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

Dorann Cafaro, one of the earliest winners of the Retirement Plan Adviser of the Year award, has retired from the practice. Her daughter, Jamie Greenleaf, says the focus hasn’t wavered since 2006.

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..

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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.”

Advisers Giving Back: Kelli Davis and CSi Advisory Services

Among other efforts, the firm dedicates significant time and resources to causes that fight hunger and support financial literacy among girls and young women in Indiana.

Art by Niv Bavarsky


Kelli Davis is a vice president of retirement plan consulting at CSi Advisory Services, where she has worked since 2008.

It is a dynamic role that involves working directly with clients and helping them solve their retirement plan design and investing challenges. Davis says the job is a rewarding one, made even more so by her firm’s commitment to giving back to charitable causes in the Indiana community.

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Though informal giving efforts had occurred earlier, Davis says, CSi Advisory Services, based in Indianapolis, opted to create a more formalized giving framework about three years ago.

“It was an organic decision based on the fact that we all felt that we needed to start doing something together to give back to our local community,” Davis explains. “We knew we were at a point where we had the ability to make the time commitment and the financial commitment. We embraced a multitier approach from that point.”

One program the team established allows staff members to “dress down” and wear jeans on Fridays, so long as they have made a charitable donation during the week. Every six months, the team submits proposals for which charity to benefit next, and the firm matches staff donations. 

“Our team puts forward proposals and we all discuss and vote on which organization we are going to support,” Davis says. “This whole approach creates such great buy-in among the staff. It has come to mean a lot to them. It’s so important and meaningful to have the staff pick the causes. They have a stake. They want to support a cause that means something special to them, and it should connect with their passions.”

The next big component of CSi’s giving is an annual service day—which the staff also gets to vote on. Most recently, the team has been working with Gleaners Food Bank of Indiana, an entity that generates most of the food bank contributions going to about a third of all the counties in Indiana.

“It is a very large population of Indianans they are serving,” Davis says. “They have a giant warehouse with about 50 people on staff, but they need about 200 or 300 people a day to fulfill the needs. They crowdsource the rest of the work from community volunteers. When we go in to serve, one of the full-time staff members is with us all day, and we get to learn about why this work is important, why this work matters. We all find it to be such a meaningful experience.”

About a year and a half ago, CSi decided to expand its giving efforts again and to leverage the firm’s longstanding focus on financial literacy and education.

“We felt we needed to do something where we could have an impact at a younger age,” Davis says. “That is how we came across an organization called Invest in Girls. They go into high schools and teach financial literacy.”

Invest in Girls had mostly been focused on the East Coast, Davis says, with no presence in Indiana.

“In fact, when we reached out, they said they were already interested in launching a pilot program in Indiana, and asked if we would take that on,” she says. “We decided to step up and we brought the program here. Now, we work with about 25 different school systems in the state. We had mapped out a curriculum that we thought would be helpful and interesting, but during the first sessions we also polled the students and asked what they wanted to know about.”

Davis says it was amazing to see the entrepreneurial spirit of a lot of the girls.

“Many of them say they want to own a business someday, and they want to understand how to do that,” Davis says. “We redeveloped and pivoted our educational plan to match what they told us, and it has turned out to be really amazing. It’s so important because the teachers don’t have the time or funding to teach any of this.”

In terms of the impact on staff, these giving efforts have been very powerful, Davis says.

“They feel good about working for an employer that is dedicated to these issues,” she says. “I know they enjoy being able to tell our clients about it. When I go to client meetings on Fridays, I explain why I am wearing jeans and I get to tell them about the work we are doing and the causes we are trying to support. Also, this is very much a part of our recruiting and hiring process. Young people coming into the workforce right now really identify with these causes and working for an employer that agrees with their values.”

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