In this illuminating episode of "The Headcount People," host Tushar Makhija sits down with the remarkably experienced Josh Rappoport, who shares invaluable insights from his extensive career in finance across tech giants and high-growth startups. From his early days at Microsoft, where he learned the art of scalable decision-making, to spearheading finance at a rapidly growing startup, Josh reveals the principles and practices that have guided his success.

🕒 Timestamped Chapters:

00:00 - Introduction to Josh Rappoport & His Financial Journey

01:36 - Lessons from Microsoft: Scaling and Decision-Making

07:14 - Transitioning from Corporate to Startup: Adapting and Thriving

15:20 - The Art of Leadership and Building High-Performing Teams

21:45 - Embracing Change and Navigating Career Growth

27:30 - Josh's Vision for the Future of Finance in Tech

🔑 Key Takeaways:

  • Understand the importance of adaptability in finance roles across different company sizes.
  • Learn how leadership principles can dramatically influence your career and team dynamics.
  • Discover how strategic finance and effective decision-making drive company growth.

Josh's journey offers a rare glimpse into the world of finance and leadership within the tech industry, providing listeners with practical advice and deep reflections on personal and professional growth. Whether you're a budding finance professional or a seasoned leader, this episode is packed with wisdom and inspiration for anyone looking to excel in the ever-evolving tech landscape.

👉 Watch now to gain insights into mastering finance and leadership in the tech world!

[00:00:00] Tushar Makhija: Hello everyone. And welcome to the Headcount People. I just want to remind everybody, this is our second season. And today as my guest, I have a very dear friend. Josh Rappaport.

[00:00:14] Tushar Makhija: Josh, you're joining us from Seattle today.

[00:00:16] Josh Rappoport: I am. I'm in Seattle and it's a rare sunny day in the fall in Seattle

[00:00:21] Tushar Makhija: today. Amazing. Amazing. So I think for all our listeners, I just want to get everybody excited that today Josh is going to talk to us about his journey in the finance function, starting at Microsoft, seeing Microsoft scale, I call it the place where people learn all the good processes.

[00:00:41] Tushar Makhija: Then he went to bill go again. Was there at 50 employees till 300 double digit or triple digit growth in revenue? He'll share that with you and now he is the vp of fbna at acumatica, which is a 600 person company again [00:01:00] triple digit million are So I think I'm just super excited to see someone sharing their information and knowledge through the lens of a long spanning career across large organization, fast growing startups, and now , an upstart mid size company.

[00:01:17] Tushar Makhija: So, welcome, Josh. Thank you. I'm glad to be here. Awesome, Josh. Let's, let's do this. Why don't we start with a quick introduction in your words. Sure. And I, I would love if you can highlight for our listeners the journey that you have taken and if there are some anecdotes like, Hey, this is what I loved about Microsoft.

[00:01:36] Tushar Makhija: Mm-Hmm. This is what I loved about Bil. Go. And like he, how it is shaping your, the, , you, you've just joined Acumatica, how it is shaping your journey here. That, that would be

[00:01:47] Josh Rappoport: great for us. O of course. And, and, and the first thing I, I wanna share is that. My journey, I think a lot like many others is not it was not a straight line.

[00:01:57] Josh Rappoport: I think there's a tendency, especially for [00:02:00] finance professionals to want to plan. And what I learned really early on, maybe I'm still learning today is that the more I tried to plan, the more I tried to control my career, the less things went to plan and the less things went as as I expected them to.

[00:02:16] Josh Rappoport: In fact, my my boss right now, our CFO as we're talking about our three, four, five year plan he likes to remind all of us, including our CEO and our investors, that the only thing certain about the plan is that it'll be wrong. And so I think it's a, it's a good parallel for the, for the way I approached my career I actually started my career a really long time ago in the late nineties as an investor.

[00:02:42] Josh Rappoport: , doing private equity and eventually early stage venture investing and realized after several years of that, that in order to be the best investor I could be, I needed an operational experience. And so when I eventually went back to business school, the idea was to, , go to school, come out of [00:03:00] school and go to work for a great company, learn what it means to run a company, to grow a company, and then go back to being an investor.

[00:03:09] Josh Rappoport: But, , as, as apparently all my plans do, that, that failed kind of failed terrifically. And I, and I realized I really liked Running and growing businesses and being an operator. And so I never went back to that venture world that, , maybe, maybe my 2nd career down the line. Maybe I'll go back.

[00:03:28] Josh Rappoport: But you mentioned, , I started. My operating career, let's say in large company, in fact, right after business school, I worked at Yahoo for a number of years and then I got the proverbial offer, you couldn't refuse to move up to Seattle and, and work for Microsoft. And, , Microsoft for me was an incredible training ground.

[00:03:48] Josh Rappoport: Sure. I, , I'm an undergrad from a great school and I'm an MBA from a great school, but Microsoft was like getting my PhD and the. Incredible luxury that [00:04:00] Microsoft has and being a couple hundred thousand person company and trillions of dollars of value value that they have the privilege of being able to be highly, highly focused and specialized.

[00:04:14] Josh Rappoport: Virtually everybody you work with is an expert in their particular function, and not only their function, but their self, self, self function. And so, , when I think about my time at Microsoft, I especially think about, , a handful of conversations I had with Amy Hood, who's, who's. An amazing, incredible CFO and an amazing, incredible person, human being.

[00:04:38] Josh Rappoport: And, , one of the things that, that she would say that really, in fact, inspired one of my leadership principles, she would say, , I've, I don't know, it was probably three, four, 5, 000 finance employees. And as a company, we're making tens of thousands of decisions, probably more than that a day.

[00:04:57] Josh Rappoport: How, , her, her challenge was how can, [00:05:00] how could she ensure that the decisions that, , this huge organization we're making every day were aligned with how she would make decisions because clearly she couldn't make them all. She would be a bottleneck. And so she talked about, , kind of having, , a mental algorithm for how we make decisions for making decisions at scale, which, which really influenced the way I think about.

[00:05:25] Josh Rappoport: A lot of of, , leadership. So one of my leadership principles is focus first on principle so that aligned outcomes will follow. And what I mean by that is if we talk about how we think about problems, what our first principles are, what, what are our, what are the things that are meaningful to us as individuals and as a business?

[00:05:47] Josh Rappoport: What are we trying to achieve? And we have a framework for what those principles are. That framework itself becomes that decision making algorithm. So we're focused less on, Oh, should, , Mary get three more headcount? [00:06:00] Should Bob get six more? Do we need to move, , this function from this location to that location?

[00:06:06] Josh Rappoport: We're thinking less about those distinct decisions and more about how do these fit our principles? , maybe we have a strategic focus on, , building new product functionality, and that principle now determines whether or not, , Mary gets three heads or Bob gets two or , maybe we have a principle around, , moving to lower cost locations, for example, that that kind of principle that we're aligned on helps anybody in my organization make a decision on a specific way.

[00:06:40] Josh Rappoport: Question or specific ask that we know reasonably will be aligned with what I would think or what my my boss or CFO would think or what John or CEO would think, et cetera. And so kind of that early time that I spent at Microsoft, amongst other really impactful learnings. One of them was really about [00:07:00] how do you.

[00:07:01] Josh Rappoport: Learn to make decisions at scale. How do you empower your organization, not just yourself to make decisions that are all line as well. And so that's just one. , one bit of, of the PhD. I, I think

[00:07:14] Tushar Makhija: I earned. Yeah. So let me, let me actually ask you the, how did you adapt these operating principles you went from a very very large organization with hundreds of thousands of employees Trillions of dollars in value to a startup which you joined will go around 50 employees, right? Can you can you help us understand like how did you , narrow your focus or try to cram all that knowledge and principles into a smaller organization.

[00:07:46] Josh Rappoport: Yeah, , the journey is interesting and I thank you for bringing me back to my career journey. Is I think one important thing. I just want to wrap up Microsoft really quickly as it relates to Bill go. One important thing at Microsoft, [00:08:00] aside from being able to learn from incredible people was the opportunity to really engage in actually different roles and different functions.

[00:08:08] Josh Rappoport: So I so what's interesting for me is or about me, hopefully is that I didn't spend my whole nine, almost nine years at Microsoft and finance roles. I did the first years. , four ish in finance roles. And then because of my focus on business partnership, because of my focus on answering the questions of why.

[00:08:29] Josh Rappoport: I was asked by one of one of my very senior business partners to come and work with him and join his organization first in strategy roles and then a chief of staff roles and then eventually in product roles, etc. And so I have this broad experience, not just in finance, but also, , a little bit of marketing, a bunch of product, a bunch of just strategy and overall business operations that I was able to bring to bear.

[00:08:56] Josh Rappoport: At Bilgo, which is a much, much smaller company where you can [00:09:00] imagine that, , you don't have the privilege of specialization and focus the, , the finance person could really could also be the marketing person and also the operations person and also the chief admin. , and so I think while, yes, it was a huge transition from a company like Microsoft to Bilgo, it was also a great opportunity to, , leverage this breadth of experience that I had.

[00:09:28] Josh Rappoport: Now, I will tell you, like, there were definitely moments early on where I was like, Oh, my God, what did I do? Yeah. Okay. Where's our data? Like, what date? What are you talking about? ? Well, yeah, because, , Microsoft in particular is a very data driven organization that, , they democratize data.

[00:09:45] Josh Rappoport: Everybody has access to it. Everybody is expected to be able to use it, understand and analyze it. I get to go go. I'm like, okay, well, where's our, , where's our performance data? How do we know how the, The application is working or, , it's a, it was a FinTech company, a payments company. So like, what are our [00:10:00] payment success rates?

[00:10:00] Josh Rappoport: And, , et cetera. And like people like there, yeah, there's no system to get the data. There are no reports, like you just need to figure it out. They pull it out of the production system, like get some engineers to help you. So, , so there, there's a little bit of like, , Oh my God, what did I do?

[00:10:14] Josh Rappoport: Because there was just not a lot of maturity and not a lot of structure, but. , what ironically trained me for that was a company with a ton of maturity and a ton of structure whereby I had lots of exposure to, to, , broad functional, , responsibilities and capabilities where I, , I could just come in and say, going back to the why I realized that it was just up to me to solve things.

[00:10:39] Josh Rappoport: Like nobody was going to give me the answers. I had to ask the questions and, and, and find out the answers myself.

[00:10:46] Tushar Makhija: Can you, while we are on this topic, there is always this question that comes to people that there is, I mean, I think there is endless opportunity in a company like Microsoft, Google, like I think, right, if we can see it in real [00:11:00] time, , in Satya Nadella's reign, the company's reorienting in breaking new grounds and doing something that even startups can't achieve at the nimble, fast rate.

[00:11:11] Tushar Makhija: What was that motivation for you to go from such a large organization to a such a small organization? Like, what were you thinking? Why did you make this decision? Maybe, maybe that's one of the guiding principles for, , younger folk who may be already at Microsoft, but now are getting opportunities to work

[00:11:29] Josh Rappoport: at startups.

[00:11:30] Josh Rappoport: Yeah, sure. Again, going back to, I think the first thing I said is, , none of it was planned. I like to talk about my careers, , being one of fortuitous serendipity. So frankly, being in the right place at the right time, but also being prepared to seize on the opportunities that are that are right in front of you.

[00:11:45] Josh Rappoport: And so it is a combination of things like honestly, like I had spent almost nine years at Microsoft and so that times feels like any like an eternity is Microsoft years maybe for me were like dog years. So, like, [00:12:00] I felt like I'd been there a long time. Now, obviously, lots of things have changed, and it was, it was pretty exciting throughout, but there's definitely a sense of like, wow, I've been here a while.

[00:12:11] Josh Rappoport: What, , it kind of, it's that grass is always greener. Like, I was kind of curious, what does that look like on the outside?

[00:12:19] Josh Rappoport: And in fact, I actually wasn't thinking about going back into finance either at that point, because I was doing, , product work in, in the Dynamics 365 org and, , ERP software where, where I am now at Acumenica, but , I, I wasn't planning on going back to finance and, and what they proposed was, hey, , we don't have a finance, we're a fintech company, we don't have a finance org.

[00:12:44] Josh Rappoport: We have a person who has, has been, , managing all the books and managing all the treasury operations and managing all the money move and whatnot. And in order for us to scale, we really need to scale our capabilities. Given your background, the highest [00:13:00] leverage role, the most value that you could probably bring to our company is, is to help us.

[00:13:07] Josh Rappoport: , build a finance organization and finance capabilities and, , it was everything from planning to controllership to treasury operations, etc. And again, for me, like, I knew, like, let me be super clear. I knew I was not at all qualified to do this. But I, , don't tell anybody that I work for, but I'm probably, I've never been qualified to do any role I've ever been hired for, but those are exactly the roles I want, because again, I want to be able to grow.

[00:13:38] Josh Rappoport: I want to learn, and I'm just delusional enough to feel confident that I can figure everything out. And so, , when I went from Microsoft to Bilgo is, yes, there's a little bit of, , is, is the grass greener. But then it was really just who are the people I'm going to have an opportunity to work with.

[00:13:57] Josh Rappoport: To learn from, to grow [00:14:00] with, to collaborate with which I think, especially early in, in career folks don't put enough emphasis on that. Don't value that highly enough. The people that you're working with are going to make the biggest difference in your career much more significantly than name on your resume.

[00:14:20] Josh Rappoport: That's a very important point. Yeah. And so kind of when I went to Bilgo, it was like great leadership. In fact, , the C suite had, I think at some, at one point, like something like five former CEOs. So there's a great deal of experience that I knew that I could, I could, , gain insight from.

[00:14:36] Josh Rappoport: And then it was just this challenge of like, Hey, you're going to go from 5, 000 person, , finance orgs to, , And, but, but that was exciting for me because I knew I was going to get to build something because even at the finance person, like I like to create, I like to build, and so I was like, okay, well, what I can build here, maybe it's not a product, but it's a function, the capability, it's an understanding.

[00:14:59] Josh Rappoport: And so that was [00:15:00] really what was most interesting to me about Bilgo. And then it, it, it bore out, like it, it, it turned out really nicely. So I joined when it was about 50 people, , about six or 7 million in revenue at the time. And by the time I left two and a half years later, , we were close to 300 people, , 60, 70 million, almost 10X growth.

[00:15:20] Josh Rappoport: And that was. That experience taught me so much in two and a half years, , maybe it was my second PhD, so to speak. , Yeah.

[00:15:30] Tushar Makhija: So, I mean, I think a nice way to come into now your role at Acumatica, you have a CFO. You went from 5, 000 people in finance to a team of one, build everything now.

[00:15:45] Tushar Makhija: It's again a 500 600 percent company a mature business, but you are building now a function within finance so more specialization. So you went from very very You went from Jack of all trades to , the leader of an org, now you [00:16:00] are becoming more specialized. Yeah. Tell us about how you first joined Acumatica.

[00:16:05] Tushar Makhija: Tell us about Acumatica. Sure. Sure. And then I would love if you can, as part of this segment, before we move on to the next segment, tie it all together in a ways that. This is everything that I'm bringing my two PhDs, I'm bringing this to Acumatica, what do you expect from this role, right? I mean, I mean, I think you're running out of topics to do your PhD in.

[00:16:31] Josh Rappoport: You never, , like, maybe I'll just be a student forever. I hope I'm a student forever, actually. Let me put it that way. , you asked me a question prior, prior to recording the episode here, and you asked me a little bit about, , the focus of finance and high growth companies and there's been a pendulum swing recently, we went from maybe 12, 18 months ago, where we're actually maybe prior to 12, [00:17:00] 18 months, 18 months ago, where it was growing all costs.

[00:17:04] Josh Rappoport: And then over the last 12, 18 months has been, , profitable growth, or I'm sorry, just focus on profitability. And now we're kind of that the pendulum is moderating a little bit and we're focusing on profitable growth. Similarly, my career is, , pendulum. So I started, , massive, massive, huge company, swing the pendulum to a much smaller, , super, super high growth.

[00:17:30] Josh Rappoport: Company and now kind of moderating a little bit. I think I referred to acumatica As I referred to acumatica to you earlier as like my goldilocks not too big not small not too hot not too cold Acumatica is a , 600 person company. We do triple digit millions of dollars in revenue privately held growing very very quickly double digit growth top line and, and, , [00:18:00] driving significant profitability.

[00:18:02] Josh Rappoport: I have to think about what I can share but, , driving pretty significant profitability and, and so we're, , we're certainly not Microsoft and Google, but we're definitely grown and developed well beyond early stage startup. And, and I think for me, it was a, an opportunity to experience a different stage of development.

[00:18:24] Josh Rappoport: But really it was, , and, and so far as proven out to be kind of a best of both worlds scenario where we have some foundation, some structure, some stability that you would see in a larger company, but also there's so much market opportunity, so much product opportunity and so much organizational opportunity that I still get to focus on growing and building.

[00:18:46] Josh Rappoport: And so that was, , that was certainly interesting going back to prior statement around the people that you work with being so important. But what struck me and really what sold me on Acumatica where the conversations I have with our [00:19:00] senior leadership, in particular, our CFO and our CEO, both of whom bring decades of experience and growing software technology companies And just a level of executive maturity and thoughtfulness and transparency that I found really important that I knew also from a personality standpoint, interpersonal standpoint, I was going to be able to work really well.

[00:19:26] Josh Rappoport: With the team. And so that that was obviously a huge, huge influence on my decision to join Acumatica. And then, , I was asked, it's funny, I was asked point blank. , why would you want to come to Acumatica and lead FP& A when you've led, , full finance organizations before? And the answer is twofold.

[00:19:46] Josh Rappoport: One is because there's always more to learn. And again, like, I think I can learn a lot from our CFO and our CEO. But Really, FP& A is kind of where I came from. I think a lot of people come to finance leadership from different [00:20:00] paths. , you get CFOs who come from investment banking, you have CFOs who come from the accounting and controllership side, you have CFOs who come from FP& A.

[00:20:07] Josh Rappoport: I have always, , had my grounding in FP& A and strategic finance. And business partnering. And so here is an opportunity to help transition a finance organization from being somewhat inwardly focused which, , maybe I have pejoratively referred to at other companies as finance for the sake of finance.

[00:20:31] Josh Rappoport: , to kind of building this business partnering mentality, outward focus towards a finance organization. , building the capability and mindset to be problem solvers and influencers of decision and influencers of business outcomes. And so even though the scope Technically at Acumatica for me is probably narrower than other scopes that I've had in the past.

[00:20:57] Josh Rappoport: It was. I think, , the [00:21:00] opportunity is even more impactful because I have this foundation upon which I can stand and still this opportunity to kind of build new perspective and new capabilities. And, , so that, that's, that's really, that was my thinking. I've, I've now been in role for two months, two months and four days, exactly.

[00:21:18] Josh Rappoport: And, and so far so good. And, and , just kind of going through my first planning cycle and the first quarterly business cycle and still very much in that, that learning phase, that consumption phase where I keep promising my boss that I'll be productive at some point.

[00:21:36] Tushar Makhija: Let me, let me, let me let's try and get a little tactical because I think the next few questions will shape a lot of your answers will shape the conversation.

[00:21:46] Tushar Makhija: To a great detail is like just walk us through the current team team size. Were you the first FBA hired? Did you have analysts?

[00:21:57] Josh Rappoport: And then what is your tech stack? Yep.

[00:21:59] Tushar Makhija: [00:22:00] So let's, let's start there. And then I, I want to ask you about your, , how you are becoming the business partner or how you are channeling the company to be more outward finance.

[00:22:12] Tushar Makhija: And what, what do you think you can achieve in the first hundred days? But let's talk about

[00:22:16] Josh Rappoport: the tactical stuff first. Sure. Okay. So the finance or, , the full finance or the CFO or finance and accounting, it's about 25 people or so round number. The FP and a team is, is, , depending on exactly how you define it, , between seven and 10 people.

[00:22:33] Josh Rappoport: Okay. So there, , there is a team in place. The team is, , largely earlier in career. Okay. And so a lot of, again, a lot of focus on reporting and providing information. And so the idea when our CFO was hired eight months ago now, [00:23:00] the idea was he wanted to bring in somebody like me to, , lean in and lead the FP& A org to help kind of a relatively early in career organization kind of learn how to business partner, how to gain trust and credibility with senior leaders.

[00:23:17] Josh Rappoport: , how to develop instinct into what questions to ask and frankly, what questions to answer. How to think beyond, well, here are some numbers in a spreadsheet to what do these numbers mean? And, and so, , we're, like I said, I'm two months into that journey. So we're relatively early into that journey.

[00:23:36] Josh Rappoport: But, but what I'm noticing, especially amongst the team is A incredibly high degree of engagement. , I'll have conversations with folks on my team. They're like, Oh, we're like, nobody's ever pushed me to think this way before, or I didn't realize it was my role to answer questions. I thought I was just supposed to, , deliver [00:24:00] reports, etc.

[00:24:01] Josh Rappoport: And so, and while that's, , potentially challenging. I think everybody's taking the perspective of like, yeah, this is really what we want to be doing. And so this is great. And people see me not as, as , creating risk for them, but rather creating opportunity for them. And, and I very much appreciate that too, because I've realized I, so I have an executive coach and, and.

[00:24:24] Josh Rappoport: I've been working with him for several years now, and I think last time I spoke to him about a month ago, I said, I said, Steve, , I, I realized something I realized that I'm actually not particularly great at finance, but I think where I have my where my real strength lies is in leading and helping to develop people.

[00:24:48] Josh Rappoport: And what's interesting is like, I wouldn't have said that 10 years ago, 10 years ago, I was like, I can create any spreadsheet you can think of, I can model anything that you want I [00:25:00] can, , help explain business outcomes, but I never really thought of myself as a leader of people and, and as somebody that could help people learn and develop their own careers, whereas today, I think that's probably more of my strength than like the technical financial capabilities.

[00:25:18] Josh Rappoport: And so that, , that's, , kind of really interesting spot to be in. So

[00:25:23] Tushar Makhija: lots to unpack there, but Acumatica itself is a CRM and ERP. So you, you, you got to eat your own dog food. Now what are some of the other tools that you're

[00:25:34] Josh Rappoport: using today? Yeah. Yeah. So, , Acumatica, as you mentioned, ERP, cloud based ERP, primarily for mid market companies in.

[00:25:44] Josh Rappoport: Manufacturing, construction, distribution, a bit of retail. , noticeably I didn't, I didn't say software. So, , kind of an, an interesting situation where we're a software company using our own product that wasn't really defined, designed for [00:26:00] our business , obviously we know how to use it really, really well.

[00:26:05] Josh Rappoport: So I feel. , we've got a really strong backbone in the core ERP and CRM. One of the things that we're doing right now, , aligned with our focus on FP& A and business partnering and forward looking planning is we're implementing an FP& A tool which I'm sure, , I know you're familiar with.

[00:26:23] Josh Rappoport: I'm sure many of your viewers are familiar with. We're implementing Planful to help with our , both are FP and a reporting and insights generation, but also, , very much with our scenario planning capabilities. So that we're not, , relying upon, , I love I love Microsoft Excel.

[00:26:41] Josh Rappoport: That's not just because I worked at Microsoft. I like I love it. But, , plan full is going to be really, really instrumental in our ability to do dynamic scenario planning and forecasting. So implementing plan full of their FP and a tool. I think that's going to be really, really important. A significant key to unlock value and then beyond that, , systems that you would think [00:27:00] about.

[00:27:00] Josh Rappoport: So we use UKG for HRIS. And, , headcount system of record. , one of the things that's. That, even with Planful and UKG and the Acumatica ERP, one of the things that, , is incredibly relevant for our conversation, one of the things that will be, that will continue to be a challenge is headcount planning.

[00:27:20] Josh Rappoport: I mean, we're a software company, so, , I don't know the precise number, but let's just say the lion's share of our expenses are headcount. And , I think one of the challenges that I see with solutions in the market today is everybody thinks about headcount and headcount expense as a, , a snapshot or a single point in time.

[00:27:40] Josh Rappoport: I've said this to you prior, like, headcount and people expenses are really, it's a flow, a flow of expenses. Not a one time, I'm just, , I need to pay for this thing, a hundred dollars and then I have it. It's like hiring somebody and now like, , someone in perpetuity, I have to continue to pay them.

[00:27:58] Josh Rappoport: But , timing [00:28:00] really matters. bow wave matters, or when you hire somebody in a year and what the impact is, not just on this year's budget, but on next year's and forthcoming years. The way, , people themselves are dynamic. So within an organization, people can take different roles or get promoted or change locations, et cetera, et cetera.

[00:28:19] Josh Rappoport: And, and all of those have an impact on our headcount costs over time. And. One of the things that I, , I feel like I've been talking to you about Team Ohana for years now. Yeah, and it's just been an incredible ride to watch, right? , one of the things that That I think team Ohana does really well is think of is help people understand The flows and the dynamic scenarios of different headcount changes and moves and decisions that we're making Whereas most of the kind of, Legacy tools really it's just like well, here's the number today [00:29:00] And as a result like we we still live and we probably will live for the foreseeable future in lots and lots and lots of spreadsheets but given Given the magnitude of, of, call it the, the percentage of costs that, that are headcount for us this is definitely an area that I can imagine that we'll we'll be investing in over the next 12 to 18 months, as soon as we get kind of our fp and a tools stood up.

[00:29:24] Josh Rappoport: And, and also just some of the organizational development pieces for, for the fp and a org in place. 'cause. , to be fair, even if you have the best tool sets, if you don't, if the organization isn't, doesn't have the exact right mindset or isn't oriented or built the right way to take advantage of that tool sets, they're not going to be terrifically useful.

[00:29:44] Josh Rappoport: So I'm moving both of these things in parallel, right? So

[00:29:48] Tushar Makhija: let's you, you mentioned something about , an FPNA software, which is planful that is going to enable. Largely your team of 10 people to be able [00:30:00] to do more, do more, be more productive, more accurate and more also most likely real time.

[00:30:09] Tushar Makhija: But there is this whole piece about business partnership is to actually partner with the business. Yes. Can you talk about where are the, and you can take a broad lens. Viewpoint from just general opportunities where FPMA can partner with business leaders directly and not just the department owners, but also HR and talent, right?

[00:30:35] Tushar Makhija: Because the answering the why around if we just, , focus on headcount for a minute is you are finance comes up with a budget. The budget needs to be translated into a plan, which is a combination of activities between probably HR, business leaders, then it has to be mapped to, can we deliver on this plan from a [00:31:00] recruiter capacity standpoint, and then it, I mean, it's, it's a constant, it's not just a flow, but it is also a cycle that you have to keep updating and keep evaluating.

[00:31:10] Tushar Makhija: So how do you think about these things about partnership? Thank you. So that you enable these business functions and help them get more productive, help them help the business grow at the pace that you want to grow. Yeah, , I think

[00:31:29] Josh Rappoport: a lot of this is a self reinforcing cycle. So Where we were just talking about, , what's the tech stack and what tools are we using?

[00:31:40] Josh Rappoport: Firstly, I should say at a high level, , I want my tech stack to alleviate as much manual transactional work as possible for my finance team. I, I, I, I want my finance team to not be the mechanics, so to speak. I want them to be the engineers. [00:32:00] I don't want them, like, , turning nuts and bolts or pressing buttons and pulling levers.

[00:32:03] Josh Rappoport: I want them asking why, again, going back to channeling, , three or five year old. And being able to kind of channel that understanding and building trust and, and kind of interactive trust with their business partner. So, , let me, let me unpack what that means for me, because that was just a lot of words, honestly.

[00:32:26] Josh Rappoport: When I think about my career to a large extent, , I talked about kind of the breadth of my functional experience as, , maybe being interesting because I've done lots of things, but where it's really interesting where that, that has added a ton of value to my finance roles is because I've, I've done other things.

[00:32:45] Josh Rappoport: I've, I've been in the seat of a marketer. I've been in the seat of a product manager. I've. Been the chief of staff of an 1100 person engineering organization. I now have both empathy and [00:33:00] understanding for the types of challenges, questions and and , activities that my business partners are experiencing on a day to day basis.

[00:33:08] Josh Rappoport: And so I can bond with them and create a great deal of trust. And also I can I have At least some insight into what's their challenge. What can I help them solve? And so, , I'm not suggesting that everybody can or should, , follow the path that I followed and go do some marketing, go to some product and go do some achievement, , but what, what I am suggesting is that it's finance people.

[00:33:36] Josh Rappoport: Once we get the core technical capabilities of finance and accounting and understanding gap and, , knowing what a P and L is and, and the like. One of the things that I think is undervalued still today is really an understanding your business partners role in a business. And so [00:34:00] when I talk to my team in particular.

[00:34:03] Josh Rappoport: For my teams, historically, I talk about finance as having, we, we sit in this privileged perch. Those are the terms I use. We basically, we're able to sit in the middle of the business and see everything that's happening around us. I can see what marketing's doing and sales and product and engineering and HR and operations.

[00:34:25] Josh Rappoport: We get, we have this privileged view of everything that's happened. But, , privilege doesn't come without a price, right? So like the price of that privilege is that we both have the capability and the responsibility to help translate what each of our partner organizations and functions and leaders are doing from their language to what I kind of call the universal language of business, which is finance, which is numbers, right?

[00:34:52] Josh Rappoport: So being able to translate what marketing is doing into financial outcomes but also not just. [00:35:00] Functional language into finance or business language. Also, we have the responsibility of helping our, our functional partners, our business partners translate amongst themselves, like truly being the Rosetta Stone, the universal translator.

[00:35:15] Josh Rappoport: So if my team understands marketing and understands product and understands engineering. We can help them understand each other as well. It doesn't have to just be a functional language to finance and back. It can be a functional language through finance to another functional language, so to speak. In a similar way, like, we also play this translation role for HR.

[00:35:39] Josh Rappoport: So I can, , because I understand either what the budgets are, the plans are for each of our functional organizations. And I can understand it holistically. I can also help translate that for HR in their language. There's maybe the engineer speaking, . A different language than your [00:36:00] recruiter is, but since I sit in the middle and I need to understand it all, I can help them under, I can help them understand each other, help them communicate better with each other, help them plan better with each other, collaborate better with each other and effectively drive better business outcomes because I've spent the time, my team has spent the time understanding our business partners.

[00:36:22] Josh Rappoport: It's really about understanding, it's about trust. Well, empathy. Finance today is so much less about the technical capabilities, the modeling, the spreadsheets. Of course, it's important, right? The data analysis. That's all incredibly important. But like the difference between good and great is understanding storytelling.

[00:36:49] Josh Rappoport: narrative, being able to kind of proactively intuit what questions are going to be asked and proactively answering those [00:37:00] questions. It's about supporting decision making fundamentally. And, and, , having this innate understanding of What information is going to be imperative for somebody to be able to make a decision for your business partners to make a decision and communicating and telling and sharing that information in a narrative that that's easy to understand.

[00:37:23] Josh Rappoport: So

[00:37:25] Tushar Makhija: I mean, extending that point to and trying to get a little more I would say narrow in in defining some goals. What I, what I want to hear is that being a strategic partner, being proactive. Right. That is you. I think that is fundamentally what you were saying. Of course, having empathy, understanding the business, but you, you cannot, you've also said that you should not be reporting the news, but you should be predicting the weather.

[00:37:55] Tushar Makhija: That's what in a way,

[00:37:56] Josh Rappoport: Yeah, your way of saying that was much more succinct than mine. [00:38:00] So

[00:38:01] Tushar Makhija: how are you, what is the outcomes that you are looking for? In the first 100 days, and I know 100 days in the grand scheme of things is not a big number, but it's also not a insignificant amount of time what so in your first 100 days with the, with the principles that you just spoke about, what do you want to achieve or what do you think you should be achieving?

[00:38:26] Tushar Makhija: Yep,

[00:38:27] Josh Rappoport: so. , I'm two thirds of the way through my first 100 days. So maybe this is unfair. Maybe I'm going to just give you the answer that makes me feel better about what I've done in the last 60 something. But, but, , I, I'll continue to go back to like, my focus is on learning and understanding it's on curiosity and so , just as a human being, so for me, the first 100 days are.

[00:38:53] Josh Rappoport: , probably, , if there, if there are five things, the first three are learn, , get to know your team. Get to know your team, get to know your team, get to know [00:39:00] your team for, for a number of reasons. One , I do have the privilege of having a team that's there, that's in seat, so there's some foundation.

[00:39:08] Josh Rappoport: So, , my team has the institutional knowledge, has the background that's going to help me get up to speed faster. So, , that's one reason to get to know your team. Two is, , these are the folks that you're going to be working really, really, really closely with. And just as we want to drive empathy and understanding and comfort and collaboration with our business partners, even more so, , think about that.

[00:39:34] Josh Rappoport: Exponentially more important for your own team. So I want to understand who's on my team. What are their strengths? What are they good at? What do they like to do? What are their opportunities for growth? , what do they want to be when they grow up? How can I provide them opportunities to get exposure?

[00:39:49] Josh Rappoport: But also what can I learn from them? And then, , also, like, there's just like the relationship matters again. We're all people. So I talked about choosing [00:40:00] companies because of the leaders and the individuals involved. , and I think we've all heard it said like people, , people leave companies because of their managers, not because of the company.

[00:40:11] Josh Rappoport: And so I want to develop personal relationships. Because I just think it's important, , it's, it's, it's important to me, but I think it's important for them as well to be able to know who I am, trust me, know that, , I have a wife and a seven year old son and two cats are, I locked them out of the office right now because otherwise they would have come and shared all their, points of view on headcount management with you.

[00:40:35] Josh Rappoport: They love Zoom calls, , like I want people to know who I am as a human being. So I think that that engenders a lot more trust. So if, if I had five recommendations, the first three are get to know your team. The second is learn the lingo. So every, I mean, I'm, I've worked for lots of companies in my life and we all generally do similar things, but we all have different acronyms for it.

[00:40:58] Josh Rappoport: Even something as [00:41:00] silly as, like, I was just, I was talking about how at Acumatica we do our monthly reporting, and instead of calling it a BVA, Budget Versus Actuals, we call it an AVB, Actuals Versus Budget. But, , it's, , it's something really small, but, like, learning the acronyms, learning the proxies.

[00:41:17] Josh Rappoport: The different reports, the teams, the structure of how the company operate literally learning the names of people but just learning the lingo and, and really closely tied to that is also learn the metrics. So we're, we're, we're in SAS, , you and I are both in the SAS world and, , we talk about, , there, , seemingly some standard SAS metrics.

[00:41:38] Josh Rappoport: ARR, NRR, Magic Number, CAC, and LTV, but the precise definitions of them are different depending on what, , who's defining that. So even if you look at, like, I forget who put it out, maybe it was one of the investment banks, like, you look at a number of public SaaS companies, They all [00:42:00] define AOR a little bit differently.

[00:42:03] Josh Rappoport: And so understand your own metrics. How do we define our metrics? What do they mean? Because it'll, it'll, it'll help you, it'll help me at least understand how our business is performing. And frankly, how you define the metrics really tells you a lot about what's important in the business. So, so, so that, , one, two, three will get to know your team.

[00:42:24] Josh Rappoport: , four is learn the lingo. And then five is actually, This perhaps is antithetical, but don't do too much too soon. Use, use your foot. Like, I like to say, like, if I'm bringing somebody on to the team, I assume it's going to take about six months for them to run. So the first hundred days is like half of what I'm expecting for the ramp.

[00:42:50] Josh Rappoport: And, and so I think there's a, , often a desire, like I need to make impact fast. And maybe in a startup, like, yeah, a hundred days is an [00:43:00] eternity. So you do, you have to like, just like get in there and start doing stuff. But in a slightly mature, more mature world, a hundred days is a short, really short period of time.

[00:43:10] Josh Rappoport: Like I'm just now getting through my first planning cycle, quarterly planning cycle. And so for me, it was like, just don't break anything, like just observe, understand. Certainly like, yeah, I've got my list of things that I think. A, I'm starting to understand, and B, I think kind of where I can, , make iterative improvements or changes but I, I, I just think it would be folly to do that too soon because, , as much as, , kind of the very first impression is really meaningful and generally pretty right.

[00:43:48] Josh Rappoport: Like, especially in a brand new environment when there's so much information coming at you, like it's worth, it's worthwhile to just take a beat and kind of take a minute to internalize [00:44:00] everything before you start taking action and potentially changing things in ways that have unforeseen consequences.

[00:44:08] Josh Rappoport: So, , if I had to take a step back and synthesize that all, it's like, get to know your people, get to know your business and don't do anything. Don't break anything. That's my first hundred days. Now, , I'll talk to my boss shortly this afternoon and we'll see what he has to say about that, but that's at least how I would approach it.

[00:44:32] Tushar Makhija: So, for folks out there who want to get into FP& A, what are some of the personal KPIs they should be tracking towards? Those. So it's, it's it's more like understanding your, like what is the advice that you would give to folks? And so that is one on personal KPIs. Then I also [00:45:00] want to know a little bit more about, , your, let's say you said six months to ramp.

[00:45:05] Tushar Makhija: So let's talk about the next a hundred days. What are the KPIs that you want to hit for your team or for your company? So personal KPIs that people should, and, , that's more advice driven. And then business KPIs. And then we'll see how we can marry them together.

[00:45:20] Josh Rappoport: Sure. Sure. I mean, , recognize that, especially as finance people at all levels, like business outcomes and the business KPIs and, , hear me out on this one.

[00:45:36] Josh Rappoport: They're largely outside of your control, but they are very much within your influence, your ability to influence. there's no prescribed path to FP& A. , finance and F.

[00:45:48] Josh Rappoport: P. N. A. is the lens through which we again, the universal language, the universal lens through which we understand a business. You can get to FP& A from an accounting background, you can get to FP& [00:46:00] A from a marketing background if you want to, you can get to FP& A, , if you want to study finance in school.

[00:46:08] Josh Rappoport: The, the, the real critical thing about FP& A is being able to quantify activity. So if I take a step back and say, like, what's a financial model, right? It's an abstraction of activity. , either that happened in the past, if we're reporting, or that could happen in the future.

[00:46:28] Josh Rappoport: So how do we quantify and understand things that are happening in real life? How do we take a business and decompose it into its, into its drivers? So I remember when I was at Yahoo pretty early on in my corporate finance career and I was working on search. And I had a mentor that like sat me in a conference room with a whiteboard and said, Okay, how do you think search works?

[00:46:52] Josh Rappoport: We went through. Well, you have users and you have number of searches per user and you have number of clicks or number of results [00:47:00] per search and number of clicks per results and, , add revenue per click in the, , and, and he really helped me understand how do you break down a business into its component pieces?

[00:47:13] Josh Rappoport: At a super high level, like the entire world is rate times volume, which is, , sounds really simple. But it's really like there's some volume of things and there's some rate at which we monetize those things. In almost everything, like it could be selling SAP software, it could be search, like everything is rate times volume, really, but how do you really understand your particular business, quantify it into its drivers, and then be able to understand structure around it.

[00:47:44] Josh Rappoport: When I think about FP& A, and I think about strategic finance. Well, yes, it's critical to understand what does a P& L look like and what are your three financial statements like that's all table stakes to me, and maybe, maybe I'm glossing over it too [00:48:00] much, but like that's table stakes. And you'll get that if you, , if you, on your own, if you want to, , study 10 Ks and, , public companies or you come from accounting or you just, , ask your friendly neighborhood finance person to walk you through your company's, , financial statements like you can learn that that's pretty standard, but what's not standard and what's Really kind of takes you from perhaps controllership and accounting and transactional based finance roles into more a PNA and strategic finance role is your ability to abstract real life into numbers.

[00:48:42] Josh Rappoport: And, and so, like, to me, it's like, I always felt, especially early in my career, I might not have been all that strong on call it financial statement analysis. But I knew I was really, I couldn't model anything because like, my mind just went to like, what are all the building blocks? How [00:49:00] do they all interrelate?

[00:49:02] Josh Rappoport: How does this end up in whatever the outcome is, , selling a widget or generating revenue, etc. And so for me, like, if you want to get into finance, you want to want to grow your career in finance and be successful, understand your business partners. Learn how to collaborate, learn how to storytell, but really fundamentally from a more technical standpoint is focus on how to, how to decompose your business into the core critical drivers and how they interrelate with each other in a really kind of geeky way Back in my Microsoft days, I was I was working on the Bing product, and Chi Liu was the president of the Bing division.

[00:49:41] Josh Rappoport: I think just being president of the Bing division, everybody should just take for granted that the guy was brilliant. But I remember being in a meeting with him, and we were talking about, I don't even remember what we were talking about, and that, and, and that's sort of the point. Like, it didn't really matter.

[00:49:54] Josh Rappoport: His question was, He said, What's the function? And, , I and [00:50:00] probably three other people in the room kind of strapped her head like, What the hell are they talking about? And then he goes up to the whiteboard and he literally drew a mathematical function. There's like, what's the function? What are the coefficients?

[00:50:13] Josh Rappoport: What's the equation that we're trying to solve? And, , I'm not suggesting that we break everything down into quadratic equations or something even more sophisticated mathematically than that, but this idea that there is an equation to what we're trying to do in business. And if we can understand that equation, And especially make it approachable for our business partners and our leaders and our investors and our other stakeholders, like you're going to be instrumental and so valuable that, of course, yes, you're going to have a great career in finance.

[00:50:51] Josh Rappoport: Wonderful.

[00:50:52] Tushar Makhija: So I think we we are coming to. I'm at my final question for you and you have spoken to [00:51:00] me a lot about your leadership axioms Right or guiding principles? Yeah, you also mentioned very generously you shared that you've been working with the coach yourself for many years and yes these principles embody you.

[00:51:14] Tushar Makhija: But I think what I'm looking for as parting thoughts from you is that for all the other VPs of finance or VPs of FBNL, any business leader who has to manage people, , because good people strategy is good company strategy, right? And leaders play a very instrumental role in that. And I think it would just be good for everybody to all learn about how you have been going about becoming a leader.

[00:51:48] Tushar Makhija: And what advice would you

[00:51:49] Josh Rappoport: share? Yeah, , sorry. Thank you for asking this question because it is really meaningful to me. , I'm [00:52:00] 20, almost 30 years into my career more than that. I don't know a lot of years into my career. Let's, , leave it at that. And I'd say for the first two thirds of my career, , honestly, and I look back retrospectively, , it's almost a little shameful.

[00:52:16] Josh Rappoport: , it was all about me. All I cared about was me. What am I capable of doing? What, how many hours am I going to dedicate to this? What is my outcome going to be? What is my work problem? And I think I got to a place where many people get , more quickly than, , some more quickly than others, where I realized that my success.

[00:52:44] Josh Rappoport: It was going to have a decreasing correlation to what I'm capable of delivering and an increasing correlation to what I can help my team deliver. And so what I finally realized, maybe like I finally had this like moment of wisdom or maturity [00:53:00] or clarity, however you want to put it. I realized that the highest leveraging that I could do was help my teams be as best as they can be.

[00:53:07] Josh Rappoport: It was not about me. It was about the team. And many people embody this, like, , servant leadership or whatnot, but like, I'm here to support my team, not vice versa. And so that, like that moment of clarity, that flipped a switch for me. And I said, okay, well, if it's not about me anymore, it's about my team and helping them be the best they can be.

[00:53:28] Josh Rappoport: How do I do that? And how do I do that in a way that's that resonates with who I am as a person? And it's authentic for me. And so, , over a number of years, , I've been working to try and articulate what, what I call my leadership axioms or leadership principles How do I help empower my team?

[00:53:50] Josh Rappoport: And, and, and, , I did, I've been working with a coach for many, many years and, , with his help, I've been able to articulate it into four principles I think are really important. The first one [00:54:00] is, like, it's always okay to say, I don't know. Like, my favorite answer to any question is, I don't know.

[00:54:06] Josh Rappoport: And that seems counterintuitive. But the reason that's my favorite question is because it invites. It, it invites us to learn, , saying, I don't know, to a question is the beginning of a journey of learning, not the end. It's not, you're not admitting fault. You're saying, okay, now, now I have an opportunity to go learn something.

[00:54:25] Josh Rappoport: And, and so for me, like that, that's really, really important there, there's a side piece here too, which is like, don't ever make up an answer. Like, I'd much rather you tell me I don't know and let me go and try and figure it out, then make something up and have it be half assed or wrong or whatever. Like, there's just, there's nothing good comes from that.

[00:54:46] Josh Rappoport: So, so embrace I don't know. Talking about embracing, so like embrace differing points of view. That's my second leadership, , principle. , I like to, , maybe earlier in my career, I might have been described as being argumentative, [00:55:00] perhaps others more kindly, , would say, like, you should have been an attorney, , but to me, like, I love debate.

[00:55:08] Josh Rappoport: Like, I love that intellectual jousting. And exercise like it's just fun for me and what I realized is that for me, like debate something to be encouraged, , often we avoid debate. I want to encourage debate. With a caveat, and that caveat is the debate needs to be about the idea and not about about our individual, , individual identities.

[00:55:33] Josh Rappoport: , it's not like, well, I don't like Bob, and so I'm going to just argue with Bob. It's about, well, I'm hearing Bob's point of view and my point of view is different, so let's try and understand the differences. And it doesn't mean that we always have to, , everybody has to agree. But by understanding differing points of view through debate, it actually can help us evolve our own points of view.

[00:55:56] Josh Rappoport: So again, kind of this learning and growing journey, these are all [00:56:00] related. My, my third leadership principle is like a bias towards simplicity. And I think a lot of people talk about simple is simpler is better. What I realized is like simple is really, really, really hard. But there's power in simplicity.

[00:56:16] Josh Rappoport: Like if things are simple, they move more quickly, they produce results more effortlessly, et cetera. But because things simplicity is hard, it's hard to divine that you really have to understand something to be able to make it simple, like try taking something complex and explaining it to your five year old, if you can, if you can explain something to your five year old in a way that they understand it, like.

[00:56:37] Josh Rappoport: You really have spent the time and effort and energy to be able to distill something complex into something very simple. And so for me, like, that bias towards simplicity, what it really says is like, hey, like, we all like, and maybe this ties back to my first hundred days. We all just need to take a step back and give ourselves permission to invest the time [00:57:00] and energy to understand first.

[00:57:04] Josh Rappoport: And now once we understand, now we can move really, really fast. But trying to move before you understand in the long run, in my experience, just slows things down. So I bias towards simplicity. And what that really says is like, I'm giving myself and everybody else permission to take the time to really understand something first.

[00:57:23] Josh Rappoport: Before they jump in and try and move forward. And then the last one, we talked about this early when I when I mentioned Amy Hood at Microsoft focus first on principles and aligned outcomes will follow again. We have to make as an organization as a business. So many decisions. Every single day that, , the CEO, the CFO, whatever, whatever leader can't make every decision, they, they become an instant bottleneck.

[00:57:47] Josh Rappoport: So by aligning on principles, we, we empower our teams so that, again, that mental algorithm to make decisions that are all kind of aligned. It's that disci decision making at scale, I [00:58:00] think is the, the term that Amy used. And, and so that, that's really been a strong influence and has really led to the, the, , final.

[00:58:07] Josh Rappoport: Leadership principle of mine.

[00:58:08] Tushar Makhija: Yeah, I think for the first time I have felt that we have not just covered the basics of whether it is planning, FP& A or finance, but we have. You in this hour long conversation have, , shown the path of how to, , I would say, live your life in certain ways, right?

[00:58:34] Tushar Makhija: And those guiding principles, I think, apply to a lot of people. So I think this is, I'm very grateful that you made some time for us today.

[00:58:43] Josh Rappoport: Well, thank you, Tisha. , I appreciate the opportunity to share. I hope that, , what we talked about sparks a little bit of curiosity in, in, in your audience.

[00:58:53] Tushar Makhija: Thank you so much, Josh.

[00:58:55] Josh Rappoport: Yeah, thank you.[00:59:00]

[00:59:00] Tushar Makhija: All right.

About the guests

Josh Rappoport
As a finance leader with over 20 years of experience, Josh helps high-growth companies achieve their strategic and operational goals by building and leading effective finance teams and processes. He has a proven track record of delivering value across various industries, including B2B SaaS, consumer and enterprise Fintech, and online media and advertising. At Acumatica, Josh oversees financial planning and analysis for this leading cloud ERP software provider, driving growth, efficiency, and profitability. He also leverages his diverse experience as a startup advisor and investor, supporting innovative ventures in the tech sector. Josh is passionate about continuous learning, culture, and talent development, and enjoys collaborating with cross-functional partners to enable data-driven decision-making and financial excellence.

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