Article Summary: This interview marks The Fletcher Group’s 20-year journey advising fintech and payments leaders through regulatory change, category creation, and industry maturation. Founder Jennifer Tramontana reflects on what has endured—trust, clarity, and consistency—and what has evolved in how financial services brands build credibility. The piece offers practical insight for fintech and payments executives focused on long-term reputation, client trust, and sustainable growth.
In 2026, The Fletcher Group marks twenty years of advising and supporting some of the most influential brands in fintech and payments. Over that period, the industry itself has transformed—from an emerging, loosely defined category into a tightly regulated, globally interconnected ecosystem shaping how money moves.
Founded in the fall of 2005, The Fletcher Group entered the space before “fintech” was common industry shorthand. President and Founder Jennifer Tramontana helped guide the agency through the early days of alternative finance, the rise of prepaid and embedded financial services, and the growing scrutiny that accompanies innovation involving money. Along the way, the firm built a reputation for having a deep understanding of this complex and technical industry, helping big and emerging brands be known across every important channel.
As The Fletcher Group reflects on two decades of success, Tramontana shares how the integrated PR and content marketing agency found its footing in payments, what has and hasn’t changed about building credibility in financial services, and the principles that have sustained long-term client and employee relationships.
Q. When you started The Fletcher Group twenty years ago, fintech didn’t exist as a category. How did The Fletcher Group start, and how did it find its way into the fintech and payments space?
Jennifer Tramontana: Like many successful ventures, it started with luck and then capitalizing on opportunity. Shortly after I launched The Fletcher Group, a referral partner introduced me to a trade association in the alternative finance industry. They needed help developing their brand, positioning and messaging for what was essentially a new financial services sector.
What I didn’t realize at the time was that I had stepped into the early formation of what would become the fintech industry. I was suddenly working alongside companies like GreenDot, Blackhawk Network, Galileo Financial Technologies, MetaBank (now Pathward), Citi, and the card networks that helped shape modern fintech. That experience gave me a front-row seat to the communications challenges and regulatory considerations that come with payments and financial services innovation. From there, I was hooked—and we built our company around this dynamic industry.
Q. Across two decades of radical evolution in the industry, what has changed most in how fintech companies need to communicate credibility to customers, partners, and investors—and what hasn’t changed at all?
JT: What will always matter is communicating clearly, precisely, and in a way that connects with your audience. Good storytelling never goes out of style. It works because a clear message, delivered by an engaging and credible brand or spokesperson, builds understanding and trust.
When you’re dealing with people’s money, nothing matters if you can’t earn that trust. That happens through consistency—saying what you will do and doing what you say, repeatedly, from every person who speaks on behalf of the brand. A viral moment might grab attention, but trust is built by showing up consistently in places people already rely on and respect.
Another thing that hasn’t changed in all these years is the criticality of being able to simplify complex topics and themes. This is an increasingly sophisticated space, and it takes a nuanced understanding of the details to make sure differentiation is clearly articulated.
What has changed significantly is how people want to consume information. The channels, formats, and expectations have evolved dramatically, and companies need to meet audiences where they are without sacrificing clarity or credibility.
For us, that shift has meant continually raising the bar on how PR and marketing are practiced. We’ve had to frequently adapt our strategies, sharpen our storytelling, and hold ourselves to higher standards as audience and journalist expectations increase. We’re never satisfied with the status quo — our work is built through close collaboration, rigorous editorial discussion, and a relentless focus on what will actually drive results. At every stage, accountability to our clients’ success is non-negotiable.
Q. Looking back, what moments—client wins, industry inflection points, or even missteps—most shaped how The Fletcher Group defines success in this space?
JT: Some of the most defining moments for us weren’t flashy wins, but inflection points where clients trusted us during periods of real pressure—regulatory scrutiny, product pivots, leadership transitions, or moments when the industry itself was changing faster than anyone expected. Being invited into those conversations—and staying there year after year—reshaped how we measured success.
We’ve also learned a lot from the opportunities we didn’t win. There were RFPs we stretched for, moments when we pushed ourselves beyond our comfort zone, and times we had to be honest about what we were—and weren’t—the right fit for. Losing some of those taught us that growth at any cost isn’t growth at all. The work is best when it’s grounded in mutual trust and shared expectations.
Over time, that clarified something very simple for me: success is retention—of our people and our clients. If talented, experienced professionals choose to stay, and if clients continue to partner with us through multiple chapters of their business, that’s the strongest signal that we’re doing our job well.
The relationships we’ve developed truly matter. Many clients have become close friends. We’ve shared late nights, celebrations, setbacks, and life milestones. But underneath all of that is consistency—showing up with integrity, doing the work carefully, and earning trust over and over again. In an industry built on confidence and accountability, that’s the kind of success that lasts.
Q. The Fletcher Group has been a fully remote agency for 20 years. What are the advantages of having a team spread out across the United States and Canada, and how have you kept the team engaged?
JT: Being fully remote from the beginning allowed us to build the company around outcomes rather than a location. When we launched in 2005, we intentionally set out to create an alternative to the traditional PR agency model. I had seen too many talented, ambitious PR professionals struggle to stay in the industry once rigid structures collided with real life, particularly after becoming parents.
Building the firm with a remote model gave us access to a much broader talent pool across the U.S. and Canada and allowed people to work in ways that support balance without compromising performance. We’ve been able to assemble a senior team that includes former journalists, folks with large-agency experience, and professionals who have spent significant time on the client side.
We hire people who are highly collaborative and self-driven, who push to raise the bar and continually share new ideas and approaches. That culture—combined with clear accountability and trust—has been central to our ability to keep the team engaged, deliver strong outcomes for clients, and sustain long-term relationships on both sides.
At the same time, remote work doesn’t sustain itself without intention. We’ve learned that while digital tools keep us connected day to day, they don’t fully replace the value of human connection. That’s why we invest in a mix of optional virtual engagement and meaningful in-person moments, like our annual retreat and smaller gatherings throughout the year. Not everyone wants the same level of interaction, so choice matters. When people feel trusted to manage their work and their engagement in a way that fits them, they stay connected, productive, and invested over time.
That longevity benefits our clients more than anything. The relationships are deeper and stronger, which ultimately leads to smarter and more efficient work.
Q. As you reflect on twenty years, what advice would you give today’s PR and marketing founders about building an organization that can not only survive the dynamic industry, but grow steadily for such a long period?
JT: At the heart of our work is client service – Don’t build a company to sell it. If that’s your goal, you probably aren’t putting service first. If you make strong relationships with your clients, they will carry you wherever they go next.
Focus on long-term, organic growth that’s sustainable and doesn’t burn out your most important asset: your people. Hire for culture fit first. Look for smart people who care deeply about their careers but also value other parts of their lives. That balance creates maturity, and it’s what allows teams to grow together and weather challenges over time.
After twenty years in fintech and payments, The Fletcher Group’s story reflects the value of consistency, expertise, and long-term thinking in an industry defined by constant change. As financial services continue to evolve, the fundamentals of clear communication and experienced counsel remain central to building durable brands.
For fintech and payments leaders navigating what comes next, partnering with advisors who understand both innovation and accountability can make the difference between short-term momentum and lasting impact.
Ready to capitalize on The Fletcher Group’s two decades of award-winning work in fintech and payments communications? Reach out today.
