely to our partners is an important part of how we continue to evolve. The questions they’re asking, combined with what our teams are seeing across their work, can point to new ways to solve problems, improve our approach and deliver more value. 

Sometimes that means refining an existing process. Other times, it becomes the starting point for something entirely new. Getting there often takes testing, feedback and iteration along the way.

We’re keeping this one under wraps for just a little bit longer. But let’s just say we’ve been thinking a lot about measurement.

The art of adapting

Each year, our offsite includes a team activity that gets us out of the conference room and gives us a chance to connect in a different way.  This year, that meant trading the 14th-floor conference room for spray cans and heading to W.I.P. Studio for a street art session that ended up echoing many of the themes we had been discussing that morning.

Before anyone touched the canvas, we got a crash course in street art. Our instructor walked us through different techniques, showed us how to work with the paint and gave us a few pointers for when the result didn’t quite match the idea in our heads. 

Then it was our turn.

From the start, there was an element of letting go: you could have a vision, but once the paint hit the canvas, you had to be willing to work with what was actually there.

The entire team was given one giant canvas to work on together, with no assigned sections or carefully mapped-out plan for who would do what. People found a place and started adding their own touches: different shades of blue, orange and pinks bleeding into each other, punctuated by our favorite things, inside jokes and nods to the places we call home.

It didn’t take long to understand why our instructor encouraged us to let go of the picture in our heads. Colors overlapped, new details appeared around what others had already painted and the piece kept changing with every person who stepped up to it.

When something didn’t turn out quite as planned, we had to work with what was there: adapt, build from it and see where it could go.

It also took more patience than anyone expected. Sometimes progress meant adding something. Other times, it meant standing back, waiting for a layer to dry or giving someone else room to contribute.

Eventually, all of those individual contributions became one eclectic piece with three words stretching across the middle:

We Are Caliber.

Every individual burst of color was still visible inside it.

That felt fitting. The goal had never been to make everyone paint the same way. The piece worked because everyone brought something different, responded to what others had already created and allowed the final result to become something none of us would have designed on our own.

The time in between

For a remote team, some of the most valuable time at an offsite happens between the scheduled sessions. It’s a chance to get to know the people behind the screens and group chats a little better.

Thursday evening gave us plenty of that. We headed to Navy Pier for a dinner cruise with views of the Chicago skyline at sunset, good food — and Caliber well-represented on the dance floor. Our competitive side came out later at Lucky Strike Chicago, where bowling and arcade games quickly became more than casual entertainment.

Those hours gave earlier conversations room to continue, but they also made space for entirely new ones. The person you usually see in a square on your screen was suddenly cheering on your bowling attempt, pulling you onto the dance floor or simply sitting across from you at dinner.

And for colleagues attending their first Caliber offsite, it was especially fun to see how quickly they settled in.

Closing out Chicago

Our final morning in Chicago included a pair of annual offsite traditions, before people started heading to the airport.

Each year, our Ask Me Anything gives team members the opportunity to anonymously submit questions to Caliber’s leadership and hear candid responses. This year, Grace, founder Harvey Hudes and COO Kristie Galvani took the hot seat, with Managing Directors Ryan Hall and Scott Paer leading the conversation. 

Then came a live edition of Pump Up My Pitch, a monthly virtual session where team members bring ideas, pitches or challenges to the group for feedback and support. For the offsite, we gave it a different spin: each group received a different scenario and had to build a pitch from scratch before presenting it for judging.

The teams got creative with their approaches, too — at one point, a team member even called one of the judges mid-pitch to make the scenario feel a little more like the real thing. Along the way, teammates shared ideas, challenged angles and worked through the story together, with a little friendly competition added to the mix. 

It was a fitting way to put one of Caliber’s defining qualities into practice: collaboration. Asked to choose the word that best describes Caliber’s work environment as part of Inc.’s 2026 Best Workplaces recognition, “collaborative” was the top response.

Before wrapping up, we turned the focus to the people behind the work with our annual Team Awards, celebrating colleagues and teams whose contributions have made a meaningful impact at Caliber, along with the milestones of team members who have now been with us for three, four and five years.

What we’re taking back with us

One image from the week seemed to capture much of what we had talked about: our mural.

We walked up to one blank canvas with different ideas, different styles and different things they wanted to add. The end result was something none of us would have envisioned on our own, and that’s precisely what made it ours.

The same is true of Caliber.

We each bring our own experiences, strengths and ways of thinking to the table. We don’t have to see things the same way to create something we’re all proud to put our name on.

Chicago gave us a chance to see more of those sides of one another than our usual workdays allow. And when we stepped back at the end, there was a lot to celebrate.

Our mural said it best: We Are Caliber.

Interested in joining the Caliber team? Check out our Career page to find your next role.