


18 Oct 2026 · 49m · 19 chapters

Kara Childress (CFO/president of Vensure Employment Solutions) discusses scaling via acquisitions—especially integration—while redesigning finance for visibility, efficiency, and growth. She also covers how Vensure uses AI in reporting, customer support, and M&A analysis, and how the company expands globally through HR/payroll services.
Childress moved from public accounting and management consulting into Vensure, initially as an outside auditor, then COO, then CFO, and now president. She emphasizes leadership lessons from CEOs and a mentor (Karen Meredith), plus a “listen and learn” approach when joining new roles. She previously worked operationally and later led finance during rapid acquisition growth.
Vensure averages ~18 acquisitions/year and has completed ~120 acquisitions in ~8–8.5 years. It uses a 1,400-step acquisition integration process and integrates into one accounting system for month-one visibility. AI should be “human-in-the-loop” and creates value when embedded into workflows.
weekly KPIs on client hiring/firing; month-one pro forma reporting; Prism AI tools in reporting; building an HR-specific LLM (“Prism intelligent model”) planned for December; using AI to compare acquisition files and flag positives/negatives. She also shares a personal example: her daughter’s stage 4 lymphoma diagnosis (2018–2020) and her support/faith work.
Written by AI. May contain mistakes.
Kara shares insights on her company's acquisition strategy and success.
“We are the leading, you know, acquisitor, if you will.”
Kara Childress discusses her career journey and transition to finance leadership.
“Our talk with CFO Kara Childress begins after this.”
Kara reflects on the influence of her mentor and her family's work ethic.
“That's onestream.com slash forwardfinance.”
Kara discusses her pivotal career leap from public accounting to corporate finance.
“And you can quickly figure out the ones who are strategically thinking about not just today, but also tomorrow.”
Kara explains how her expanding roles have changed her leadership perspective.
“Were they taking a leap with you or were you taking a leap with them?”
Kara shares insights on evolving leadership and organizational improvement.
“Oh, I know that I think extremely differently today than I did a year ago, five years ago, 10 years ago.”
Learn how leadership and personal growth parallel organizational development.
“put myself in their shoes, I can make a difference.”
Explore how Vensure has successfully completed over 100 acquisitions and its professional approach to M&A.
“And so, you know, those things, you know, come to light with all of our acquisitions and the way that we've grown the business, which I'm sure we'll discuss.”
Discover how Vensure generates revenue through technology and global services.
“and that's what we've done differently to really make sure that if you're going to do 120, you better get really good at it.”
Understand the KPIs that provide insight into Vensure's business performance and economic trends.
“I mean, with so many services and businesses, which operating signals perhaps give you the earliest read on how the company's performing?”
Learn how Vensure evaluates potential acquisitions and investment opportunities.
“Now, Venture raised another$450 million this year for M &A.”
Explore how Vensure incorporates AI into its compliance and service tools to enhance client experience.
“where are customers seeing meaningful value already?”
Learn how AI is integrated into human capital management and its impact on efficiency.
“You don't just have to go out to Google or go out to Claude and try to figure out what they're saying.”
Explore key insights from M&A that shape financial strategies and decision-making.
“Well, thank you for a wonderful overview.”
Hear personal stories of leadership challenges and resilience in tough times.
“We always like to ask about your first 60 days after you stepped into the CFO role.”
Kara shares her personal experience with her daughter's cancer diagnosis and the support she received.
“Sometimes I just need to get my mind off of it.”
Discussion on how 'Seven Habits of Highly Effective People' has influenced Kara's leadership approach.
“I think it's important that you do step forth and talk about it.”
Kara emphasizes the importance of a win-win mindset in both business and personal relationships.
“I mean, when you say win-win, that's one of his principles.”
Kara outlines her priorities for the upcoming year, focusing on client retention and organic growth.
“We're And what we want to know are your priorities for the coming 12 months.”

Get the gist, explore an idea or ask about something said.
On CFO THOUGHT LEADER, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Support for CFO Thought Leader comes from OneStream, Trusted Data, Faster Decisions, and Salesforce. Explore new research on the future of finance and AI at Salesforce.com slash CFO report. Hello, this is Ken Stilwell, CFO of Pegasystems, and you are listening to the CFO Thought Leader podcast. This is episode 1222. too.
0:29Kara Childress: We've done about 120 acquisitions in about eight years, eight, eight and a half years. So we're on that. We're averaging now about 18 acquisitions a year. And, you know, we lead really our industry. We are the leading, you know, acquisitor, if you will. We are usually the buyer of choice to most in the payroll HCM and PEO sector. There's more than 14 ,000 businesses. So we've only bought 120. So we got a long roadway ahead of us. But I'll tell you something, Jack. We have professionalized the M &A industry by really systematizing and giving ourselves a process. We have a 1400 step process for every single acquisition we do.
1:20Hi, it's Jack. On today's show, we speak with Kara Childress, CFO of Venture Employer Solutions.
1:36There's something interesting about companies that grow through acquisitions. Buying a business is one thing. Absorbing it, understanding it, and making it part of a larger organization is something else entirely. And the faster the acquisitions come, the more difficult that second part becomes. At some point, finance has to ask whether the organization itself is built to keep growing. That's a question that comes through in today's conversation with Kara Childress. Her company has developed a remarkably systematic approach to acquisitions, but what caught her attention was how the same growth forced her to rethink the finance organization itself.
2:20Our talk with CFO Kara Childress begins after this. What is a forward finance organization? Finance leaders are under pressure to move faster, adopt AI, and guide decisions across the business. But here's what most people miss. AI doesn't create value on its own. You need the right operating model behind it. That's what Ford Finance is. It's the blueprint for building trusted data with finance and IT actually aligned. and AI working right where decisions are made. OneStream brings this to life. As the AI operating system for modern finance, it's all in one platform. Your financial and operational data in one place with purpose-built AI embedded across planning, close reporting and analysis.
3:20The result, faster decisions, less busy work, stronger governance, and more value from AI, explore the Forward Finance Blueprint at onestream.com slash forwardfinance. And see how to turn AI ambition into real business value. Visit us at onestream.com slash forwardfinance. That's onestream.com slash forwardfinance.
3:58Hello, CFO Cara Childress is with us. Her career has taken her from public accounting and management consulting to an expanding leadership mandate at Venture Employer Solutions, first as COO, then CFO, and now president. Along the way, she's gained a front row view of how businesses scale, integrate, and evolve. Kara, welcome.
4:26Kara Childress: Thank you so much, Jack. I'm glad to be here. So, as always, take a look back for us, Kara. Try to identify some of those experiences you feel prepared you for finance leadership. What would come to mind? Yeah, absolutely. I mean, when I kind of think back on how my career evolved, you know, starting in public accounting, I was really able to see different types of businesses. Public accounting is about kind of serving, you know, small and medium-sized businesses in the areas of tax accounting, audits. And you get a good view and a good exposure to different CEOs who tend to operate their businesses differently.
5:11Kara Childress: And that really helped me kind of know and understand there's different ways to do things. There's different ways of how people think, especially at the leadership and ownership level. Still, as you look back, what were you unsure about back then? Oh, I was unsure about many things, right? And a lot of things sometimes were driven by the transaction, the dollar amount of the discussion, the tax liability, the accounting treatment. There's probably multiple examples I could give you that you're unsure, is this the right decision, right? I mean, in finance, there's gray areas. Not everything's black and white.
5:50Kara Childress: A lot of things are, but you get into that gray area and that as a leader is where you have to really discern, is it more black or is it more white, you know, and how do I, in that gray area, and how do I navigate those when you become unsure? So you, from early in your career, had the opportunity to sort of sit across the table from leaders, observe them up close. How did your opinion on leadership change as you grew and got more responsibilities yourself. Yeah, I mean, I think I was able to see CEOs, owners, other finance leaders approach business, approach their business and how they made decisions.
6:37Kara Childress: And you can quickly figure out the ones who are strategically thinking about not just today, but also tomorrow. We're not making a short-term decision, we're making a long-term decision or we're looking at a 50 ,000 foot level. And that really helped shape me that the question you ask me is not about the answer that's maybe like right this second, but it's also thinking more broadly about the bigger picture and not just should I take this deduction today? It's should I build something that builds this deduction to recur, for instance? And I'm not asking you to name someone necessarily, but was there someone in your past who made you think about your career a little differently?
7:32Or were you always sort of had sort of a grasp on what career building was about?
7:40Kara Childress: You know, I could probably name her. She was the first person who hired me at this public accounting firm. I call her my mentor. I give her all the credit of who I am today. Her name is Karen Meredith. She's out of Dallas, Texas. She's an amazing woman. But she herself was in the Big 12 back in the day, and she learned a lot, and she really instilled in me the desire to build my own career and to really elevate and not just limit myself. She never limited me, which I felt was so extremely important. Like, this is your job and this is what I need you to do. No, do what you think. Let me throw you in the deep end and see how well you swim, which was just amazing for me.
8:25Kara Childress: And I also just kind of have to add one more thing. My parents instilled in me this work ethic that I think a lot of times we're missing today. and I've tried to instill in my children, I'm not sure I did as good a job as mine did, my parents did, but my parents had five kids and they were really almost forced to some degree, my parents both went to college, but they worked multiple jobs and they just showed us kids that like working hard pays off and that really instilled in me and that really drove me to want to build a career along with a mentor who was willing to say, you know what, I'm going to give this girl a chance.
9:05Kara Childress: I'm going to let her sink or swim. And if she sinks, I'm going to pull her up and make sure she doesn't drown. But that really helped my stepping stones to build that and give me confidence that I could really take this to the next level and the sky was the limit. What career decision perhaps felt like the biggest leap? Oh, that's a great question. I had been in public accounting from 1993 roughly through, you know, the mid 2000s basically, 2012-ish, 2013. And really where I'm at today, Venture gave me an opportunity to kind of take the leap and really leave public accounting. I had left momentarily in 2008 while I was doing management consulting for a very large client of mine, but always had the intention of rolling back to the public accounting.
9:58Kara Childress: This particular opportunity really gave me kind of the springboard to say, you know what, I'm going to go into corporate, which is very different than public accounting. I'm going to focus on one industry. I'm going to be the leader in this one industry, guide my team, you know, to the decisions we need to make. But that was really pivotal for me to say, you know what, I'm going to take this leap and get out of public accounting where I wear many hats. Right. And I'm going to get into corporate accounting where I wear one hat in this industry. And you also got into operations when you joined the company.
10:32Is that right? I did. Were they taking a leap with you or were you taking a leap with them? I mean, your operations experience, clearly you had done many different things. However.
10:46Kara Childress: Yeah, no, great question. At the time, I was actually the outside auditor for Venture. and their COO had decided that after 20 years of being in the business, he wanted to actually go into sales and not do operations anymore. And so it opened the door for me to come in that you already had a CFO. But reality was I was really already playing a major finance role. And I had told our CEO, by the way, I really enjoy helping people more than I help in moving numbers. A number is a number to me. Not how many zeros. It's really helping people remove roadblocks, helping them get to their next level because if I help them, they're helping me concept.
11:34Kara Childress: And so it really was us both taking a leap, although I knew that I could do finance in my sleep. I really wanted the opportunity to dig in on the operational side because I had done a lot of that in public accounting. I had moved into full consulting role where I would come in and look at operations and kind of see what are the areas you're being inefficient, where could you save money, with the finance mind at the forefront. And so this just kind of, it really very smoothly transitioned me because I had already been doing it for a lot of our clients and now I was able to concentrate on it and really not necessarily have to worry about the numbers because they had a CFO.
12:20so i want to just point out as you come through as a the door as a coo you take on the cfo role roughly three years or four years later roughly and then you become president as well um and and and for the last three years you've been cfo and president so this broadening is just a fact of your career i mean it just seems like it's always been a journey of how to broaden. How am I doing? Would you look at it differently?
12:52Kara Childress: No. Yeah. I think you said it perfectly. So, has becoming a broader leader, how has that changed you? How do you think differently? Oh, I know that I think extremely differently today than I did a year ago, five years ago, 10 years ago. I think, you know, if you're not evolving, then you're probably just in a stagnant, you know, area, right, or position. But really, it has helped me as a leader, not just think about the area I'm in. How am I affecting, you know, what's happening in different departments? Well, how are the decisions I'm making really affecting the organization as a whole? And when you start thinking more broadly like that, and you're willing to ask more questions, I'm a pretty inquisitive person and I want to dig in and I want to know did we really figure out if this affected this this and this and are we really following our SOPs or is that something that we need to address and you realize that you are one person that can really affect the organization's thinking you start to really go okay if I think about the way that we should be doing this and I put myself in their shoes, I can make a difference.
14:11Kara Childress: And I think that's really in broadening my career when you think about, I'm not just here to do a job. I'm not just here to report the numbers. I'm not just here to report the state of the affairs. I'm really thinking about what are we doing as an organization that's working and not working, right? And I think every company, we all are, none of us are perfect. We have things, Microsoft's not perfect, Apple's not perfect, Venture's not perfect, right? but we all strive to do the best for our clients and the service we provide. And we want to make sure that, you know, if we do have a flaw, that we're working on those things.
14:47Kara Childress: And as a leader, you've got to be able to listen and recognize, ooh, is that systemic to our organization or is this a one-off? And I also want to just sort of make that parallel comment that as you broadened over the last 10 years, so too is venture. Venture has really become a broad HR technology and services business today. So there's two evolutions happening here. Tell us about venture. How do you describe this company today and the opportunity that lies ahead? Yeah, we are the largest privately held organization in HR technology, in HR and payroll services, what we'd call human capital management services.
15:33Kara Childress: We're a global company. So we're in 77 countries directly, but we service like 180 plus countries. So we have expanded tremendously to not just the US, but really COVID taught a lot of us that you can be global because we all went remote and we quickly realized that we really wanted to expand. So as you point out, my career has grown as venture has grown as well, right? Like if I didn't grow, I wouldn't be in the position I am today because venture was growing at a very rapid pace. So we are in an exciting time. I'm in an exciting company, which we try to fly under the radar as much as possible because we're really not here to pound our chest.
16:18Kara Childress: We just wanna build an amazing company built on a good foundation and great values and great customer service. We're starting to get noticed. And so, you know, those things, you know, come to light with all of our acquisitions and the way that we've grown the business, which I'm sure we'll discuss. But what it's done is it's forced a lot of us leaders and given us an opportunity to really take our career and say, are we thinking of this in a bigger and better way? And how can we scale this business with a solid foundation? Wow. I was looking at a stat. I mean, Venture has completed more than 100 acquisitions.
16:56I don't know what the span of time is, but that's quite a number. I'm wondering how, you know, can you reflect on how M &A has really shaped the business you have today?
17:08Kara Childress: Yeah, absolutely. I mean, kind of to answer your question, because I'd love for our listeners to know, we've done about 120 acquisitions in about eight years, eight, eight and a half years. so we're on that we're averaging now about 18 acquisitions a year and you know we lead really our industry we are the leading you know acquisitor if you will we are usually the buyer of choice to most in the payroll HCM and PEO sector there's more than 14 ,000 businesses so we've only bought 120. So we got a long roadway ahead of us. But I'll tell you something, Jack. We have professionalized the M &A industry.
17:54Kara Childress: We process payroll for a living. You know, no one pats us on the back for getting their paycheck right. I'm sure you didn't thank anybody, neither did I, for getting my paycheck last week, right? But we have, because we have amazing technology, we have amazing customer service, we really strive to bring clients, small and medium-sized businesses, the solutions they need. But at the same time, as we are those businesses that we run very in our sleep, we've also built this amazing engine to acquire businesses, roll up our industry, if you will. But we've professionalized our industry, excuse me, we professionalized the M &A industry by really systematizing and giving ourselves a process.
18:41Kara Childress: We have a 1400 step process for every single acquisition we do. That is our integration process. So when most private equity firms listen to our story and what we've done as a business, they are blown away by the fact that we have really taken what a lot of people do. They make, they acquire businesses, you know, and everything, but it's integration and it's synergizing is the key. and that's what we've done differently to really make sure that if you're going to do 120, you better get really good at it. So building those processes and procedures were extremely important to us.
19:21We'd like to understand better how the company makes money. I mean, where is the sort of the more important story today? Is it the technology? Is it the services? What's the story here?
19:34Kara Childress: Yeah, I mean, it's all of it in the sense of we provide a technology as our underlying platform, but our services domestically and globally is really how we make our money. When you think about a business today that operates in the U.S. that sees the opportunity to go globally, and maybe they see an opportunity to sell in Spain, for instance, it's hard to get into the country of Spain. You gotta set up a company, you gotta do all these things that get you there. One of the really ways that a lot of companies, even our competitors that we work with, we fill in for each other in countries that each other may not be in.
20:16Kara Childress: We have understood that we can provide a service to companies that they can be global on a very economically solution-based service that allows us to expand our services and continue our revenue streams that doesn't just limit us to one region or one country, but allows us to really broaden that. And that's today where we are, where five years ago, even 10 years ago, we were only thinking US. So you would have asked me, and I would have said, our services are strictly in the US. We're providing administrative services. That's how we make our revenue. And we provide HR. There's a lot of rules. You've got states that have compliance, very heavy compliance, and you have to follow that.
21:02Kara Childress: That's what we specialize in, right? Now, globally, there's a lot of compliance, too. It may not be so much, you know, on the tax side. We're very complicated tax-wise in the U.S. You know, globally, there's much more complication on onboarding and offboarding employees. So that's where, you know, we come in to provide those services, and that's where we have more revenue opportunities. You always like to understand how you look into the business, your revenue visibility. I mean, with so many services and businesses, which operating signals perhaps give you the earliest read on how the company's performing?
21:42Kara Childress: Yeah, we've got several different KPIs we look at on a weekly basis, on a monthly basis. You know, data is key in today's environment. 2026, everything is about AI, but that's really, you know, data driven, right? If you've got the data, you can start measuring things and knowing, hey, what's an indicator? What's a leading indicator? One of the things for us is we measure weekly. what are our clients, how are our clients hiring and firing? If we see a trend that the clients are hiring more employees, we know that the economy itself is picking up. We know if we see, when we hear in the news Amazon had a layoff, but we don't see that trend, that same trend in our weekly KPIs, we know that maybe the small and medium-sized businesses, it's just not a leading indicator for us yet.
22:35Kara Childress: So it's those types of KPIs that we see that tell us how's our business doing? Also, how is our economy doing as well? And what is it reading and telling us about what's happening or getting ready to happen? The concern would be, you know, every one of those acquisitions are at a different stage, perhaps. And your visibility might be, you know, solidified with some of them, but others are a little checkered. As you integrate these businesses, how do you make certain that your lines of sight into them are going to be, you know, established and
23:13optimized? Yeah.
23:14Kara Childress: So first and foremost, from a finance standpoint, we integrate into one accounting system. You don't have a choice. You know, part of our 1400 steps, you know, there's probably, I haven't counted them, but a couple hundred that apply to accounting and finance alone, right? You know, some are technology, some are operations, right? So those steps include integrating into our finance reporting. That is 100 % key. I have visibility from month one. I know exactly. And we also load all the pro forma from the prior history as if we've always owned them so that I can see truly how the acquisition is performing.
23:54Kara Childress: If yesterday you had 10 clients and today you have 12 clients. I know you're doing amazing. You picked up two clients. I can see that. So reporting for us and integrating into one accounting finance reporting solution is at the top of my priority list. I have a completely separate integration accounting team that that's their job. And of course, with as many acquisitions they do, they're plenty busy. That's what they go do. They go get those companies and those acquisitions accounting data, and it gets pulled in, eventually they migrate completely in. Of course, that doesn't happen day one, but they know month one, you're going to report in to ours.
24:36Kara Childress: And over time, it takes six to 12 months, depending on, to your point, there's some that are smaller, there's some that are bigger, that may take longer. We will migrate you completely over into our accounting system. But definitely reporting is key. Otherwise, you just don't have visibility into what you should. Now, Venture raised another$450 million this year for M &A. Is that right? That is correct. How do you decide where the next investment creates the most value? Yeah, we have a pipeline of acquisitions. And as those acquisitions come in, like those potential prospects, we have a process.
25:21Kara Childress: We have an LOI phase where we evaluate the companies, right? And I think I kind of mentioned we're the buyer of choice. So we see a lot. We don't pick them all. They don't always pick us either, right? They may have, you know, a different opinion on the value of their company. But that first initial phase of that LOI phase is extremely important. And that's how we determine, hey, we have a sweet spot of, you know, what we think the average, you know, a company we like to acquire looks like. but we have smaller and we have bigger. And we don't turn those away because they're not in our average.
25:56Kara Childress: We look at everything because we see the opportunity. If there's opportunity, if you can imagine in a company our size today, if you could bring in a product and we touch on an indirect and direct basis, 4 million employees in the United States of America on an either weekly, bi-weekly, semi-monthly basis. And we can bring in a product that will help them or their employer. it's okay if it's small. If we can scale it and we can offer it to all of the employees or all of the clients, that's a great add for us, right? Because we own that technology and we own that product now. So we look at it from that view and that lens that it doesn't have to be just because you're small, you're outside our wheelhouse, and that's not how we're going to deploy our 450 million, we look at it as what is the opportunity that we can bring you into our ecosystem, right?
26:50Kara Childress: And grow your revenue. Our goal is to help grow your revenue and make sure, because a lot of times our acquisitions, Jack, are in 80-20. We will buy 80 % of your business. We want you to remain in for 20 % because we believe your second bite at the apple could be bigger than your first because you're going to come into an ecosystem that's much larger. You may have been concentrated in Florida and that's all you've been, or Southeast, and that's all you've been able to really do, we're going to open up the whole United States. We're going to open up global to you. So it's that opportunity and how we look at things to see if this is a good fit into, you know, what we're trying to do, you know, from a venture standpoint.
27:27You're putting, I want to touch on AI now with you. You're putting AI into compliance, into recruiting, workforce tools. where are customers seeing meaningful value already?
27:43Kara Childress: Yeah, I mean, we are putting it, we rolled it out at our user conference this year in June. Our, you know, our Prism AI tools, it's in their reporting. So clients of ours can get in. They can ask it to build a report. We all know kind of about like chat GPT. You can go ask it to build something. It'll go build you a PowerPoint. It'll go build you an Excel. we have that built into our reporting centers now we've got you know chat bots that will now answer questions for you more quickly than you having to put in a ticket and waiting for a human to respond we're in the process of building our own llm that all human capital related we're not going to put a man on the moon and we're not going to you know cure cancer but we're we're building a learning model that will be specific to human capital management so that our clients can quickly get answers, right?
28:32Kara Childress: You don't just have to go out to Google or go out to Claude and try to figure out what they're saying. We're going to have a very specific, what we're calling our prism intelligent model, PIM. We'll be rolling it out in December that we've built purely for human capital. So as we're evolving as fast as AI is coming out, we're putting it into our report center. We're building into client facing so that they can feel and get more answers, be more efficient, quicker. We're also going to the next level and getting them our own learning model that will allow them to kind of really hone in on what we're doing for all of our clients.
29:07Just for the AI enhanced capabilities of the platform, has anything surprised you as far as how customers actually are using it?
29:19Kara Childress: No, I don't think so yet because, you know, two years ago we were all kind of talking about AI, right? Maybe a little. Now it's all we talk about, right? I mean, every day, it's probably all all of us talk about. And so I guess the most surprising thing for me is how fast people are adopting it. You know, and I kind of think back to how technology has evolved. This is just another step in a technology movement. It's just a little more powerful. And of course, it gets faster and faster. But you know, I imagine, and I remember when I first started in my career, that we barely had the www, like I like to call it, you know, right?
29:59Kara Childress: You know, that we all were very, you know, intrigued by, but we didn't really use it. We didn't know how to use it. I mean, just think about that. It was the early 90s, you know, and think about where we are today, right? You know, so just incredible, incredible, you know, growth, but also today it's just moving even faster. How fast did we adopt the internet versus how fast we're adopting AI? That's probably the most surprising thing for me. Has sort of the M &A framework that you've established, this machine, has AI become a component there as well, we would imagine? I mean, how can AI be used in the M &A realm?
30:43Kara Childress: Oh, yeah. I mean, absolutely. The analytics that need to be run, the comparisons, the finance data. You can upload that into AI and ask it to go do that comparison. Tell me what you see as your conclusion. It functions as a human. I like to say you should treat AI like another person in the room. Get their opinion. They need to be at the table with you as you're making decisions because it's gathering intelligence from other companies, from the things they're scraping out there that are built into these models. So asking it to give it, you know, a different layout, a different view, you know, asking its opinion is highly valuable.
31:30Kara Childress: It will give you things you weren't thinking about, right? Because we're all limited to, you know, what our experience is and what we know and, you know, what our expertise are. And so absolutely in the M &A area, you know, we use it for analysis of tell me what you see, tell me what are the positives, What are the negatives we're not seeing? You know, point out to us and help it. It's just another step. It'll actually do things much faster than I was doing some things this morning, comparing, you know, two files and asking it to tell me. And it was just quickly, you know, within seconds, not even minutes, seconds telling me, yep, here's your differences.
32:03Kara Childress: Here's what I think. Here's what's causing it. Here's what's driving it. Amazing. What about as AI becomes more embedded in more of venture offerings, Do you see it changing what customers ultimately pay for? We've been having lots of discussions on that, right? And to make sure that we were sensitive to that, right? One of the things that we've done within venture, which is probably, you know, is going to go against maybe even what you're asking and thinking, but I think it's a good point. We have built a tool that actually created a new department. so we didn't become efficient and and let people go because we were using ai to do a job that someone else a human did we actually created a tool that created a new department and created more jobs and i see that happening just just as much if maybe if not more than the other because it's going to give us humans more time to analyze you have to have a human in the loop You have to.
33:11Kara Childress: AI is going to make mistakes. It's not going to tell you all. It's not 100 % accurate. So it's interesting that really the approach, and by the way, we've rolled this out to some of our clients, some of our other service provider, other payroll, HCM, PEO service providers, because they saw the value. That created jobs for them too, but it was an AI tool we built.
33:34Well, thank you for a wonderful overview. we are up to what we like to refer to as our finance strategic moment. And this is where we ask you to look back and just choose a moment of insight or an aha moment that you've had along the way. What comes to mind for you?
33:51Kara Childress: Yeah, I mean, I think I actually have two, if I can share them both. One, from a finance standpoint, as we've had all this incredible growth through M &A and acquisition, myself and our other finance leader we had a structure within our accounting organization that was very regional and divisional driven as I explained to you we have an 80-20 I don't just roll them all in and it becomes one number I get to report I still have to report to all of the sellers their individual 20 percent and so we were really duplicating a lot of efforts by kind of keeping all this accounting functions individual.
34:34Kara Childress: It was really a moment I had that said, you know what, we need to think about this differently. And I think for me strategically, and I touched on this earlier, you have to be able to kind of step back, like push your chair back from the table for a second and think bigger. And I said, you know what, we're this M &A engine isn't slowing down, we're going to get bigger. And if I keep doing the way I'm doing it today, someone's going to come along and go, Kara, your finance organization is so large, but it's just simply because I was duplicating efforts. We were all doing the same job. So we spent some time two, three years ago reorganized and said, you know what?
35:14Kara Childress: And you know what? I don't think I lost more than 10 people out of the 400 people I had. It was not a process of I need to shorten, but I wanted to be more efficient. But what it did do for me is I wasn't going to need a higher in the future as we had more acquisitions because I stepped back and I said, you know what, the way I'm structured is not going to be built for growth as we continue on the scale we're on. And that was really strategic for me from a finance standpoint is to really recognize, hey, you may think you have one way to do it. You need to step back and say, is there another way?
35:48Kara Childress: That was kind of my first one. And And then secondarily, I think just from a president operational standpoint, we were getting, being in the U.S. primarily, and we were going global and we had brought on our own global teams that were outside the U.S. I was getting a lot of concern that we were offshoring. And I was like, you know what? The message isn't right. That's not what we are. If you can imagine other employees in other countries want an opportunity just like we do in the U.S. to be employed. And we have some in South America that they are thrilled to be part of a U.S. company. We are the greatest country in the world.
36:30Kara Childress: We are by far. You know, we have the greatest economy. We are the greatest country. We have so many things to be thankful for. If you never go outside the U.S., you need to, you know, because it'll open your eyes. But what I realized as a leader is the message within our organization was like, oh, we're offshoring. And I thought no I've got to change that because that's not what we're trying to do and i'm so thankful I did that It was probably about I think that was 2019. So seven years ago And I came up with a term for us That no, this is our team. That's global. We are global number one. We're global number two This is our team.
37:07Kara Childress: That's part of us and as I said that enough it infiltrated through the whole organization Everybody says it now and I shut off that narrative, which was my goal because I was concerned that they were going to always look at as an outsider. And they're part of our team. By the way, we go there, they come to us. I got a full team here in my office. So it was a really strategic moment to say, you know what, I need to think about what the message is here and make sure that they understand what we're really trying to do. And make sure they understand the positiveness in it and not the negativity. So those two things for me were really key is just really being able to step back and think a little bigger and outside of what's just sitting directly in front of me.
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38:54Great, great insights there for us. Thank you for those. We always like to ask about your first 60 days after you stepped into the CFO role. How did those 60 days surprise you? What about the role, as prepared as you were? There must have been something about the role that you never expected, something you wish someone had mentioned to you. Anything? thing?
39:24Kara Childress: Well, I will tell you, I was really already doing the role. So our CFO at the time didn't have the experience to stand in front of our private equity firm. And so I had already been doing it for a while. So as the COO, I was giving financial advice, I mean, excuse me, financial presentations to our board and our investors early on. So that it was just a natural fit. But if you had asked me, which I'm going to pretend you did, what were my first 60 days when I stepped into the COO role? Because that's really kind of where I got my, this is interesting. I came into that role into an organization where I was the outside auditor.
40:02Kara Childress: Okay. I only knew the numbers and I knew the fun. I didn't really know. I knew some of the people, not all the people, but here's what I decided to do that paid off very well for me. I was not going to be a bull in a china shop. I was not going to be a heavy hand. And I said, I set everybody down. I said, look, I'm here to listen and learn. I want to know what works well and what doesn't work well. And I promise you, I am not going to just come in and think I got to bulldoze and change everything. And they really received that well. I have an amazing staff. We have amazing people we work with.
40:34I think if you interviewed a hundred people, you know, out of 200, all of them,
40:40Kara Childress: I just talked to a brand new employee who is a new C-level for us. And she's like, The people are so welcoming and they're so kind and they're very willing to help. And I think it's because the leaders at the top, we want to establish the right message that we're not here to be a bull in the china shop. We're here to help people and get past that. That was my first 60 day aha there. More than anything, I think as coming into these roles, because like you said, the other ones, well prepared for, I was really actually already playing them. In both cases, I just naturally got the title and they said, hey, can you be our CFO?
41:15Kara Childress: And I had groomed a COO and she's amazing today that whole time, which really helped kind of, you know, naturally let me pass that off so I could kind of do what everyone felt like I was really good at, which was the numbers. And then also into the president role, which I do today. Yeah, wonderful. Great, great insights for us. Hey, Kara, we always like to ask our guests to reflect a little on the personal side. You've been there 10 years, so your colleagues must know most everything about you, but maybe there's something out there that a lot of people don't know about you. Anything come to mind?
41:49Something from your past, way back when, an interest that you had, something you did a little differently?
41:55Kara Childress: Well, I'll actually share with you just something a little bit that happened to me in the last 10 years that will really sort of, it'll kind of let you know a little into me a little more. My daughter in 2018 was diagnosed with stage 4 lymphoma And so we went through two years of treatment Thankfully, she's 22 today, doing amazing But a lot of people don't know that about me You know, in the role that I'm in If you were with me at the time from 2018 to 2020 Venture was amazing They were very supportive They gave me all the time I needed I said, you know, staying in hospitals is kind of boring sometimes Because you're just watching the medicine go into your child which is not, you know, like all that.
42:34Kara Childress: I can't, there's not a lot I can do. I'd like to work so I can stay busy. Sometimes I just need to get my mind off of it. And sometimes I needed to be right there with her. And they gave me that flexibility. But a lot of people don't know. And as leaders higher up, right, our lives are, you know, are pretty private, you know, and because we don't, we're not, you know, we have a lot going on. So, you know, going through that, but really, you know, I help people today. I've served on pediatric cancer research boards. That impacted me as well and in my career. But it is something that's very personal that I do share with people because I think that I want to make a difference.
43:15My daughter was very fortunate, but it took a lot
43:18Kara Childress: of prayer and hard work and a lot of support to get through that time. But it is something that's difficult to talk about as a mom, you know, but like as a leader, you know, like we all are moms and dads and, you know, and brothers and sisters and all that, that go through these things in life and know that, you know, I can relate. I can relate to you. You know, my child had cancer and, you know, she survived and is thriving, but it was scary, but I had a lot of support that really helped me. And so that's just something that I, you know, openly do share about. And I have a platform that, you know, and venture where we raise money during pediatric, you know, cancer research month in September and we go gold and all that, which is really awesome.
44:01Kara Childress: You know, but a lot of people that wouldn't necessarily, if you look at my LinkedIn and you look at my business career, you don't know that about me, but it's very, very impactful and it changes the way I look at the world today. Well, thank you for sharing that. I think it's important that you do step forth and talk about it. There's so many people impacted by cancer and all types of things. Hey, we always like to ask also for a business resource. And I should just say a book or that's influenced your thinking or actually maybe it's not related to business. Maybe it's something you escape with.
44:34Anything? Yeah.
44:38Kara Childress: It's definitely a book and definitely business, but Seven Habits, of highly effective people. Stephen Cuthy, oh my goodness, I live and die by that. I really do those principles. I've taught classes on it, but I just think if people in business grasp those concepts, and maybe sometimes just even two or three, I think the world can be a different place. I think those foundational principles are just so key that have just really propelled me in my business career. I think on a personal level, I just have a lot of faith and faith has just driven me on that side, which is helpful because I'm telling you, business is hard and business at the end of the day, you have to sit down because you have a family.
45:21Kara Childress: And sometimes I need to be grounded and I just need to be grounded in faith. And so sometimes I tell my leaders, I need to go to church. I need some Jesus. I need a little bit, because I just get so wrapped up in business, right? But I need to just sort of ground myself. So from a personal standpoint, it's faith. But from a business standpoint, man, Seven Habits of Highly Effective People. So I think if people grasp it. Why is that book still so relevant? I mean, when you say win-win, that's one of his principles. You think about how many times people in, you know, it could be in our departments or arguing about something.
45:58Kara Childress: But am I really thinking about the other person? How can we both win in this situation? It's all we do as leaders all day long. it's all we and it's what you should be doing but if you could impact that to the rest of the organization and the downline to think when when to begin with the end in mind what are you trying to accomplish you know and that's why i think it's so still unpack pulling around is because those principles i don't care if it's 21 35 and we're all gone now that i don't don't think those are ever going to go away you know you and the human race it's just so applicable to the human race, you know, that it's, it's thinking outside of ourselves, right?
46:39Kara Childress: Thinking about others, you know? So it's just, it's just one of those things that I just get super motivated and passionate. As you can see, I can just tell you, you know, I have to go in and have an open mind and not like I'm getting what I want and I don't really care what anybody else's want. Well, guess what? Nine times out of 10, that's not going to work, you know? No, it doesn't. We all know that doesn't apply in your marriage, you know, like we can do everything, right? So if you think it's going to work in business, it's not going to work. It really doesn't. You know, I think that's why it's just, it's staying the test of time there.
47:15It's stood the test of time. Wonderful takeaways for us there as well. Thank you for reminding us of a selection we hear a lot about, but you said it better than most. So thank you for that. We are up to our final question.
47:30We're And what we want to know are your priorities for the coming 12 months.
47:35Kara Childress: Yeah, for the next year, I mean, we're really focused on retention. Client retention is very important for us. Organic growth. For us right now, we're really looking for, you know, investing into our sales. And so, you know, AI is just going to continue to be at the forefront for everything that we're doing. you know being more efficient providing more services to our clients so you know we're really looking for you know the next year for the economy inflation interest rates which we could probably talk about for the next hour you know to you know improve in a lot of areas and to help us continue to fuel our economy as a business and you know and giving back into our clients and the services we're providing.
48:24Kara Childress: So we're just really looking that one year forward as client retention, organic growth. Those are our focuses. Kara Childridge, thank you for joining us on CFO Thought Leader. Yes, thank you so much.
48:54Hello, 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.
49:24Thank you.
At Vensure Employer Solutions, completing an acquisition is only the beginning. The company has acquired roughly 120 businesses in eight years, and each new addition enters an integration process containing some 1,400 steps. For CFO and President Kara Childress, the challenge is not simply bringing more companies into the fold. It is making certain the organization can absorb them without multiplying its own inefficiencies.
That challenge has become familiar territory for Childress, whose career took an unusual turn when she left public accounting to join Vensure as COO. Having previously served as the company’s outside auditor, she knew its finances. Operations offered something different: an opportunity to remove roadblocks and help people perform better.
As Vensure expanded into global payroll, HR technology, and human capital management services, Childress’s responsibilities broadened to include finance and the presidency. Along the way, she confronted a finance organization whose regional and divisional structure was duplicating work.
The acquisition engine was not slowing down. The finance organization needed to change before further growth made its existing structure untenable.
“We need to think about this differently,” Childress recalls.
The resulting reorganization reduced duplication and positioned finance to support additional acquisitions without continually adding staff. Meanwhile, a dedicated integration accounting team now brings acquired businesses into a common reporting framework beginning in their first month.
Today, Vensure is also expanding its AI capabilities while Childress concentrates on client retention, organic growth, and sales investment.
For a company accustomed to acquiring businesses, the next test is making its growing organization work better.







