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A part-time college job that was never supposed to last. More than 30 years later, Stephanie Kaster is still in the industry, having gone from certifying print vendors during the shift from manual print to electronic data transmission to serving as Chief Revenue Officer at CompuMail Inc. She has also volunteered as a search and rescue diver for a county sheriff’s office, which means that when she says she enjoys untangling complex challenges, she is not speaking figuratively. Read on to learn more about Stephanie, including the leader who told her to act like she owned the company, the event venue she would run in another life, and why her husband says her real superpower is remembering every conversation they have ever had.
Name: Stephanie Kaster
Job Title: Chief Revenue Officer
Company: CompuMail Inc.
Length of time at current company: 10 years
Length of time in industry: 30 years
How did you get your start 30 yearsin the industry?
While attending college, I was looking for a job to help supplement my income and joined Columbia Ultimate, a collection software company. At the time, the industry was beginning a major shift from manual print processes to the electronic transmission of variable data directly from collection software to print and mail providers. My role was to certify print vendors, onboard clients, configure their systems to generate production files, and ensure the quality and accuracy of the data being transmitted. It gave me a front row seat to one of the industry’s biggest technology transitions and, just as importantly, a firsthand understanding of the operational, compliance, and communication challenges that organizations in the ARM industry face every day.
What I expected to be a temporary college job turned into a career spanning more than 30 years. Along the way, I’ve had the opportunity to work with incredible people, witness remarkable innovation, and help organizations navigate the ever-changing landscape of customer communications. Looking back, I’m grateful that a job I took to pay for college ultimately led me to an industry and a career that I continue to enjoy.
What is your career highlight so far?
It’s difficult to point to a single career highlight because, for me, success has never been defined by one sale or one title. I’m proud to have helped a small company grow into one of the largest providers in our industry, to have joined one of my vendors and contributed to its growth into what is now RevSpring, and to have earned opportunities to work with some of the nation’s largest financial institutions, healthcare organizations, and the third-largest cable provider in the country.
But if I had to choose one highlight, it would be the relationships I’ve built over the years. I’ve always believed that your reputation is your most valuable asset. By leading with honesty, keeping my word, and focusing on what’s best for my clients, even when it wasn’t the easiest path, I’ve built relationships that have lasted decades. Many clients, partners, and even competitors have become trusted friends. Knowing that people continue to call because they trust my judgment is something I value far more than any single contract or achievement.
When or how are you most productive?
I’m most productive during the quiet hours either very early in the morning or late in the evening—when I have uninterrupted time to think strategically. I do my best work when I’m trusted with the freedom to execute and focus on outcomes. I enjoy untangling complex challenges, especially when there isn’t an obvious answer. I’ve learned that the best solutions usually come from listening more than talking, asking good questions, and working with others. The variety of the work is what keeps me energized because no two days are ever the same.
Which industry professional do you admire most?
There really isn’t a way to answer that with just one name. I’ve been fortunate to learn from a few exceptional professionals throughout my career, and I simply can’t single out one individual. Some taught me the technical side of our business, others showed me how to lead with integrity, and many challenged me to think differently. If there’s one quality I admire most, it’s a willingness to share knowledge, invest in others, and help them succeed. I’ve been fortunate to have had these mentors who have done exactly that, and each has played an important role in shaping my industry experience. The greatest compliment I can give them is to try and emulate those qualities.
What is one thing you do better than everyone else?
I don’t know that I do any one thing better than everyone else. I try to be fully present—whether I’m listening to a client, supporting a colleague, spending time with family, or volunteering in my community. I’ve found that taking the time to understand people, ask questions, and appreciate different perspectives lead to better decisions and stronger relationships. My husband might tell you my real superpower is remembering every conversation we’ve ever had… especially the parts where he was wrong.
What do you like most about this industry?
The people! I’ve had the privilege of building relationships throughout this industry that span decades, and many colleagues, clients, and even competitors have become friends. I enjoy that our industry is constantly evolving, requiring us to learn, adapt, and collaborate to solve new challenges.
What is one thing you wish you could change about this industry?
I hope we continue to embrace innovation while finding ways to simplify the ever-changing regulatory landscape. Compliance is fundamental to our industry, and consumer protection should always remain a priority. At the same time, clearer and more consistent regulations would allow organizations to spend less time interpreting requirements and more time delivering secure, effective solutions for the businesses and consumers we serve. Since credit and debt touch virtually every industry, improving that balance benefits everyone.
If you weren’t in this industry, what would you be doing?
Something very different. I’d probably own an event venue and planning business. I’ve always enjoyed decorating and planning the layout of an event, but I also like coordinating all the moving pieces behind the scenes. There’s something satisfying about seeing an idea come together exactly as you imagined it.
If money weren’t a consideration, my second choice would be an animal rescue property. I’d love to provide a safe place for animals in need, help them recover, and find them loving homes. I can’t think of a more rewarding way to spend my time.
Describe a typical work day.
I’m not convinced there is such a thing as a “typical” workday! I wear a lot of different hats, so one day might be focused on strategy and client meetings, while the next is all about solving problems, mentoring, collaborating on new ideas, or working on business development. Many days are also spent traveling to client meetings, conferences, or working our booth at industry events. The one constant is that no two days are ever the same—and that’s exactly what keeps the job interesting.
What is your guilty pleasure?
Give me a day to sleep in, wear comfortable clothes, snack all day, and binge-watch murder mysteries or Dateline, and I’m perfectly content. Some people may find it a little concerning that I can relax while watching crime shows… but I promise I’m just fascinated by the mystery, not taking notes!
What is the best advice you have ever received?
One of the best leaders I have ever worked for told me to approach every decision as if I owned the company. He trusted me to make decisions with that mindset, and that confidence shaped how I lead today. He also taught me that it’s okay to say “no.” Not every opportunity is the right opportunity, and protecting your time, your team, and your values is just as important as saying “yes.”
What are you currently reading?
I’m currently reading “The Pretender” by Jo Harkin. I read widely across genres—from historical fiction and mysteries to biographies and business books—so my next read is usually something completely different from the last.
What is one fact you’d like everyone in the industry to know about you?
Many people don’t know that I was a volunteer diver for The Umatilla County Sheriff’s Underwater Search and Rescue team. It was one of the most challenging experiences of my life and gave me an even greater appreciation for teamwork, preparation, and serving others. I eventually had to step away after a serious eardrum injury, but I’ll always be grateful for the experience.
Who would you like to see answer these questions?
Tim Stapleford, Spring Oaks Capital
