Above: Me with Jennie Fisher at The Cannata Report’s 11th Annual Elite Partner Dinner this past May at private club, Tiro a Segno, in New York, NY.
Following her retirement announcement at the Executive Connection Summit, Jennie Fisher, group president, Office Technology at GreatAmerica Financial Services, and I had the opportunity to converse about leadership, culture, talent development, and the evolution of the industry over the course of her more than three decades in the dealer channel.
As the majority of senior executives, thought-leaders, and dealers who have worked with and developed relationships with Jennie over the course of her highly impactful career would likely agree, her experience and perspectives are thought-provoking and relevant. In my opinion, the manner in which she authentically expresses her viewpoints are specific and direct, while thoughtful, humble, and respectful of others.
In the first installment of this discussion (the first of two), Fisher discusses the values that shaped GreatAmerica’s growth, the importance of developing people and future leaders, and how the role of women in the industry has evolved throughout her career. I hope that you enjoy reading through our conversation as much as I enjoyed having it with her.
CJ: Jennie, congratulations on your upcoming retirement from GreatAmerica. After more than three decades at GreatAmerica and many years of leadership within the industry, what leadership philosophies or practices do you believe most contributed to GreatAmerica’s long-standing success and reputation among dealers?
“Think about all the challenges we’ve been through in the 33 years we’ve been in business: the good times, tough markets, industry changes, the floods, the pandemic and many other challenges. Dealers saw and felt that consistency that GreatAmerica brought to the market, and they rewarded that with long-term loyalty.”
– Jennie Fisher –
JF: If I step back, I’d say probably the biggest thing was discipline around who we are and how we show up—and never letting that slip, especially as we grew. From the very beginning, with Tony Golobic’s [executive chairman of GreatAmerica Financial Services Corporation] leadership, we were clear that values, integrity, and relationships weren’t just slogans; they were operating principles.
We talked a lot internally about earning trust every single day. Our customers want partners and organizations that understand their business, understand strategically where they’re going, and focus on how they can help drive continued growth and success. That has always been a mantra at GreatAmerica.
There was also a very consistent desire to win—showing up every day, every month, every year in the same fashion. Think about all the challenges we’ve been through in the 33 years we’ve been in business: the good times, tough markets, industry changes, the floods, the pandemic and many other challenges . Dealers saw and felt that consistency that GreatAmerica brought to the market, and they rewarded that with long-term loyalty.
The Cannata Report recognized and featured Jennie Fisher (center) as one of three Woman Influencers in our 3rd Annual Women Influencerissue of 12 to date.
CJ: GreatAmerica has long stood out for the number of women in leadership and sales roles. How did you help build that culture, and why was it important?
JF: Honestly, having women in leading roles was not really a strategy in the traditional sense. It was about talent and opportunity. If you want a strong organization, you hire the best people—whether they’re male or female—and create an environment where they can learn, grow, and become passionate and dedicated to the organization. That’s what we truly believe.
I am extremely proud that we have so many talented women in sales and leadership. That makes me very proud, especially considering the male-dominated industry that we serve.
I believe women bring an incredible perspective, relationship depth, and thoughtfulness that creates diversity in thinking and makes teams stronger and conversations better.
“I’m very proud that GreatAmerica built that culture from the start—not as an initiative, but as a natural outcome of who we are—and that we’ve continued to drive and enhance it as we move forward.”
– Jennie Fisher –
I’m very proud that GreatAmerica built that culture from the start—not as an initiative, but as a natural outcome of who we are—and that we’ve continued to drive and enhance it as we move forward.
As far as building the sales organization, early on we were very intentional about developing people based on capability and character, not profile. As my career evolved, I became more aware of the importance of sponsorship—making sure individuals had access to colleagues in different roles, visibility inside and outside the organization, and leadership development, not just mentorship.
Today, we have a much more sophisticated sales operating system that includes in-depth training, identified development opportunities for advancement, and strong mentoring and guidance. It integrates the relationship-based selling we’ve always believed in with disciplined planning, strategic thinking, and data-informed decision-making supported by the tools and resources people need to be successful.
We also developed a Sales Leadership Academy during the pandemic that has become a core component of our sales operating system and leadership development process. We’ve already seen multiple participants move into leadership roles, which I consider a real success.
The Cannata Report featured Jennie Fisher up close in 2016’s 3rd Annual Women Influencers Issue.
CC: Attracting new talent has become one of the industry’s biggest challenges. How is GreatAmerica responding, and what broader challenges do you believe dealers face when recruiting the next generation?
JF: Acquiring talent has been a challenge everywhere—in our market and markets across the country and around the world. As technology continues to evolve, the talent needed is changing and evolving as well. It looks very different from what it did twenty or thirty years ago.
At GreatAmerica, we’ve responded by doubling down on our culture, our development programs, and clarity around career paths—communicating from the beginning so people understand the opportunity they have and what they’re coming into.
People want to know they’re growing and developing, that their work matters, and that they’re part of something bigger. Communication and marketing around that are critically important.
“For dealers, I think the challenge is partly perception. This industry is not viewed as a growth destination for new talent despite its evolution into advanced services. However, many dealerships are far more advanced than the market realizes, but they just don’t always tell the story well enough.”
– Jennie Fisher –
We’re also revising our benefits to better attract younger generations that are looking for more tech-savvy organizations and more flexibility around work-life balance. For example, after conducting our employee survey, we introduced expanded maternity and paternity leave benefits. We increased the value of maternity leave and expanded paternity leave from one week to a full month.
For dealers, I think the challenge is partly perception. This industry is not viewed as a growth destination for new talent despite its evolution into advanced services. However, many dealerships are far more advanced than the market realizes, but they just don’t always tell the story well enough.
If dealers did a better job presenting the value they bring to customers and the market, people would be much more excited about joining these organizations.
The Cannata Report featured Jennie Fisher with Carol Cannata in 2016’s 3rd Annual Women influencers Issue.
CJ: How have you seen the role of women in the office technology industry evolve since the beginning of your career?
JF: It looks very different today than it did when I started in the industry more than thirty-five years ago.
Twenty or thirty years ago, women in this industry had a limited presence without power. They were significantly underrepresented in visible leadership roles. Many women contributed meaningfully in finance, sales, administration, marketing, and support functions, but few held executive positions or had a prominent voice in industry conversations.
Cultural norms probably helped shape those expectations. Many women entered the industry while balancing young families during a time when workplace flexibility simply didn’t exist the way it does today.
“Today, women are no longer just participating in the industry—they’re leading. They’re leading conversations, shaping strategy, collaborating, sharing knowledge, and influencing the future of the channel in ways they never had before.”
– Jennie Fisher –
Today, women are much more confident in their roles. They understand the value they bring to organizations and the voice they have. It’s incredible to see how women in office technology have evolved in meaningful and encouraging ways.
Today, women are no longer just participating in the industry—they’re leading. They’re leading conversations, shaping strategy, collaborating, sharing knowledge, and influencing the future of the channel in ways they never had before.
You’re also seeing more women in leadership roles, which is exciting to me. I believe the industry has embraced the value of relationship-driven, collaborative, servant-style leadership, and that’s exactly what this industry needs to continue evolving.
Mike Stramaglio, CEO, Stramaglio Consulting, presented Jennie Fisher with an award for Extraordinary Contributions & Leadership at the Executive Connection Summit this past February on behalf of the ECS team.
CJ: As you prepare for retirement, are there any final thoughts you’d like to share about GreatAmerica, the industry, or the relationships you’ve built throughout your career?
JF: While I’m retiring from day-to-day responsibilities, I’m not stepping away from the industry or the relationships that matter so much to me.
I’ll continue supporting connections and cheering on the next generation of leaders who will carry this industry forward.
If I had to leave one message, it would be that this industry has always been resilient because it’s built on service, relationships, and adaptability. The hardware will continue to change. Offerings and business models will continue evolving.
“What I value most [about my experience with GreatAmerica] is not the transactions or titles—it’s the people. This industry has always been about relationships, showing up, doing what’s right, and helping one another succeed over the long term. That’s what I’m going to miss the most.”
– Jennie Fisher –
But the need for trusted partners who help customers run better businesses will only grow. Personally, I find myself reflecting with deep gratitude on the relationships that shaped my career and, in many ways, shaped who I am today.
For more than three decades, it’s been a privilege to work alongside industry partners, peers, and especially dealer organizations. We’ve learned together, solved challenges together, celebrated successes together, and navigated change together with trust and mutual respect.
What I value most [about my experience at GreatAmerica] is not the transactions or titles—it’s the people. This industry has always been about relationships, showing up, doing what’s right, and helping one another succeed over the long term. That’s what I’m going to miss the most.
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Jennie Fisher’s last day in her current full-time role at GreatAmerica and in the office technology industry is Tuesday, June 30. In our next installment (Part 2), which launches next Tuesday, Fisher speaks to her future involvement with GreatAmerica and the office technology industry along with other personal plans, among other pertinent business topics.
Me with Jennie Fisher as I welcomed her back home on the Patriot Pack‘s ride’s final stop at GreatAmerica’s headquarters in Cedar Rapids during the summer of 2023.
