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CFO THOUGHT LEADER

16 Sep 2026 · 50m · 18 chapters

Episode artwork

1215: Building Finance for the Long Game | with Jessica Somers, CFO, Aledade

In short

How CFOs should make “long game” investment decisions when projects are interconnected (not independent ROI stack-ranking), especially with AI opportunities that may take years to pay off. Also covers Allidade’s value-based care model, capital allocation, and how AI is used to drive measurable outcomes and savings.

Guest backgrounds

Jessica Somers is CFO of Allidade. Career started in mergers & acquisitions and investment banking, then private equity, then nearly nine years at Elevance Health (corporate development to CFO leadership). She later became CFO of an acquired business unit, and has been at Allidade for over two years. She has an MBA from Harvard Business School.

Key claims

Isolated ROI ranking is too simplistic; investments compound when planned across product strategy/roadmap. Finance should tie strategy to numbers and act as a thought partner via listening and deep business understanding. AI should be used to drive outcomes, not just efficiency.

Notable examples

Allidade’s Medicare Shared Savings Program: 2024 benchmark $15.2B vs actual $14.1B for 1.2M members, creating $1.1B savings; CMS keeps $327M, Allidade recognizes $700M+, with ~50% of revenue paid to practice partners. AI examples: using AI to structure unstructured clinical notes for predictions; “Allidade Assist” overlays recommendations in physicians’ EHR workflows at the right time.

Written by AI. May contain mistakes.

Chapters

0:28

The Complexity of Investment Decisions

Understanding how interconnected investment opportunities can amplify results.

“Right, there is so much nuance to running a business.”
3:48

Introducing Jessica Somers

Meet Jessica Somers, CFO of Allidade, and learn about her career path.

“Jessica's career began in M &A before taking her into private equity and investment banking, followed by nearly nine years at Evelyn, where she moved from corporate development into CFO leadership.”
4:30

Jessica's Journey in M&A and Value-Based Care

Jessica shares her experiences in M&A and the shift to value-based care.

“So, Jessica, as always, take a look back for us.”
7:58

Transitioning to CFO Role

Jessica discusses her transition to the CFO role and the challenges faced.

“to kind of move into this area of the economy.”
9:21

Insights from M&A to Operational Excellence

Jessica reflects on lessons learned from M&A to enhance operational strategies.

“I had never, you know, been in an operating role before and it pushed me out of my comfort zone.”
14:03

The Role of Analysis in Decision-Making

Learn how analysis can enhance decision-making within organizations.

“There's a reason for certain things, but how do you use analysis to unlock understanding about the business, right?”
15:04

Taking Risks in Career Growth

Explore the importance of stepping outside comfort zones in career advancements.

“was there a career decision that felt like a gamble at the time?”
16:14

Leadership Insights from Experience

Understand how leadership perspectives evolve through experience.

“And again, I really try to think about that as I develop the team around me today.”
18:06

Overview of Allidade's Services

Discover what Allidade does and its mission in healthcare.

“We are now want to talk to you a little bit about Allidade.”
20:28

Investment Principles for Long-Term Success

Learn about the foundational principles guiding Allidade's investments.

“And we've actually built it into our governance model as a public benefit corporation.”
Show all 18 chapters
22:25

Understanding Allidade's Revenue Model

Get insights into how Allidade generates revenue through value-based care.

“I mean, what capital allocation matters most?”
24:07

Metrics for Measuring Success

Learn about the key metrics Allidade uses to gauge its success.

“We're the largest participant in the Medicare Shared Savings Program.”
28:00

Measuring Outcomes and Financial Impact

Learn how Allidade measures healthcare outcomes and financial results over time.

“And then there at the end of that whole chain is when we see the actual kind of financial outcome, right?”
36:20

Investment Strategies and AI Integration

Discover how Allidade balances long-term investments and immediate financial results while integrating AI.

“We've had all types of finance strategic moments.”
43:20

Transitioning into the CFO Role

Jessica shares her experiences and learnings from her first days as a CFO.

“Could you tell us, was there something unexpected, something as prepared as you were for the role.”
44:45

Personal Insights and Background

Jessica discusses her diverse upbringing and how it shapes her leadership style.

“I continue to try to, you know, remember, even when things are busy on a day-to-day basis to pause, to listen, to create space for really paying attention to the business, not just the finance team.”
46:20

Recommended Reads for Escape

Jessica shares her favorite books and interests outside of work.

“Doesn't have to be a book Might be something you escaped with Don't know, anything come to mind?”
47:22

Future Priorities as CFO

Jessica outlines her focus areas and priorities over the next year.

“We're going to ask you to look 12 months into the future and tell us what your priorities are for that period.”
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Transcript

Automatic transcript. May contain errors.

0:00Jessica Somers: Support for CFO Thought Leader comes from Salesforce. Unify selling and billing for a seamless customer experience. And one stream, trusted data, faster decisions. Hello, this is Martin Urich, I'm CFO of Thrillbridge, and you're listening to the CFO Thought Leadership Podcast. This is episode 1215.

0:28Right, there is so much nuance to running a business. And so many, at least for us, of these investment opportunities are highly interrelated. And what we've had to do in Mature Jack in our kind of planning and our decision making is look across, get people who lead different areas talking to each other in a much more meaningful way and saying, these two investment cases actually work like this and they compound on each other. Like doing one makes the other better. Doing the other kind of compounds on each other. And stack ranking, you know, individual isolated investment cases is insufficient and is too simplistic.

1:14So we spend a lot of time in investment decisions, doing things like debating product strategy, doing things like debating, you know, roadmap prioritization, what comes first, what comes second, how do they interact?

1:34Jessica Somers: Hi, it's Jack. On today's show, we speak with Jessica Somers, CFO of Allidade.

1:45Jessica Somers: What happens when the smartest investment isn't necessarily the one with the highest ROI? For CFOs, that question is becoming harder to answer, especially as AI creates opportunities that may take years to fully play out. The traditional approach says evaluate the projects, rank the returns, and fund the winners. But what if the investments are connected? What if one makes another more valuable? Today's conversation gets into that tension, how finance can bring discipline to investment decisions without allowing the numbers to oversimplify the strategy. Jessica Somers has an interesting perspective on why sometimes the bigger picture may require the bigger bet.

2:37Jessica Somers: Our talk with Jessica Somers begins after this.

2:48Jessica Somers: As finance leaders know, revenue operations is no longer just a sales conversation, especially when the quote, contract, and invoice somehow tell three different stories. Agent Force Revenue Management brings pricing, quoting, contracting, and billing together on one agentic revenue platform with a single source of commercial truth, proven workflows, and built-in governance. It gives people and AI agents the context to make smarter deals across every channel. The result? Finance spends less time playing revenue detective and what your business sells is exactly what it invoices. Learn more about Agent Force Revenue Management at salesforce.com slash CFO.

3:42Jessica Somers: That's salesforce.com slash CFO.

3:53Jessica Somers: Hello, CFO Jessica Summers is with us. Jessica's career began in M &A before taking her into private equity and investment banking, followed by nearly nine years at Evelyn, where she moved from corporate development into CFO leadership. Today, a CFO of Allidade, she brings that deal-making and operating experience to a healthcare company focused on value-based care. We'll explore how those different chapters shaped director thinking about investment growth and the role of finance. Jessica, welcome. Thanks, Jack. Great to be here. Thank you for having me. Yeah. So, Jessica, as always, take a look back for us.

4:37Jessica Somers: Try to identify some of those experiences you feel prepared you for the CFO role. What comes to mind? Sure. As you mentioned, I started my early career in mergers and acquisitions as an investment banker, spent a couple years in private equity, and then actually returned to investment banking. And for me, M &A has always been strategically interesting, right? Like, how do we think about two businesses coming together and doing more than they could individually? And I personally, in kind of M &A and investment banking roles, really liked the impact I felt I was having on individuals and teams who founded and ran businesses, right?

5:18Like navigating one of the most impactful moments in their professional careers oftentimes, and sometimes personally, right, as founders. So I loved that work. I enjoy kind of, you know, getting deals done, working through the complexities. But over time, you know, while that can be very satisfying, I realized I was really increasingly interested in understanding what happened after the deal closed? And after my role as an advisor ended, right, did the strategic thesis pan out? Like, what worked? What didn't work? And that really led me to move from an advisory role to going in-house to a corporate development team at Evalent Health, as you mentioned.

6:01This is where I got introduced to the healthcare industry and value-based care more specifically. And as you noted, I spent almost a decade at Evalent and I've been at Allidade for more than two years now, and both operate within the value-based care segment of the healthcare industry. I think for a little bit of context for listeners, I think everyone knows healthcare is one of the largest and most complex sectors within the economy, 18 % of GDP, 5.3 trillion of spending and growing at a rate that in many ways is unsustainable for this country. And I think, unfortunately, I expect many of your listeners have experienced the system and found it to be deeply broken, right?

6:53And value-based care attempts to change that approach to healthcare that we have in this country, which is that our doctors get paid on the volume of care that they deliver. uh you know fee-for-service health care if you will and in value-based care we really look to reward providers when they deliver high quality proactive preventative care and that ends up costing the system less so imagine right like your doctor getting rewarded for preventing a stroke or a heart attack instead of getting paid to treat one um so i didn't actually specifically seek out a role in value-based care, right? I was kind of leaning on my M &A background, that transition to corporate development.

7:40But as I spent time at Evelyn and then now at Allidade, I came to really appreciate kind of the hard work that these businesses are working on, the impact that we're trying to have on the healthcare system. And at this point, it's really hard for me to imagine working in a different space. It's been really rewarding to kind of move into this area of the economy. So going back, I mentioned starting at Evelyn in corporate development. As part of my role there, we bought a business. And it was a meaningful strategic addition to the Evelyn portfolio. And the questions I had always wondered, I was able to see what happened when the deal closed.

8:26And luckily for us, the strategic thesis was indeed working. The business was growing meaningfully, and we decided, you know, probably given that growth, it made sense to put a little bit of more financial rigor around that business. And that led me to take on a role as CFO of the business unit. that was a super interesting moment, Jack, right? Like having run diligence on the acquisition, having led that process, I very quickly realized once I was, you know, in the operating role, how little I had really understood as a dealmaker. And, you know, the financial results of the business were really a representation of hundreds and thousands of like individual small decisions and actions, right, that the business is doing every day, which was, you know, I think has helped shape how I approach my role today.

9:20And I'll admit that transition was a little bit scary for me, right? I didn't have a playbook. I had never, you know, been in an operating role before and it pushed me out of my comfort zone. And I remember in particular one line that someone said to me, which is, well, Jess, if it's not a little bit scary, are you still learning? Is it interesting enough? And that really stuck with me. So, you know, there was a lot that I had to figure out on the fly. There was a lot that I had to learn. And I think in that moment for me, it was about being really curious, right? Admitting what I didn't know, what I didn't understand asking a lot of questions and, and most importantly, uh, again, listening, listening to the answers people are given, uh, but also a lot of times listening to what's not said, right?

10:14What's in the space in between. Um, and I will say it also involved Googling a lot of acronyms and trying to get up to speed.

10:23Jessica Somers: Um, one of the things I think that, uh, you didn't mention, which I think is interesting as well. I, I know you went back for an MBA, you went to Harvard business school. You were only in the workforce, maybe you're in private equity, I guess, at that point in time, you decide to go and get another degree. Tell us about that decision and what you were hoping the types of doors it would open for you. Yeah, look, I think what I knew at that point in time is that I didn't see myself in private equity long term. And there was a lot that I really liked about that type of work and getting, you know, going from investment banking advisory role to kind of making investment decisions.

11:12But, you know, for a variety of reasons, wasn't the right fit for me. So part of my, you know, transition to get my MBA was just to have more exposure, right? Meet different types of people doing different types of work from all over, not only the country, but the world. And to really think about, again, was there something that would really pique my interest in a different way? And look, I had a fantastic experience at HBS. I learned a lot. I value the network, you know, deep friendships I made and professional connections. But what I ultimately came away with was that I really liked the investment banking work I had done straight out of undergrad.

11:59I loved advising businesses. And so for me, I wanted to explore different versions of that work. So I went to a different institution that provided, you know, different types of deals, different types of industries, different size, if you will. And I wanted to kind of test the thesis of like, you know, might I be a long-term investment banker, which is not the path I have ultimately taken, but became kind of clear to me as I was evaluating, you know, different options, you know, after my MBA program.

12:32Jessica Somers: And soon, corporate development becomes the lane that you occupy. And you enjoyed, or what can you tell us as you got deeper into some of these financial deals and within the operating side of the business? Yeah, so I mean, I still love doing deals. Again, I think it's doing M &A from inside a corporation allows for just such unique strategic perspectives that you don't necessarily see from advisory role or from kind of a pure financial rationale or financial analysis? Like what is the unique combination, right? Between businesses that make it, that lead you to stretch, to make sure you can win the deal or get a deal done in a competitive process.

13:25So coming up and really interrogating the strategic thesis, I find just fascinating and is so much more nuanced and subjective than just, you know, running a DCF model, right? And I think a lot of that learning from my M &A work has been helpful in kind of the operating roles, you know, I've had since then, right? So, right, the importance of connecting the business and the strategy to the numbers, right? Like, it's a story that ties together. I believe in the value of kind of structured thinking and analysis, right? There's a reason we do a DCF analysis. There's a reason for certain things, but how do you use analysis to unlock understanding about the business, right?

14:12Not just analysis for analysis sake, you know, how do you bring that analysis to help make a better decision, make a more informed decision? And the last thing, you know, investment banking or private equity, there's a fair amount of discipline, right? There's a way that processes tend to run. There's an arc to a deal. And I do think there's also value in that. So in the sense of process discipline as bring structure and kind of unlocking capacity for an organization. And so I spent a lot of time thinking about that here at Allidade as we mature, right? Where do we need to be nimble and responsive to what the business needs?

14:52but where can we also bring structure and discipline, again, to in many ways simplify the work that we do.

15:01Jessica Somers: You've provided us a nice overview. I'm just, which, I'm wondering, was there a career decision that felt like a gamble at the time? Yeah. Because actually you look very calculated. You look very driven. M &A's you're laying, corporate development, it all makes sense. But was there a gamble here somewhere along the way? For me, getting pushed out of the comfort zone from the corporate development role and that lane in which I had spent a lot of time and had a fair bit of comfort to actually taking a CFO role, a business unit CFO role to start. As someone who's maybe more risk averse with the background I have, like I said, it was a little bit scary.

15:44And what I really appreciated and try to pay forward now is people who just believed in me. people who said, scary is normal. Scary is okay, but we have confidence in you and we're here to support you. And so some ways, right, Jack, that was a scary move, but I was doing it in a very, what I would call safe environment around folks that had supported me in my corporate development role and who I knew would support me as I made that transition, as I learned and went up that learning curve. And again, I really try to think about that as I develop the team around me today.

16:21Jessica Somers: Just curious too, from your very earliest days, you likely perhaps sat at tables across from C-suite members who are making these big decisions about deals and what have you, and you would advise them, you'd provide insights. I'm wondering, as you observe that leadership, how your own opinion of leadership today, being that person, how your views of leadership may have changed? What have you learned as you take on the responsibilities? Yeah, it's a great question. I mean, I think a lot of what I have learned from being in those rooms and having those opportunities is how much leadership is about listening and watching as opposed to doing.

17:12uh right kind of um i'm a big believer in you know finance as a support function to the business and that means learning about the business deeply um again i talked about kind of not just financial analysis for its sake but kind of what does it help us understand and unlock about a business's potential um and and making sure that you know i'm diving in my team is diving in that we view ourselves as thought partners to the business. And that's what's going to allow us to be most successful and impactful. And like the best way to learn is to listen, in my opinion. And so I've seen folks, you know, do that really effectively, build trust, right, from leaders, peers in that way.

18:03And I try to think about that, you know, as I'm engaging across the organization.

18:07Jessica Somers: Nice. Well, nice overview for us. As I said, thank you so much. We are now want to talk to you a little bit about Allidade. For someone new to this company, what does the business provide exactly? Who does it serve and where's the opportunity here? Awesome. Well, I'm always excited to talk about Allidade and the work that we do. So for you and our listeners, Allidade is a technology-driven physician-led organization and we work to empower primary care practices to succeed in value-based care. So what this really means, right, there's a lot of kind of buzzy words maybe in that line, but what this means is we're helping, we're working to help make the healthcare system work more effectively for seniors all across the country.

18:56And we're doing that by helping the primary care doctors that care for those seniors. So as I mentioned earlier, value-based care attempts to change the standard approach to healthcare where volume is how providers get paid. And so instead, we bring technology, data, predictions, insights to our providers that encourages proactive and preventive care. so we try to stop a stroke from happening so that a patient doesn't have to let's say first go to urgent care then go to the er then end up in a hospital then perhaps getting discharged from the hospital but getting readmitted uh you know which is very common in this country um and when we do that well uh it actually saves the system money all right um you're preventing that entire chain of what is both very expensive care, but frankly, a lot of human suffering.

20:02So, you know, for us at Allidade, you know, we have a very simple but lofty mission that is our North Star, and that is to deliver better health, better care, and lower costs by building a solution that is good for patients, good for practices, and good for society. We deeply believe in this mission. It shapes, I would say, every decision we make at this organization. And we've actually built it into our governance model as a public benefit corporation.

20:35Jessica Somers: Now, Allidate has grown considerably. How have its investment choices shaped what the company has become? Yeah, I think there are a number of fundamental, what we would call first principles decisions that our co-founders made when starting the business, you know, more than a decade ago that continue to hold true for us today. Which brings a certain amount of clarity, which helps a business growing and operating in a complex environment. So some of those fundamentals are that we are long-term oriented. And I think that's represented through our status as a public benefit corporation. We care certainly about our shareholders and our investor base has supported us over the years.

21:25But we also take into account what our decisions mean for our practice partners, for the patients that we have the privilege to serve, for our employees. and we have that long-term mission-oriented lens as we make investment funding decisions for example you know over the last dozen years we've become one of the largest independent value-based care platforms in the country we serve more than 3 000 practices we touch more than 3.6 million patients. And our goal is to, you know, multiply those numbers over time. How do we let every senior in this country have the benefit for the type of, you know, proactive and preventive care that we help to deliver?

22:15And that's our guiding, that's our guiding light.

22:18Jessica Somers: When you have this long-term view, how does that, you know, translate into capital allocation? I mean, what capital allocation matters most? Yeah, look, I think we are always talking about reinvesting in the business. And it allows you to make, again, those long-term bets, those long-term decisions because you have conviction around the impact it'll drive over time. It's also led us to be focused on really controlling our destiny. And that shows up in a bunch of decisions like we've built our own technology platform since the very beginning. We didn't want to be beholden to someone else's roadmap, right?

23:01We wanted to control that critical part of how we deliver our product to our partners. And so there's a, I think, again, as I've said, there's a clarity that comes from having missions so clearly at the forefront in being able to say, you know, yes, that might be a short-term, you know, hit, but long-term valuable. Like, I know where that decision is going to land every time, right? So again, we're deeply committed. And I think that long-term lens ultimately has worked. And again, we're committed to it going forward from here.

23:41Jessica Somers: So when it comes to the revenue model, Can you help us understand how Allidade makes money, very simply? Which part of this model best reveals the opportunity, the economics? Sure. So, Allidade is the largest, I'm going to use one of our value-based care programs, our largest program, as an example here to answer your question. We're the largest participant in the Medicare Shared Savings Program. And this is a program for traditional Medicare members. So, you know, seniors across the country who are in traditional Medicare, it is administered by CMS, so it's a government program. And again, we're the largest participant.

24:26In the program, effectively, we take accountability for the total cost of care for members that are seen by our practice partners. So I'm going to use, Jack, a 2024 example That's the last year in which there were kind of final published results for the program And in 2024, we had accountability with our practice partners For 1.2 million members For their total cost of care And what we try to do is bring down The cost of their care relative to what CMS would otherwise expect That's our medical spend under management. So in 2024, those 1.2 million members, CMS expected them to have total health care expenditures of$15.2 billion.

25:19dollars, right? Like astronomical numbers. And our responsibility was to bring down that number at the end of the day. And what we did was ultimately by engaging with these members through our practices, the actual costs for those same 1.2 million members was 14.1 billion. So we created$1.1 billion of savings for the program. CMS, or the taxpayer, ultimately is going to keep their share of that. In this case, CMS kept$327 million of that$1.1 billion. The remainder, $700 plus million, that's what Allidade recognizes as revenue. So the actual savings we created against the benchmark we're measured at after our customer, or CMS in this case, keeps their share.

26:18And the largest cost we have, and we celebrate this every year, is that just about 50 % of that revenue gets paid out to our practice partners. And so the ability to send out more than$350 million worth of payments to independent, community-based primary care across the country is, again, like I said, a moment that we celebrate every year at Allidade. And it's critical to kind of making the business model work.

26:50Jessica Somers: Well, we're curious about your lines of sight into the business, the visibility into the business, and what tells you early that Allidade's model is working? I mean, is it physician participation, patient outcomes, or is it another measure? It's all the above. So we are, what I would say maybe is an understatement, a very data-driven company. Curiosity is one of our core values, right? Looking deeply and interrogating every piece of information and data we can get our hands on. And so, you know, we look at a cascading, I guess, set of metrics, if you will. So the first things we do is, again, and we have more than a decade of experience of knowing what works, what actions, if we do them, our employees do them, our practices do them, like what actions result in those savings I just described.

27:49So the first things we track are kind of action metrics, right? Are the activities that we know work, Are they happening at the rate and in the right places where we expect them? The second thing we track is then kind of what are outcomes measures, right, that those activities drive, whether it's reduction in hospital stays, reduction in ER visits, those actions, again, we've learned kind of drive specific outcomes. And then there at the end of that whole chain is when we see the actual kind of financial outcome, right? That savings math that I just described, that$1.1 billion of savings relative to the benchmark, that happens, you know, months and months after those actions.

28:35So again, we're looking at, you know, all of these metrics, all of these key indicators. And, you know, fortunately, over, you know, a decade of learning and growing to the scale we have, we have pretty good kind of prediction between kind of the connection of actions to outcomes to ultimately financial results.

28:58Jessica Somers: we always like to try to understand sort of the uh decision mechanics within an organization and we wonder since becoming cfo if there was an investment decision that might illustrate for us how alliday makes its bigger bets let's say anything come to mind yeah yeah look i think we're kind of always in this, you know, strategic review process of kind of how we think about bets for the future, right? If you're not, especially when, again, we build our proprietary technology and like that takes time, you know, we're not going to just go out if it really matters and and kind of buy something from someone else, which means those cycles, you know, take time.

29:54So we have to think about, you know, not only what are we trying to accomplish in, you know, this year, next year, but three years from now, you know, what do we need to start building today? What are the data elements that three years from now, we're going to wish we started collecting today to allow us to do something different. And so that's a very kind of natural part of our, kind of leadership discussion topics, developing kind of an investment committee, if you will, to think about what are the latest ideas that the business has? How do we balance opportunities that might have a near-term ROI or a longer-term ROI?

30:37And thinking about, again, a portfolio of opportunities that will impact the business over time.

30:43Jessica Somers: Yeah. We want to also touch on AI, with you. Where is AI already creating measurable value at Allidade? Yeah, this is a, it definitely is. So I can say that for sure. And as I mentioned, you know, Allidade has been tech first since day one, right? Our founders were really committed to having impact at scale and were big believers for a bunch of reasons. And in their past experience that to really do things at scale, you need to leverage technology. And so for us, AI is super, super exciting, but also just a natural evolution of that tech first mindset, right? We are not having to, I would say, shift how we think about using technology.

31:34We're simply leveraging the latest and greatest. The way we've always thought about technology, including AI, is how do we leverage it to drive better outcomes, which as I described earlier, like leads to savings, which leads to our financial results. So everything we have focused on to start with AI is about how do we apply AI to the platform that we have today? And I'll give you a couple of examples. We obviously have over more than a decade, millions and millions of pieces of data. We get tens of millions a year. We also have access to hundreds of millions of unstructured data files. Think of things like clinical notes, right?

32:20That historically have been pretty hard to access the insights. We can now use AI to kind of read, if you will, like those insights and turn them into structured pieces of data that then we feed into our interoperability engine, which then feeds our ability to make better and better predictions, which ultimately lead to insights that we deliver to our practices. So that's like one example of just unlocking data in a way that's super compelling. You know, another way that we've leveraged AI is something that we call Allidade Assist. And this is our effort to put our insights into the physician's workflow in their normal course patterns.

33:12So they're seeing a patient. We are actually using visual language models to kind of read the screen. So we sit on top of a physician's electronic health record, and we kind of watch what's happening. and if there is a natural place for us to kind of share an insight share a recommendation that we want to make sure the doctor sees it pops up at the right time and that's really important right because you know we've all been to the doctor they're trying to you know run through a million things at once and and like more information at the wrong time is not actually helpful like the more information is not always better how do we bring it at the right time to get their attention, to help them remember something that they maybe want to ask the patient about in that right moment.

34:05And again, that ability to do, to kind of create that overlay was unlocked by visual language models, you know, that didn't exist, you know, a number of years ago. So those are a couple of examples. But again, overall, how do we use AI to drive outcomes? Of course, we're all also thinking about how we make it, you know, ourselves more effective, efficient internally from an operating perspective, but that's certainly not our primary use case.

34:33Jessica Somers: What about, just to get narrow our lens on finance, you know, where has AI maybe moved beyond efficiency? And, you know, this is what we're continuing to drill down on. Is it impacting how you make decisions in finance? Is there evidence of that? I would say that the way we think about using AI and technology, kind of systems at large, including AI, is starting by simplifying the work. And we talk a lot about with my team kind of reimagining the work. So, you know, not just using AI to do something 5 % or 10 % faster, but kind of can we approach it totally differently? And by doing that, I would say, can we create capacity that is then deployed to strategic partnership to the business?

35:29How do we use AI to kind of look at data sets and help us see insights that we then have to go interrogate and we bring the judgment and the understanding of the business to bear? but how can we again just leverage uh information um see more insights more quickly um and again ultimately be partners to the business not just sit kind of what you would say like off to the side in our lane doing reporting or forecasting um uh and so you know we're we've you know examples all over uh the finance team about kind of simplifying process um using data uh analyzing trends in new ways, but ultimately bringing those insights again back to the businesses is where it really matters.

36:16Jessica Somers: Great. Well, we are up to what we like to refer to as our finance strategic moment. And again, this might have happened any time during the course of your career, but we're looking for a moment of insight or that you experienced that may have led you to think a little differently or do things differently. I don't know. We've had all types of finance strategic moments. What comes to mind for you? when we ask for a finance strategy? Yeah. You know, I think an example I'll talk about, you know, relates to a little bit of what I've mentioned earlier in the conversation, but really I would say highlighting, you know, how we think about ongoing strategic investment for the long term, as I mentioned, which is kind of, you know, part of what we do every year.

37:03But how do we balance that with thinking about the financial profile and trajectory that we're trying to accomplish, right? There's a kind of a push and pull, right? You can invest more or you can drive, you know, profitability faster. And kind of how do we think about that push-pull, that balance? You know, I joined Allidade again a couple years ago and in the first, what I call kind of budget or investment cycle, a lot of what I did was watch, right? It was listen, as I mentioned earlier, kind of learn how it worked. And then last year, really, I think, had a much more meaningful opportunity to help drive change and different ways of thinking and decision making.

37:45And so, you know, I'll go to a moment last year where, you know, we were making, we were excited about AI. We were also, you know, committed to continuing to progress our kind of march towards, you know, profitability and kind of expanded financial profile. And we had this moment to think about what's the size of the bet and how do we balance that for near-term financial results? And I think that's a tension I would expect a lot of your listeners struggle with. At some point you do, I think, seek to kind of mature your financial profile. You reach profitability, you reach cash flow break, even all of those things that businesses are on the trajectory for.

38:34but particularly in this moment of AI and as I described kind of how meaningful we view it to be as kind of the next evolution of our our tech first approach is should we rethink how much we invest in in the future versus how much we would I would say invest in near-term profitability And that took us really, I would say, taking a different look at how we thought about investment cases. I think the simple, what I would call maybe plain vanilla way to think about allocating investment dollars is you look at ROI, right? And you say, the business comes up with a variety of ideas. A lot of them are great.

39:19There's probably more that a business wants to do than we can kind of quote unquote afford to do. And you stack rank, right? Highest ROI to lower ROI. And I think what we've realized is that's too simplistic, right? There is so much nuance to running a business. And so many, at least for us, of these investment opportunities are highly interrelated. and and what we've had to do in mature jack uh in our kind of planning and our decision making is look across get people uh who lead different areas talking to each other in a much more meaningful way and saying these two investment cases actually work like this and they compound on each other like doing one makes the other better doing you know the other kind of compounds on each other.

40:09And stack ranking, you know, individual isolated investment cases is insufficient and is too simplistic. So we spend a lot of time in investment decisions, doing things like debating product strategy, doing things like debating, you know, roadmap prioritization, what comes first, what comes second, how do they interact? And then ultimately, again, focusing decision making on the highest compounding investment requests, which might look different than if you took things one by one. And ultimately what that's led us to make decisions around, including last year, was to make bigger bets, right? Understanding are you in a unique moment in time?

40:55We have a ton of conviction around AI and the value it's going to bring to our practices and patients in the near and long-term. And we should go bigger. we could use our position to extend our advantage, if you will, and probably made some different, bigger bets than we might have otherwise. And we're learning from that experience. We're learning from how did those bets a year ago pay off as we go into this season's budget and investment cycle. But I think the common thread here is that you have to tie strategy, whatever that is for us, it's again, tech-led product dev as fundamental to our strategy, you have to tie that to the numbers.

41:39You have to tie that to the financial decisions as opposed to viewing them as kind of isolated decision points.

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43:19Jessica Somers: Just turning back the clock a little bit, really, your first 60 days in a CFO role. Could you tell us, was there something unexpected, something as prepared as you were for the role. There may have been something you wish you knew more about. Well, I mean, there is a never-ending opportunity to learn, particularly within healthcare and value-based care. I would say, I don't know, if I could have used AI more aggressively to learn about primary care BBC before I started. But I think something our CEO says to everyone that joins, which is, you know, learn to love us before you try to change us. And that, you know, that I think holds true for how I, you know, try to show up at Allidade and with my team, which is, again, going back to the fundamentals, coming with an open mind, be curious, and really dive into the business.

44:23Like, from my perspective, if you don't really understand the business and the nuances and, you know, the type of things I just mentioned, which is like interconnected, you know, product value, then it's hard to be a valuable, you know, partner to the business and making key, you know, financial decisions. So that was really important. I continue to try to, you know, remember, even when things are busy on a day-to-day basis to pause, to listen, to create space for really paying attention to the business, not just the finance team.

44:59Jessica Somers: Jessica, we'd love to have you reflect a little on the personal side with us. We're wondering if there's something your colleagues might not know about you, something from your past, a feat of some sort, an interest that you had. I don't know. It could be anything anything yeah so it's um uh i grew up um as a kid in the foreign service so i spent a lot of my uh my formative years living abroad in in asia um so so first off like i will eat asian asian food for any meal at any time and if anyone's in the dc area and wants wants recommendations You know, I'm your gal. But secondly, I think perhaps more relevantly is that I grew up around a lot of diversity.

45:46You know, I also had to learn to adapt, right, moving to new countries, being the new kid. And I think that has helped shape how I engage in new environments and with new people. I think it shapes, you know, a lot of what I just mentioned about, you know, starting with an open mind. I know what it's like to be the new person in a foreign country who looks different and doesn't speak the language And so I think again that shapes how I approach a lot of my interactions with all sorts of different people in the world

46:18Jessica Somers: I always like to ask if you have a book selection for us or a resource you might recommend Doesn't have to be a book Might be something you escaped with Don't know, anything come to mind? Yeah So, Jack, I will say, you know, I think culturally we spend a lot of time at work and thinking about work. And so, honestly, if I'm reading, it's most likely to escape and to think about something fun. Not that work, you know, isn't fun, but something of personal interest that also gives me a mental break. So my favorites are any book related to tennis. I'm a huge tennis fan. I'll be watching the US Open matches coming up.

47:02And also any chef-related bio or autobiography. So if I had to put a couple of specific recs out there, I would say Rafa about Raphael Nadal and The Apprentice about Chef Jacques Pepin are some personal favorites. So maybe a little bit of a different answer than some of your other guests.

47:21Jessica Somers: We're up to our final question. We're going to ask you to look 12 months into the future and tell us what your priorities are for that period. What come to mind as a CFO? What are your priorities for the coming 12 months? Yeah, look, I would say one thing I try to talk to my team a lot about is that the things that end up mattering are kind of each of the individual micro moments that we all participate in every day. And like our job is to do all of the small things well. And I believe like that ends up stacking to big things done well. And so I spent a lot of energy keeping people focused on building the right small habits.

48:05Again, working towards building a world-class finance organization, building that foundation. And so that stays true. And that is kind of always a big part of my focus. On a more macro level, you know, piggybacking on a lot I've talked about today, which is what is AI doing, right? How is it going to shift? What AI is doing for us today is dramatically different than what it could do six months ago. And it's going to be dramatically different six months from now. And so we're investing, as I talked about, in AI in a bunch of ways. But how do we develop those muscles to leverage AI while knowing we will have to leverage it differently in the future?

48:47And building with that in mind, I think, is a key priority for the business and myself and my team.

48:55Jessica Somers: Jessica Summers, thank you for joining us on CFO Thought Leader. Thanks so much, Jack. Great to be here.

49:11Jessica Somers: Hello. 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.com slash benchmarking.

From the publisher

At Aledade, CFO Jessica Somers is helping finance navigate a business where investment decisions can take years to fully reveal their value.

The technology-driven, physician-led company works with more than 3,000 primary care practices and touches more than 3.6 million patients, using data and technology to support proactive, preventive care. Its value-based model also creates an unusual finance challenge: connecting better patient outcomes with healthcare savings and, ultimately, financial performance.

That long-term orientation shapes how Somers approaches capital allocation. Aledade has built its own technology platform rather than relying on another company’s roadmap, reflecting what Somers describes as a desire to “control our destiny.” Today, that same thinking is influencing the company’s approach to AI.

Rather than viewing investments as isolated projects to be stack-ranked strictly by ROI, Somers wants leaders to understand how different investments interact and compound. That became particularly important as Aledade weighed continued progress toward profitability against the opportunity to make larger AI investments. The result was a willingness to make bigger bets where leadership saw the potential to extend the company’s advantage.

Somers’ perspective is shaped by an earlier career in investment banking, private equity, and corporate development. Moving from advising on transactions to operating inside the businesses themselves taught her that financial results reflect countless everyday decisions—and that finance creates the most value when it deeply understands the business behind the numbers.

Her agenda now extends that philosophy to AI: not simply using technology to make finance faster, but reimagining work so the team has greater capacity for judgment, insight, and strategic partnership.

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