Dan Bolsen doesn’t do small talk when it comes to broken systems. He sees gaps, then he takes action to fill them.
Following a decade of production as a record-breaking fundraising professional, securing major and principal gifts to impact nonprofit organizations, Bolsen has made a career path pivot.
“Calculated risk-takers are the people who change the world,” Bolsen says. “If we only look for the sure things in life, innovation will never occur.”
For the past several months, he has been applying that philosophy to pharmacy benefits management reform, a rapidly evolving arena ripe for reinvention and fueled by innovators Bolsen has learned from and deeply respects. Bolsen contracts as Chief Impact Officerwith AffirmedRx, a Public Benefit Corporation in Louisville, Kentucky.. He also recently wrapped a similar role with Bowtie Therapeutic Benefits, a cell-and-gene therapy focused benefits solution for affordability, gaining valuable experience executing a new company playbook from the ground up.
The work is technical, the stakes are high, and the problems are personal. All of his work in Louisville requires the kind of stamina he first developed as a farm kid and an all-state athlete in a small Central Illinois town, where he set records on the basketball court that eventually landed him in his high school’s hall of fame.
“I am at a point in my career where thoughts about my older family members’ health, as well as my own health, are more at the forefront of my mind than previously,” he says. “We must find a suitable healthcare path if we want the best life possible for each of our children going forward. As someone who also has a passion for entrepreneurship, I value the leadership I am able to collaborate with in Louisville. It has been a remarkable several months together.”
Bolsen’s sense of urgency is new, or at least newly spoken. For years, Bolsen’s professional identity was shaped by donor conversations, council meetings, and the rhythms of higher education fundraising. He managed teams, mentored staff and connected passions to secure gifts endowing scholarships, funding research labs, and establishing faculty chairs.
But he also saw something else over the years: a comfortability with the status quo and resistance to modernization. Most of the time, the root cause of a situation was an infrastructure problem.
So, starting with healthcare, Bolsen has made it a personal mission to build bridges.
When Bolsen made the decision to join Greg Baker’s efforts with AffirmedRx, he saw a leader in Greg who had an unbridled passion to change an industry rooted intentionally in opaqueness.
“I was able to see the pharmacy benefits world from a very unique perspective throughout my time as a fundraiser across many health-related disciplines,” Bolsen says. “Admittedly, the PBM world is so complex I barely understood it for a long time. Then, I met Greg, who was on a relentless mission from day one to make America a better place for employers and their employees. His desire to actually create meaningful change was and still is magnetic.”
It’s an ambitious play to transition to the for-profit realm with a young family and a transition away from the security of large organizations like those at the pinnacle of the nonprofit ecosystem. However, Bolsen has always been a learner, and to that end, he’s in the process of completing a Certificate Program in Financial Planning and Services at Boston University. The credential adds another layer to a foundation that includes a master’s degree from the University of Illinois Urbana-Champaign and dual bachelor’s degrees from Eureka College, where he graduated cum laude.
Bolsen also graduated from Eureka as a Reagan Leadership Program Fellow, a detail that hints at his inclination toward civic-minded frameworks and structured idealism.
But idealism is tempered by experience, real experience.
“In my earlier career, I saw instances where a lack of transparency was a way to dodge an uncomfortable reality,” Bolsen says. “Blame was shifted to individuals who did not deserve it to re-direct from people who did not want to accept accountability. The result of such a situation can be catastrophic for innocent people.”
That observation has become a cornerstone of how he leads now. When everyone is aligned, he says, transparency, governance, and accountability unify naturally.
Leadership in high-stakes environments requires listening first. Bolsen is adamant about that.
“Listening is the most important thing that can be done in those scenarios,” he says. “Evaluate the input from various stakeholders and then synthesize.”
But synthesis alone doesn’t move the needle. “A strong leadership cabinet to rely on is most important as various paths forward are constructed,” he says. “In the end, a decision has to be made. I am not afraid to make the decision.”
That confidence didn’t come out of nowhere. It was built over years of frontline fundraising, where donor conversations required real-time strategy adjustments and relationship management under pressure. It was reinforced through team leadership roles, where he had to balance institutional priorities with individual development.
And it was shaped, in part, by the people who believed in him early.
“I have been blessed to have tremendous career mentors in my life from my earliest days on the farm to now,” Bolsen says. “Individuals who poured themselves into me. They instilled a confidence in my core traits, and they taught me how to lean on trusted people in my life when uncertainty becomes the daily theme.”
That mentorship didn’t just build his skill set, it gave him permission to take risks, to step outside the traditional career track and build something new.
He takes particular pride in developing talent himself. Over the course of his fundraising career, he mentored team members who went on to close transformational gifts in their own right. That legacy matters to him as much as any dollar figure.
Bolsen knows his personality can be misunderstood upfront.
“As my career grew rapidly at a younger age, my high-energy and passionate personality was sometimes viewed as ‘too much’ by a person I have met for the first time,” he says. “People then come to realize I am truly filled with that much energy.”
His energy isn’t performative, it’s foundational and rooted in something deeper than professional ambition. He grew up on a multi-generational family farm in a small community. Business ownership and entrepreneurship weren’t aspirations, they were table stakes.
His time as a collegiate student-athlete helped, too. The discipline. The team-first mentality. The hours spent running drills that didn’t always make sense until the game was on the line and muscle-memory made a highlight outcome a reality.
“I genuinely want the best for each person,” Bolsen says. “My hope is that the rest of my career is defined by pouring myself into the teammates who share those values. When the right people come together, there is no ceiling to what can be accomplished.”
When asked for his input on the modern day importance of ethical leadership, Bolsen says it isn’t abstract, it’s operational.
“Ethical leadership begins with doing what is right,” he says. “It requires you to put your personal bias, if there is one, to the side and focus on what is best for the employee and the organization.”
That means protecting employees, positioning them to succeed, and rewarding their accomplishments. “My father taught me from a young age that you do not have to be a brilliant mind to tell the truth. It is much easier to remember the truth than to manufacture it,” Bolsen says. “Eventually, the truth will come out.”
That conviction has shaped how he approaches governance, accountability, and team dynamics. It’s also influenced the kind of work he’s willing to take on now.
The contract roles he has held in Louisville are not just consulting gigs, they’re opportunities to champion cross-sector collaborations and build organizations that operate differently from the start. To embed transparency and patient-centric values into the foundation rather than retrofitting them later.
“Currently, I am driven to do everything I can to help with the affordability crisis in pharmacy benefits and healthcare,” he says. “Connecting people is what I have spent my career doing, and it has been very rewarding to help bridge like-minded leaders together to forge a successful path forward for the benefit of all Americans.”
It is a different arena than higher education fundraising but the skills translate. Relationship building, stakeholder alignment, long-term thinking and the urgency is real.
Now and in the future, Bolsen’s goal is straightforward: build something robust and sustainable.
It’s ambitious, but ambition without execution is just noise, and Bolsen has a track record of turning strategy into structure.
Bolsen was named an Almabase/Blackbaud “50 Under 50” Award winner in 2023, a recognition that speaks to both his professional impact and his potential to keep building.
Accolades aside, what drives him now is something simpler. He wants to create systems that work, that last, that make it easier for the next generation to do meaningful work without reinventing the wheel every time.
“If we begin working with the end in mind, the path forward will reflect the goal,” he says.
That philosophy applies to donor strategy, to business planning, to healthcare reform, to legacy, and it applies to the way he’s building now. One relationship. One solution. One step at a time.
The internal grit of a true leader will prevail in most situations, he says. It’s not a platitude. It’s a pattern.
