Where Are They Now? A Mother-Daughter Team at Cafaro Greenleaf

Jamie Greenleaf, lead adviser and principal at Cafaro Greenleaf

Dorann Cafaro, lead adviser and principal at Cafaro Greenleaf, was one of the very first people to win the PLANSPONSOR Retirement Plan Adviser of the Year award, having received the accolade in 2006.

She has since retired from the practice, and so Cafaro referred us to her daughter, Jamie Greenleaf, to tell us about how things have evolved. Greenleaf is now a lead adviser and principal at the practice..

While it has been 14 years since her mother received the award, Greenleaf says the focus has not wavered at all.

“We are advocates for helping people retire with dignity,” she says.

One notable development for the practice came early this year, when OneDigital bought several established retirement advisory practices, including Cafaro Greenleaf. This, Greenleaf says, has enabled the firm to offer its plan sponsor clients a more holistic view of their benefits spend—including health care and ancillary benefits.

As to how the practice has grown in these past 14 years, Greenleaf says that, in 2006, there were only four members of the team; today that number is 25—and OneDigital has more than 2,000 employees.

Cafaro Greenleaf continues to specialize in the middle market.

“These companies tend to be the backbone of the workforce in America and tend to need the most help with outsourcing fiduciary liabilities,” Greenleaf says. She adds that she finds it rewarding to serve this market because these companies “are open to creative ideas about controlling costs and enhancing benefits.”

While Cafaro Greenleaf’s service model has not changed, Greenleaf says, the firm has branched out in a few areas, leveraging the experts at OneDigital.

“Now we can help with health care spending, human resources [HR] outsourcing and payroll evaluation,” Greenleaf says.

Reflecting on how the industry has developed since 2006, Greenleaf says advisers truly have become experts about retirement plans.

“We have really had to hone in and focus on this area,” she says. “There are now many more specialists, as opposed to generalists.”

Asked whether she is optimistic about the industry, Greenleaf affirms.

“Absolutely. People are still retiring, and they will be for many years to come,” she jokes. “People need guidance, and employers need help with benefits, which are complex. Plus, the regulators are not going to stop what they do. These challenges present us with a great opportunity to help employers and employees.”

Greenleaf says she believes it is not just financial wellness that has become holistic, but that, in general, retirement plan advisers no longer work “in silos.”

“Benefits have moved from silos to a more holistic view of individuals and budgets,” she says. “Sponsors realize that if an employee is not financially well, their productivity will go down and their health care costs will go up. They want to offer them all of the right benefits so that their employees can thrive and their organization will benefit as well.”

While the fundamentals remain the same, Cafaro Greenleaf has updated its messaging since the onset of the coronavirus pandemic.

“We are trying to hold employees’ hands since the market became so volatile. It is the first time in 11 years that we have seen volatility of this nature, and the younger members of the workforce have never seen a negative return,” Greenleaf says. “We are also trying to be good listeners and hear about the challenges they are facing. Our message is that this, too, shall pass. Sit tight and let things work themselves out. Stay focused on your long-term goals.”

In ongoing conversations with plan sponsors, Greenleaf and her team are asking them about their challenges and seeking solutions the practice can bring to the table.

“Some of them are in survival mode,” she says. “Others are thriving. Each has a unique challenge. We are trying to be good partners. In the face of challenges, advisers have to be bold and have an opinion. Employers are relying on us to help them and be the expert in the room. Our job is to disrupt the norm so that we can get people to a comfortable retirement.”