Insights From The Outside: Reuniting Together

I had zero intention of coming to a credit union. But when I interviewed, I felt something I hadn’t felt in a long time — sincerity.

Dylan Wyatt spent nearly two decades in corporate banking before taking a leap of faith into credit union culture.

As chief information and strategy officer at Together Credit Union ($2.5B, St. Louis, MO), he now leads a 40-person team and has used that platform to help build and sustain a forward-thinking culture rooted in collaboration, care, and innovation.

He didn’t come alone. Wyatt brought in longtime colleagues Jonathan Roberts and Siomara “Sio” Galaviz Herrera, both of whom he had worked with at Santander Bank in past lives on —  as they somewhat jokingly call it — the dark side.

Roberts joined Together in 2024 as vice president of strategy and DEIB (diversity, equity, inclusion, and belonging) after several years as a researcher and strategist at Forrester. Herrera, Together’s director of digital and AI, came aboard in 2022 after a decade in financial services.

Their reunion brought fresh energy to the credit union’s leadership team and a corporate sensibility that’s finding a new purpose in a member-first environment. Although their roots are in banking and consulting, the trio says they’ve found more than just a new employer — they’ve found alignment.

Each brought a healthy skepticism with them but say they have since bought into the credit union difference. Along the way, they’ve redefined how a remote, cross-country team can function, built trust across the org chart, and learned to lead with both urgency and empathy.

How did the three of you end up together at Together Credit Union?

Jonathan Roberts: We all go way back to our days at Santander Bank in Boston. Dylan and I sat next to each other at one point, and I first met Sio at a Northeastern University career fair — I actually recruited her for an extended internship.

Over the years, we stayed in touch as our careers evolved. I eventually became an analyst at Forrester, but I stayed connected to Dylan, even doing keynotes at Together’s leadership conferences before joining.

Dylan Wyatt: Bringing people into a new space is never just a job offer — it’s a trust exercise. I’d seen how both Jonathan and Sio worked, how they solved problems, how they communicated.

When the right roles opened up, I knew they’d be a good fit, but I didn’t rush them. They both came in after taking their time to understand the mission and culture. We weren’t just rebuilding an old team — we were reshaping how we work in a new context.

How has your experience as recovering bankers — as you put it — shaped your perspective on the credit union world?

Siomara Galaviz Herrera: I like to say I’m fully recovered. I came in skeptical, for sure, but the more I talked to people in this space, the more I saw alignment between personal values and organizational values.

I was floored by the openness — not just within Together, but across the industry. Credit unions actually call each other to share solutions. That spirit of collaboration wasn’t something I’d seen much of in the for-profit world.

Jonathan Roberts: We each had different reasons for leaving the corporate grind, but we also brought some muscle memory — strategy, speed, urgency. That stuff has value here when applied the right way. The key is adapting it to a culture that genuinely prioritizes members over margin. You’ve got to recalibrate without losing what made you effective.

CreditUnions.com’s “Insights From The Outside” series shares the experience and perspectives of newcomers to the credit union industry. Read more today
How do you make the on-site/remote/hybrid dynamic work, especially in an industry that’s traditionally more in-person?

Dylan Wyatt: When I got here, remote work was basically non-existent. Now, my team of about 40 people is about 40% remote. We’ve created intentional moments for connection — off-site, team-building events, a group art project that still hangs in our HQ. We’ve proven that if you design for connection, geography isn’t a barrier. And without that approach, we wouldn’t have Sio or Jonathan on the team.

Jonathan Roberts: I split my time between St. Louis and Nashville and Sio is in New York. But even those of us based in St. Louis operate on a hybrid model, so remote collaboration isn’t just for out-of-towners. It’s become part of our muscle memory.

Dylan’s also been great about making space for bonding that’s not just performative. That includes quarterly gatherings and plenty of moments to just be human together. It’s not remote versus in-person — it’s intentional versus accidental culture-building.

How is Together Credit Union’s internal culture different from the member-facing culture? How do those two interact?

Jonathan Roberts: They’re connected by purpose. Internally, there’s a shared language around why we’re here and who we’re serving. That clarity creates cohesion across departments and roles. It’s not just a branding exercise — it’s real alignment. Our internal work around DEIB, for instance, reflects the same empathy and intentionality we want to bring to members.

Siomara Galaviz Herrera: What stands out is how deeply people care, even behind the scenes. The values that show up in member service — empathy, transparency, accessibility — also drive internal decisions. There’s a feedback loop between how we lead internally and how we show up externally. And that makes it easier to make decisions that benefit both teams and members.

We each had different reasons for leaving the corporate grind, but we also brought some muscle memory — strategy, speed, urgency. That stuff has value here when applied the right way. The key is adapting it to a culture that genuinely prioritizes members over margin. You’ve got to recalibrate without losing what made you effective.

What did you bring from your corporate careers that’s helped elevate your work at Together?

Dylan Wyatt: Two things: a sense of urgency and accountability. We’re not running to meet shareholder demands, but that doesn’t mean we shouldn’t aim high. There’s a divide in our industry between those who want to perform and those who don’t — and I want to be on the high-performing side. My goal is to set a high bar while staying true to the mission.

Jonathan Roberts: I think our corporate backgrounds help us cut through the noise. We skip the theater of work — the over-polished presentations and unnecessary meetings. There’s a shorthand between us that lets us go straight to execution. That makes room for real conversations, honest feedback, and better outcomes. Familiarity isn’t just convenient — it’s a strategic advantage.

What surprised you most after joining the credit union space?

Jonathan Roberts: How real the mission is. I’ve worked with Fortune 1000 companies that talked a big game about customer centricity, but the profit motive always won. Here, when we’re in a room making decisions, member impact actually drives the outcome. It’s not just talk — it’s practice. That’s rare, and it’s refreshing.

Dylan Wyatt: Same. I had zero intention of coming to a credit union. But when I interviewed, I felt something I hadn’t felt in a long time — sincerity. People here care deeply about their coworkers and their members. And that mindset shows up in small things, like how we treat one person’s problem with the same urgency we’d give to a systemwide issue. That kind of care scales in a different way.

What advice do you have for someone coming to a credit union from a corporate background?

Jonathan Roberts: Check your ego at the door. In corporate settings, it’s often about being the smartest person in the room. Here, it’s about being the most aligned, the most collaborative, the most mission-focused. Don’t assume your old playbook will work. Be humble, be curious, and learn how to succeed in a culture that values purpose over polish.

Siomara Galaviz Herrera: Start talking to people in the industry. The openness here is real. Go to a credit union event, strike up conversations, and listen. If you lead with curiosity instead of credentials, you’ll learn a lot. And if you care about meaningful work, there’s a place for you here.

These interviews have been edited and condensed.

Make Your Leadership Development A Priority The first step toward fulfilling your promise to members is building a strong team of leaders, and Callahan can help with that. Callahan’s Executive Roundtables give C-suite executives the chance to talk with and learn from like-minded leaders about industry hot topics, roadblocks, strategies, lessons learned, and more. Give your leaders the gift of inspiration through collaboration. Read more today.