# From accounting to operations, how Brad Silicani became COO of Anrok Brex’s CAO Erik Zhou sits down with Brad Silicani, COO of Anrok, to talk about his journey from Big Four accounting to leading operations at a fast-growing tech company. **URL Source:** https://www.brex.com/resources/controllers-classified/season-2/episode-10 --- Episode 10 From accounting to operations, how Brad Silicani became COO of Anrok [Spotify](https://open.spotify.com/episode/4UbK66yHARTGAxEK15jfmO?si=907beb076e7f4955) | [Apple](https://podcasts.apple.com/us/podcast/controllers-classified/id1712897034?i=1000696193996) Episode summary On this episode of Controllers Classified, host Erik Zhou sits down with Brad Silicani, COO of Anrok, to talk about his journey from Big Four accounting to leading operations at a fast-growing tech company. The discussion begins by covering Brad’s transition from audit to client side, and highlights the myriad of roles he held at Dropbox. In his time there he was Controller, tasked with landing a sound revenue recognition method, Head of Tax, focused on developing the right international tax structure prior to IPO, and Treasurer, responsible for managing $2B in cash in a changing interest rate environment. In covering all this, Brad shares how these experiences set him up for success in his current role as COO at Anrok, highlighting why a background in accounting and finance makes him the operations leader he is today. And of course, no modern finance conversation would be complete without tackling the AI revolution. Erik and Brad dig into how automation and AI are reshaping accounting, tax, and treasury functions—not just making processes smoother but fundamentally redefining the role of finance leaders. Whether you're a CFO- OR COO-in-the-making, or just someone who loves hearing behind-the-scenes war stories from hyper-growth companies, this episode delivers sharp insights and great conversation. Show notes - The journey into accounting [00:50] - Early career and experience at E&Y [02:04] - Joining Dropbox: revenue recognition methods [05:03] - Scaling Dropbox: tax challenges [06:54] - Transition to Treasurer and preparing for IPO at Dropbox [20:12] - Becoming COO at Anrock [21:49] - The evolution of financial software [25:55] - Finance leaders are are fun too [36:14] Guest bio ### Headshot ![Brad Silicani](https://brand.brex.com/m/25f4b8cefffbcd44/webimage-Brad-Silicani.jpg) ### Bio Brad Silicani, COO, Anrok Brad is currently the COO of Anrok. He got his BS and Masters in Accounting from USC, and began his career at E&Y. He’s held a myriad of roles across finance and operations in his career. “My career goals changed from CFO to COO because I loved getting exposed to all of the different parts of a business.” ### Transcript [00:00:00] **Erik:** Welcome to Controllers Classified. I'm your host, Eric Zhou, the Chief Accounting Officer at Brex, and I'm really honored to have our guest today. Uh, this is Brad Ani, the COO at Aroc. Um, we haven't had a COO on the show before. Um, this is a show, it's called Controllers Classified. We're really talking about accounting and finance and tax and treasury and all this stuff. Brad's great because he has an accounting background. He was a big four person. He worked in accounting. He was a controller at a large company before worked on tax and somehow made its way. Into the operations of his new org at Anorak. Um, welcome to the show, Brad. **Brad:** Yeah. Thanks, Eric. Excited to be here. Appreciate you having me on. **Erik:** maybe just to get kick started for the audience. Give yourself an intro to everyone. How, how did you end up as the COO of a company, giving your background? **Brad:** Yeah, um, well, maybe origin story on the accounting side of things to tie in for the controller audience here. I like to joke that I was born that way. So my father was [00:01:00] a partner at KPMG for, uh, you know, his whole career. My sister, my older sister, had started at KPMG as well. And I, uh, went to college and took my first business class with no intention of being an accountant. And, um, yeah, for me, it was like almost a clairvoyant moment that I like saw Davidson credits and everything just made a ton of sense to me. So, um, I kind of quickly that freshman year figured out that I could, um, go out, get my accounting degree, get my master's accounting, um, do that very quickly. And it just made so much sense to me that. That got me into, uh, accounting in the first place. And yeah, roll forward to where I am today. Um, you know, Anrock is a company that helps support accountants and, uh, supports folks, uh, within tax to be able to solve a problem around sales tax and VAT. So, um, I've, uh, been able to kind of use my experiences from those even early days on the accounting side of things at UI all the way, uh, to make my journey here to Anrock today and get into lots of other things, exciting outside of **Erik:** just for fun. I, I love, I just want to ask this question. I didn't realize that your dad was a partner at KPMG. Okay. And then you just told me your sister, uh, [00:02:00] is that KPMG or I don't know if she's there anymore. And then which firm did you join? **Brad:** Yeah, I joined Ernst Young. Uh, I look a little much too, too much like my dad. And so, um, I wanted to, you know, step away from the, the family from there, if you will, and, um, ended up with Ernst Young. I, uh, they also encouraged me over that. Um, For my internship, I did that internship in San Francisco, and then they offered me the opportunity to start actually in the National Accounting Group for my first year out in New York. So, um, that made the decision pretty easy. Got to skip the first year audit experience there and do technical accounting research instead. So that, that helped as well. **Erik:** But then you came back to the San Francisco area. And did you get involved in like tech while you were at Ernst and Young? Or how, how, how, what was your intro into that? Like I grew up in New York. Right. And naturally for me, when I went back to New York and worked at Price Waterhouse, Oh, financial services, like, no, but go someone else for me in New York. So I'm just curious about your experience. **Brad:** Yeah. Um, maybe that also like leads into why you're so young, [00:03:00] which is, um, yeah, I grew up here in the San Francisco Bay area. So tech, uh, of course is the industry here. So I knew I wanted to work with tech companies. So, uh, when I came back to San Francisco, uh, got assigned to work on Oracle and Salesforce as pretty much my only two clients, um, snuck in a few smaller private tech companies here and there. Um, but yeah, that was, I think, an intentional choice on my side to try to get exposure to, to those companies and understand that the industry a lot better. Um, and yeah, work with, I think, some of the companies that were the brightest there. My Salesforce reference, which may be dating me here was, I remember being on the audit. As an intern and their controller came up and he was very excited about their progress and he was, you know, came to the office and he was like, you know, one day we are going to hit 500 million in revenue. And I remember looking around at the like senior and the manager and they're like, no way, not going to happen. Hey, he was right. Look at Salesforce today. **Erik:** , it's really interesting [00:04:00] that you say that, you know, the, um, And I'll just share this with the audience as well. I, I, I'm the chief accounting officer at the company. I recently also became the SVP of finance. So I look after corporate FBA and, and, uh, strategic finance as well. And then there's that side of me where I look at all the numbers and I'm looking at other projections and like, you know, we have very big dreams at Brex too for revenue and the whole company, et cetera. And in my heart, I'm just trying to reconcile like, okay. With what I see in the field today and what's with, what's like going on, are we really going to be able to hit this objective? And I think that's the thing that's, that's really interesting at the end of the day. When you're running the business and leading the business, it's not just about everything that you see in the field, but it's what you can envision and imagine them to be and what they'll grow to be, um, that will get you to that number. And so, and so there's still a part of me, like, you know, the accountant in me just keeps looking at the past, the finance piece in me, like, yeah, I'm looking towards the future and trying to build this company now. Uh, that's really [00:05:00] exciting. I I'm really **Brad:** love that. Yeah, **Erik:** Yeah, I'm really curious. Um, you joined Dropbox pretty early stages. I think **Brad:** yeah, um, that's right. So, uh, maybe picking on the UI that, uh, stayed there for maybe four, uh, five years, I kind of looked at myself. I obviously had my dad who I could look at as well. I love my dad, uh, to death there. But, um, yeah, I knew that I didn't, yeah, he's going to love it. When I get this next one, or she's like, I knew I didn't want to be a public company partner, um, to me that, um, you know, didn't fit with the curiosity that I had about it, just like. Trying new things, testing, iterating, um, you know, as you kind of know within the big 4, you got to follow the process and stick to what's going on. Um, so got interested in thinking about joining a tech company. Uh, to be honest, I had no idea what Dropbox was when I applied. Uh, I was. Mid interview process with them, and then they came out and announced that they had raised a series B, uh, that was 250 million and a 4 billion valuation.[00:06:00] And I was like, okay, well, product makes sense. I can understand, you know, file, sync and share there. And, uh, wow, they're an 80 person company with this valuation. This seems like a good choice. So, um, decided to, to join there and, um, yeah, uh, had a, a long journey there about nine to 10 years before I, **Erik:** I can only imagine what that was. It must've been like 80 people, 4 billion valuation, growing bananas. You need all these new people to come into the company every month to start building what you've promised to these investors and building the revenue. You know, it's chaotic, right? Like when you're growing so fast. And I believe you were the controller there for a bit, right? As they were starting out, like, like, how did you? Put it all together. Like, you know, payroll is expanding, maybe opening new entities and like other countries, you know, there's like, I'm just curious, like, what were your focus areas during that time there? **Brad:** Yeah. Um, so when I, when I joined, uh, we were in a county team of two people. And then, [00:07:00] um, at the time I stepped away, um, being the controller there and the county team was about 25 people. And so, um, one thing that was like, uh, has stuck with me through today that has opened here is, um, the main priority we had to get an order was what was going on on revenue and in order to cash there. Um, the company, like, yeah. Um, I had no records about what was happening on, you know, how to record revenue or, or kind of recognize what's going on. And, um, that was definitely our biggest journey to figure out. I like vividly recall my very first day having to go talk to an engineer, um, about, Hey, can I get a report on revenue? And we had this like very gruff conversation, um, where they gave me a lot of feedback about what the hell I was talking about, um, that I was wasting their time and that this data didn't exist. Um, and to me, that was like a big transition from being in an environment where I was around a bunch of accountants who knew kind of the language, the acronyms, the ask them, you know, if you asked another accountant for a revenue report, they know exactly what you're talking about. And then being in this world where you [00:08:00] had to learn how to communicate with people who had no experience or background on accounting or finance. Um, and how to find a common set of language there. So, um, that I think was a challenge, you know, address on the revenue side of things, we had to get a sales tax and VAT system in place, a billing system in place. Um, we had to convince engineering to make a ledger, uh, immutable transactions for what a historical ledger will look like. Uh, And, yeah, continue to grow from there. So, um, revenue, I think was definitely the biggest challenge given their small transactions and high velocity there. Um, and then that expanded into, you know, as we got to 25 or so on the accounting side of things, like how do we start addressing international? How do we localize for currency? How do we start thinking about the tax structure and what the implications of that are going to be for the longterm as well? Yeah. **Erik:** right? Like you're building the plane as you're flying it. Like, that's a, you know, common expression, I think, but it applies here. [00:09:00] Um, how long did it take? So you asked for a revenue report. It doesn't exist. What was your first month of revenue close then? How long did it take before you could get all the revenue kind of like into your GL comfortably knowing it would be complete and accurate. Like, like maybe size that for the listeners. **Brad:** Oh, I think to like get to a process that we were comfortable with was like probably close to a year, um, to be able to like go through getting the reporting, you know, ticked and tied. Uh, like, what did it look like? Um, the beginning, which is, I think, a common experience across like many things with. Accounting in a startup, which is like, you have to work with what you have, right? Um, and take the information that is available. Um, that may mean that like, uh, you're going to come back to it and true up or make adjustments. And so, um, I think in the beginning, yeah, what can you start with? You can start with cash, you know, what the cash is in your bank account, um, and try to parse from there. So I think we kind of comically tried to look at the bank statement and see the credit card charges come [00:10:00] again and categorize. Each one is a monthly charge or an annual charge and figure out amortization. And then. You know, maybe 12 months on, we got to a place where we could get to an internally produced report because they had built their own billing system that gave us maybe a more structurally the ability to answer those questions and, you know, get through a revenue close that may take **Erik:** What, what you just share with me reminds me of an episode I did last year. We had the controller of open AI on the show and she was explaining how, I mean, she's, she's like in house, right? So she. There was no concerns by her of using the tool and all the privacy stuff that like other, uh, potential buyers are worried about. Anyway, she, they, they went to getting revenue like overnight, right? It was a free product. And all of a sudden they started charging like 20 a user a month. And like, they had like a hundred million users. Like just, let's just say two, three, 4 percent of the users are paying. And **Brad:** Yep. **Erik:** like no revenue one month, next month, 4 million lines. Of credit cards. [00:11:00] Yeah. 4 million lines on a CSV file for like credit card charges. And, and, uh, I, I, I, I'm not sure if that's, it's definitely a large data file. That's what she said. She not give me like the exact details. Um, but you know, she, you know what she did? She wanted to reconcile that credit card statement with what she had in her GL. And she fed both sides. Into chat GPT, ask chat GPT to write, um, a SQL query to restructure the data in both sides so that they can be comparable and then put the new sets of data in there and ask chat GPT to run a Python code so that you can reconcile the two and she had like, you know, what are like jet brains or something and some other engine to run Python, uh, to run the, the, the code and just did it. **Brad:** That's amazing. Yeah, I, **Erik:** In one month, figured **Brad:** born too early for it. **Erik:** No, yeah, no, like, like, I've, Dropbox was obviously, like, you know, years [00:12:00] ago, but **Brad:** Yeah, yeah. I wish. No, I, I'm being jealous here. **Erik:** that's, and I thought, I thought it was so impressive, like, just to **Brad:** that is, **Erik:** that order to cash so quickly for such a large, uh, accelerated business to some extent. **Brad:** that is, uh, awesome. I think it speaks to like, like the flexibility of. Uh, being successful right at those early stages is just like finding new methods and approaches and working with what you have. If you can do that, then you're going to find success on being able to navigate and push the company you know forward if you can't and you get stuck in like it has to be this way and this is the You know the ideal process or outcome you're going to go too slow and not be able to keep up with that business **Erik:** So one of the things that you mentioned was, okay, so, so you're, you're in the org, you're, you're, you're now creating a bunch of entities in different countries and different locales. When did you get introduced to tax? Was that when you got introduced to tax? Like, and started working on that at Dropbox, **Brad:** , great question. So my first exposure and kind of what drove my, um, eventually becoming the head of tax [00:13:00] at Dropbox actually started back at the audit days. So, um, I was working on Oracle. Oracle is even then and definitely now like a complex global company. And, um, I got assigned, uh, you know, the audit team job of going to coordinate with the tax team. And, um, Um, I think many people found, uh, would look at that job and be like, oh, this is the worst. I actually found it probably to be one of the most interesting things I've worked on my career, genuinely, because I think what that taught me, um, uh, you know, my friend knows is like how the world works. And I genuinely think that tax, uh, drives a lot of, uh, how the world works. And what I mean by that is, um, I had no concept of, What a legal entity was. I had no concept of why a company would establish a different legal entity. No concept of how income got attributed across the globe. No concept of the geopolitical considerations of how that all worked. Um, and the mechanics which fall into transfer pricing and all these other wonderful things. And just being able to get exposed to that, I feel like it was really a light [00:14:00] bulb moment for me on. Understanding why a business would make a decision about where they're going to place their people, why they're going to produce their products, um, how they're going to, you know, uh, become profitable, why they would acquire a company and do it in a certain way. Um, yeah, I think really understanding that is like a serious light bulb moment for me on, uh, you know, better understanding business context in general. And so I enjoyed that experience at Oracle, started poking around on that on the Dropbox side of things. And, um, yeah, this was maybe, uh, 2014, 2015 at that point, Dropbox was always 18 months away from going public. And so, you know, we were constantly ready to, you know, pull the trigger there. Um, and we knew that an important activity for us to think about was our international tax structuring, uh, before we got to the IPO, primarily because of evaluation differences that happened pre and post IPO. Um, so, yeah, I, New, we had to take this project on and, um, yeah, ended up switching over to start our tax team, [00:15:00] uh, and implement our international tax structure there. And, um, I thought that was particularly, you know, interesting, um, again, on, like, tying back to that theme that I learned at Oracle about just really understanding the considerations of, um, not only accounting and finance aspects, but just like. Um, why is Ireland interested in offering this tax rate? Why does America think about that? What are going to be the considerations when, um, those governments come to look and think about different transactions? Um, how should we think about other alternatives like Netherlands, et cetera? So, um, that was really an enjoyable experience. **Erik:** uh, maybe just to give some context to the audience as well. And this like, okay, so you're 18 months. So we have a saying to, we're like two years away from being two years away. **Brad:** Yeah. **Erik:** right. Like always 18. Yeah. And, and so you're 18 months away. Let's just say that that's, that's like, what's the starting point where you guys decided, like, okay, like we got to get this stuff going to make sure we have the right legal entity structure. When we're a public company, right. To kind of, cause at the end of the day, and I've heard this [00:16:00] from many people, right, tax is important because ultimately it does impact your, like your bottom line significantly, especially as you become profitable. And especially as you earn revenue in different jurisdictions with different rules. And so. You know, you take two companies that could be in the same business, same revenue, if one company just spent the time they needed to invest in the right tax structure, this is going to have a higher valuation because their bottom line is going to be the day. And so like, what, what, what was the, what was the timeline? Where when you guys decided like how long did you think it would take like, you know what I mean? like just trying to just trying to Level set with with with the audience like how they should be thinking about it if they if those are their aspirations as well. **Brad:** yeah. I mean, project wise, I think it took about 9 months to be able to get there. That was a fast 9 months from knowing that we want to be prepared to enter that that timeline. Yeah, I think the important considerations is just like, you don't want to do it too [00:17:00] early, um, if you do it too early, uh, before, uh, one, you become profitable, or two, you have a transaction, um, what you're doing is giving up the generation of net operating losses for paying income taxes here in the U. S. Assuming that you're not profitable, right? So you don't want to do that too early. You don't want to do that too late. Say like post an IPO because then likely your value, um, at a minimum, it's just like very publicly known. It's very clear. You can look at a stock price and see what the value versus private company valuations and two, it's likely to be higher just by nature of waiting. So for us, like we wanted 18 months before an IPO. Of course, Dropbox didn't public or, uh, Dropbox didn't end up going public for about three years after that point, uh, for different reasons. And so 18 months was the kind of timeline where I said, hey, we would feel comfortable 1 being able to do this and then to giving ourselves some distance between that transaction and, uh, you know, um, a public offering event, uh, to have confidence in the valuation [00:18:00] side of things. **Erik:** What what sorry just just so I understand to and for what do you mean by the valuation? What's so important about? The private company valuation that you would be using for some of these tax decisions versus like a public company valuation. Um, knowing that, okay, what you're saying is like, okay, the public company valuation is higher. That's not the right time to do it. You want to do it maybe when it's lower, but why? **Brad:** Yeah. Um, so like to try to simplify what you're doing in this, uh, these types of transactions, you're going to essentially sell a portion of your business to another affiliate or subsidiary there. And to sell it, you have to value it. To value it, you need to determine what that value is, and just by nature of private markets, value is more ambiguous. Um, there's not, you know, literally the stock price, uh, ticker there. And so, uh, you know, oftentimes those private company valuations, at least back in that period, um, significantly lagged kind of what you were able to achieve on the public markets. And so being able to do [00:19:00] that in a period where, uh, there wasn't a stock price that's gonna draw a straight line on that value, um, You know, what's helpful? Um, and so that's really what you're thinking about. There is like, hey, can I get this done? Um at the lowest price possible to make that transfer to make it the most cost effective uh, and then taking that in consideration with that future public company, you know valuation and Yeah, the literal stock price that's going to be available on on working that transaction **Erik:** And once you, and once you transfer that value, basically that's how you're able to kind of record revenue in a certain entity and then take advantage of the local tax rate there. Am I, am I kind of like getting that **Brad:** Yeah, you're right in the red ballpark there. Yep. Yep. So you come to an agreement about how you're going to pay for that. And then, um, at that point, you know, the say Irish entity or foreign legal entity there has the rights to then go sell your product internationally. And so you record revenue over there and, um, yeah, you're, you're off and away. **Erik:** maybe maybe just to round off [00:20:00] like just talking about your Dropbox experience **Brad:** Yeah, **Erik:** So now you guys are going up to the IPO like what I did you move on to even something else at Dropbox? That's what I recall from talking to you previously **Brad:** uh, spent about a year as the head of tax there, completed that international tax transaction. Um, we were even close to the IPO at that point. Um, and, uh, yeah, I think interest rates were starting to come off of zero. And, uh, we took a look around and, um, I had actually, even though I was controller and had a tax, it was very common, like I was responsible for the bank accounts. Um, and so we had a few, you know, a few hundred million literally just sitting in a cash account because previously there were zero interest rates. Um, that was changing. And so I wanted to take on optimizing that for, for Dropbox. So, um, stepped over and became the treasurer there. Um, taught myself or, or, you know, got an education on how to become a treasurer, which was. Exciting and fun and, um, you know, credit to our partners on, uh, JP Morgan, Goldman Sachs, many others who, who spent hours on, uh, helping and [00:21:00] answering lots of my questions. Um, and yeah, I ended up, uh, being the treasurer there for about five or six years, uh, through IPO. Yeah, I ended up managing about 2 billion in cash, which was a fun experience to, again, learn about like a new area of the world, which I hadn't, um, had that much exposure to on interest rates and corporate debt and, uh, financing. So that was another area of excitement, uh, for me. And maybe like putting a theme on like maybe, uh, my experience was like a non traditional experience on the accounting side of things. Like my goal during that period was, um. Prepare myself as best as possible for the point one, I need to become a CFO. And so I knew that if I wanted to do that, the best path was to be able to speak to every part of the finance work, um, you know, with expertise. And so I was working hard to ride out my experience in that way. **Erik:** um, I Okay, so that begs the question You are now not a CFO, but a COO, still C level. That sounds great. Right? Like in some, in many [00:22:00] orgs, actually, CFO may even report to a COO. You know, you're actually running all the parts of operations of the business. Um, how, how did that come together for you? Like, like what drove, what drove you to this kind of role versus staying in finance and accounting and tax and treasury and, you know, all that stuff. **Brad:** yeah, um, as I was a maybe like the later years there, there are dropbox. I think my career goals changed from being a CFO to, to a COO and it did that because I was like, uh, exposed and interested to even learning more and more about different parts of the business. Um, I got a, you know, great opportunity at Dropbox to, you know, work closely with the legal team, work closely with the HR team, um, managed our real estate and workplace services. So it started to get some exposure on, on operations outside of finance. Um, and I, in my vision would, uh, wanted to jump to a, you know, a startup, do that, uh, early stage chaos there again, um, and be able to broaden and learn about, you know, different areas of the business and so, um, [00:23:00] Yeah, got connected with Michelle, who's a, uh, CEO here at NROC and, um, what she had started working on just immediately resonated with me as a problem that I knew well, which was, uh, solving the risks around sales tax and VAT. Um, going back to that story on, you know, early stage revenue there at Dropbox, I had to deal with that from, from day one there was a big problem and cost that business like 15 million in historical liabilities. And we built our own tax engine. Um, so I knew this was a problem that, uh, was out there to be solved. And it also gave me career wise, the opportunity to be able to explore and learn new areas. And so here it was maybe a secret advantage for me, which was I could jump into and rock and actually be our first salesperson, um, and learn about sales and how that worked. And I could do that because I could speak to our buyers, um, and resonate with the same background. Right. So it gave me a like technical advantage on that sale, um, to then. Uh, while I did that, learn how to sell, learn how to market, learn how to, um, you know, take on [00:24:00] these other aspects of the business, which I previously hadn't had an experience to. Yeah. **Erik:** I love that. I, um, one of the big reasons I joined Brex, um, man, six years ago at this point, and one of the big draws actually for my team members to continue working out at Brex is that we're the first users of our users of our own products, right? We use our own card. We use the spend management software. We're using our banking platform, et cetera, for payments, et cetera. Um, and at the end of the day, like, you know, because we're customer number one, we're also like really credible folks within the company, the product order comes and asks us first, Hey, does this make sense to you? Because if it doesn't make sense to us. Like why would it make sense to have a vast range of different companies that we're trying to market this new product or feature to, um, so it's like a really meta job in that way for me. Like you have this tremendous, I would say pedigree already all the way going to your family on accounting and finance too. And so like, you know, I, I gotta imagine you got a pretty big voice at the company on [00:25:00] like how, how like. And rock should be solving these particular, uh, tax and finance and accounting, et cetera, problems, uh, for your customers, **Brad:** Um, yeah, I mean, team effort always, but, um, you know, uh, from those early days and still now, like, uh, able to work closely with our engineering and product team on, yeah, uh, being that voice of, you know, the user experience, being that voice of the pain points and the problems to be solved, uh, to help us make sure we're really, you know, addressing that and solving that effectively, uh, for our customers, uh, is something that I really enjoy about that process and maybe takes me back to what I was describing Uh, about the Dropbox experience of those first days of being able to just really step outside that accounting and finance world and speak with people across the business, um, in that Dropbox case, the engineers and, and here at Anirock, we get an engineers and explain to them, like, what is the pain point, what is the problem? Um, is, uh, exciting, like, uh, a fun challenge to walk into every day. **Erik:** I would say. Okay. So I, I have a different topic that I want to talk to you about. It's related to rock and [00:26:00] actually Dropbox to some extent, when I think about tech evolution over the last, call it 20 years, um, and especially like, you know, uh, I would say software solutions. Um, for within the cloud, like I think maybe when you started working and certainly with Salesforce, like, you know, you're talking about cloud 1. 0, to some extent, the first service providers that were putting software onto the cloud so that you can access it through the web or an internet interface versus like having on prem software. Right. And, and so that in and of itself was great because. You can now bring your work with you anywhere on the laptop, you can access things that you need applications that you need to access at home to do work and it just made productivity across many different companies much better. I think from that perspective. Um, I think we're in the second wave of cloud and it's been going on for a few years. Um, but you know, you guys are in it. I think like, you know, [00:27:00] you're taking advantage of cloud. And providing software as a solution, but with consumer grade features and user interface versus, you know, I, I mean, I, I love all the services that I have from called the cloud 1. 0 days. Um, they were built back then. So there's just a little bit clunkiness. Uh, some of those, uh, which I mean, they're now those people are like scrambling to try to keep up with all the new, new software solutions out there that are giving people, giving people a better user experience. I'm curious about your views and like, how you think about that being an NROC and how you're serving your customers. **Brad:** Yeah, I love that. And I would agree with the perspective there. That's like, I think the generation of, uh, you know, cloud companies before this are all about, uh, yeah, just taking things from the data center and being able to access it. Right. Um, and I agree that there's definitely elements of the new aid, which is better about better UI and workflow improvements for me. What really stands out even beyond that is like, um, [00:28:00] providing software that actually, uh, not just has like a bias towards action, but just like allows you to go out out of the box and solve that problem. And maybe an example that I give is like, thinking about when we installed that sweet Dropbox. We got our general ledger and, and put it in there. And then, um, you know, next question is, okay, how are we going to put data in there? Okay, well now we need to go build our own integrations to be able to bring in a bank statements or revenue. Okay. Now the revenue is in there. Um, how are we going to go about amortizing it or how are we going to like run appreciation? Okay. Now we need to like bring in this other stool set or manually address moving things, these things forward. And it really, to me, like lacked the. Active, um, management of those transactions and their life cycle like sure you could put the data in there and you could click a bunch of buttons to, you know, get it to where it needs to be. But when you're doing that at mass, the scale of number of transactions that that a business needs operated, you're not really automating what is happening there. Um, [00:29:00] I think the approach that, you know, we're taking, uh, here at Anrock and I think there are other companies, um, and other spaces that are taking this approach as well as think about the entire problem that you need to solve here. Uh, which for finance folks is building a transaction, um, through that process and how can we ensure that the data that you need, um, is all included within this platform and that the transaction can actively move through that process as efficiently as possible with, um. You know, the right configurations as little touch as possible. So going from a place where for our industry, like a legacy player, where you might get a tax calculation, but then need to go work with your accounting firm to figure out where the next place you needed to register for or get that return filed. Um, interlock can come to the market and provide a solution that gives you from visibility from when and where all the way through to execution. Um, In one single package, right? And I think that is this next generation of software. I think you see that come with, um, other companies that are, uh, [00:30:00] within the AI space as well of trying to, you know, take large, large pieces of data. You given that open AI example, which, which comes to mind there and like, how do we actively move from not just ingesting data to like making it usable and processable and getting to our outcome, right? Um, if we take that back to the core of what we are trying to do on the accounting side of things, um, we're trying to sell the customers and bring the cash in, uh, and then we're trying to, uh, buy things and send cash out, right? So how do we make sure that those functions are as efficient as possible and provide an experience to somebody who's buying your software, um, that. Doesn't require them to buy a bunch of other tools along with it. Doesn't require them to have a bunch of professional services or manual processing around that. Um, and yeah, we're a brexit user. I think you guys take on that philosophy as well. **Erik:** I love how you're describing the goal, which is like through your software, even more can be done. As a service provider, we can be doing more for you to improve your quality of life [00:31:00] as a customer, etc. Um, I'm curious, you know, Since we did touch upon AI a bit, what is your view on like the use of AI, whether it's in your software or within the operations of your business? Um, how are you guys thinking about, about the technology yourselves? **Brad:** Yeah, I think it's a super important area for all businesses that if I take that to like in rock level for us, the core problem that we're solving is a deterministic one. So there is a absolutely correct answer to what we need to do to follow the laws and support our businesses and executing. That doesn't, for today's AI, end up being a great use case, uh, for going through and handling maybe that, that core process of, uh, executing the job to be done. The place where AI really fits, uh, in supporting, I think, Anirog and generalizing other businesses is how do we make our operations more efficient. And, um, you know, how can we make sure that as we go to execute on the accounting side of things, as we go to execute [00:32:00] on support, as we go to execute on, um, customer success or sales, that we are leveraging AI to make sure that we can, um, yeah, see large bodies of data and get the right outputs and insight that we can, um, see the patterns of language that we're using in our communication with customers and surface the right insights to them. And so we're super focused in on how to, uh, and today, you know, using that, uh, pieces of data to be able to help support those functions. Um, and yeah, that's, I think, a super important place for all businesses to think about, because, uh, if we can, you know, take on many of those examples of how we can, uh, address doing our jobs faster, uh, and being able to see better insights, we can reduce the risk for our businesses and, um, be able to, uh, You know, spend more time probably doing other things that we love doing. **Erik:** How many people are in Anorak today? **Brad:** Yeah, we're 75 today. **Erik:** It's like the perfect size. Right now where you guys are still building out a lot of processes. [00:33:00] I I'm, I'm assuming you can correct me, of course, but you know, yeah, uh, you guys are nimble, you can create new processes. You can consider the use of AI for your kind of foundational operational processes to build off of, um, versus, you know, if you had started the company, uh, or, or if you're already been, if you're already at 500 people or a thousand people, it is just a little bit more difficult. To steer this bigger ship, so to speak. Um, **Brad:** agree. And, uh, yeah, I've seen that a Dropbox on the large side of things, which maybe want to come to these earlier stages for me, what's really exciting about our stages, like, um, we know our business pretty well. And we're able to hire now experts within, you know, functions of our business who can then yeah, dive deep on being able to solve that problem. Um, so it's a super exciting time and yeah, I think that has been the places where we've been able to implement a lot of these exciting solutions as you bring in the person internally who has the technical functional expertise of the job to be done, pair them with this, you [00:34:00] know, modern set of, of tools there and they can go further and faster than, you know, they, they had ever previously, which was super exciting to see. **Brad:** Well, for me personally, I'll answer that side first. Uh, yeah, got into running in the last year. So, uh, gonna work on my first, you know, half marathon, a marathon during this year, which is, is pretty exciting. **Erik:** That's awesome. Yeah. **Brad:** yeah, uh, so I'm excited about that once the rain goes away. Um, yeah, and on the business side of things, yeah, for us, it's, uh, it's all about, you know, growing really, really quickly here. So, uh, continuing to expand the team, make sure that we can get out there and support every business that, uh, needs to solve this risk. Uh, that means being able to expand the types of customers that we support and being able to, um, provide them better and better tooling to be able to do that. So we're super excited about that, and we'll have some fun announcements coming up here in the coming month or two **Erik:** Yeah. I got to say sales tax is one of those things where, yeah, there's these exceptions and [00:35:00] then these things, but like if you, if you start selling to more customers and more States and you don't keep track of it all and, you know, it'll creep up on you when you start to expand quickly and yeah, it becomes a, uh, it can be pretty troublesome at the end of the day. **Brad:** Yeah, and I really love sales tax. Like my plug here for this issue is like, it probably isn't an issue that is more financially consequential to your business that is within your control as a finance person. Like if you think about the problems that are out there, there are very few for which, uh, you know, on the sales tax side, 8 percent of revenue or VAT 20 percent of revenue that you have like complete control over being able to solve. Um, And so I love that we're able to bring that solution for, for our customers and be able to help them bring that plan of, uh, again, passing that cost onto their customers so that they're not taking that hit to their bottom line and cashflow. So, um, been, been good in that regard. **Erik:** I mean, at the end of the day, like, you know, I I'm still a finance practitioner. I think you [00:36:00] are as well in your role still. Um, and yeah, I, I just want to make sure I'm managing the finances of the company appropriately and risk and risk adjusted, risk mitigated way, so to speak. And you can't get away from this. So, so it's definitely important, All right, Brad, we always end our show with a little section called finance leaders are fun too. Um, so I'm just curious if you have any like accounting debacles or finance debacles or maybe tax jokes. I don't know. Like if you can share with the audience. **Brad:** yeah, uh, I'm light on the jokes, but maybe, uh, my best accounting debacle or worst accounting debacle. Um, I was, uh, getting married, I was at Dropbox and, uh, we had turned over a payroll person. So we had, uh, in a contractor, um, the team overall was about 20 people. So they were being managed by somebody else on the team at that time. I got married on my honeymoon and when I came back on Monday, um, I walked into the, uh, the company and see the accounting team just like seriously on the [00:37:00] phone and, and working on their computers and kind of calmly come back after being away on my honeymoon for two weeks, you know, what's going on, what's happening here. Um, and they let me know that the contractor had, uh, paid about 20 people at their company, their entire salary in one payroll cycle. And we had to unwind and deal with that. Uh, so. Decently financially problematic there and definitely operationally problematic. It was like this fast switch from, you know, highlight of my life getting married and being on the honeymoon to then coming back and having to deal with that one. So, uh, that was, that was pretty bad **Erik:** Oh, that sounds like a nightmare. Oh my God. And then there's these different like payroll and labor laws in different States that it's, you can't really call backness. Oh **Brad:** Yeah. Oh, exactly. It was a whole mess. Um, but, uh, yeah, we worked through it, but that one definitely stands out as a big debacle. **Erik:** my heart's **Brad:** And to me, it also like anytime you're dealing with paying people, that's the most important thing. So, um, [00:38:00] you know, you don't want to mess things up for employees. So that one hurt extra bad in terms of the debacle. **Erik:** Like maybe one of them, like, I don't know how much these people were paid, but like all of a sudden they see their direct deposit, like, Whoa. **Brad:** Yeah, no, there was, there were some nice payments in there. Yeah. **Erik:** okay. Well, Brad, uh, thank you so much for being on the show. It's been a pleasure having you. I love your experience, uh, and talking about it. So thank you. **Brad:** Thanks again. 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