1214: The CFO Checklist Keeps Growing | with Jack Gordon, CFO, Harri

0:00Jack Gordon: 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 Ross Granger, CFO of Nasuni, and you are listening to the CFO Thought Leader podcast. This is episode 1214.

0:28in arguably one of the toughest SaaS funding environments that existed in the last decade coming off of the highs of 2021 middle of 2023 the market was just repricing assets and repricing them on a daily basis we met with at least 70 funds as part of the process fortunately for us You know, it only took about another four months. We found the right sponsor. We got the round closed in October of 2023. But it was, you know, it was really, really challenging time for me. You know, having never run a fundraise to run in one that failed that then had to repivot. it. So, you know, you learn like the old adage, never counting chickens before they're hatched.

1:15Like that was, that was one that I reiterated a number of times, but, but other things that I learned that are really important to how I look at the world, you know, always hedge against risks, or at least as best as you can. And then always, always, always understand the downside scenario and build contingency plans.

1:39Jack Gordon: Hi, it's Jack. On today's show, we speak with Jack Gordon, CFO of Hari.

1:48Jack Gordon: AI is creating a new question for finance leaders. What happens when technology doesn't just change how work gets done, but begins changing the economics of the business itself? Suddenly, familiar assumptions around pricing, margins, investment, and scale may need another look. And for CFOs, there's another challenge closer to home. Before AI can improve decision-making, the underlying data and systems have to be ready for it. So where does a finance leader begin? And how do you separate real capability from ambition? Jack Gordon has been confronting both sides of that equation, and his experience offers an interesting window into what comes next.

2:40Jack Gordon: Our talk with CFO Jack Gordon begins after this.

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4:19Jack Gordon: Hello, CFO Jack Gordon is with us. Jack's finance career has taken him from early analyst roles at IBM and RBS to acquisition and integration work at OneMain before a six-year run at Wiley broadened his experiences across planning, transformation, M &A, and divisional leadership. Today, as CFO of Harry, he brings those experiences to a growing workforce technology company where capital allocation, operational discipline, and an increasingly AI-enabled business are shaping the finance agenda. Jack, welcome. Thanks, Jack. Good to be here. So, Jack, as always, please take a look back for us. And we're interested in those experiences you feel prepared you for finance leadership.

5:15Jack Gordon: What comes to mind? Yeah, I mean, as I reflect back on my career journey very early on. So I started my career at IBM, 440 ,000 employee, massive technology organization, great for a lot of things, but not great for being able to see how an analyst level role can make an impact on a business. And so, I mean, I learned a lot of great things at IBM, how to run a planning process, how to have capital discipline, how to understand ROI, your basic foundational FP &A skills. But you couldn't really see the impact you were making. And I realized pretty early on, I wanted to be a CFO. So I sort of sat down with one of my mentors and put together what I would later refer to as the checklist of the things that I thought were really necessary in order for me to get to the next level.

6:17And then each progression in my career, each role that I took, I wanted to make sure that it was checking at least one of those boxes along the way. So it was a really deliberate path from IBM to RBS, where I learned a lot about financial services and capital allocation across the financial ecosystem. But also, this was on the back end, this is 2012, back end of the 2008 financial crisis, And so we were also involved in, RBS was impacted by mortgage-backed security challenges at that time. And so what does it look like to assess a business unit and to divest an asset and to find a buyer and to price an asset, which ultimately led me to also realize I needed M &A experience, right?

7:09And so I could go into each of my roles throughout the way, but each one was really a deliberate step in sort of checking those boxes off. And they're still not all checked off, by the way, but in order to get myself to a place where I could sit in the CFO seat and really drive an organization.

7:29Jack Gordon: I'm wondering if you recall, thinking back maybe to IBM even, was there a belief that you had about finance that would change as your responsibilities grew beyond IBM as you went into these other roles? Was there an original belief about finance that you outgrew? Yeah, well, so my original belief about finance was really grounded in investment banking. Like that was finance. And when I went into corporate finance, I realized very quickly that that was not, you know, wasn't all Wolf of Wall Street type stuff. Right. And so it's really about the finance individual in the room is the one that brings, you know, rigor and precision and analytics to the table.

8:20And it's deeply rooted in those foundations. and so as I progressed through my career, aligning myself with individuals who were sort of foundationally built in that way really helped me understand how do you tell the story through the numbers? That's the foundation of FP &A, which is where I built most of my career and so the paradigm shifted from, you know, stocks and bonds and trading and sort of that view, you know, the outside end of what finance is to what corporate finance really is and how it helps to shape and drive an organization and the deep ties into strategy and to all the other executive functions.

9:07It really is a service role. The finance team is a service provider for the rest of the organization. And so we take that lens, you know, and I talk to my team a lot about that. You know, our customer is the rest of the organization. And so that's how we should be positioning ourselves in finance.

9:26Jack Gordon: I'm wondering, as you move from one of these positions to the next and changed companies, now you're at Wiley six and a half years. So you did invest some time in these different companies. But I'm wondering what might have been a gamble for you? Was there ever an assignment that soon became a role that wasn't necessarily what your mentor had pointed out to you as being the milestone on the way to the CFO office? I don't know. But was there anything, some sort of gamble that you took maybe? Yeah, for sure. I mean, when I left RBS to go do the one main transaction, it was really a deliberate M &A position.

10:10I stepped into this role knowing a company called Springleaf Financial was going to buy, or was on the cusp of buying a company called One Man Financial, which is part of Citigroup's bad bank on the consumer lending side. And it was a four plus billion dollar transaction. And so the gamble here was I had not really participated in any M &A prior to coming to the organization. And I really was grounded in FP &A, which was a good basis. but the fundamentals around M &A transactions and synergy modeling and really operational execution on the other side of a transaction, I knew very little about.

10:51But when I talked to some of my network and my mentors about how I should be thinking about this, they all sort of came back to the same thing, which is like, you're never actually prepared to take the next role. you just need to jump in. You're smart. You'll learn to figure it out. It'll be really painful. And then on the other side, there's a lot of benefit to the experience. And so this one had me on an airplane every Monday morning at 6.30 a.m. to Evansville, Indiana for six months to go do due diligence and build the model and understand the business. train rides back and forth to Baltimore, which was the headquarters of OneMain, to get the transaction done.

11:36It was a private equity sponsor transaction. It was a huge deal. And so it was a big gamble. And I was there for only a little over a year. It felt like 10. But ultimately, that experience was one that really shaped the way that I think about analysis and transactions and really paved the path for my next couple of roles.

11:57Jack Gordon: What about as far as leading teams and your leadership experience, how that began to grow? Was that along the same time? Yeah, I mean, yes, but most of my leadership capabilities were built when I was at Wiley. So I joined Wiley. It was really an individual contributor role during the M &A transactions. I had one or two analysts working for me. But at Wiley, I took on a more broad set of responsibilities. The first director of corporate FP &A across a$3.5 billion organization with a team below me that supported me and then dotted lines into all the divisions. So a lot of my leadership skill set was built is sort of midway through what I would call my career now.

12:48And it's not easy. For someone who spent a lot of time building on my own foundations, analytical capabilities, business acumen and understanding and relationships to move into that role where you had to trust and rely on people to deliver for you and to your standard, that's a really hard shift to make. And a lot of people, that's where they fall down and fall back into individual contributor roles. So I relied heavily on my network, my managers, the global CFO, to really help guide me into how to become a good manager, one that people, we used to joke, you want your people to want to run through a brick wall for you.

13:34That's how you know you've got a good team and you're a good leader. There's still a lot of lessons for me to learn on that one.

13:42Jack Gordon: At Wiley, you advance into a VP of finance role and into a divisional CFO role. It's obvious what the next step you're going to look for is perhaps that CFO role, perhaps in a smaller company. What's your mindset? Share with us what was it the logical next step? were those opportunities. The other thing is those opportunities are still really hard to get. You have to get a CFO appointment. You need to be a CFO. That's what we always hear. Yes, you were a divisional CFO, but you're still taking a leap. How was that? How did that all come together for you? Yeah. I mean, yes, we in my CFO network, I'll joke the hardest CFO role is the first one because the person who's hiring you as a first-time CFO is taking, you know, you talk about gambles, is taking a huge leap of faith on your ability to step in.

14:41When you're at a public company and you're in a divisional CFO role, you have a lot of support and infrastructure behind you. There was a dotted line, but there was an accounting team, there was a risk team, there was a legal team, there was an HR team, all there to support you as well as the other divisions and the global CFO. When you're in the CFO seat, it ends with you. And so, yeah, ultimately my goal was to get into a smaller company CFO role where I could really learn and grow and help drive a business. I'm a, you know, in sort of the schema of CFOs, I lean much more heavily towards operational than I do towards technical.

15:24and so I like to get my hands dirty. I like to get into the business. I like to drive business. I like to own business and so that's why coming into a smaller organization, I oversee the HR, legal, finance, accounting, revenue operations, commercial partnerships and enterprise transformation, right? So like it's a very wide remit. It's the many hats culture of a scaling organization but I did that at Wiley as well. I stepped out of finance into an enterprise transformation role about halfway through my time there to drive an organizational-wide, basically cost optimization program. I partnered with BCG and I was the internal, they were the external and we drove this program for about 12 months and realized real cost efficiencies and transformed the business.

16:21but as part of that role, I really realized that I like to get my hands into the operations. And so I knew ultimately I wanted to be a CFO, but I wanted to be a CFO at an organization where I could really own a broad set of capabilities across the organization and drive the business. So my role now is one part CFO and two parts really business leader. And I'm starting to actually build out business lines that I own now, more on the financial side of things, which we can get into if it's interesting.

16:56Jack Gordon: Well, that happened four years ago, 2022. You step in to the CFO role at Harry's. So there's a four-year track record behind you now. Lots undoubtedly happened. But for someone new to Harry, tell us something about this business. What does the business provide? Who uses it? you know what's the opportunity you're pursuing tell us about it yeah so um so harry so we're an ai powered workforce operating system uh verticalized and very focused in hospitality um so what that means is we unify the employee life cycle onto a single platform that helps mainly restaurant operators, hire faster, optimize labor, and maximize what we call four-wall EBITDA, which is the EBITDA that lives within a restaurant.

17:52We exist because no company had ever built workforce software, like no company that understood what it feels like to run a busy restaurant on a Friday night. And our roots really are in operator our history. Our CEO ran restaurants for a number of years before he started the company. And so we didn't stitch together a whole bunch of tools. We built an operating system, which is truly a platform that today, you know, McDonald's and Shake Shack and Jack in the Box and 14 of the 20 largest hospitality groups in the U.S. have chosen us to run on. And it's just a story about growth, the really interesting thing, you know, our opportunity is to own the economic relationship with an entire industry.

18:47You know, this is a$15 billion TAM. Restaurants, you know, are there a massive, the largest employer frontline employees in the U.S. And it gives us the opportunity to own the industry for a wildly overlooked workforce in our country. You know, we're just a click deeper. We are a system of record, which means we displace point solutions. And, you know, I assume at some point we'll talk about AI and moats and what gives us the right to win. System of record software that's built on years of data foundations that span across multiple mission-critical workflows. that that's where we exist today and that's where we believe uh companies have the right to win in

19:42Jack Gordon: an ai world so uh just looking back in time here around the time of your arrival harry raised 43 million i believe shortly after uh you were entering the cfo office what did that capital allow the business to do exactly yeah that's right so that was uh october of 2023 so about a year after I joined the company. So this capital allowed us to, practically speaking, complete our platform. And what that means is we spent a long period of time from 2020 until the middle of 2024 building enterprise-grade workforce management. Fortunately for us, We built it alongside McDonald's. So we signed a contract with McDonald's in 2020 to be their workforce management solution.

20:39And then over the course of the next almost four years, effectively co-developed what is now the industry leading workforce management platform. And when I say workforce management, I mean scheduling, time and attendance, compliance, communications, and all the workflows that go into managing the people side, the day-to-day operations of a restaurant. You can imagine building enterprise-grade software as capital intensive. And so there was a big slug of CapEx that we spent, which this capital helped underpin to complete that part of our platform. And then to start building on the next component of the platform, which is our engagement suite, which has just come live just recently now.

21:28And so we operate across what we call talent acquisition, which is sourcing hiring, workforce management, which is scheduling time and attendance and compliance, and now employee engagement. So it truly has gone from a single point solution to a platform asset over the course of that period of time. That capital really underpinned mainly R &D build and go-to-market capabilities.

21:57Jack Gordon: Before, let's say, the financial results show up, what tells you Harry's growth engine is working? What are you looking at? Yeah, so I mean, ultimately, it starts with the customer. So we measure everything. Customer satisfaction, MPS score, what's coming through our support tickets, you know, how happy are our customers? What is customer usage? these are my leading indicators. They're the ones that we look at to better understand whether what we've built resonates with our customer, they're using it, and they're getting the outcomes that we've presented to them in the ROI case is why they bought the software to begin with.

22:50And so when we think about how leading indicators impact our business and how we make decisions, we spend a lot of time as a management team unpacking the nuance in customer satisfaction between a restaurant manager and an employee. Both are using Harry, but in very different ways. And so understanding usage patterns, satisfaction, and ultimately outcomes across sub-segments of our user base is critical for us. Financials are outcomes of a good product and happy customers. And so we spend a lot more time on the leading indicators than the lagging indicators.

23:36Jack Gordon: I want to understand your sort of decision mechanics within the company. You know, is there an investment decision that was made that maybe wasn't obvious looking at the numbers, but it proved correct? there's there's been a number uh and the reason why i say that is because it's never really out when you're building software uh especially software that is providing capabilities and features that don't exist in the market you're always sort of guessing right um i mean one One example, and this one was a little bit before my time, but in COVID, you can imagine there was a significant impact to restaurants just given the shutdown.

24:31A lot of restaurants went under, a lot of them had to close doors for a long period of time. But one critical missing gap as people started to come back into restaurants was restaurants were required to test their employees to make sure that they were safe to interact with customers. And there was no software capability set that existed for them to report the outcome of their testing. And so we pivoted very quickly and very aggressively to build out something that we called the health check, which effectively lived within our platform that allowed the employees of our customers to submit their test results to prove that they could come in and they weren't going to be infectious to anyone.

25:21on that product um helped to stabilize the business when it was in a very instable time um that product we also just sunset right and so it was it was a point in time when we needed to pivot uh create something very quickly because the market needed it and no one else was doing it but ultimately resulted in something that we would throw away and so um now was there roi in that yes So ultimately, these decisions that we're making, a lot of them are calculated gambles.

25:58Jack Gordon: Today, Harry describes itself as an AI-first workforce operating system. That makes us wonder, where is AI today creating measurable customer value within that operating system? Sure. Yeah. Well, the first answer is everywhere. But I'll be much more specific in terms of how we think about where AI will and will not play a role in our ecosystem and where we've really invested because we saw early returns coming through from our customers. So we've invested in a gentic layer that lives across the Harry platform. We call it Sally because naturally when Harry met Sally. And what Sally does for our restaurant managers is a number of things.

27:04but some of the important things are it can provide a knowledge base for our managers to ask questions really about any of the data sets that live within Harry. So it can be sort of a reactive chat interface. What it can also do is serve up ideas or potential actions that a manager can take on their own. So say, for example, we've seen that your four-wall EBITDA is lagging when a certain manager is in place. You might want to look deeper into this and hear some of the data analytics. Now, we've taken it a step further for it to be truly agentic in which Sally will actually ask, you have two employees who are unavailable at a certain time.

27:58We know you're going to be busy. do you want me to go reach out to these other two employees, ask them about their availability and bring them into the shift? You click yes, it goes and takes the action on your behalf. So, I mean, these are just some quick examples. There's a multitude of use cases that we've built out through the Sally platform to allow a manager to be more effective at training their people and spending time with customers and less time in the back of the house doing like pushing paper. The other and potentially more impactful product that we've just released is what we call our autonomous scheduler or the hairy one-click schedule.

28:42If I sort of rewind a year, generally what our customers will be using to schedule is either an incumbent scheduling platform, which is not built for the industry, or quite honestly, Excel, right? So it's analog, and anything is better than what they have. So they move on to Harry, they're able to see measurable impact in efficiency and productivity in creating a schedule. And we have demand forecasting capabilities, and we have the ability to automate the process in a very streamlined way. But now that we've implemented the autonomous scheduler, which is a AI-driven demand forecasting module, so you can't create a schedule unless you know the demand, right?

29:36And it's all about matching supply, which is labor, and demand, which is how many burgers are you selling, right? And so we have a AI-derived demand forecast, which runs off of an immense amount of historical data, but it also pulls in things like weather, right? If you have a patio and it's going to rain, you're probably not going to have a lot of demand for people sitting on the patio. So you may not need to schedule someone to be a server on the patio. So it pulls in an immense amount of internal and external data, generates a forecast, drives that into the AI schedule optimization model, which takes into account the intrinsic details of that restaurant and employee availability.

30:23And it runs something like 57 million permutations and then spits out the perfect schedule. So what we've done is we've improved schedule accuracy by 98%. We've reduced the time to create a schedule by 93%. We've reduced weekly labor costs in some instances by multiple hundreds basis points. And we are creating a 100 % compliant schedule. And that means wage hour, minors, which is the bane of the existence of restaurant operators, these regulatory frameworks that can be wildly expensive if they have infractions. And so we're able to deliver this schedule that creates immense value. And we can do it now in four minutes in some instances where it used to take three to six hours.

31:17So we're seeing real ROI, both in terms of maximizing throughput through optimal labor, but also through bringing the right people into the seats at the right time. So you're not always minimizing the amount of people on staff, but you have the right people on staff at the right times to maximize throughput.

31:42Jack Gordon: I'm wondering whether you have a SWAT team of, I don't know, maybe it's in the go-to-market realm or what have you, but insight into how the customers are accepting and adopting and leveraging these types of AI enhancements. There's so many of them. And we know restaurants, very often the employees turn over, the people who know the system come in cold and they have to relearn it, I think. I'm making some guesses here. But one would imagine that you folks have to be paying really close attention to, okay, we're getting traction with labor insights. But it looks like the communications piece is a lagger in some way.

32:27Jack Gordon: What can we do differently to educate them to begin leveraging it more? I don't know, but I mean, is this an ongoing conversation perhaps? It's more than an ongoing conversation. It's a multi-double-digit number of internal communications on a daily basis in a Slack channel internally, right? And so our role in this as the innovative disruptor, which we are in our market, is to sort of test the bounds of what is acceptable within our industry. So this has been a laggard industry in terms of technology adoption. And then over the course of the last five to seven years, restaurants have had no choice but to adopt technology because margin compression has really impacted them.

33:26If you think about inflation and wage costs and food costs, regulatory requirements, they've had no other choice other than to go to the labor line and implement technology to try to optimize that labor line. And so our role in this is really to deliver innovative technology to learn from our customers and really take customer feedback and insight into how far they're willing to adopt. And there really is an extreme adoption curve. We have some of our customers who come to us and say, you know, we can't get enough of this. We want more and here's what we want. And then we have some customers that say, I don't even want to talk about AI until I can get myself off of spreadsheets.

34:15Right. And so it's our role to really lean in where our customers are leaning in, the early adopters, learn from them, and then take those stories to the rest of the industry and show them. You know, it's very much a very insulated industry and they all, all restaurant operators talk to each other. And so the most important thing for us is getting real alpha customers who understand how technology can really impact the industry and have them evangelize on our behalf. And so that's the model that we've taken. But yes, internally, we're looking at usage data. We're looking at number of interactions per user, amount of time spent within each of the AI solutions, the output and the efficacy of the solutions that are coming through, potential bias concerns, because in HR tech, there's always potentially AI bias concerns and making sure that we're well audited and well insulated from that.

35:20And so there's a number of considerations when you're on the leading edge of delivering these AI solutions. And we truly believe AI will be an enabler for restaurant managers, above store managers, franchisors, owners, and the employees. and fortunately for us, we believe we're really far away from AI flipping burgers. It may be there one day and robotics is taking leaps and bounds, but fortunately for us and fortunately for our constituents, there's going to be a need for people-centric operating systems for a really long time in the industry that we operate in.

36:07Jack Gordon: So let's step away from the customer realm for a little bit. Inside finance, we've been speaking to our guests about how AI has, you know, getting beyond the saving of time, the automation, what have you. We're wondering, have you begun to see how AI is improving your decision-making?

36:37Yes, but... So, and I'll give a little bit of background here. When I joined the company in 2022, I was the first, not only was it my first CFO job, I was the first CFO of this company. And so, as you can imagine, a company that's been scaling and growing rapidly, there wasn't a lot of attention put on the foundations, the infrastructure, the data, sort of what I would call the back office. And so over the course of the last four years, it's been a real journey to get ourselves into a place where our data was organized, accurate, and structured in a way where we could use AI to actually drive decisions or even not use AI to drive decisions.

37:34And so we've just crossed that chasm, I would say, last year. We've started to implement a real data lake architecture. We've started to move a significant amount of our data into the data lake and put agentic layers on top of that. We've opened up MCP server connections that allow us to do analytics. We've not taken the next step, which is agentic or autonomous AI within finance. We are just sort of at the very early stages of that. I can't express enough, and I'm sure other guests have said this, and it's widely known, but can't be understated. the data is the most important like ai is irrelevant without the data being accurate in the right place and and somewhat structured um and so that is the most important thing in order to drive decisions uh you know we've tried and failed a couple times to just put ai on on our data sets without doing that work um and so we've not yet you know made that leap uh but we're I think we're on the cost.

38:51That's certainly early 2027. We expect real decision-making capabilities coming off of AI internally.

39:01Jack Gordon: One last one here. As AI becomes part of the product itself, has it begun to change how you think about pricing or monetization going forward? Is there maybe, who knows what lies ahead? Yeah, within my network, and more broadly, if you read the articles on the topic, I don't think anyone really knows how to package, price, or bring to market these AI solutions that are building on top of non-AI native enterprise software. Right. So even Salesforce and and some of the big, you know, legacy enterprise software solutions, I think are struggling really to understand, you know, is it a is it a seat fee?

39:53Is it a hybrid seat and usage? Is it outcomes based? But I think what we all know sort of intrinsically, and we do start to see it come through in the numbers, as you start to gain adoption in your solutions, and you start to drive more customers into more AI solutions within your product, the shape of your business changes, right? So your gross margins ultimately will erode because you're moving from a model where you spend a lot of time creating a CD and then you sell a lot of CDs. That is sort of the legacy SaaS model where your marginal cost to deliver to the next customer is next to zero to something where your marginal cost is more than zero.

40:42And if they're using a lot of tokens, it's a lot more than zero. And so we've thought a lot about this. We're testing a few different models. And I think ultimately for a solution like ours, where AI is not displacing workforces, it's enabling workforces, but there's true economic value and economic outcomes coming off of our AI solution, we will likely land in a hybrid model, which is seat plus usage and usage with usage caps, right? So you think about how you use Claude today and you get a certain amount of usage within your seat. And if you go over the usage, you pay for that usage. That's likely the model that we will land at.

41:27But we're testing a few different models. What's clear to me is customers, sort of more broadly, are not yet willing to pay for outcomes-based pricing. And I'm one of these people, right? Even though I know I'm getting positive ROI and outcomes from some of the AI solutions that I'm using, it's too unpredictable and too unknown to move towards outcomes-based. It also creates a little bit of a disincentive because you know the more you use it, the more you're going to pay. And so we have thought a lot about it. I've talked to a lot of other CFOs about it. And, you know, we'll see, but I think that's ultimately where we'll land.

42:16Jack Gordon: Yeah, great, great insight there for us. Thank you for that. We are up to what we like to refer to as our finance strategic moment question. And this might have happened to you anytime during the course of your career. But what comes to mind when we ask for a finance strategic moment? Yeah, sure. So you asked about our Series B fundraise. Um, so this is, so, uh, I'll rewind to June, 2023. Uh, we're a week away from signing and closing on our series beat fundraise. I'm sitting at my desk, uh, in New York. I get a call from one of our board members who is helping me. So we didn't use bankers, uh, for the fundraise.

42:59It was, it was me and, and one of our board members. Um, and he called me and he said, the deal is dead. this is two weeks before closing um and so i said what do you mean the deal is dead and he said well you know how the sponsor needed to close their fund in order for them to fund the investment well they're they had a european lp who had a capital call issue and pulled uh pulled his funding out of their vehicle and they can't close they can't close we can't close great so uh and And sort of back up to November 2022, when I joined Harry, I joined Harry, I mentioned, you know, I was the first CFO.

43:40There's a number of operational challenges at the organization. We had, you know, we were running four, globally, four entities, all on QuickBooks. Nothing was connected. No order to cache system. I didn't have a controller in place. And so I had a lot of operational stuff that I had to sort through. And I was thrust into a Series B fundraise, which we kicked off. about a week after I got to the company. Um, and so I was really stretched, um, you know, had to really aggressively do time management, uh, and sort of call on some skills that I had from, from, from my past in order to do that. Um, but, but, but June, 2023, the deal is dead.

44:23Um, so pivoted very quickly, uh, restarted the fundraise, went back to some of the funds we, We spoke to in arguably one of the toughest SaaS funding environments that existed in the last decade, you know, coming off of the highs of 2021, you know, middle of 2023, the market was just repricing assets and repricing them on a daily basis. You know, we met with at least 70 funds as part of the process. Fortunately for us, you know, it only took about another four months. We found the right sponsor. We got the round closed in October of 2023. But it was, you know, it was really, really challenging time for me.

45:07You know, having never run a fundraise to run in one that failed that then had to repivot. So, you know, you learn like the old adage, never counting chickens before they're hatched. Like that was one that I reiterated a number of times. But other things that I learned that are really important to how I look at the world, you know, always hedge against risks or at least as best as you can. And then always, always, always understand the downside scenario and build contingency plans just in case. When I talk about what are the core tenets of a CFO, and in particular a CFO at a founder-led organization, it's really about being that backstop and making sure that you can manage the highs and you can manage the lows.

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46:57Jack Gordon: That's salesforce.com slash CFO.

47:06Jack Gordon: We always like to ask about that first 60 days in the role, if there was something, and we're just touching on a little bit of that. But what didn't you know? If you could go back in time and give yourself a piece of advice, what would it be? Oh, well, there was a lot that I did. There's still a lot that I don't know. And I'm learning every day, which is great. You know, I think there's a couple of things that I would, you know, if I'm giving advice to someone who's about to step into a new CFO role, one is certainly do your due diligence and know what you're stepping into. You know, nothing's good and nothing's bad, but knowing what you're getting into and making sure that you have the support behind you and the network to rely on for the things that you don't know.

47:58So for me, you know, some of the things that I was unfamiliar with was dealing with the banks. So we have venture debt on our business and I had to step into the banking relationship. I had never done that before. So all of the collections work. So I managed that widely. We had a lot of support that underpinned us. One was a global collections team that managed all of our outstanding AR. We don't have that here, right? It's me and the controller and we have a few analysts. But, you know, it's the really like tactical stuff that I learned on the job, that I'm happy that I learned on the job around capital management, around technical accounting, and really about how to be the leader in the room when things go sideways.

48:52You know, and all, by the way, all those things happened in my first 60 days.

48:57Jack Gordon: well those are great uh examples for us hey um we always like to ask our guests to reflect a little on the personal side jack and you've been there four years so your colleagues must must know most of everything about you but what's one thing people might not know about you something from your past an interest that you had a pursuit uh outside the professional world perhaps don't know anything come to mind yeah i mean i got into this um you know the finance function because i you know good in math but also i liked solving puzzles i like solving problems right um and so uh you know in my personal life i also like solving problems and solving puzzles so when i moved uh when i when i bought a house and had some space uh i built a workshop uh and i actually started building furniture.

49:52And so for me, you know, in the, in this world that I operate in, where it's like various shades of gray and it's sort of moving the ball down the line, but you're never actually done in, in, in, in innovation and disruption. You're never actually, you never actually cross the finish line. Right. In my personal life, I like to have things where I can actually cross the finish line. And so I started, I started building things. So I built some of my bedroom furniture. I built some bookshelves and dressers. And it sort of takes my mind out of this sort of thing. But it also, it's precision. It's puzzle solving to some extent.

50:37And at the end of the day, you can step back and actually have something. And so in the same way, it's sort of like building a business, but on a much more micro scale, So anecdotally, right now, I've moved from building furniture to restoring some 1980s arcade games that my father-in-law was getting rid of. So when you think about circuitry and root cause analysis and that sort of thing, it's where I like to spend my time. As funny as it might sound, but that's how I spend a lot of my free time.

51:14Jack Gordon: Yeah, those are great. Thank you for those. What about a book or a resource for us? Or maybe it's a book you escape with. It doesn't have to be a business book. Anything come to mind? Yeah. So probably the book that's made the single biggest impact on how I live my life on a day-to-day basis was a book that I read a couple, two years ago or so, called Atomic Habits by James Clear. I mean, a lot of people have read it. It's a super popular book. Yeah. But the principles are principles that I talk to my team about and my wife and my family about all the time, which is like, sometimes it's not about massive step change from point A to point B, right?

52:04Sometimes it's about micro changes that you can make, like the 1 % every day. 1 % every day leads to, at the end of the year, you're 37 times better. And on the reverse side, it could go the other way. So that was one part of that book that really resonated. The other was around systems. So I talk about this a lot. in the finance world, but it works everywhere. A goal is an outcome. A system is the process that gets you to the outcome. And so as opposed to focusing on the goal, let's focus on what are all the steps required. And they might be big, they might be small in order to get us to that outcome.

52:55And how do we raise, instead of lowering the ceiling, how do we raise the floor on how we think about making these changes. So that book was tremendous for me. And it's about consistency and the compounding of consistency, which I live, or at least I try to live in my personal life as well.

53:16Jack Gordon: Yeah, wonderful. We've had, of course, had this book before, but you highlighted some parts of it a little differently for us that made it very interesting. So we'll have to go back and refresh many of us. Hey, we are up to our final question. which we ask you to look forward, and we're wondering about your priorities as a CFO for the coming 12 months. What would those be? Yeah, we hit on some of these. So we are in full launch of our AI platform and really deeply understanding the unit economics of our business in this new world is a key priority for me. So on a day-to-day basis, what are we learning?

54:03How does that change or alter or inform the thesis that we had going in? And so really understanding that from a business performance perspective. The other thing that we're really driving to more on the finance side is automations everywhere. So the playbook has now already been written for finance. I believe 75 % to 80 % of the activities that my team is doing today can be 100 % automated or near 100 % automated to free my team up to actually deliver better insights to the business. you know we've made a commitment that we will not add headcount to our organization until we get we have we have a revenue goal that we're working towards um and so it's really about uh you know if we come back to systems like how do we build the systems that allow us to scale the organization without negatively impacting the unit economics so so that's huge for me the other thing i mentioned early on, I'm actually taking the lead as a pseudo product owner of a product that we're building and bringing to market over the next six months.

55:21And so for me, this is intellectually stimulating and rewarding to actually be the one who's doing market analysis and meeting with partners to build out partnerships for part of this tool that we're building, go deep with the product team on scoping and specking and the engineering team. And so, you know, that for me, you know, to talk about like things on the, on the checklist of things that are important for me, building and launching a successful product is the next thing on that list.

55:53Jack Gordon: Jack Gordon, thank you for joining us on CFO Thought Leader. Thanks, Jack. Appreciate it.

56:14Jack Gordon: 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.