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Past, present and future Jenni Bickerstaff’s vast experience on both sides of the aisle has helped her build a book of business from the ground up and evolve into an industry leader and mentor.

By Dan Cook | Photography by Kevin Garrett

Jenni Bickerstaff was being drawn toward her future career before she even realized it.

“My mother worked for a large medical health plan and hospital system in Virginia Beach,” she recalls. “I would often listen to her talk about how hospitals and health plans worked together and I gained a very early understanding of how health care works and how insurance integrates with plans and providers.”

That little girl would grow up to become senior partner and senior VP of employee benefits at AHT, where her resume now includes 27 years of experience in the benefits industry, 17 years with national medical carriers, and 15 years with a national broker.

But going back a bit, after graduating with a business degree from Virginia Tech, she returned to Virginia Beach to learn more about health care.

“My first job was at my mother’s company,” she says. “I answered 100 calls a day from members who had Medicare, Medicaid or the commercial health plan, so I quickly discovered a need that wasn’t being met: proper education about how health plans work.”

She listened and empathized as members shared personal stories about not being able to afford prescriptions or the cost of a hospital visit.

“I found more enjoyment and fulfillment in helping them understand how they could better utilize their benefits than by just reading off their copays and getting to the next caller,” she says.

Bickerstaff then moved to Washington, D.C. for a role at a regional medical carrier. Working directly with employers helped her recognize which needs were not being met by brokers.

“Either rates were too high and renewals were not effectively negotiated and marketed, and/or employees had no effective way to understand their limited benefits choices,” she says.

Bickerstaff later worked with a national medical carrier for several years, where she interacted directly with brokers, providing valuable insight into the experiences of her clientele.

“I saw firsthand areas in which employers were not getting the information needed to best position their health plan and make effective decisions,” she says. “The focus was predominately on rates, when I knew there were so many other factors impacting why an employer would select a carrier or a particular plan and funding arrangement.”

After the birth of her second child, Bickerstaff decided to again work directly with employers so she could help them better manage their costs, create a customizable communication plan, and effectively put in place a benefits strategy that would allow them to retain and attract the best talent.

“As a consultant, there were no loyalties to any one carrier. As health care got more and more complex with the passage of ACA, I had to provide my clients with the peace of mind that I was solving problems that they didn’t realize they had.”

In fact, this became her mission statement.

“My biggest successes have come from working with a talented team who shares my vision. Each year, we continue to evolve and go back to the drawing board.”

While consistency is key, subtlety is also required.

“One of the biggest flaws within our industry is complacency. It doesn’t take long for a client to realize you are saying and delivering the same message and results.”

She recalls an email from the CFO of a large tech company: “I don’t know how you and your team do it, but you make us feel like we are your only client, and I know we are not.”

This sentiment is echoed by one of Bickerstaff’s other clients, Mike Jewett, senior manager, total rewards at Appian.

“They provide better service and more support than any brokerage we’ve worked with before. They feel like an extension of my team.”

When Jewett joined Appian, he envisioned big changes in the benefits package and Bickerstaff was ready to help.

“We weren’t content with our carrier; they didn’t seem to want to work with us or do anything extra to improve the plan. Jenni was able to bring us a proposal that included tremendous savings.”

“I never had that one mentor who changed my life. So I decided to be that mentor.”

The company reinvested those savings back into the plan to reduce member premiums and add other enhancements. And, Jewett notes, the transition went smoothly.

“A large carrier switch can bring turmoil, but this one was painless. She not only brought in someone who saved us money, but they provided much better customer service, as well,” he says.

Much of Bickerstaff’s magic can be traced to a network willing to help. She often reaches out to other successful advisors within AHT.

“We recently formed an ‘elite advisor group’ that meets regularly to share what works and doesn’t, and leadership is involved to help facilitate next steps and takeaways,” she says. “Our compliance and actuarial leaders provide added support and problem solving on a daily basis.”

Each new year provides a complete re-work of the prior year’s open enrollment communication, with customized themes used throughout the year.

Bickerstaff specializes in international benefits and is one of the few brokers in the region who manages both domestic and international risk.

In a male-dominated industry, Bickerstaff realized early that she needed both an impressive skill set and a unique approach in order to succeed.

“Whether pitching a new client, serving on boards, or presenting to the C-suite, I was often the only female in the room,” she says.

She has prioritized empowering women to speak up and understand their value and power.

“I never had that one mentor who changed my life,” she says. “So I decided to be that mentor.”

Bickerstaff’s vast experience on both sides of the aisle has helped her build her book of business and maintain momentum through the pandemic.

Whether her children will follow in the family’s footsteps has yet to be determined. But from her beginning as a receptionist at her mother’s company, Jenni Bickerstaff has discovered that learning from the past and listening to clients in the present creates opportunities to provide for those who need it most.