1193: Building Finance Functions That Shape Outcomes | Jesse Waldron, CFO, Thyme Care

Jack: CFO Thought Leader is made possible by Sage High Performance Finance Software and Intuit QuickBooks bill pay. Say goodbye to manual bill entry.

Andre Mansell: Hello, this is Andre Mansell, CFO of neom and you're listening to the CFO Thought Leader podcast.

Jack: This is episode, uh, 1193.

Jesse Waldron: What the big moment was really thinking about. Okay, how do I take the financial profile of Propel in the board meetings that the, that ResMed is now sitting in, where they are seeing our, you know, are seeing our quarterly results and how do you transform that into a way that gets them excited about the potential future of what, of what Propeller plus resmed could look like. Right? It wasn't, you know, wasn't as you think about like financial reporting can often be not that fun but you know, thinking about like they are not going to care about how we performed last quarter against our budget, whether we did 2.5 million or 2.8 million of revenue. They are going to care about like think long term into 2029 and the market that we might be able to impact if we use uh, what propeller services are across all of ResMed's different devices and how we think about the long term view into the company.

Jack: Hi, it's Jack.

Andre Mansell: On today's show we speak with Jesse

Jack: Waldron, CFO of timecare. One of the challenges facing finance today is figuring out where technology truly creates leverage and where human judgment still matters most. For years, CFO have talked about automation, efficiency and scale. Now AI is accelerating those conversations in ways few people anticipated. The question isn't whether finance teams will use AI, the question is how far it can go before something essential gets lost. And that's particularly interesting in health care, where the stakes are measured not only in dollars, but in human outcomes. Our guest today has had a front row seat to both rapid growth and rapid technological change. Along the way, he's developed a perspective on finance that extends beyond reporting results to shaping strategy and helping organizations see what's possible. We'll why the most effective finance leaders don't simply measure value, they help others recognize it. Our, uh, talk with CFO Jesse Waldron begins after this. And so it's been said, growth in business comes from data driven forward momentum and without time, clarity and control, it can be impossible to move when and how you need to. Intuit QuickBooks, bill pay, automates, accounts payable so you can see clearly, act with intent and remain in control for your finances. Their powerful platform brings bills, vendors, payments and 1099s together so you can make smarter decisions and reclaim precious time. And energy. With QuickBooks Bill Pay, you choose how and when money goes out instantly. See what's due, control who needs to approve it, and see how it hits your cash flow. Vendors add their own payment details, but you don't spend time chasing them down. You stay in control and confident, making it easy to chart your own leadership path and move forward the way you need to. And so it's been said yet again, reclaim time and control so you can move forward. Making the switch to, uh, QuickBooks Bill Pay today. Learn more@quickbooks.com BillPay Again, that's quickbooks.com BillPay terms apply. Money Movement services are provided by Intuit Payments Inc. Licensed as a money transmitter by the New York State Department of Financial Services.

Jesse Waldron: Hello.

Andre Mansell: CFO Jesse Waldron is with us. Jesse's finance journey has crossed healthcare services, digital health, startup ventures and value based care organizations, navigating rapid growth and major transactions along the way. He helped guide Propeller Health through its acquisition by ResMed and later helped Cricket Health merge into Interwell Health in a multi billion dollar deal. Today at Timecare, he's helping scale a company focused on improving the cancer care experience while navigating the operational realities of modern healthcare delivery. Jesse, welcome.

Jesse Waldron: Thank you very much, Jack. Appreciate you having me on the podcast.

Andre Mansell: If you wouldn't mind, I'd love to, uh, just go back to one of your early chapters, or perhaps the earliest chapter. I didn't include this in my intro. But you were at IBM for four and a half years. I have to believe that was your launch pad. Maybe you look at differently. Um, but that finance organization of course has launched, uh, quite a few CFO careers. Having interviewed so many over the years, what is your memory of that experience? Was that a big deal when you got the phone call and found out you had a job at IBM?

Jesse Waldron: Yeah, it was definitely a big deal. I was a college kid and, uh, I got the letter in the mail. This was, I think this was even before email. This is how old I am. I got a physical letter that said, we are offering you the job of a financial analyst. Uh, and I was super excited to take the role. I was at IBM for about, I think, four and a half years, which was a really great experience. Taught me a ton about, uh, how finance operates at a big company. Um, so I really enjoyed my career journey there. I had quite a few different roles throughout the time there. Sort of, um, as you might imagine, a very big organization where you can plug into a bunch of different places.

Andre Mansell: Was IBM recruiting on campus?

Jesse Waldron: Yeah, they were recruiting on campus. So I went to the University of Wisconsin. And so at the business school uh, they came and interviewed folks, they sort of went through the rounds and uh, you know, everything was uh, great from there.

Andre Mansell: Where did you land? What office geography wise?

Jesse Waldron: I was in Rochester, Minnesota. So it was actually a pretty interesting start to my career. IBM's big uh, idea was hey, we have acquired many, many companies over the course of the last couple of years. Uh, we have finance leadership roles and finance roles throughout the country. Uh, what we are going to do is we are going to go and find a bunch of college kids who just graduated college. We are going to recruit them and we are going to bring them to Rochester, Minnesota, smallish town, low cost center where they had previous ah, facility for manufacturing. They created a big ah, center of excellence where they hired ah, you know, a bunch of, a bunch of ah, people who sort of looked, looked and acted a lot like me at 22 years old. Um, uh, for better or for worse, um, ah, and they, and my first week there it was you know, hey Jesse, like you know, we're excited you're here at IBM, like your role. You are, there is a, there is a woman um, in North Carolina who has a job, whose job you are taking. She is leaving in two weeks. You, we're going to fly you out there, you're going to go spend as much time you can with her. It's a bit of a, you know, touchy situation, um, but learn as much as you can and then you know, when you come back here that job is basically yours to do. Um, and so that was my first experience at a big company, uh, which was uh, all sorts of exciting and a big, a big opportunity. Um, but it was a big, kind of a really interesting first lens into like how a big company operates Now.

Andre Mansell: Were you serving health care customers at IBM? Because I know that the next door that swings open for you, you're in the health care realm I think. Did IBM experience overlap with that or was it a new sector for you?

Jesse Waldron: New sector, yeah. So I didn't, I didn't touch any healthcare when I was at IBM. Um, what I found at IBM. Like I think my one thing I, a big thing I learned at IBM was that it was very hard for me to have influence over the company. Right. There are um, you know the response, even though the responsibility that I had was very big and broad in scope. I was managing you know, a couple hundred million dollar P and L that ultimately rolled up to you know, a bigger P, L that Rolled up to someone else that ended up being one number on one, one financial statement that people maybe cared about a little bit. Um, so I, I struggled a lot with having a really big impact and so over my career I had tried to go smaller and smaller in terms of having a bigger impact in my career over time which led me into health care. I didn't, I didn't intend to get into health care. I uh, I moved to. We were in uh, in Minnesota and I had met a, I met a girl and she was moving to Denver and I decided that I was going to go with her. We were dating for a couple months. She got into an accelerated nursing program out there and I'm not sure if she actually offered for me to come with her but I joined her and uh, uh, we moved to Denver and I was working from home uh, for IBM sort of. This was way pre Covid before sort of work from home was a big thing and I wanted to get back into the office and found, found my way to a company called healthgrades, uh which is a public company out in Denver, was taken private by private equity group.

Andre Mansell: You would make a uh, five and a half year investment there. I just want to point out so similar size investment as you made at IBM maybe a year more. But still you're someone who's investing career years all along the way. You are a, by the time you leave you're a vice president of strategic finance. Did you enjoy some promotion within that company? Uh, more experience coming your way?

Jesse Waldron: Yes, I definitely did. That was a great experience for me. So the company was, it was a public company, it was taken private by private equity. Um there was, when I joined there was a ah, finance team which was sort of quickly replaced with folks from the private equity team to come in and become uh, the cfo um of the entity. So I learned a lot about uh, the private equity world and how they operate and how they think about uh, running companies that were run by operators before. Learned a lot of good, learned a little bit of bad, uh, but was able over the course of uh the five years to sort of like really grow my uh, skill set and my experiences to become uh, a couple promotions over time and sort of was the number two there at healthgrades for a long time. But learned a lot about not only healthcare and how healthcare operates. But how do you really, how do you really use finance as a way into making really big operational decisions within the business and how do you use that as a lever to make sure that cross functional areas are all operating with the same information and making decisions that impact the financials of the business over time in a really meaningful way. So I would say that is a huge learning opportunity for me early in my career, uh, and got me really excited about healthcare.

Andre Mansell: I would say by the time you're leaving health grades, you're locked in on the CFO path.

Jesse Waldron: Yeah, that was my path. So as I was thinking, and, uh, I was definitely like, I want to be a CFO over time. I think my next jump from health grades was to the place where I could go run finance independently. Um, I didn't yet have the title. There was no CFO at Propeller Health when I joined. There was only a. It was a pretty small company. So, uh, I was sort of the. The head of finance there. Um, but that was. That was my next path into. Into really taking the step of being the. The number one at the organization.

Andre Mansell: So were you thinking that even back to your IBM days, were you thinking, I'd like to be a cfo?

Jesse Waldron: Yeah. And actually, to go back to your earlier. Your earlier story, uh, about, you know, when I got recruited from, from business, from, uh, from college, uh, I remember very vividly in an interview, uh, of a job I did not get, uh, with a Fortune 500 company where they asked what I wanted to be. And I said, listen, I want to be the CFO of a Fortune 500 company. And the guy looked at me and he said, well, you know, there. There are like 500 of those in, in the world. And so, like, that's like, pretty unlikely that that would happen. I said, yeah, I understand that. I understand that's what I want to do. Um, and I've always had that, you know, obviously didn't get that job because the guy thought I was crazy, but sort of always been my mindset of, like, I want to continue to progress my career. I want to continue to prove to myself and to others that I can operate and be a CFO of a big company over time.

Andre Mansell: So we're. Now you're at Propeller health. You're really 10 years away from where you are today. There are multiple CFO roles coming your way. Uh, this is where you really become the CFO and you become a leader. Can you reflect a little bit on your leadership development or when you felt the full weight of the role on your shoulders?

Jesse Waldron: Yeah, for sure. The. So the company Propeller was founded, um, it's in Madison, Wisconsin, which is where I live now. It's where I went to. Went to college also. So I sort of used the Opportunity to move back, back home, closer, uh, to home. The uh, the company was founded by two co founders, a a scientist and a, and a technology person. Uh, and when I met them the company had, was a, ah, really great idea, had not scaled meaningfully in any sort of way, but had a bunch of good investors and had a bunch of, had put a bunch of time into research and development and was just on the cusp of commercialization of the product that we ultimately went to market with. Um, and they came to me and said, you know, our board is telling us that we need to hire someone to run finance. We actually have no idea what we're doing. We, we use an outsourced accounting firm and that's kind of the extent of what we do. But we, you know, we, we need someone to, to come in and do it. And so I use that as, really as a, as a, as an opportunity to propel, propel myself at Propeller Health into a uh, leadership role of actually taking on the full finance organization, being able to build everything from the ground up, right? And there's essentially nothing that existed when I, when I came and was able to build from, from scratch to kind of, you know, put my own mark on, on what a finance organization should look like at a, at a, you know, VC backed dealing company.

Andre Mansell: If we were to look at your network, you've already talked about the PE executives, you know, board members, you know, PE executives, you know, other, you know, the CEO. I mean all these people are perhaps influencing you and giving you confidence to step up and take on this role. Or how would you describe it?

Jesse Waldron: Yeah, definitely. I think, uh, another thing I've learned over time is like being able to use your network around you and being able to understand the sort of the good, the bad and the ugly from everyone that you interact with over the course of your career to help shape sort of how you think about how you want to operate. Um, so I've had the fortune of working for a bunch of different finance leaders over time and a bunch of other CEOs and got to see how executive teams operated, um, got to be in a lot of boardrooms, uh, throughout my career to understand sort of uh, what is the best way and how can I take the information that I have to make the best decisions to help really guide this company. So I sort of use that mindset and I still do today of like, you know, everyone I meet, everyone I interact with, I pick up little things of things they do well or things that I see them, um, able to do what they want to do and help use that to guide, guide me as I think about it.

Andre Mansell: But this is gonna be, it's gonna be a tough question. We've been just going over these different chapters, these different companies. Where and how was your, how you lead finance teams today most influenced? Was it IBM, was it your Propeller Health? When you think about how your mindset as far as leading finance teams, where did it happen?

Jesse Waldron: Yeah, that's a very good question. I would say. I uh, don't think there is like one specific moment or place where it's happened. I think it really happened over time. I think it's really been a career, a journey. And as I think about like where we operate today at timecare, which is you know, a much bigger company than Cricket or Propeller or even health grades, right. The company has gotten, gotten pretty big. Um, it is like all of the different aspects of things that I have learned and seen over time kind of shaping the narrative into what we do today. So um, you know, taking a lot of the like early mindset of building things our own, but also like thinking about in the back of my mind, oh, IBM operated at a huge scale and these are the huge, these are the processes and procedures that they thought about as they did that and sort of merging all that into, into one I think has really helped me. So I would say, you know, maybe a bit of a cop out answer, but no specific moment. Just kind of the learnings of the journey. I would say.

Andre Mansell: Uh, and again it's an interesting chapter because you're at IBM, uh, where there's a lot of perhaps senior finance, senior executives, IBM senior executives around you, opportunity for mentorship. You go into these smaller environments, you're sort of more on your own as a networker. I would say you have to sort of understand cross functional areas much more than, perhaps more exposed to them than you were at IBM.

Jesse Waldron: I suppose I've been really fortunate in my career. I've been able to be at um, a lot of successful companies with really great founders and CEOs that I have been able to get a lot of mentorship from. So thinking back to the Propeller days, so David Van Sickle was the founder, CEO of uh, Propeller Health. Even though he was not able to mentor me on a, like from a finance capacity. Just the mentorship of like, you know, how to go about and operate a startup company, how to think about these things, how to gain trust throughout the company, how to gain leadership skills. Um, so David was very influential to me over time. At Cricket Health, the CEO Bobby Sipuka was very influential and a great mentor in terms of, you know, how do you bring operational rigor into the, into the company, how do you grow and scale this business in a, in a value based care world? Um, and fast forward to timecare where I've been super fortunate. The leadership team here is fantastic. So Robin Shah, who's the CEO, there's uh, Brad Diepeis, who's our president, have been able to work hand in hand with these two gentlemen over the last almost three years to really uh, learn a ton about the oncology landscape, to learn a ton about rapidly scaling a business from you know, series B and quickly, uh, growing beyond in the last couple of years, uh, to really scaling a business into um, something really special. So I've been fortunate to have a lot of really great sort of senior leader mentors over time and I've also been able to pair that with a lot of investors that are investors in the company who I've been able to work with, uh, and gain a lot of uh, insight and great relationships and learnings from them sitting on the other side of the table. Um, as well.

Andre Mansell: We might have a few more career related questions for you, Jesse, a little later, but right now let's find out about timecare. What is this company about?

Jesse Waldron: Yeah, uh, so timecare is an oncology care navigation company. Um, we help patients that are undergoing their cancer journey. So patients that are diagnosed with cancer often, uh, are going through this terrible journey. They are recently diagnosed and they are put into this uh, experience in the American healthcare system which is very overwhelming both financially and emotionally. Um, so what timecare does is we partner uh, with health plans and with oncologists to help manage members that are going through their cancer care journey in order to help them have a better experience and ultimately to bend the cost curve for um, uh, the health plans that we partner with.

Andre Mansell: Very interesting. I mean I can't imagine there's quite a few listeners who are familiar unfortunately with the cancer journey of a loved one. I want to ask, often you're hospitalized or what have you, it's discovered, um, do you partner with the large healthcare institutions? How do you come into the equation?

Jesse Waldron: Uh, yeah, so we really sit at the center uh, of the ecosystems. We think about the way in which our business model works. We partner with the health plans so the insurance companies or um, um, entities that are taking risk on populations, uh, of patients. So we go to the plans and we say, hey look, we can help manage the members that are going through their active cancer journey. We can Help lower the costs that ultimately go to you. Uh, the health plan to help ease the burden of the rapidly rising oncology costs over time. Uh, we then partner directly with uh, patients who are undergoing their cancer care journey. So the health plan gives us the members and say yes, like we have 5,000 members that are going through the journey. We're going to send you their information. You can go and manage those members on our behalf. Um, we then partner also with oncology practices, think, uh, community oncology or health systems that are actually giving the care or giving uh, the treatment to these patients and help work with them to help navigate their patients through the journey. We do that through, uh, we've got a virtual care team. So we've got about, I think 550 members today of nurses, social workers, lay health navigators that help manage members sort of in between appointments, uh, making sure that we can reduce uh, the total uh, cost to the, to the plan to help make sure that the members are getting their appointments on time, they are uh, on the right medications, they're doing the right things and happy through their journey. Um, and then um, ultimately we sort of help, uh, sit at the center of that contracting vehicle between all those entities, um, to help us as our fundamental business model.

Andre Mansell: Now are most of your, and I'm just thinking of the patients, are they in the major metro areas?

Jesse Waldron: We serve patients all over the U.S. so, uh, both in rural and in major metro areas, um, what timecare's business model allows us, you know, is a virtual care navigation service. So our model works very well, especially in rural areas. We think about places where folks don't have access to large academic hospitals, uh, medical centers where they are seen by community oncology practices that are in, you know, rural Tennessee. Uh, we are able to help manage those members in a way that has uh, a meaningful impact on their journey. We serve, uh, as of Today, just over 120,000 members that are actively going through their cancer journey, uh, which is a meaningful amount of the American, um, population that has diagnosed with cancer today.

Andre Mansell: Just from a numbers point of view, if we look at cancer and the notion, some of the largest, most esteemed, uh, hospitals that are serving patients today, there are only so many doctors, there's only so many oncologists. The fact is, is during your cancer journey or during the time or the period a patient is being served, they might only see that doctor infrequently and they might only receive service, uh, a few, maybe it varies patient to patient. What am I getting at? I guess the Opportunity. I'm trying to understand better. It seems to me we'd all like to believe that there's a doctor who's very much aware of you, but the fact is that Dr. Today, even in the most esteemed organizations, the doctor to patient ratio, uh, isn't what it needs to be. So how do you achieve a greater level of care? How am I doing? Am I close? Or do you look at people differently?

Jesse Waldron: Yeah, exactly. You think about, uh, someone who's undergoing their cancer journey and on chemotherapy, for example. We will go in to get their chemotherapy. Maybe it's, maybe it's once a week, they go into the office, they sit in the chair, they get their chemo and then they go away and they come back. They have a next scheduled appointment, maybe in a week. There's no one that's checking in on them. There's no one to make sure that they're doing all right after their appointment. There's no one to make sure they're on the right medication. There's no one to make sure that they can answer any questions, right? So by, uh, timecare, what we offer our virtual care services. So we have nurses that are on the phone 24 7, where you can call, you can text, you can do a video visit, say, hey, you know what? I got done with my chemo. I just don't feel right. I'm feeling nauseous. Should I get some medication? Should I go to the er? Like, I don't know what to do. Um, and so we offer, we are that really high touch, um, very personalized support that is in between appointments where we meet patients, where they are. Um, and so the unfortunate part of the American healthcare system, as you're probably aware, and I think many listeners are probably aware, is like, we still live in a very fee for service world. And so if the healthcare institution or the doctors are not incentivized to reach out to patients or not able to bill for whatever services, right. No one is going to. No doctor can bill for telling a nurse to call a patient to check in on them. That's not a billable event. So there is no reason for them financially to do that. And so we are the care management sort of wraparound services, uh, that support all those members going through that journey.

Andre Mansell: We want to understand your visibility into, uh, the business then and whether you have all the visibility you hope to achieve. What are you looking at to understand whether you're succeeding?

Jesse Waldron: Yeah, so our business operates very much in the value based care world. Um, and so to go back A little bit to our, our financial profile or the profile of how we structure a lot of the contracts where we work with the health plans. Um, we structure our agreements with health plans in a way in which we guarantee them medical cost reduction on the population of patients that we are managing. So we often go to them and say, uh, we guarantee we will reduce the cost of all these patients that are undergoing their cancer journey, um, by X percent, we want you to pay us Y percent. Um, and we guarantee that we will reduce the, everything by, we will reduce the medical expense by our fees plus some sort of guarantee on top of that. Anything above and beyond goes into sort of a shared savings pool or a program where we split that with the payer sort of 50, 50, 70, 30. Sort of just depends on the, on the nature of the agreement. But, um, having information about how our contracts are performing is a little difficult, especially early on. Right. We are not able to see, uh, the experience that comes through our claims experience, uh, until a few months after. Right. Because patients have to go into the doc, they have to get diagnosed, they have to get their treatment, they have to then have it bill their insurance company. The insurance company has to take time to process it. And then we get a data feedback that shows us on a monthly basis like what is the medical expense for these patients relative to the baseline that you are benchmarking them against. That doesn't happen instantly. And so we operate with imperfect information for a period of time as we're serving our members. Um, so we've had to create a bunch of what are the leading indicators or metrics that are driving success in our contract so that we know from day one whether or not we are saving against that cost benchmark that we are put against. Um, and so it's been a really interesting journey to find ways to figure out leading indicators to understand if you're operating in the meantime while you're trying to navigate this sort of like claims run out period where you don't know for sure if you are in the red or green or somewhere in between for a period of time. Um, and so that's been a really, a really big learning for the company to over time to continue to grow and scale our operations, uh, to really make sure that we are appropriately, um, you know, we are taking risk on, on these patients and to make sure that we are appropriately doing so.

Andre Mansell: What we want to know is when you're deciding to invest, Jesse. Uh, we know that there are so many areas that are demanding, but as the finance leader, you have Visibility and you know, okay, these dollars are uh, where we're likely to create more value. So naturally we want to dedicate them there to you. When a big investment decision is being made within timecare, how does that happen and where is Jesse?

Jesse Waldron: Yeah, we think a lot about capital allocation. So we've, timecare has been in a fortunate, we've been uh, very fortunate in terms of our ability to both raise capital, to have a lot of cash on the balance sheet, to make strategic investments over time. Um, and so we've, you know, we've, we've raised about under $50 million over the course of time. We are, we are free cash flow positive now. So we have uh, we are in a position of strength, I would say, to make those decisions or make big bets in terms of how we impact the cancer ecosystem over time. So as we think about the oncology landscape, where we want to play right now, it's been a lot in value based care and the contract structure that we talked about earlier, but the company is taking big bets in terms of how do we get further into drug distribution, how do we get further into utilization management, how do we play in the clinical trial space? Um, and so we operate very, um, we've got a, uh, you know, the executive team who works very closely together to figure out how we make decisions about what dollars we want to invest into these new strategic initiatives. Um, I would say sort of Jesse and the finance team takes a lens of like we need to model this thing out. We need to really understand what the long term, uh, economics might look like to make sure we are making appropriate bets and resourcing and allocating capital in the right way so that when we, you know, unlock 3, 4, 5 million dollars into this new initiative that we want to staff against and put a bunch of resources to that, we think that there is a long term and we think that it's going to play out and broaden, not only bring value to timecare as its own entity, but as a, as an individual investment pays off, uh, in the long run.

Andre Mansell: When you are surveilling, let's say your operating metrics, what signals trouble the earliest?

Jesse Waldron: Yeah, I think, you know, fortunately for timecare, we have been in a very up and to the right growth mode for, you know, sort of since I started, knock on wood. Um, things have been going very well, we've been scaling very rapidly. I think a lot of the metrics that we think a lot about and making sure that we are um, all over is what is our cost of care, what are the cost to serve members over time. So as we think about our very people intensive business in terms of the people that are managing the care model or the people that are actually interacting with patients, how do we make sure that we are using AI and technology in a way that is augmenting our people so that we can deliver care at a really healthy margin so that we can continue to grow the business as much as we can over time. So think a lot about sort of operating metrics from a cost of care to serve and a lot in terms of on the other side of the business, um, in terms of revenue like how do we ensure that we are generating as much sort of revenue on a PMPM or a per member per month basis, uh, so that we are optimizing for driving as much cost savings as we can back to our, back to our plan partners, um, so that Timecare benefits and they are also happy as well.

Andre Mansell: You've now been there two and a half years and I want to coming in, I'm wondering if there was a business assumption that you had that has proved less true over the time you've been there.

Jesse Waldron: Yeah, the biggest thing that proved to be not true was uh, so we had always, when uh, I like I joined two and a half years ago, the business was, we were managing less than 10,000 members. So we've 10x, you know, more than 10x the business in a couple of years. Uh, when I looked at the financial model when I first joined. So I sort of, when I joined I took the lens of like, you know, let me pretend like I'm an investor. I'd love to see your data room show me the financial model. Like give me the pitch. Um, and so I got into the financial model and the financial model was uh, very, very driven by ratios over time. So as I was just talking about earlier, the cost of care to serve members. We had always assumed that we would need to hire, you know, for each, for each 500 members we had, we would need to hire a nurse, we would need to hire two care partners, et cetera. So it's very ratio driven over time. The thing that has proved to not be true was uh, the revolution that technology and AI or the ability for us to quickly adapt and adopt uh, into our own homegrown technology to better serve those patients at a lower cost has driven our gross margins up from you know, mid-50s, which is where it was when I joined and where we thought we would maybe get up to 60% to 70% plus with a path to getting to somewhere near 80% in the long run. Um, that has been sort of a big realization of something that I didn't even think was possible over time, just given the nascency of what AI, uh was at two and a half years ago, which is kind of scary to say.

Andre Mansell: Did you. And again those numbers you just mentioned being driven by AI solely?

Jesse Waldron: No, not driven by AI. I think AI is definitely helping, helping to enhance our cost profile right now. I think AI will help us, uh, it helps us from the way in which we gather data to the way in which we serve members. I think it will help us operate more efficiency efficiently over time. But I think from a sort of like contract new revenue, new growth in the business has been much more about proving to the ecosystem that we can actually not only drive better clinical outcomes to all of our members, but can do it at a lower cost, uh, to the plan so that they are actually saving costs in a world in which costs are rapidly increasing for the oncology world.

Andre Mansell: So how is AI, uh, perhaps changing finance work? Yeah,

Jesse Waldron: it's been really interesting to see. So a lot of the team right now, they don't love when I get into Excel because I'm an old man now and they're a lot better at it than I am. But there is a CLAUDE plugin for Excel that can build financial models at the click of a button that would take people days or weeks to gather inputs and to make assumptions and to build out all the formulas, et cetera. So I have seen a huge revolution in terms of the ability um, of CLAUDE specifically to plug into Excel and to a lot of the other tools to make our monthly financial reporting done in a click of a button versus sort of having to screenshot, uh, a bunch of templates and a bunch of uh, assumptions. I think it does not replace the intelligence that one needs to understand the true drivers of the business, but can help with a lot of the operational aspects. Um, so I've seen big improvements in the finance organization from like a modeling perspective. I think the other area that's really been exciting for me to see is from our accounting team, uh, in our accounting, like the way in which, you know, as you think about like the value that AI drives, it is a large, there's a large database of information. So as we think about super technical accounting memos and if, and writing a memo about, you know, stock based compensation and some secondary transaction that happened a year ago, right. It is like, you know, type into CLAUDE like all of the information and it is like here's an actual memo with all the accounting guidance and all the backup you still need to validate and vet that things are correct. But like as a starting place to give you a 95% good draft that can take you know, one minute versus actually like hiring a third party big four audit firm to like come in and understand what happened, sharing a bunch of information. Like the process has just gone from weeks and months to like instantaneous. And it has been a huge unlock for us in terms of the ability for us to really rapidly grow and scale the finance team.

Andre Mansell: What about AI perhaps still feels unclear to you?

Jesse Waldron: Yeah, I think the biggest thing that is unclear to me in AI and I think the biggest thing that we think a lot about, like at the core of what we do, we interact directly with members. We don't use AI in any way in which we use, you know, there are companies that have sort of like AI nurses who will call and actually have like phone interactions or video interactions. I don't think we will ever be to the point where we are doing that. I think a lot of the value that we bring is in the highly personal touch, uh, and human to human interaction that we would provide. Um, so I think the role of AI over time for me that is unclear is like how much more is there to give than we see today. I think we've seen a rapid evolution in the last nine to 12 months. Um, predicting that in the future I think is really, really difficult. It'll be exciting to see, but I think there is still, you know, there's still a lot unknown as to what, what possibilities there might be. No worries.

Andre Mansell: This is where we ask you to look back over your career and just identify one moment of insight that you experienced along the way. What comes to mind when we ask for a finance strategic moment?

Jesse Waldron: Yeah, I think the, the, the big moment for me or the biggest big learning that I would say here is uh, when I was at Propeller Health, um, as I talked about earlier, it was a pretty early stage company when I joined, we had raised some capital and we're just getting to commercial commercialization of our product, still figuring out how, how and where we wanted to take the business in terms of uh, who is actually going to pay for our services. So uh, just quick background like Propeller, we built a digital sensor that attaches to inhaled medication to track when and where you took it. It connects to a smartphone, uh, app and then tells your doctor, pushes notifications to your doctor. Uh, and so we had a big thesis early on about uh, the value that this Might bring to someone who has asthma or copd. What we didn't have insight into was like who is actually going to pay for this service? Right? Are the health plans going to pay for it? Are the docs going to pay for it? Will um, health systems pay for it? Will pharma pay for it? Um, and so we tested a bunch of business models over time, uh, which was fun and interesting and helped to start to scale the business. Uh, sort of throughout that journey we had gotten um, a company called ResMed interested in the company and what we were doing. They're a very big public company, 20 plus billion dollar public company. They joined one of our financing rounds uh, as a strategic. And the big insight for me or the big moment was sort of like okay, there's a very clear path here in which RESMA is excited about acquiring Propeller. We, Propeller are a very small company doing you know, less than 10 million of revenue and burning, you know, burning over a million a month. So the financial profile is not, it is not a like compelling financial transaction here. There is no, no meaningful way in which we are going to convince ResMed that they need to acquire Propeller based on the merits of our sort of like standalone business. Um, and so what, what the big moment was really thinking about, okay, how do I take the financial profile of Propeller in the board meetings that the, that ResMed is now sit, they're seeing our quarterly results and how do you transform that into a way that gets them excited about the potential future of what Propeller plus resmed could look like. Right. As you think about financial reporting can often be not that fun. But thinking about they are not going to care about how we performed last quarter against our budget, whether we did 2.5 million or 2.8 million of revenue. They are going to care about, think long term into 2029 and the market that we might be able to impact if we use uh, what Propeller services are across all of ResMed's different devices and how we think about um, uh, the long term view into the company. And so really like got me, got me thinking, got me excited about how do you use the financial reporting in a board setting to start to shape the thinking of strategic entities around the table into getting them excited about what their future vision might be uh, over time. So that kind of like was a very big moment in my career of like wow, there is a way to tell the narrative here that doesn't need to be black and white, that can be very much more creative or strategic. Uh, and ultimately sort of that thesis played out and ResMed got excited about the business and put in an offer to acquire Propeller and the rest is history. But um, that was the big moment for me of like, wow, there is a way here to be much more strategic and to build a narrative around something uh, that that can help accelerate the business in a meaningful way.

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Andre Mansell: We want to know what if you could go back in time and give yourself a piece of advice, what it might be. Again the idea is you had observed CFOs, um, up close. You thought you knew everything about the role, perhaps, or quite a bit. But then when you were in it, what piece of advice do you wish someone gave you?

Jesse Waldron: Yeah, I think the biggest piece of advice I wish someone would have given me earlier is that time, uh, is your most valuable asset. Um, I think I have learned that over my career as I have now. You know, I've gotten older, I've got three kids. It is um, a big part of my life to be present, you know, to be a present part of my family. And so now that I have got, you know, a bunch of responsibility at work, there are a bunch of decisions to be made. How do you make sure that you are ruthlessly prioritizing the things that need to get done so that you can be successful in your career but also have a, ah, presence in your, in your home life as well. And so that has gotten me, um, you know, ah, a big thing to say, like, okay, I wake up in the morning and I am like, I need to know what I need to get done. I need to understand what needs to happen. I need to know the decisions that need to be made. I need to be able to sort of like, delegate appropriately to people, to do things in a meaningful way so that I am not, you know, at the office 17 hours a day and not able to like, be part of, uh, be part of my, you know, my. My family journey as well. So that has been a big thing for me that, uh, that. That, you know, back in my early career, I didn't, didn't have that concept, but have learned over time as I've had more responsibilities, uh, outside of work.

Andre Mansell: That's nice. That's a great share for us. I want to keep you on that personal side of things. What's one thing maybe your colleagues don't know about you? Something you did in your past? Some interest that you had? Something. I don't know. What would you tell us?

Jesse Waldron: Yeah, um, I would say that you, uh, know something that people don't know much about me is I, you know, I grew up in central Wisconsin, a very small town, um, a lot of people. I kind of maybe give off more vibes of someone from one of the coasts, I've been told. And uh, not a, uh, you know, a small town. A small town guy. But, uh, my, My first job, my first ever job and a job I had for four years, um, since when I was in freshman in high school, all the way through was, uh, I worked on a farm. Uh, so I worked on a ginseng farm in, in rural Wisconsin doing everything from driving tractors to, you know, carrying buckets of roots and building, uh, you know, the things that need to get built around the farm. So, uh, you know, I've got a. I've got a bit of, uh, you know, hard work Midwest, uh, you know, side to me that people don't really. Don't really see when you, you know, and see me up front.

Andre Mansell: Now, the question we're all waiting for, and one I might have to edit if I don't get the response I want. Um, the nurse that was in Denver. Did you marry the nurse in Denver, uh, who you travel to in Denver? You did?

Jesse Waldron: I did.

Andre Mansell: Largely a listening audience. You can't shake your head.

Jesse Waldron: She's still here. She's still putting up with me. Yep. We've got.

Andre Mansell: You have three children with. With.

Jesse Waldron: We've got three kids. We, uh. Yeah. Everything has been everything.

Andre Mansell: You are a CFO of a. Of. Of interesting healthcare company and of course you're married to a nurse which.

Jesse Waldron: So she's actually an oncology nurse as well. So kind of.

Andre Mansell: Is she really? Wow.

Jesse Waldron: Yeah. Full circle. She stopped. So when we had our third, uh, our Third kid. She decided to stay home.

Andre Mansell: Yeah, well, thank you, uh, for that. Wondering. What about a book, Jesse? Anything? Um, doesn't have to be a business book. Might be something you just influenced your thinking along the way. Anything?

Jesse Waldron: Um, yeah, I'm not a big, I'm not a big business or finance business book reader. I like to, I like to very, I very much like to sort of when I have time to read, I like to get into a different world. So I am a big, uh, reader of fiction. Um, okay. I just started, uh, the Will of the Many. Just, uh, recently I started that. It's very good so far. Um, but uh, yeah, I, you know, try to, when I have time to get away from the other world, I like to sort of, you know, find myself in a different land or somewhere else where I can divorce uh, myself from all the, you know, stresses of the day to day life.

Andre Mansell: I thought we were going to get a time management book selection from you, but maybe that'll, maybe that's yet to come. We are up to our final question, uh, which asks you to look forward and uh, what we want to know are your priorities as a CFO for the coming 12 months.

Jack: What would those be?

Jesse Waldron: Yeah, I think the big thing, as I talked about earlier, we're scaling very rapidly. So uh, I think for me the big things on the 12 month roadmap are scaling the financial infrastructure to meet the demands of the rapidly scaling company. Um, we manage, uh, just north of $8 billion in medical spend across our whole book of business, uh, which is quite a lot. And so we need to make sure that we are building the infrastructure from the finance lens to make sure that we are able to continue to grow and scale that part of um, the business. Um, I think the other part is just like continuing to keep the mission funded. So at the core thesis of like why TimeCare was started, right, we started TimeCare to help patients that are undergoing this horrible journey in their cancer journey. And how do I make sure that that mission continues into duration? How do we make sure that more and more people can get time care services? So how do we scale into more health plans to work with more oncologists? How do we make sure that this mission lives on even 5, 10, 15 years beyond? Um, and that's like a big thing that we think a lot about, uh, in terms of how do we get this into more members, uh, hands.

Andre Mansell: Jesse Waldron, thank you for joining us on CFO Thought Leader.

Jesse Waldron: Thank you very much, Jack, I appreciate you having me.

Andre Mansell: Foreign.

Jesse Waldron: Hello.

Jack: We're Benchmarking the CFO path join 500 finance leaders, helping define how today's CFOs rise and lead. If you're a CFO or senior finance executive, contribute your experience. It takes just a few minutes and you'll receive early access to the findings. Visit cfothoughtleader.combenchmarking.