In this episode of 401k Real Chat, Fred Barstein spoke with Jamie Greenleaf, co-founder of Fiduciary In A Box and longtime industry veteran, to talk about the growing convergence between retirement, wealth, and health benefits in the workplace.
While ERISA has long governed both retirement and health plans, Jamie explained that we’re now seeing real fiduciary scrutiny extend into healthcare—driven by rising costs, new transparency regulations, whistleblower activity, and even class-action lawsuits. For plan sponsors and advisors, this shift is less about products and more about process.
“Employers are being asked to act prudently with employee dollars, not just for retirement but for healthcare too,” Jamie said. And that’s where retirement plan advisors come in—many of whom already live and breathe fiduciary governance.
After years as a top retirement advisor, Jamie launched Fiduciary In A Box to guide employers—and the advisors who serve them—through a structured, documented fiduciary process on the healthcare side. She likened the platform to “TurboTax for healthcare benefits,” offering step-by-step guidance whether you’re fluent in fiduciary speak or still learning the ropes.
Fred asked how retirement advisors without deep benefits experience can get involved. Jamie’s response: lean into what you already know. Advisors don’t need to master healthcare—they just need to ask the right questions: How are vendors getting paid? Who’s on the committee? Where are the conflicts?
And while few healthcare TPAs or brokers are stepping up as fiduciaries (yet), advisors can still bring tremendous value by helping employers stay ahead of emerging risks. “We made retirement plans better by applying fiduciary process,” Jamie said. “We can do the same for healthcare.”
To learn more, visit: www.fiduciaryinabox.com.
Read the Full Transcript Here:
Fred Barstein:
Greetings and welcome to 401k Real Chat. My name is Fred Barstein, contributing editor at Wealth Management and CEO at TRAU, TPSU and 401kTV. Today, we are speaking with Jamie Greenleaf, Co-Founder of Fiduciary In A Box, and former principal at Cafaro Greenleaf, a leading retirement plan advisor. Welcome, Jamie.
Jamie Greenleaf:
Thanks for having me.
Fred Barstein:
Thank you.
Jamie Greenleaf:
Excited to have the conversation.
Fred Barstein:
So Jamie, our PAs or retirement plan advisors and plan sponsors are really hearing a lot about the convergence of wealth and retirement at the workplace, but not so much benefits. What does convergence of wealth and benefits actually look like?
Jamie Greenleaf:
So if you think about it, ERISA, which was formed back in 1974, has always covered retirement plans, as well as health and welfare plans, but we haven’t really seen ERISA get into the health and welfare area for a number of reasons. In the past, employers paid 100% of employees’ medical benefits, and now because of the expense they’re having to share that cost with their employees. And therefore, ERISA now is coming in and saying, “Hey, you have to be prudent with your employee dollars.” And then we’ve had some new regulations that came to fruition in 2020 by President Trump then, that are really having an impact on the transparency in the healthcare space. So where I see the convergence is really more of a fiduciary conversation as opposed to the individual benefits that we think about.
Fred Barstein:
Right. And ERISA is Employee Retirement Income Securities Act of 1974.
Jamie Greenleaf:
Yes.
Fred Barstein:
We always fine our ERISA geeks for using acronyms without defining it, but we’ll give you a pass there.
Jamie Greenleaf:
Thank you. I figured most of your plan sponsors are familiar with that, but you’re right.
Fred Barstein:
Yeah. Why should retirement plan advisors and plan sponsors be paying attention to this? How is it affecting their lives on this?
Jamie Greenleaf:
Great. Well, where to begin? That’s a good question. But let’s talk about the employers. Recently, we’ve seen some class action lawsuits against employers. We also have President Trump doing executive orders around the enforcement of the pieces of regulation that he put into effect back in 2021. We have some whistleblowers that are reporting bad behavior in the marketplace around TPAs and brokers, and we’ve just recently seen actually a very landmark ruling against Blue Cross Blue Shield of Michigan. And it’s really saying to employers, “Hey, you need to have a prudent fiduciary documented process in place.” So that’s why employers need to be paying attention. For the retirement plan advisors, who knows the space better than those of us that have done it our full working career? We are experts in the fiduciary process, so having that expertise behind us is going to be extremely important to employers moving forward.
Fred Barstein:
Yeah, I mean, the big wave of retirement plan advisors started with the fiduciary advisors acting as a fiduciary and co-fiduciary on that, so a big, big change on the benefits. So I know you transitioned from being you and your mom and leading, she was the first woman retirement plan advisor in the industry, a great advisor, as well as you. But you transitioned to this. Why did you? And how are you addressing the opportunities and challenges here?
Jamie Greenleaf:
Well, again, as I said, I think who better than to sit on the same side of the table as the employer during these healthcare conversations than somebody that understands fiduciary process? And that’s really why we built Fiduciary In A Box, to really guide employers through a fiduciary process on their healthcare plan. And just like we were able to improve benefits on the retirement side by taking a fiduciary lens to that benefit spend, we can do the same thing on the healthcare side.And I think for employers, there’s a lot of people sitting at the table, but having somebody that’s unbiased and conflict-free sitting on the same side of the table is very important.
That said, this has to be a collaborative effort. You have to have a proactive employer. You have to have that fiduciary process in place. And then you have to have expertise from people like your benefit brokers and TPAs. But it’s a collaborative effort, and the reason that I transitioned to that, is because I felt that I could have more meaningful impact on my employers by helping them through this process.
Fred Barstein:
Are you seeing your traditional healthcare TPAs, third party administrators and brokers taking on that fiduciary responsibility? Do a co-fiduciary? Because they haven’t really in the past, right?
Jamie Greenleaf:
Absolutely not. There aren’t really any vendors out there at this moment that are truly taking on that co-fiduciary status like they do on the retirement side. That does not mean that a retirement advisor cannot help and coach an employer through that fiduciary process and oversee that process. It’s just at this time, until we see how the courts weigh in, most are not comfortable taking on that fiduciary status.
Fred Barstein:
A lot of our PAs, and I know your former firm, OneDigital, they’re owned by a benefits firm, so those advisors might have more exposure, understanding, and certainly collaboration on that. What about an advisor who doesn’t really have that much experience and benefits, or not owned, or even those that are owned by a benefits firm like OneDigital or Hobb or Marsh Mac, but don’t really understand how should they get involved? And how do they get involved?
Jamie Greenleaf:
Again, I think the expertise of somebody that understands the fiduciary process is extremely important. They don’t need to understand the healthcare industry to understand how to ask the right questions. How are you getting paid? Who’s paying you? Is that considered reasonable? Have you formed a fiduciary committee? Are you taking minutes? Where are the conflicts within your contracts? All the things we’re used to asking on the retirement side, it’s just applied onto the healthcare side. That’s why it’s a collaborative effort, because you’re going to need the expertise of some of those benefit brokers and those third party administrators and pharmacy benefit managers. But what we really bring to the table is that fiduciary process and asking the questions that nobody else was.
Fred Barstein:
Fiduciary In A Box guides that advisor that may not know the healthcare and all the questions they should be asking in the process and the documents. That’s what your software and service offers.
Jamie Greenleaf:
Correct. So if you can’t spell fiduciary, that’s okay, the system’s going to walk you through exactly what you need to do to adhere and establish and document your fiduciary process. If you can spell fiduciary, but don’t or understand the fiduciary language, but don’t understand the healthcare benefits, that’s okay too, because the system’s going to tell you exactly what questions you need to ask in the lingo that a healthcare benefit consultant would understand. So think of it as almost like TurboTax for healthcare benefits, is what most of our employers and others have said it’s like.
Fred Barstein:
Again, your website is what?
Jamie Greenleaf:
fiduciaryinabox.com.
Fred Barstein:
That’s all the time we have today. I’ve been speaking with Jamie Greenleaf, who is the co-founder of Fiduciary In A Box. Thanks for your time today, Jamie.
Jamie Greenleaf:
Thanks for having me.
Fred Barstein:
And thank you for watching 401k Real Chats.
