The Modern CFO:
Navigating AI, Data, and the Future of Finance

to the Agent CFO podcast. I'm here today with Caitlin Haberberger. She has been a rock star in the CFO world.

And I've always been want to talk to her this formally on a podcast. I thought this would be a great venue to share our ideas with the world. Welcome.

Great, thanks, Ashok for having me.

And what's going on in life these days?

Gosh, just trying to keep up with rapid pace of change everywhere between professional life, personal life. And I'm just trying to figure out how to keep up and where to focus my time and attention.

And I see you're very active in the AI world as well. We'll cover that space. By the way, Caitlin is one of the CFOs probably is in the forefront of looking at all various AI technologies.

She's an investor as well in many companies. So I think it will be a great conversation, you looking at various AI products and we want to know what you think about all this new AI functionality that is coming.

It's funny, having been in this world for longer than I care to admit, the pace of innovation and change right now and the impact that all these new tools and platforms can have for accounting and finance professionals is really exciting. 25 years ago, it would have made my life so much easier.

And I think back to all the painful lessons that I've had to learn along the way and how I think that can be so different for people coming up in their careers now.

Now we have it. To be honest, I work in AI day in and day out, right? And I've seen how finance can change.

I think with the current tools that we have, we are barely scratching the surface. ⁓ We are probably at five or 10 % of what is possible in finance with AI. And there are endless possibilities.

And it's not just about automation, right? It's about...

There lot of things we are not doing right now just because we are too busy. I had this conversation with the finance leader for a really large public company and I asked, what's your motivation of AI? Why do you want AI in your process?

And her response is that we have this bunch of things that we are not doing right now because my team is very busy doing this mundane manual work.

I have that big list of things that now if I can come solve all these problems, all this manual work, my team will focus on it, which has a direct impact on the bottom line.

100 % and I love that. you know, obviously focus on the bottom line. And alongside that, I think about the direct impact that this can have on like the quality and the interest, like the interesting amount of work there is to do and the value that can be added.

And of course it has to translate to the bottom line, but I also think it's going to be such more like more interesting work for everybody. And I think that's really exciting.

And when we hear about maybe people not wanting to go into the accounting profession right and not enough people and stuff, we're thinking about it, well, we'll use tools to help bridge the gap, like where we're missing people.

But I think maybe more people will look at this as a career path when they see the opportunity to add significant value to organizations. I think that's really exciting.

I think even probably you and me, you have been in this space for more than me. But what we have seen, again, I don't think it is probably, it is much bigger than our imagination at this point of time, what can be done.

Yeah. You know, I'm glad you said that because while we're all talking about all these tools right now, I know we're not seeing exactly what can get done. Like it's going to continue to improve, but the possibility is there.

Whereas I think the possib- it did not feel like the possibility was there three years ago. Right. And we're, it's like, okay, we're to have to keep slogging through and sure we can connect this system to that system and it'll make incremental improvements.

That's right. I think it's also the evolution of thought that happened in the last three years. I just wrote an article about it.

End of 2024, if you remember all our conversations, we all thought world is changing at a much more rapid pace. We thought finance will change. Even though I know all the nuances of it, I still thought things will rapidly change in the next 12 to 18 months.

But the pace has been fast, but still the change has been incremental.

I think we are just naive to think that it will be a big bang change rather than incremental. It's because humans are involved in it, right? We don't want the change to be that fast.

We want it to be much more incremental so that we can cope up with it. I think that pattern will continue in 2026 and 2027 as well. We'll see much more incremental changes.

We'll all get used to it. And we will think it's not a big deal. But like how chat GPT or this AI has changed our world, how we write, how we do things now.

Now we are all, we have accepted that fact, right? We don't think it as a big bank change. It's just incremental change that happened in our life.

It's the same thing that's probably will happen in finance as well. I know you live in Silicon Valley. Things go at a different pace here in the enterprise world and also in the finance world.

I know you're extremely busy when you do things. What keeps you sane? Do you have a morning routine that keeps you sane?

gosh, I feel like every podcast I listen to is telling me what my morning routine should be. Outside of, know, making my bed and things like that that everybody says is the right way to start the day.

Look, I mean, they're sort of my, like to keep myself sane, honestly, for me, it's I have to get out into nature.

And so sure, there's certain professional things I do around. read my business update, email updates. I check my Slack to make sure nothing's blowing up, X, Y, Z.

But I'll tell you, just as a human being, I try to get out for a walk. I try to see some trees, hear some birds, breathe some fresh air, at least move my body. That's my way of staying grounded, for sure.

Okay. That's right. All right.

Caitlin, so before getting into the CFR all, what was actually your first job?

Yeah, so my first job was actually working in public accounting with one of the big firms, Arthur Anderson. I'll really date myself there because the firm is long gone, but I worked as an auditor. So that's how I got my start.

We previously interviewed Jason Yocum. He also came from Big Four and audit firms and looks like that's a very good path, right? Is it like it instills some kind of discipline in you being in an audit firm?

Yeah, that's a good question. think, yes, it certainly does. ⁓ I mean, it's a very structured way to start your career, right?

And I know, some people started banking, there's different ways to get started. It also helped, think, with there were technical skills that I learned, but I think more than anything, it was learning how to operate in an environment with certain expectations, how to show up, how to communicate.

regularly, I had to incorporate that feedback. So I think all of those things were really just foundational, just operating in the workplace. And I think when you're coming out of college, like I didn't have any professional types of internships.

think most of the, did a lot of ⁓ community service work, working with nonprofit agencies. So I didn't have that traditional. corporate experience before starting my job.

And so I think for me, it was just a really good grounding in existing in that world outside of college. And that foundation really helped me, has helped me throughout my career.

Right, I don't know if anyone did this survey with all the CFOs and just to see where they started, I'm assuming it's going to be a public accounting, right? It's going to be, that's where if someone starts their career, they'll have a good chance of being a CFO.

think public accounting and would be the best. Yeah. Exactly.

Investment banking.

and banking, Investment banking probably, right? And things will change as well. With AI now coming into play, we don't know how that's going to evolve.

But that would be a good survey to do and figure out what's the best way it was earlier.

So in terms of when you're thinking about as a CFO job, what is something that people go wrong about that role? When you say you're a CFO, what is something that they get wrong about it?

my gosh. I mean, so many things. know, sometimes people think that the role is just purely around risk mitigation and reporting numbers.

You know, other people see the role as, you you're there as just like, as the backstop. against everything else.

think, and this has really changed over time and maybe isn't so much of a misconception anymore, but I think the strategic nature of the role and how cross-functional, like to be a successful CFO and by successful I mean to have real impact in your organization.

You have to be super cross-functional and really understand what the business is doing and how to work with everybody else, with other teams to get things done.

And I think sometimes people think the CFO sits off in the corner and is just managing the numbers part of the business where I'd say nothing could be further from the truth.

In the CFO role, you take statistically, how many initiatives, like strategic initiatives for the company actually starts from CFO?

Hmm.

Does it happen?

It does. I mean, certainly, right, if there are goals around profitability, around cash flows, right, it could start from a high level that there are these. economic outputs we want these financial metrics that we need to hit.

But I'd say for companies that do a good job of strategic planning, it's really incorporating the entire leadership team into the process and that you're going to have some financial parameters that you're trying to work within.

Everybody should be involved in having some sort of input right into the process of setting strategy and strategic initiatives. So I feel like sure the board obviously the board's going to have an opinion. CEO should be driving a lot.

think this CFO certainly can be a great partner. to the CEO and the board in those. But I think to be successful, the whole leadership team has to embrace those strategic initiatives.

So I think about it less, where did they actually originate from? the CFO can play a really strong role in driving that alignment and focus across the executive team.

That's right. And are there initiatives that a CFO directly oversees, which are not related to just finance? Like let's say, if it is about improving profitability, are there initiatives CFOs directly oversee the whole exercise of it?

or does it have to go through CEO or the other leaders?

Yeah, I mean, I think it has to involve any truly strategic initiative. I think would involve all of the rest of the executive team. you know, as we already started talking a little bit about AI, but data, right?

Like data quality is still an issue, I'm guessing for almost every CFO. if you kind of zoom back from that.

you have to have integrated data across the whole organization. It's not just, know, finance might be reporting on it, but it originates often that data originates outside of the accounting and finance teams.

And I think about that as one that if the whole executive team and their teams aren't working together.

to solve some of these challenges. You're not gonna be successful if it's just seen as a CFO initiative. It has to be a business initiative and imperative.

Right. Let's say if you're getting into a company, is there a red flag in the finance process that instantly tells you this will struggle, the company will struggle? Is there a red flag like that?

Yeah, I think one is if budgets are a finance exercise in a vacuum, that is a huge red flag to me. you know, if it's, we approach budgeting that finance goes out and creates this bottoms up model and either goes and collects a bunch of inputs from people without some strategic

overlay or constraints or finance just creates something and then goes out and tells the rest of the company what they can spend and what headcount they can add. Like that's a huge red flag to me and I have definitely seen that before.

It's a great insight. I I've all been budgeting, but I never actually thought about that part where if budget is only a finance activity and if the rest of the company is not participating in it, I don't think it works. No one is following it.

And also we discussed about this in the earlier episode as well. Budget actually gets outdated pretty fast.

I mean, there's a whole other thing on actually if you're only doing an annual, sort of the annual planning cycle is really getting outdated or already is outdated anyway, because it's, yeah, the minute, the joke is always like, the minute your budget is set, it's out of date because you're having real business information come in that's gonna change that.

I think about it, mean, there's so many, there's a zillion different frameworks out there, right? But really, if you don't have strategic initiatives that everybody's aligned behind and that you're resourcing, right?

The budget should be a way of resourcing, allocating dollars within certain constraints, allocating dollars to those strategic initiatives. And everybody has to be bought into that. Now that doesn't mean everyone's going to be happy all the time.

Of course, most leaders are going to come back and say, need more people or I need more dollars for this or whatever. Like I'm not, you know. living in a bubble about that.

But if there isn't that engagement and alignment on what is most important as an executive team, as a leadership team, and then explicit connection drawn between resource allocation and the budget to achieving those strategic initiatives, you're going to fail.

⁓ But then also the overlay on top of that is, of course, you've got to be adopting a more agile

process to continually refresh your forecasting and budgets. And if you're just doing this on once a year on an annual basis, and then you set it out, you set it and kind of put it on a shelf, like you're also going to fail in this world.

And luckily there are more tools available to us now to make that easier. Although I'd still say, you know, I'm sure there's companies out there. And again, like I also should frame that my perspective is that

high growth startups, let's say series B to post series D. And so that's a different environment than a huge company. But at that size of company, you're still gonna have challenges with data flows and all that in real time.

And I think that's improving. Yeah, but I think that world, that's one area where I think it's really exciting to think about. Instead of sitting down and having these cumbersome, processes that you can make it more lightweight but real time, which then allows a business to react more quickly.

That's right. So if we think about it, you're on Twitter and other platforms, or X and other platforms, basically everyone keeps saying AI is going to replace a lot of teams, a of executives. But this is one example that you give of aligning goals.

There's high level goals, strategic goals, and then there's the financial goals and the financial plan to achieve those goals and the resourcing goals. Aligning all this, which involves number of people, lot of Excel sheets, a lot of data at various levels, right? It's not just granular data.

Sometimes you need granular data. Sometimes you need aggregated data. Aligning all this, this is a huge process.

And there are a lot of nuances that needs to be taken care of this, because if you're a SaaS company, it's different. Manufacturing company, different. So all these things, considering.

These are the processes where they will be last to get automated, where there is a lot of complexity and nuance that is involved.

So my point is that coming back to the incremental advantage of AI is where we should start with things that are much easier to automate, not the things that almost looks impossible, the alignment example.

We can always have that goal, but we should always start with something that we can, like Monday and repetitive tasks that we should automate, should let AI do it. But on top of it, as humans, we'll take care of the alignment problems, the goals, the resourcing, et cetera.

Yeah, no, that makes a lot of sense. Like get some easier wins further down the complexity stack. And look, at the end of the day, I mean, I'm not a futurist.

So I don't sit here spending all my time thinking about like these, know, do we, know, will CEOs be replaced by AI, right? Like I live in the more near-term realities myself. And in the near-term realities, humans talking to each other to negotiate.

Right.

around how we're going to resource things, around what's most important, what's going to most move the needle with our product, with our customers.

While we might be using new technology to help us have deeper insights, to understand all this better, to be able to more quickly aggregate data across multiple sets to help us make a more informed decisions, like absolutely, but I still think humans are going to be having those...

That's it, right? Yeah.

discussions and debating that. so the more you looking to like automate all of that right now doesn't make sense to me, but looking to improve how we're spending our time to free up the time to engage in those discussions.

So I think there's a lot there we don't discuss enough because we're spending so much time collecting our data.

the stream. That's true.

And then you have not enough time to analyze the data, and then you often really don't have enough time to sit down with other people to thoroughly understand and debate that information and use that to then inform your decisions.

Thank ⁓ No, that makes sense. If you could erase one outdated finance process from your process, right, from all the finance process that you do, what would it be and why?

Yeah, mean, look, there's a lot. mean, easy, like low hanging fruit is just lots of things where you're matching things together to reconcile or things like that. Whether it's expense reporting or things like that.

reconciling data between different systems. ⁓ mean, gosh, I'd love to not be spending that kind of time. But at a higher level though, I think about there's so much that is still, if you think about it, like on the accounting side, you're going through a monthly closed process, right?

There's these things that are happening point in time. You're reconciling accounts, you're closing the books.

Or from the finance side, you're doing this annual budget. I think these things that are point in time, like I would love to see those become more fluid and rolling so that it's not like you're kind of waiting for this buildup and this point in time.

Everybody's super busy for a few days doing these point in time activities. I mean, I don't see that going away completely.

But I think there's a lot like that notion and there's like just a mindset around that, right? Like, yes, our value is added in these couple of days that we're doing these point in time things. And I think that starts going away as tools improve and there's a, I don't know, just like a shift there.

So that part feels pretty, I hope that that's pretty outdated in the next year or two.

I think closed process is something that can be automated a lot, probably I would say 80 to 90 percent.

I think the best way to look at closed process and also in a futuristic sense is it should be automated, but there should be enough transparency for the team involved to look at where the process is.

you're on, let's say, BD plus two or you're in BD minus one, you should be able to know what is really happening that day and are there any issues that are just recurring every day so you know what is happening. I that would be a great place that CLOS should be.

Automate everything, but still have the transparency and visibility for a controller or a FLC, a photocopy, where things are.

Yeah, no, absolutely. yeah, think, you know, sometimes people can think of pieces of accounting as like this black box. And I totally agree with the transparency and visibility.

I mean, yeah, that's really important.

That's right. And one way to achieve it is the problem with automation and so far what we have seen is it is rigid. It takes a long time to implement it and also it's difficult to manage or you need a specific skill to manage.

So that has always been automation even with all the tools that we had. We always have, oh, we have this automation tool but we also need these experts to do this kind of automation. With AI, I think that's going to change where the end user will be able to do automate their work by themselves.

Whether they will do it or not is a different story. But now they have the ability to automate by themselves. are a bunch of tools in the market.

where you can buy, you can start using it. You can basically say, prompts, right? You're asking the system to do this work for you.

And you can also say, repeat this work every day or every end of this month, do this activity for me, whatever I said right now. So that is the kind of automation I think that's gonna change. It makes things much easier for the end user to automate their work and then do a higher level work.

Now they are also the owners of that automation as well as the output of it. I think that's going to change how finance works.

Yeah, no, I think you're right. And that's where I start getting really excited about the future. And I think it means the nature of the work is different, the skills are different, all of that.

Yeah.

⁓ If I know we have a lot of tools in finance. We did this survey. And within finance function, let's say if you say accounting and finance function, we at least use 12 different tools to get our things done, right?

You have GLs, you have expense management software, and you have FP &A tools. So at least there's an average of 12 tools, and that's the company as the business grows, the number actually grows big. Do you think there are, are there any unnecessary tools that will go away in the future?

Yeah, actually you just named one that I had been thinking about, is, yeah, some of the expense, like expense reporting tools as a standalone tool. I mean, we're already seeing it's getting subsumed into, you know, credit card, what was initially like credit card platforms, right?

And so I think that's certainly one, yeah. So expense reporting tools as a standalone thing I think goes away. probably also some point specific, point solutions around analysis or BI that maybe go away and we have a more of an all encompassing analytics platform.

Those are two things. also, another thing that we've definitely invested into these integration or ETL tools.

I think some of that starts going away as we have systems that can talk to each other better, or we have an AI layer that's translating between tools. You don't need all these connectors between all the systems.

sure. That's right. Yeah.

I think that's going to be a big change as well. The kind of integrations that we have done because at that moment we want to get that work done, right? We really didn't think about how this will impact the whole architecture, the resources needed to support it.

But with new AI tools, I think it will become much easier to integrate systems and also build those point solutions. I think one of the trends that I'm very bullish about is AI can integrate a lot of point solutions into one platform and you don't need many point solutions to get things done.

Because if you have more point solutions, you need integration. Now if you have more integration, you need more people to support this. So that, as you eliminate more and more point solutions and integrate them into a single platform or a few platforms, we're going to make it much more efficient.

And just in terms of how we capture data. how we transform them, how we report them, how we automate all this process.

Yeah, it's an interesting point though, right? Because I think I said, I think some point solutions will go away because they'll be part of something bigger.

But you're making a point that it should be easier to have, if you want to have more point solutions, there's less manual work in connecting all those solutions up, right? And so it should be easier in some respects.

And I think I've been through this, seen this cycle many times in my career where, Needs aren't being met by bigger systems. The thing I think about though, cause I also think about the procurement side of all of this and it might be easier to manage lots of different tool.

You don't have to go hire somebody to build all these things, but you still have contracts that need to get, you know, negotiated and reviewed. And even if that's all, that's all getting more automated now, right? With other tools, but renewals happen.

And I, as I just think about the complexity, Right. I think about how can we start eliminating some of the complexity and compliance and all these other things.

And every additional software product is something that has to go through, even if it's automated, some sort of compliance review and do they have all their, you know, SOC 2 compliant, all the things that you might need. It'll be interesting to see.

There's things that make it easier and then, you know, you could easily build back up your complexity.

I worked with finance teams ⁓ a lot. I was on the other side of it and now with ChatFend we help companies use AI in their finance process. One thing that I feel is change is very difficult with finance and finance teams.

I still can't find the root cause of it. Is it just finance teams? Is it probably marketing?

I'm not sure about it. Why is change such a difficult thing in finance?

There's a few things I think that could be behind that. First of all, especially on the accounting, if I think about accounting and finances related, but... You know, different disciplines in accounting, you know, you're having to undergo things like audits.

you know, you're held to a level of rigor and accountability that other teams at a company might not be. And perhaps not only is there the different level of accountability, but maybe people choose to go into the work because something about them likes that environment.

And so I think that's one piece. And then there's, yeah, what if

we automate this in a different way or use AI tools on top of things and then they don't work as they're supposed to and I'm on the hook for that. And I think some people, instead of seeing possibility, they might come from a place of fear, right?

And like, well, I'm going to be responsible, so I need to control it. Like they're kind of pulling that control layer in and that might be getting in their way. And you know, there's just, the overall risk.

aversion layer on top of all of this, right? If cash goes missing, if something goes undetected, you know, like you're again, it's maybe it's coming from that place of fear or risk. And like you're the check at the company on some of that risk.

And so I think if you're too far into that mindset, I think an antidote to that though is really like changing, getting people excited about the impact, the change in impact that they can have, that their impact can be far more than we didn't fall into this risk. category or we passed this audit.

I mean, I always joke, if an accounting team is doing a great job, you might never know it because it means things were functioning really smoothly. means audits were being passed. ⁓ But we could choose to celebrate all of that.

But generally, the better job you're doing, potentially, the less people notice the work that you're doing.

Thank you. Okay.

But flipping that on its head to, yeah, we're using tools to take care of a lot of this. And now people are seeing the impact we're having, because we have time to go out and talk to our business partners and our stakeholders, really understand the business I think that's really exciting.

And I think so there's, but there's a mindset shift that the impact is going to look different.

That's right. That's right. And we see that every day.

know, Chatfin does a lot of finance work, accounting work, controller, AI takes over. We asked the leaders after a few months how things are working. They totally forgot about the product because it is working so well and the teams are using it.

⁓ what do you think is a CFO skill that no university is actually teaching right now? I don't think any university teaches CFO skills. I'm probably 100 % sure about it.

But what do you think that a university should teach for future CFOs?

You know, a couple of things come to mind and, you know, possibly these things are being taught and I'm not aware of it. But one I think is really understanding how data flows across the entire organization, not just within finance and accounting. I think that's really critical.

And I think sometimes we've, you know, it's easy to get into your day-to-day world. And so your role in the organization is not just to sit off in the corner and, you know, or the virtual corner and produce a bunch of data, but it's really to think about how is that information being used?

How could it be used? But it's not being used that way today because you didn't treat it as a product and you didn't look across the company and see your internal customers and users of the information that you're producing.

All right, so I'll ask you a bunch of rapid questions now and hope they'll be fun. What is one habit or trait that gave you an unfair advantage in your career?

You know, I think one thing might be, my education was not in accounting. And so I always felt like an underdog. And I think that just kept me on my toes and kept me really wanting to learn because I didn't come in with a knowledge base.

I had to learn everything on the go. But I think that just gave me a different, it gave me a different approach to my work.

What's one skill that finance leaders often underestimate?

empathy. data, like that product approach, like empathy. You have to think about everybody else and how they're going to interact with you and use that information.

Sometimes you can get frustrated because why didn't so-and-so understand that this margin was really important or that this spend was going to impact things in this way? But everyone's got a very different lens on the business.

And so I think you need to really, as a finance leader, put yourself in everyone else's shoes and think about their starting place and their knowledge base and meet them where they are.

Yeah. sense. What's one metric you care less about now than you did earlier in your CFO career?

Hmm. I don't know if I have an answer for that.

All What's one finance process that you think will look completely different in the next three years?

Well, something we've been talking about, the month-end close. I think it will look really, really different. And I don't know how it's going to look, but I'm open to the idea that it just is fundamentally something very different.

What's one misconception about AI and finance right now among finance leaders?

I think one misconception is that we are going to improve current workflows because I think that workflows, everything's going to look really different. I mentioned that with a month in close. I just think the way we can work is going to be really different.

And so a misconception is that, you know, we're trying to improve things kind of how they look today. But I think people who are willing to radically reimagine the roles and the impact and look at the body of work that needs to get done, not how it's getting done today.

What's one thing, I know you work with lot of finance leaders, what's one thing great finance leaders do outside finance? What makes them great? Is there anything that you have seen?

deeply understand the business and have a passion for the business that they're involved with.

That's a great answer. I think it's also the passion to work. That probably defines a person.

Once they start enjoying the get, they have fun working. I think that really defines a person and their career.

absolutely.

mean, you know, I find for myself sometimes some of the most fun I have is not, sometimes it's on things like, you know, unlocking some strategic insight, but sometimes it's just like solving a seemingly small problem through some analysis or looking at piece of data a different way and unlocking something like.

That's like good nerdy fun. And I think people who can find that, who can find ways, it's not just rote drudgery, like getting through stuff, but you know, being able to have that impact and unlock and like taking pleasure in that and finding joy in some of those things.

right. Finally, what's one advice you give to your younger self?

Probably to step back and get to know people more across the company. I think earlier in my career, I was so heads down on just like the doing the stuff in my job and delivering maybe. What was asked of me rather than stepping back and thinking about, is there a different way to do this?

Are there people outside of my team at the company who I could get to know who could help me learn more about the business so that I could approach my work differently.

Even in general, we all think we need more friends. We should have made more friends when we were younger,

That's true.

No, I mean, you know, I think I think early in my career I approached things as you show up You work your butt off You do what you're told keep your head down just work really hard and good things will happen I think that's how I was raised and I wish I'd realized earlier on in my professional life that Those things they served me to some extent But the real, when I was able to make incremental jumps in my impact, I wasn't following that.

I was actually going out and having more conversations with people. was actually stepping back from my work and thinking about things from a different perspective. And that's what unlocked things.

So I probably wasted a lot of years earlier in my career.

All right. Great conversation, Kathleen. Enjoyed it a lot.

And we'll keep having these insights and conversations again.

Great, thank you so much for the time. This was really fun.

Thank you.