How Listening Became a Career Strategy: Lessons from Nonprofit Leader Ashley Diersch
by Ryan Brown
Careers in nonprofit fundraising and communications rarely follow a straight line. More often, they evolve through experience, reflection, and a willingness to pivot when something doesn’t fit. That’s what makes Ashley’s journey—from a high school movie theater job to Chief Advancement Officer at Paws With A Cause—a useful blueprint for anyone building a career rooted in purpose and impact.
The Unexpected Value of a First Job
Before we talked about Ashley’s career in communications and fundraising, we took a trip down memory lane to her high school days. Her high school job was at a movie theater in Southgate, Michigan, where she spent three years selling tickets, working concessions, and cleaning theaters.
It may sound like a typical high school job, but it laid the groundwork for everything that followed. She learned customer service, how to multitask under pressure, and how to navigate real-time interactions with people—skills that translate directly into careers in nonprofit development and communications.
Realizing the “Right” Path Isn’t Always Right
At Central Michigan University, Ashley initially pursued physical therapy, a path that made sense given her background as a competitive figure skater. But over time, she realized it didn’t align with her personality or how she wanted to make an impact.
Instead of forcing it, she changed direction.
That decision didn’t come with a detailed plan. It came from being open to new possibilities. A conversation with a college advisor introduced her to fundraising as a career—one that combined communication, relationship-building, and meaningful impact.
Breaking Into Nonprofit Fundraising
Ashley’s first professional role at Special Olympics Michigan gave her hands-on experience in nonprofit fundraising, corporate partnerships, and event planning. She worked on large-scale events like the icy and iconic “Polar Plunges,” which required more than logistics.
Success depended on understanding what motivates people and how to connect them to a cause. Convincing someone to jump into freezing water isn’t about the activity—it’s about how invested they feel in the mission behind it.
Why Listening Is the Core of Fundraising
Fundraising is often viewed as asking for money. In reality, it’s about understanding people.
Ashley’s approach is simple: if you’ve done the listening upfront, the ask becomes the easiest part. By the time you make it, you already know what someone cares about and how they want to contribute.
That mindset applies well beyond fundraising. In communications and marketing, the most effective strategies are built on audience insight, not assumptions.
Growing from Execution to Strategy
After Special Olympics Michigan, Ashley spent nearly a decade at Kids’ Food Basket, where she expanded into more strategic work. She became involved in long-term planning, forecasting, and capital campaigns—shifting from executing initiatives to shaping them.
This transition is a key inflection point in many careers. It requires thinking beyond immediate tasks and focusing on long-term outcomes, aligning day-to-day work with broader organizational goals.
The Value of Stepping Back
Before taking her current role, Ashley made a decision that’s increasingly rare: she took a three-month sabbatical.
That time gave her space to reflect on what she actually wanted in her next role—not just the title, but the mission, structure, and environment. By the time she re-entered the job market, she had clarity that allowed her to evaluate opportunities more intentionally.
Leading at a National Nonprofit
Today, as Chief Advancement Officer at Paws With A Cause, Ashley oversees fundraising, marketing, and strategic communications for a national nonprofit that trains assistance dogs for individuals and communities across the country.
The role brings together everything she has developed over her career: relationship-building, strategic thinking, and the ability to connect people to a mission in a meaningful way.
What This Career Path Teaches Us
Ashley’s journey offers a few clear lessons for professionals exploring careers in nonprofit fundraising, communications, or marketing.
Early experiences matter more than they seem, because foundational skills compound over time. Recognizing when something isn’t the right fit is just as important as finding what is. Listening—whether to donors, audiences, or yourself—is a strategic advantage. And sometimes, the best career decisions come after taking the time to step back and ask better questions.
Her advice is straightforward: find work you love, and if it’s not working, don’t stay.
It’s simple, but it’s also what makes the rest of the story possible.