Diana Miller’s journey is a story of resilience, determination and an unwavering commitment to doing what’s right. Her path — including moving to a new country at the age of 17, navigating the U.S. immigration system and building a career in finance and health care advocacy — has been shaped by her passion for justice and her ability to bridge gaps for Latino communities and others.

Miller grew up in Colombia during a time when the country was waging war against drug cartels. Her father, a politician in Colombia’s House of Representatives, was heavily involved in the turmoil, which Miller says heavily impacted her upbringing. Her mother was a teacher, and the family often participated in civic advocacy and engagement, attended protests, and watched her dad speak in front of the House.

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“My childhood was a bit unique in the sense we were always being escorted by security,” Miller says. “We always had to be careful, but I watched both of my parents fight for what they believed in and refuse to be quiet. That will stay with me forever – the importance of seeking out what's right.”

Leaving home

Miller graduated first in her high school class at Colegio Santa Francisca Romana in Bogota, which earned her a scholarship to her choice of three colleges in the United States: one in Iowa, one in Minnesota and one in Wisconsin. She chose Loras College in Dubuque, Iowa, because she thought it would get the least amount of snow.

When Miller graduated in 2005 at the age of 17 and moved to Iowa on a student visa, it was her first foray outside of the country where she grew up.

“We never really went out of the country due to safety concerns,” Miller says. “Dubuque was very, very different from Bogota. I grew up in a city of 10 million people and moved to a rural farming community of 60,000 people. When I landed and started looking around, there were cornfields everywhere.”

She acknowledges it took courage for her to make the move, but says she also didn’t have much choice.

“My dad didn't think it was safe for me to stay and try to develop a life there,” says Miller. “I wanted to be a lawyer, and he said if that’s what I wanted, I had to go somewhere else to do it.”

Although it was painful for Miller to move away from her family, the scholarship allowed her to be somewhere safe until the turmoil in Colombia passed.

That said, “none of us were thinking that I would stay here,” she says.

But life had different plans. While in college, she met her husband and decided to stay in Iowa, where they now have three children who are nine, five and 21 months old. In 2013, Miller and her husband, a chiropractor, purchased a practice in Dubuque, where he handles patient care and she heads up marketing and financial tasks for the practice, in addition to her role as mom and full-time benefits professional.

Miller and her family return to Colombia each winter to visit family, escaping the cold and snow of Iowa for the warmth of her native city for a few weeks. In the summer, her parents come to visit her family in the U.S.

Path to citizenship

Reaching this level of success and stability has been far from easy for Miller and her family. When she graduated from college in 2009, it was the height of the recession, and Miller struggled to find a job. Faced with having to return to Colombia if she wasn’t sponsored by an employer, Miller and her husband married so she could remain in the United States. But even that process was long and difficult; Miller was not allowed to leave the country for a year after she submitted her paperwork for a green card. Meanwhile, she and her husband were interviewed extensively by the U.S. Citizens and Immigration Services (USCIS), and took out a loan to pay the required $5,000 in fees in order to be approved.

After five years, she became eligible to apply for citizenship, which meant even more fees and interviews. But Miller and her family were often separated when traveling because of their different citizenship status, and more importantly, she wanted the right to vote, a vital privilege for Miller, given her upbringing in a political environment. After a long and arduous process, Miller became a U.S. citizen on the Fourth of July, 2014.

Aspirations

Growing up, Miller’s dream job was to work for the World Bank. She was attracted to the idea of helping people in third-world countries through the power of financial aid. When she started college, she decided to major in finance because she thought it would provide her with skills that would be universally applicable and hopefully bring her closer to her dream job.

But while in college, Miller had a life-changing experience that would reshape both her career and mission in life. When she was hospitalized overnight for an illness, she didn’t have health insurance due to her status as an international student. She was shocked to receive a bill for $40,000 for a stay that would cost only $1,000 in Colombia. With no way of paying, Miller received help from Loras College and was able to negotiate the bill to $10,000, which she paid off via a 10-year payment plan.

“That experience shaped my views on health care in the U.S.,” says Miller. The hospitals and facilities in the U.S. were comparable to those in Colombia, and the doctors had the same training, so why was it so much more expensive to treat a patient in the United States than in Colombia?

“That kind of stuck in my head,” she says.

Launching a career

As a college student, Miller honed her sales skills at a summer job selling burial plots door to door in Latino neighborhoods in Los Angeles. The next summer, she was recruited to sell encyclopedias door to door in California, a less successful endeavor due to the availability of Google.


Her first job out of college was at a bank, where she started as a trust specialist and moved up to its retirement division. As she simultaneously worked toward her MBA at Clarke University in Dubuque, a classmate encouraged her to apply at a local insurance agency. She started at the firm in 2013 as a marketing representative, launching her career in the employee benefits space.

It was during this time that she began to question some of the industry’s business practices, including bonuses paid by insurance companies based on retained business. She also witnessed employees walk out of client enrollment meetings, frustrated by high costs and difficulty navigating their benefits. Miller decided there had to be a better way.

The right fit

While attending an industry conference, Miller sat down at a lunch table next to Ben Conner, an encounter she says changed her life forever. Over lunch, she shared her thoughts about finding a better way to ensure people could access high-quality health care at an affordable price. Conner told her about his company, a third-generation family agency based in Indianapolis that provides employee benefits, commercial insurance and personal insurance. The longer they talked, the more they discovered how closely their thoughts aligned about ways to fix the health care system.

Shortly after the conference, Conner reached out to Miller and offered her a job. She became the company’s first remote employee and the only team member who didn’t live in Indiana. Conner says the experiment has been a complete success, thanks largely to Miller’s self-motivation.

“It has allowed us to expand our footprint and solidified that we are growing into a regional firm,” says Conner, president and CEO of Conner Insurance. “She has an internal drive for justice and doing the right thing. She is courageous in her approach and she's also super prepared and organized. She gets rave reviews from her clients.”

Miller has now been a benefits advisor with Conner Insurance for three years, working with employers across the country. She strives to understand their needs and then marry those unique details with the providers and vendors that make the most sense for their employees and their bottom line. One client, a manufacturer with about 410 employees, has a special place in her heart.

“Their CFO is from Mexico, so we have a connection and always interact in Spanish, which is kind of nice and refreshing,” Miller says. “We took over their existing plans in 2022 and from the time we started partnering with them until now, we have saved them $3.8 million.”

The company also received a Rosie Award last year, a recognition highlighting employers and unions that provide high-quality, low-cost health plans.

Deep roots

Miller’s roots have influenced both her professional and personal life. She is actively involved in the Presentation Lantern Center in Dubuque, a nonprofit that provides resources to immigrants. Their services range from basic needs and English instruction, to helping people open a bank account, pay utility bills, and apply for permanent residence or citizenship. Miller’s background has helped her become a more effective advisor because she can communicate with Spanish-speaking employees and relay their concerns and needs to employers.

For example, she was recently working with a manufacturing company where several employees were carpooling to work in an unreliable car that was on its last legs. The employees were increasingly worried that if the car broke down, they wouldn’t be able to get to work. Miller communicated the problem to the employer, and the company collected money to buy them a van.

“My background has helped me create a heightened level of empathy and be able to bridge a lot of communication gaps between Spanish-speaking people and the companies they work for,” says Miller. “It has also helped me create more impactful health benefit programs focused around their needs.”

Client strategy

Helping employers save money is an important aspect of Miller’s work, but she says the most valuable service she provides is helping clients understand the needs of their employees and then connecting them directly with independent pharmacies, primary care physicians and other providers. Employees crave interactions with primary care physicians who spend more than seven minutes with them and can follow their health concerns over the long term, which helps reduce chronic illnesses and improve outcomes. While direct primary care has gained momentum in some parts of the country, Miller and the Conner Insurance team are working to build that model in Iowa.

“The need that is out there for high-quality direct primary care has been an eye-opener,” Miller says. “DPC is gaining momentum across the country, and now being able to incorporate that into more health plans for employers and their employees in a cost-effective way is very satisfying.”

As she looks back on her career so far, Miller says she is most proud of being able to make an impact in the lives of so many people.

“I am helping people get the medications they need for no cost, or cancer treatment that they couldn't otherwise afford. I’m so proud of that — and I can't wait to help more.”

The 2025 Advisor of the Year will be announced at the BenefitsPRO Broker Expo, May 6-8, 2025 in Boston, MA. The winner will be further profiled after the announcement.

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Kristen Smithberg

Kristen Smithberg is a Colorado-based freelance writer who covers commercial real estate, insurance, benefits and retirement topics for BenefitsPRO and other industry publications.