2026 Advisor of the Year Finalist: Alex Dampf

But after graduating from Lipscomb University in Nashville in 2010 with degrees in finance and economics, Dampf had to consider his options. A chance connection at a youth softball game resulted in a job offer he couldn't refuse, mainly because he didn't have any other opportunities. He told himself he'd give it six months and then move on, but that temporary stop in the benefits world instead became nearly a decade of hands-on experience, providing deep exposure to plan design, self-funded models and the intricacies of employer challenges.

Early in his career, Dampf discovered what drove him: the financial side of benefits. He realized that the established structure often didn't make sense from a dollars-and-cents perspective and so began to question why services couldn't be self-funded to help employers save money.

That inquisitiveness, combined with conversations with colleagues and mentors, eventually developed into a philosophy that benefits should be transparent, flexible and tailored to each employer's needs — breaking free from the one-size-fits-all model.

Turning vision into plans

When he started Oakmont Benefits, Dampf built it around the concept of giving employers control over their benefits. He focused on unbundled, self-funded plans for mid-market companies, typically 100 to 500 employees that were frustrated with cookie-cutter insurance.

"I just wanted to build and focus on plans that gave employers the opportunity to design it how they truly wanted it and give them control over how it operated," says Dampf. "And then to be able to explain to them how the financial side of it was very similar to other parts of their business."

His finance background has helped him translate complex plan structures into understandable choices for clients.

Dampf also prioritizes flexibility. Employers select their own administrators, networks and pharmacy benefits managers, layering in specialized point solutions, when needed. For some clients, this means fine-tuning an existing plan; for others, it calls for a complete redesign. Oakmont currently employs five team members and serves clients headquartered in roughly 15 states, with employees in 35–40 states. All clients are on self-funded or level-funded plans, with none relying on traditional fully insured models.

First-year engagements typically deliver $1,000–$1,200 in cost reductions per employee,while self-funded clients finishing their first 12 months average a 3.4% reduction in costs, with only a 1.2% renewal increase. Many maintain renewal increases under 5% for multiple years — often without changes to deductibles, out-of-pocket costs or employee premiums.

Dampf works directly with providers to negotiate contracts, ensuring savings are reinvested into health plans, rather than lost to inefficiency. A signature element of Oakmont's approach is its community-owned health plans. Partnering with national professional employer organizations, Oakmont serves mid-market clients who have outgrown master policies, creating self-funded plans that feel familiar to employees while delivering enhanced insights and flexibility for employers. Most arrangements are guided by shared philosophy, allowing Oakmont to scale solutions without sacrificing consistency.

Making benefits understandable

Dampf has long emphasized that employer clients should understand the details of his compensation and have access to the data behind their plans. Oakmont operates as a guide year-round, meeting with clients monthly on data, strategy and implementation. In addition, employees are supported directly, navigating a system full of jargon and acronyms.

"The industry is great at creating multiple phrases for the same thing," Dampf jokes. "Our role is to simplify it and guide both employers and employees through this often complicated process."

Employees particularly benefit from Oakmont's hands-on problem-solving. Life-changing diagnoses, complicated claims and pharmacy issues can arise long after open enrollment — and one-time communications rarely prepare employees for these circumstances, Dampf says. Oakmont tracks metrics showing how often team members coordinate with providers to resolve issues in real time, investigating workflow disconnects to ensure claims are processed correctly.

"We have insights into both sides of the system and use that to figure out where the disconnect lies," he says.
A focus on clarity and transparency has also enabled Dampf to see and understand the industry's systemic challenges more clearly.

"Everyone knows the industry is broken at its core," he says. Employers often try to fix individual pieces with third-party vendors, creating additional complexity. Dampf's approach centers on identifying two or three realistic improvements per year and then building on them gradually. If it becomes too convoluted, he says, employees will tune out.

Looking ahead, Dampf envisions steady, focused growth for Oakmont rather than chasing every trend. Oakmont isn't seeking scale, or a sale or acquisition. Instead, it concentrates on key areas where it can add maximum value, focusing on expertise, guidance and impact. For Dampf, success is measured in his clients' long-term stability and tangible cost savings.

There are easy ways to reduce costs by 15% or 20% in certain areas,he says, but the real impact comes when they can build plans that keep multi-year trend lines.

"When we have an open enrollment with an employee and for the fourth year in a row, we can tell them, 'your deductible isn't changing; your copays aren't changing; what comes out of your paycheck is not changing,' that continuity and consistency makes a huge difference," he says.

Better together

Dampf is also active in the benefits community, including his role as a charter member of Health Rosetta, which fosters collaboration with like-minded consultants nationwide, testing ideas and sharing successes and missteps. Collaboration has also been crucial to his success. A small network of peers offers advice on complex client issues, innovative designs and emerging trends. He co-brokers accounts with other firms, reinforcing the philosophy that collaboration produces better outcomes, even among competitors.

"Alex is generous with his knowledge and collaboration, and he genuinely wants others to succeed," says Justin Leader, president of BenefitsDNA. "In an industry where information is often guarded and relationships are transactional, Alex does the opposite."

Dampf recognizes that while the benefits industry is highly competitive, consolidation has created a vacuum for employers with 50 to 500 employees, a void that collaboration can help fill.

Dampf's personal volunteer work includes coaching youth sports for his two children and volunteering with the Special Olympics of Middle Tennessee. He is particularly proud of his role on the Advisory Board for Lipscomb University's Master of Public Health Administration program, where he is the sole representative from the insurance and benefits sector.

In this role, Dampf brings a practical perspective to future health care administrators, helping them understand how patients navigate insurance and billing, how money flows through the system, and the ways direct contracts and community-owned health plans can create sustainable, localized solutions. He emphasizes continuity and collaboration in health care, aiming to restore the kind of connected relationships between hospitals and communities that have been lost through decades of consolidation.

Dampf stresses that insurance plans should support, not hinder, clinical care, giving patients and providers clear guardrails, while avoiding unnecessary interference. By sharing these insights with students, he prepares the next generation of health care leaders to think critically, ethically and creatively, and to design systems where plans serve both people and communities, not the other way around.

"If we can help one future hospital administrator understand how the money works and be willing to have conversations about direct contracts or community health," he says, "we've done our job."