Diana Miller Named 2025 Advisor of the Year Finalist by BenefitsPro

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Diana Miller’s life has been shaped by courage, compassion, and an unwavering sense of justice. Her path—from growing up in Colombia to building a successful career in finance and healthcare advocacy in the U.S.—is a powerful example of how personal experience can fuel systemic change.

A Childhood Marked by Advocacy

Raised in Bogotá during a time of intense conflict with drug cartels, Diana’s early years were steeped in political awareness. Her father, a member of Colombia’s House of Representatives, was actively involved in reform efforts, and her mother worked as a teacher. Their home was a hub of civic engagement and activism, with safety often a concern.

“We were always aware of our surroundings. My childhood taught me to speak up, even when it’s difficult,” Diana recalls. “Both of my parents modeled what it meant to fight for what’s right.”

A Leap of Faith

At just 17, Diana left her home country after earning a scholarship to study in the United States. She chose a private college in Iowa, trading the bustling city of 10 million people for a rural town surrounded by cornfields. “It was a culture shock,” she admits. “But it was also an opportunity to pursue the future I wanted—one that wasn’t possible in Colombia at the time.”

That leap of faith was the beginning of a new chapter—one that would eventually include a family, a career, and U.S. citizenship. But the journey wasn’t easy.

Overcoming Immigration Hurdles

After completing her finance degree during the 2009 recession, job opportunities were scarce. Without employer sponsorship, her options were limited. Diana and her now-husband made the decision to marry, a step that allowed her to remain in the U.S. and begin the complex process of applying for permanent residency.

“It was stressful. We took out a loan just to cover the paperwork fees,” she says. “But it was important to me to be part of this country—not just live in it. I wanted to vote, to participate.”

Five years later, Diana became a U.S. citizen—on the Fourth of July.

A Passion for Healthcare Advocacy

Diana’s interest in healthcare reform was born from personal experience. As a college student without insurance, a brief hospital stay left her with a staggering $40,000 bill. “In Colombia, it would’ve been a fraction of that,” she says. “I realized then how broken the U.S. healthcare system can be—and I wanted to be part of fixing it.”

She entered the employee benefits industry after working in banking and finance. From the start, she challenged the norms she saw—questioning monetary incentives, pushing for transparency, and advocating for access over profit.

A Turning Point

At a conference, Diana met Ben Conner, CEO of Conner Insurance. Their conversation about healthcare reform sparked an immediate connection. Soon after, she joined the firm as its first remote team member, helping expand its reach and solidify its mission.

“Diana brought a new level of insight to our team,” says Ben. “Her empathy, experience, and drive to do what’s right have made her an incredible asset to our clients and our company.”

Now three years in, Diana supports employers across the country, tailoring benefit plans that prioritize affordability, accessibility, and meaningful care. One manufacturing client has saved nearly $4 million since partnering with her team.

Grounded in Community

In addition to her work, Diana stays deeply connected to her roots. She volunteers at a local immigrant resource center, helping others navigate the very systems she once struggled through. She also plays a vital role in bridging communication gaps for Spanish-speaking employees, advocating for solutions that resonate with their unique needs.

Recently, she helped a company step in when a group of employees was at risk of losing transportation to work. With Diana’s help, the employer provided a van—an act of compassion that rippled through the workforce.

“These small actions make a big difference,” Diana says. “My job is more than numbers and plans—it’s about people.”

A Vision for the Future

As the healthcare landscape evolves, Diana is championing the integration of direct primary care—giving employees access to doctors who know them, spend time with them, and focus on long-term health outcomes.

“High-quality care shouldn’t be a luxury,” she says. “And it shouldn’t bankrupt families. We’re showing employers there’s a better way.”

Her journey—from Bogotá to the Midwest, from immigrant to citizen, from student to industry leader—is a powerful testament to what can happen when empathy and expertise collide.

“I’m proud of where I’ve come from,” Diana says. “And I’m even more excited about who I get to help next.”