Season 2, Ep. 19 | How Brandy Thompson Is Reinventing Employee Choice Transcript

[00:00:08] Jason Rudman: There's a health benefits technology company that has grown to two hundred and eighteen million in premium volume across all fifty states in roughly three years.

They partner with Blue Cross Blue Shield, Kaiser Permanente, Gallagher, Lockton, and Hub. And when it came time to staff the team that guides employees through open enrollment, the CEO didn't hire insurance professionals. She hired former teachers and nurses.

That one decision tells you everything about how Brandy Thompson thinks. She didn't build BenefitBay to make benefits more efficient. She built it to make benefits make sense to the person staring at four plan options on a screen, trying to figure out which one won't bankrupt them if their kid breaks an arm.

This is More Elephant. I'm Jason Rudman, and today's conversation is about what happens when you redesign a broken system from the human out.

Welcome to the More Elephant Podcast, Brandy.

[00:01:01] Brandy Thompson: Thanks, Jason. Thanks for having me.

[00:01:03] Jason Rudman: So excited to get into this conversation. We're going to cover a lot of ground. I would say that your path is unconventional. You love to rewrite the playbook. There's the future of AI in all that you're doing. You fundraise, you lead, and as we talked about, you are also a mother of six. So you do all of this and that. I'm so excited for the audience to hear from you. Let's jump into this thing about the unconventional path. As you shared with me, you went from staff accountant to COO and you're now the CEO of a health benefits technology company. Everything in your path is not a straight line.

[00:01:43] Brandy Thompson: No. 

[00:01:43] Jason Rudman: Walk us through the moment you realized the system you were administering was the system you needed to rebuild.

[00:01:50] Brandy Thompson: I think it was a complex journey to get there. I think we've all seen the healthcare ecosystem evolve. And when I first got out of college, this is really going to age me, deductibles were one hundred dollars for a PPO product that your employer could afford for about ten thousand dollars a family, okay?

So I'm aging myself, that was the nineties.When we had to move up to a five hundred dollar deductible, everyone was outraged, right?

We evolved over to the HSA high deductible health plans, and we've gone all the way to offering bronze products with limited networks and point cost-saving solutions that are still not working—at a cost sometimes to a family of thirty to forty thousand dollars a year before they can really access their benefits. That is crazy.

Add that the employer is just really struggling to make ends meet for their employees and the humans they care about. That is what really drove me to care about impact in this industry. The combination of both of those things, being a consumer of healthcare and being an employer trying to deliver the impossible outcomes for the employees you care about.

[00:03:04] Jason Rudman: So simply, the system clearly didn't work and you felt compelled to change it. 

[00:03:09] Brandy Thompson: Yeah. 

[00:03:10] Jason Rudman: You've got lots of great lines. One of them, which I really loved—you've said in the past, “you don't have to have followed the yellow brick road to get to where you are.”

In practice, and we talked about this unconventional path that you've traveled down, how often did the unconventional path feel like an advantage versus a liability, especially when you were raising capital or trying to build this company?

[00:03:34] Brandy Thompson: When trying to raise capital or being evaluated on your resume or your credentials, it is impossible to have the non-traditional path. It adds a lot of adversity to the path to success. However, having that adversity, having the non-traditional yellow brick road is what sets you up for success in operating a business. So both.

And, one led to success in one version of the company, the other was a harder story to tell and gain trust to an investor to bet on me, a non-traditional CEO or a non-traditional path to the CEO. I think what I experienced in my career has made me into a fantastic leader and operator, but that's not necessarily what somebody's looking at who needs to check an IC5, right?

[00:04:31] Jason Rudman: You shared with me you were at the company before you got the call to be a CEO, and I sat back and listened and it was just remarkable. It truly is an unconventional moment. Would you take the audience through your history at BenefitBay and how you got to the CEO seat?

[00:04:48] Brandy Thompson: Yes. So I joined on day one as the vice president of operations. That role was going to hold HR, operations, fintech, financial leadership, and start the organization from each of those disciplines.

I was so excited to be able to own multiple disciplines from day one. I had been a transformational executive, where I come in and help companies improve retention, reduce churn on customers, look at diagnose, improve.

And so, being able to deliver from the very beginning was something I was really excited about; the first year at Benefit Bay, that's what I did. I got to own standing up our team, our tech from a fintech perspective, our backend operational structure and scale.

And one year into the company, our CEO was asked to step away from the company, and I was asked to step into that seat—I think, at first, probably from a interim thought of saving the company and raising some survival capital—and I'm here five years later.

I've had lots of learnings in that process, and one of them is really how hard it is to be that number one and hold all of the accountability, but also how hard it was to raise capital as a female or as a non-traditional path to the CEO seat.

[00:06:13] Jason Rudman: And also drive growth, right? 

[00:06:15] Brandy Thompson: And drive growth, absolutely in a new industry, driving growth and selling and stretching into…I had never been a salesperson. The CEO is the top salesperson of an organization. Whether that's in your title or not, you are selling and you are allowing people to trust your organization.

So, that's a lot of external, extroverted behavior as an introvert accountant, right? I've been leaning into that area of my life of growth for the last five years. I absolutely would not have done it had I not been asked. I know that about myself. Gently pushed into the deep end of the pool. 

[00:06:52] Jason Rudman: Gently pushed or prodded.

[00:06:54] Brandy Thompson: Yeah.

[00:06:55] Jason Rudman: Thinking about the rewriting of the playbook there's going to be many listeners who don't live in the benefits world. So could you explain the individual coverage health reimbursement arrangement, the ICHRA, the way you'd explain it to your neighbor. 

And then tell us why you believe it's going to eventually replace group health insurance the way that 401Ks replace pensions.

[00:07:17] Brandy Thompson: Yeah. So, I try to take the "ick" out of ICHRA when explaining it, and I try to take it to where people can really understand.

Benefits are the last place that we as the consumer get to make the decision. These dollars are our benefits dollars. This is portion of our compensation, right? And our employer is deciding each year with their broker which carrier we get, which network we get, what type of plans we have offered to us.

They are forced to purchase a five XL t-shirt or a Wagoneer because they can't adapt to where people are. They have to solve for the entire population. When they solve for the entire population, they're not solving for anyone, right?

And so this allows us to move to a defined contribution model and allow the employee to be the fiduciary of their funds and decide what is best for them and their families. We all live different lifestyles. We are all at different stages. We come from different socioeconomic backgrounds. We live in different geographies that have different healthcare outcomes. We should be able to purchase where we live and where we're at as individuals, and that's what ICHRA does.

It allows choice for the consumer with their employer benefit dollars, decouples the employer from being in that control, and allows the individual employee to be in the decision-making and adds competition.

Right now, there's four BUCAs who employers are purchasing group insurance from. In the individual choice market, there are up to thirteen carriers in the average market that an employee's gonna be shopping from, and a lot larger selection of plans.

[00:09:07] Jason Rudman: This is very different. So I have a health savings account, an HSA, but the HSA doesn't free up, the premium part of it, right?

I'm contributing before-tax dollars there and getting the benefit of not paying the taxes on the, on how I use them. This is different, right, because this is leveraging the premium piece?

[00:09:25] Brandy Thompson: Well, yes, it's different but both/and. You can still have an HSA plan. There are sixty-four HSA plans in the average market. So you get to pick from different carriers that have an HSA product that vary in deductible size, and you still get to benefit from the HSA savings and deferral from your payroll.

This is accessing those premium dollars to pick the right plan at the right cost for you and your family.

[00:09:49] Jason Rudman: Got it. And so this strategy's clearly working. As I mentioned, you've grown Benefit Bay to service all fifty states, two hundred and eighteen million in premium volume, and you've done that in roughly three years, which is remarkable. What's the growth strategy that made that possible? And where did you have to say no to grow that fast responsibly?

[00:10:10] Brandy Thompson: So what's made that growth possible is that we're go-to-market through the broker channel, and we have an agency software as a service model. We are and have built tooling to allow the consultant, which is where the average employer is purchasing their benefits, to add their consultative value at the table. Those consultants become our sales arm.

We have a sales team of four people on our team, so very small sales team. That allows us to be efficient. We sell a software as a service agreement to the broker agency, and then their agents become super users of our technology and deliver BenefitBay's employer tooling to their clients.

BenefitBay is then the benefits administrator for the employer, and that came by way of trust of their trusted partner, the agent, who is objective, presenting different tooling, and BenefitBay hopes to win in that scenario with that employer. And then, with the employees, we've really grown a CSAT service improvement in the industry against others because we own the service people who are answering the phone, and we can also be tech plus human, right?

And that's where we found, nurses and educators are building that trust and helping humans through this decision. 

We are in a software platform technology ecosystem. We are delivering technology value, but people still make healthcare decisions in a very anxious way. They want to feel heard. They have lots of medications, various physicians. They want to make sure that they're making the right financial decision: it's very complex. They want to be able to talk to somebody if they need to. And so we stood in that gap and delivered the human piece of the business as well.

That's really been our growth story. We didn't begin the agency till twenty twenty-four, but that agency and having licensed agents answer that phone and improve outcomes in the nervousness of being able to decide on our own plan, has allowed us to organically grow by referrals. And we're not losing customers— we have a high retention rate in the market that allows us to continue to grow without losing people off the back from not servicing well and really moving upstream. So, that premium volume growing so quickly for BenefitBay has been about average customer size moving rapidly up into what's considered mid-market or enterprise. Each customer that we're signing has a bigger life volume and a bigger premium volume per customer than the industry, which is typically in a micro SMB outcome.

[00:12:48] Jason Rudman: Yep. I went to Stanford's d.school, so I'm a huge fan of human-centered design, and you just described human-centered design. Probably one of the best stories that I've actually heard in a very long while.

You also rely on brokers, right? There's a broker channel part to your strategy. And again, I do a little digging here. You've described your philosophy as helping brokers quote, "differentiate or die."

Why choose to build for the broker?

[00:13:15] Brandy Thompson: One, I think a lot of people have misunderstood the broker's value at the table. I come up the ranks as a CFO, right? I had purchased benefits from a broker. I understood their value from a property and casualty or an employee benefit space. They bring ERISA attorneys with them. They bring various cases that they've solved.

They bring complexities for ancillaries to the table. BenefitBay [is] able to solve well for medical, bringing medical choice from a group experience to an individual's experience. I don't understand how anyone thinks they're cutting the broker from the table when an average employer has another nine products at the table, 

Two, I really understood that the back-end of the ecosystem that we service is carriers, and carriers have long relied on brokers to be their service arm and their sales arm, And so, coming into an industry and wanting to make impact is about understanding the ecosystem or industry that you are wanting to add value and drive impact. [You] can't step into the ecosystem and bite all of the hands in the industry and hope to have impact. I think that's shortsighted. So understanding the industry that you're servicing we built for that agency model. I do believe brokers need to evolve or die, and I think they're terrified of ICHRA if they're not evolving. Those who are in the game and actually learning to drive the consultative outcome for their clients when it matters are the ones winning here.

It's just I understand if you've been successful one way, it's easy to believe it's not coming. It's easy to believe AI is not coming if you don't want to believe it's coming. And in the same respect, payers still require fax in some scenarios. So we might think, "Is AI really here because we have until twenty-twenty eight to fix faxes?"

[00:15:22] Jason Rudman: Okay, youngest kid's thirteen—do they even know…

[00:15:25] Brandy Thompson: No. 

[00:15:25] Jason Rudman: [what] a fax is?

[00:15:27] Brandy Thompson: I don't think she knows what a fax is.

[00:15:28] Jason Rudman: If I said to one of my two kids, "What's a fax?" They'd be like, "A what?" 

[00:15:31] Brandy Thompson: But some payers only accept fax. 

[00:15:35] Jason Rudman: Right. But it is not unlike when we said that checks were never, ever going to be written again, right? I mean, people still write checks, and faxes still exist.

[00:15:44] Brandy Thompson: Yes, every time I go to the DMV and there's a four dollar service charge for using a credit card or you can write a check, but they don't take cash, I'm going to go find that checkbook, right?

[00:15:54] Jason Rudman: There you go. 

You briefly mentioned, so I want to pick up on this: you made a deliberate hiring decision that I think many of us will find fascinating. You hire former teachers and nurses to guide employees through open enrollment rather than using temp or a generalist.

What does a former second grade teacher or a nurse bring to a benefits conversation that, as you've learned, a traditional call center agent or a generalist simply doesn't?

[00:16:20] Brandy Thompson: Listen, nurses are tasked with ridiculous amounts of juggling. They're juggling very high complex cases. They're juggling various audiences. They may have a physician, they may have a family, they may have a charge nurse, they may have somebody from the insurance certification department, they may have a husband to deal with in the delivery of a baby, right?

So it's a lot of different audiences. They also have EMRs to enter data into. They also have drug deploying technology. They also have systems that are monitoring their patient. They have to then go calculate a drug dosage and not harm a patient. 

They are cool as a cucumber under pressure. They are highly intelligent and they can multitask.

Let's shift to a teacher. Well—nurse is undervalued as well out there in America—teachers are undervalued in America. They're risking their life every single day. They're juggling twenty to thirty students in a classroom of all different socioeconomic differences. They're showing up to that classroom at different stages of learning, different capacity of ability to learn, and different socioeconomic backgrounds. Some people are showing up in nice clothes, some people haven't showered and haven't washed their clothing. It is not that child's fault. They are a product of their environment.

Our industry is similar. Some employers are giving a high contribution, some are giving nothing. Some employees are making very limited income. Some employees are making a large income. Some employees have eight children, can barely make ends meet. Some employees have every ounce of disposable income they could have. Some are healthy, want an HSA plan, never going to the doctor. Some have one hundred health outcomes, and they're very anxious, right?

And do we need people who can empathize and do that well without panicking? What I have seen in our industry is people are hiring temps on a regular basis or contractors or temp services and staffing services, and they don't care in that six-week window how they treat the humans who they're picking up the phone for.

Our brand is how people are treated on that end using employee user. And that is why we have found that it is really successful. To be honest, how we stumbled on it, my daughter's a registered nurse. I'm a founder. We're gritty. My son-in-law's a registered nurse. I asked people to help during open enrollment when we didn't have a lot of income, and I had a few retired school teachers in my network. We stumbled on it. It was an accident, but also immediately understood that the profile we were hiring before was not able to immediately feel great once licensed and being on the phones.

Took about thirty days to license the average nurse or teacher. It was taking ninety days to license someone else because, again, they had to take complex exams. They went through their education cycle, right? They're constantly testing, and their kids are testing every year. They're keeping up their academia in both of those scenarios because they have to. And that's just really evolved into our strategy now and we've moved pretty much clinical because our director of education, she's an occupational therapist by trade.

Really, anyone who was delivering that same outcome is the right fit. It's not necessarily just nurses and we've also leaned in on those who are providing clinical care coordination for other software toolings because they also had clinical backgrounds originally and serviced in a similar area.

If you think about it, it makes sense, right? We are juggling so much in this: a broker audience, employer audience, employees, all different industries, all different language skill sets, technology skill sets, right? It's the same outcome. 

[00:19:54] Jason Rudman: Makes so much sense to your point.

What you described there is there's the rational part of healthcare, and then there's the emotional part of healthcare, right?

And, that six-week period you described is when, the EQ of the person on the end of the phone needs to be off-- through the roof.  and that building that empathetic trust conversation…incredibly important. 

So, you had mentioned AI very briefly when we were talking about faxes. I do want to go down the ‘AI and the future of benefits’ path. I know you've already integrated AI into the BenefitsBay platform for things like plan recommendations, claims process, and customer support.

We just talked about this element of the human connection and trust, right? Somebody on the end of the phone or even, looking you in the eye and saying, "This is the right plan for your family." Guidance in what is a really hard and complex decision. 

How do you think about where AI should make that decision easier versus where it should take a step back or where it should step back and let a human lead?

[00:20:57] Brandy Thompson: Yeah, I think it's a good question. I like to talk about AI responsibly here. 

A lot of people talk as if AI could be flawless in this scenario, and I don't believe it can yet. There's a lot of language learning and models that need to go on for some period of time and exposure, and each year the plans change, right? And so then there's a new set of tools that everybody needs to look at.

What we do here is we're using AI in engineering, in PR releases and supporting from a cloud enterprise perspective through Anthropic. In a HIPAA world, we're relying a little more on Copilot actually in recording and transcribing of our meetings because of the security controls and parameters within our company.

And then from a servicing the end-using employee, we have a hybrid approach, right? As they're navigating the platform, it's constantly trying to suggest things that would answer or solve their problems or scenarios that they may want to look at.

It's not going to the point of telling them exactly what they need because we don't see the accuracy rate there by the AI—very much like UHC launching it for their pre-authorizations and having, you know, a fifty percent accuracy, and they've had a lot of deaths, right? 

We're not going to do something that's irresponsible financially for BenefitBay or that member. We want to make sure it's the right outcome. So it's in the responsible stage of recommending what our team should ask and finalize and make their job better or more scalable.

But it's not to the place of we're going to absolutely tell you which plan you should have and select it for you because I think it's only as good as the recommendation of that individual taking the time to put in the platform.

So m, we're not at the place where we're ingesting every single medical background of that employee. One, the employee would have to authorize it; two, the technology isn't there on the individual side of the house, the individual family products that are used in ICHRA. I think it may be getting there from the group insurance side because you just have to load one carrier and three plans, right?

On our side, there's three hundred-and-six carriers across the nation, a massive amount of plans, and they change every year. So it's important that we do that responsibly, making sure that the company's continually moving forward from an AI perspective and an AI native from a team and training each individual contributor of how they can improve their day and their work life, and also how can they use it to support that end user.

But we're not to the point where we're just autopilot telling someone how or what to do based on a limited amount of information and only five years of the ICHRA industry, right?

We do not feel the data is there or that the risk profile is there on the reliability of the network searches or the drug data in American healthcare in general.

[00:24:01] Jason Rudman: The thesis on AI as given by Brandy Thompson.

So, I was in a conversation last week and somebody said this, which resonated with me, and it was the simplest way, and it's not earth-shattering. A computer is deterministic. AI is probabilistic. And what we're dealing with is probabilistic odds in something where you'd want much more security that you're actually getting the right plan. So that was the light bulb moment for me as I was hearing you talk.

You also mentioned HIPAA. For the audience listening and I say this often, Brandy and I did not get together, and she's not teeing this up for me.

But however, she did mention HIPAA, and so healthcare data, some of the most sensitive information that exists. And you have been vocal about data privacy. As AI gets more capable and obviously more hungry for data, where do you draw the line between personalization and what I'll call good governance or surveillance? Because got to believe that the same data that helps recommend a better plan could also be used in ways that would feel invasive. 

[00:25:06] Brandy Thompson: I believe so, and I'm very vocal because in our current self-insurance profile inside of an employer, they are able to gather your personal health claims and health information as an employer. And, I would like to believe that no one ever lands on a reduction in force list over their healthcare outcomes but I actually unfortunately know that it happens. 

I had been an employer's pre-ACA where it happened regularly on group insurance renewals, and it was quite disgusting. And as part of my passion for this industry, I think we need to care about our data, and we need to care about protecting that.

And one of the positives of the move towards this ICHRA or defining the contribution in individuals choosing is they own their healthcare plan selection, and they own their evidence of benefits and their claims process, not their employer, right? 

And so, allowing that individual to pick a plan because they're planning to have a baby, allowing them to pick a plan because they know they need hip surgery without having to go through HR to discuss what they should be doing for the cost containment of the employer's health plan, right?

And I think that private health information, PHI, private identifiable information, and HIPAA is something that software companies out here are not doing well and they're not protecting. And I think sometimes,  employers and employees are unassuming and don't realize that not everyone has to have those things to turn on a technology and sell some business, right?

It's very much the Wild West when new industries are coming to life, and then regulations follow risk. So, after people had risk outcomes, then we get regulations in an environment. I'm very passionate about people getting really intelligent about how these things work, and at least caring, right?

Moving this to consumer-based and also moving the motivators, because we know that humans are motivated by things that affect them personally, and by the rewards that go to them. 

Individual products, if they have healthcare outcomes that are positive, they receive the rebate. The employee receives it, not the employer, right? There's money back to me for doing better? I think that's another place of maintaining privacy, those rewards and those dollars inside the individual, instead of having motivators that are maybe going to a broker or an employer for those cost containments.

Let's motivate me to cost contain, but look it up on my own phone and not bother HR for that, right?

[00:28:00] Jason Rudman: Feels like you're ahead of the curve. So with that in mind, I'm going to ask you to sprint forward to twenty thirty (2030). AI can guide an employee through enrollment, answer every question, compare every plan, optimize every dollar, maybe. Does BenefitBay still employ former teachers and nurses? What's the human role when the machine can do a lot of the technical work?

[00:28:24] Brandy Thompson: I think there's still a human role in that. I think maybe the technically aptitude employee gets through the AI-only journey, right? But I think that there will be trust, and probably more so as things fail through practice in the AI and robot world that we'll be moving to.

There'll become some distrust and people will want to talk to a human. Also, I think that there are scenarios where an individual's going through cancer treatment, and they're feeling very anxious about their employer's change from one plan to a choice option, and they're going to want to talk to an individual and not just accept accountability from a computer that they can't feel or touch.

I think that will be important in twenty thirty and I think overall, individuals will become consumers of healthcare. They'll be a lot smarter individually about what they want, and they may be able to make that decision as well with limited or no support from AI; let's not give up on people being able to evolve into making their own healthcare decision without a lot of support from AI. 

[00:29:32] Jason Rudman: We are not giving up on humans.

[00:29:34] Brandy Thompson: We are not giving up on humans. And their physician can help them consider plans that are actually taking care of the physicians and approving pre-auths and making payments on claims quickly. 

There can still be a human element to how this gets decided, and I think it still will be here.I think it's still teachers and nurses. I think it's also those who want to make an impact in healthcare, anyone who has that passion, deep to the core of their being, to survive when fax is no longer a thing at payers. So let's see how they do on the next stage.

One of our engineers likes to say, "It's great to talk about all this innovation, but the carriers have been around for a long period of time, and they are at different technology evolutions, and they move like cruise ships." So there will still be some human element to make sure that people are stewarded well in this process, because data integrity is lacking for AI to be accurate.

[00:30:25] Jason Rudman: I think what we're talking about, and it is similar to financial services, is an elevated, more advocacy-based guided conversation given the subject matter that we're dealing with, whether that be your healthcare or how you make ends meet or build wealth or live better tomorrow than you are today.

I think to your point humans will always need humans, even in an increasingly digital AI-enabled world.

[00:30:56] Brandy Thompson: Right, Jason. That's a good parallel there to the pension to four-o-one (401K Plan) that a lot of people say that's ICHRA of healthcare, right? That's the defined contribution moment of retirement.

Most of us could a little ways ago, when E-Trade started, we could have all became personal day traders and everyone said the whole financial services industry is going under. It's not true. There are still brokers in financial services. We can get recommended plans for our retirement. We can go into age-based products. We can even have it suggest how it diversifies our funds. We still want to talk to an advisor.

So, the broker is not going anywhere, and BenefitBay having a human talking to somebody through the complexities of the HSA decision and my employer's giving me money versus this decision versus that decision versus my advisor over here on financials tells me XYZ.

They want someone to help them make the decision in complex ways at some times. Now we're all mostly doing our taxes on our own. Tax is a complex decision we never thought we would do without going and sitting down with our accountant in a box. Most of us are doing our taxes on our own; there is a human-guided side if we need it, even inside our software solutions, or some of us still prefer to go see a tax accountant, talk through strategies at a higher level, like you mentioned, Jason, right?

So I think there's lots of examples through all of those various pieces that have had evolution that a human is still needed sometimes, and sometimes we still have to call the dreaded IRS and wait for two hours, right? And so, it can't be changed—there's no AI that can solve that problem for us. We still got to solve it.

[00:32:37] Jason Rudman: I just want to go on record that I need a human to do my taxes, and I don't even start in a digital world, and I don't want to contemplate answering. I don't start, I don't end. I still need a human. 

[00:32:46] Brandy Thompson: I'm in Kansas City, who's to say we were gonna be the H&R Block of healthcare. 

[00:32:49] Jason Rudman: So I want to pivot to leadership and fundraising  and you actually talked a little bit about this in the open. So, you raised a five million seed round in twenty twenty-five, and you have an oversubscribed round before that. 

You hinted at the beginning about being a woman founder and that the fundraising experience is different. We've had many women founders on the More Elephant podcast, and I think you're likely to affirm some of what they've said and then share some other things that have been unique to your experience. So what was that fundraising experience actually like, and what did you learn about who gets believed in those rooms?

[00:33:30] Brandy Thompson: I refused tobelieve that the male-female dynamic before doing this role. I've worked in highly male-dominated industries, and I was in finance, and it's a highly male-dominated industry. Most of my bosses at the CFO seat or the CEO seat have been men. I've actually never reported to a woman outside of one controller in my entire career.

So I really didn't see-- I mean, we could say we don't see gender, right? I didn't really see that as being a problem. However, I quickly found out in this seat it's different. Ninety-nine percent of the money goes to a white male, one percent of the money goes to women and minorities. I would have great conversations, and I would secure the buy-in of the first three levels, and then I would get to the managing director level and I would lose confidence.

And, I started to notice a pattern; there were very few women in any room in VC or investing at all. I've met five out of hundreds. Five out of hundreds. So it's the same sitting across the table, right?

What I did find—I once hired a fractional CFO to sit beside me in meetings. The men in the room look to the man in the room to validate what I've just said. Now, he was married to a very high-powered lady in finance, and he would often say, "I'm watching what you say all the time, and it is happening. I am watching her articulate the vision and mission. I'm watching her articulate all of the numbers, and they look to me to validate it," and he'd been there a week the time I brought him. 

I recently witnessed it. I've brought two C-suite gentlemen beside me, super high caliber careers and resumes and CVs, and raising capital this time, which it's not public yet, but raising capital this time was the easiest it has ever been for me. Yes, I'm on a hyper-growth trajectory, so maybe that has a little bit to do with it. Second, possibly because it's been three years now since the CEO transition, or four years now in total, right?

So, that first year, people are testing you out. Can the company survive a CEO transition? Second year, we have to buy him out; you're using new capital to buy someone else out. It's non-deniable, though, that there's been more excitement about others in the room who've just joined the org than those who have built it, right? So that is something that I've experienced and I've seen firsthand.

I'm very motivated that post Benefit Bay twenty thirty (2030), when I'm wildly successful, I hopefully get to sit on the other side of that table and make a difference. That's what I'm motivated for. It really motivates me to one day be on the other side and give some, with adversity in their background or with non-traditional profiles, that capital. 

[00:36:38] Jason Rudman: That is on some level the only way it will change. So interestingly in the story, the accounting roots in your history, I'm going to pull a thread because I think the financial discipline shows up in how you built BenefitBay.

So, the company grew organically before you raised capital. You were profitable before you scaled. In the startup world, where I would argue there's a lot of burning of cash, what gave you the conviction to build that way?

[00:37:05] Brandy Thompson: Really it was twofold. One, we didn't have the luxury of a choice, so I'd like to assume I would've done it that way regardless. I have only worked in companies that were profitable. EBITDA was king. That's what we measured to.

I didn't know there was a world where you burn cash, go get more cash, sell off your company to continue to build. I didn't even know that existed. So it was out of requirement. We had burned four million dollars in year one under Zach's first year, and so we hadn't made the traction that justified another round in that first year.

And we then had a non-traditional CEO take the seat in a transition under dire circumstances. So, we had to overcome that adversity by being very lean and very smart and very focused. I also have a board of investors who are very path to profitability focused, so they kept me focused on I could still compete and build a great business without raising eighty million dollars as a competitor is doing, right?

So they kept me focused on the goal is outcome for team and investor and build a profitable business that is self-sustaining, that can control its own destiny They kept me focused on it when I would get really—I would think I needed the capital to win. So that was really important that I had those investors and that profile at my side.

I think the financial discipline, yes. I don't think the average person could have built this business under the limited capital that we had because we had to really be smart about everything. Cash flow is really important, and understanding where every dollar is going was really important when you're building lean. And I think a lot of people haven't had to do that.

I've worked in regular companies that don't have a line of credit or that don't have an investor lined up at the door; that have to survive cash flow ups and downs and seasonality.

So that is a skill set I could pull on easily as a muscle that had already been stretched a lot in my career, especially when I was in manufacturing and construction. They're constantly out a bunch of capital before they collect, complete the job, right? So you've got to be advancing cash to complete a job, and no one's giving you the money to do that. So, making sure that work is something that I did have exposure and experience with and which did lend to success here. I am excited that this team will have an outcome because we didn't build that way. 

You also are making an impact in an average person's life who didn't have the traditional resume in a way, and you're changing that passion to change lives and to allow people in the Midwest to have an experience that only people in the [Silicon] Valley or New York traditionally understood is something that's really driving and motivating for me on the hard days. It's just the impact this team has as owners, right?

[00:40:08] Jason Rudman: Your quotes are luminous. You've described, which I think is a bookend to what you said, you've described “benefits as a lever for empowerment, equity, and financial wellness.” And so, you talked about the impact in the Midwest that changes things for the hourly worker, the single parent, the person who never's really had a choice in healthcare.

Everything you're doing ties back to that legacy of empowerment, equity and choice.

And I think, so it's incredibly important. I mentioned, and you acknowledged that you're a mother of six and you have built this company while raising your family, which is remarkable.

And I think we often reduce this to balance, right? How did you balance all of that? But I'm not gonna go there— instead, I'm actually going to go in a different direction, which is how has being a parent of six shaped the actual decisions you've made about what kind of company Benefit Bay is and will be?

[00:41:05] Brandy Thompson: That's a good question. I think being a mom of six and six different personalities and still raising children to be good humans and have an impact in society is so very cross-functional to leading a company and a team with all different humans who you are trying to raise up to their highest potential. I think I've been stretching that skill for three—my oldest is thirty two, my youngest is thirteen, and… 

[00:41:33] Jason Rudman: You told me it was thirty two and I literally dropped on the floor. I was not ready for thirty two.

[00:41:38] Brandy Thompson: Yeah. And I think the other thing is I didn't realize how much it would drive me to know my girls are watching me with this opportunity that I got pushed into the pool, right? 

Early on, I didn't really tell people I was the CEO. I didn't update my LinkedIn. I had a bit of fear of failure and imposter syndrome, and my girls would hype me up—they would say, don't know if I can cuss on your podcast, "She's a badass CEO." 

[00:42:09] Jason Rudman: You can say that on the More Elephant podcast.

[00:42:11] Brandy Thompson: So yeah, they were calling me Boss Babe and things. And I'm a very humble person, so people would ask me where I worked, and I'd say, "Oh, I work for a software company."

I was married in February of twenty five, and if he ever heard me say it, he'd say, "She's being humble. She's the CEO of the company." 

So, people helped me to really lean into the impact you can have, but also the weight of that. And at first, I was uncomfortable with leaning into the weight of it all, I think, is a little bit of it. I think having those girls is highly motivating; not failing is highly motivating. Also, giving myself the grace that you are integrating your family and six kids and life, and there's ups and downs, and you're not balancing all the time. Sometimes it's out of balance. And being able to have those cheerleaders that I did have, six of them, has been very motivating, humbling.

My thirteen year-old says, “you're not anybody because you're not viral on YouTube or something." But, their generation is very different and...

[00:43:17] Jason Rudman: Mom, you're an influencer in different ways. 

[00:43:19] Brandy Thompson: She said, "Yeah, you're not an influencer. I don't see you on House of Kids."

So you know, that has been a fun experience as a mom, really. It keeps me motivated, and I think that is something I didn't realize—you really need is somebody.

You don't have to be a parent. You need someone in your circle who's rooting you on because we all can lean into feeling like we're not good enough or we have a fear of being successful in that role.

It doesn't matter if you do have the resume. It's a lot of pressure, right? So being able to have somebody in your corner helping you to lean in and accept the weight of it all is really good, and to know that you have them to vent to if you need to, you know, a little more elephant, that somebody will be there to listen on the hard days and challenge you to get back up there the next one.

[00:44:08] Jason Rudman: Do you recognize this quote? "Don't wait for permission. Lead with conviction."

[00:44:15] Brandy Thompson: I do.

[00:44:16] Jason Rudman: That you do. I know, because it's yours. When was the last time you had to take your own advice?

[00:44:23] Brandy Thompson: This round of capital. It was somebody across the table said, "All I've heard you talk about is what's best for the company or the team. You don't talk about what's best for you." So, back to always leaning into that leading with conviction and not asking for permission. I was leaning back in on asking for permission to ask for my value in those conversations. and had to be reminded by the person across the table.

We need that, though. We need people like that out here because we can all start to slip in those ways, right? We gotta be reminded of that. Yeah. 

[00:44:57] Jason Rudman: I love that. This has been a remarkable conversation.

[00:45:00] Brandy Thompson: Thank you Jason. 

[00:45:02] Jason Rudman: Brandy inspired. I know everybody that's going to listen to this is going to be incredibly inspired. You're taking something that is complex, trying to make it easier for people and give them choice.

How do people find out more about Benefit Bay and the amazing Brandy Thompson?

[00:45:20] Brandy Thompson: They can follow me on LinkedIn. I have a little bit of content that I put out there maybe once a month. I'm trying to lean in on that for thought leadership. And then for social handles, it's 6girls13, the number six girls13. And then for BenefitBay, it's benefitbay.com. Obviously, sales@benefitbay.com if you're interested in getting a free quote.

That's free for your employer or if you're an agent, if you want to take a look at our technology. And yeah, just follow some of our team. BenefitBay is on LinkedIn as well. We're not very good at the BenefitBay socials yet, but I just recruited great people on marketing. 

[00:45:54] Jason Rudman: You got a thirteen year-old to rope in, I think.I think there's a roth IRA contribution waiting to happen. Come on. Like that's, you know.

[00:46:02] Brandy Thompson: I think so. Yes, absolutely.

[00:46:04] Jason Rudman: Brandy, thank you again for your time. And we cannot wait to continue to follow the amazing trajectory of Benefit Bay. It's been a pleasure.

[00:46:11] Brandy Thompson: Thank you, Jason. 

[00:46:12] Jason Rudman: Thanks.

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