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The Margin is a podcast from MGI Research that explores the evolving world of business monetization. Hosted by MGI Managing Directors Andrew Dailey and Igor Stenmark, the show features candid conversations with founders, CEOs, product leaders, and industry experts at the forefront of pricing, billing, and revenue operations. Each episode dives deep into the strategies, technologies, and trends shaping how companies generate, capture, and grow revenue—from subscription and usage-based models to AI-driven monetization. Whether you're in finance, product, or IT, The Margin offers practical insights to help you navigate complexity and drive growth in the digital economy.
Andrew Dailey: Hello, and welcome to The Margin, a podcast exploring the forces shaping business monetization. I'm Andrew Dailey, Managing Director and Analyst at MGI Research in high growth companies. Finance is often perceived to be the Department of Business Prevention. Sales teams need finance to sign off on deals and get paid. And finance has to keep the business and the accounting in line with auditors and regulators. The accounting world talks about wanting to be a strategic partner to the business. Is this really possible? What's the reality inside revenue accounting at hypergrowth software companies? Can finance emerge from the back office and take the lead when it comes to improving things like the order-to-cash process? Joining me today is Jane Koltsova, a seasoned revenue controller and ordered a cash leader with experience at companies like Salesforce and PagerDuty. She'll share her perspectives on what it takes for finance to get buy in, for investing in cross-functional processes like order-to-cash, and how finance can collaborate effectively with it. We'll also discuss common finance pitfalls in engineering driven companies, and practical strategies for attracting and growing accounting and finance talent. Jane, welcome to The Margin.
JK: Thank you, Andrew. Wonderful to be here. So maybe you could just give us a little background, your background and kind of backstory. Yeah, absolutely. I started my career in spades at Salesforce. Ten years with the revenue recognition team, which meant a lot of conversations with sales folks in order to figure out how to structure a transaction and deals to not run afoul of ASC 606, specifically, with an additional piece of understanding of how the operations work on the back end, our friends and sales do not tend to care too much about what the backend has to do. So it was my job to make sure that they understood the impacts and decisions were made appropriately in order to, by the way, maximize revenue, maximize ACV as well.
AD: And then more recently, at PagerDuty.
JK: That I expanded to run order-to-cash. So it was beginning to end, or the first time I got to see the entirety of the flow and of the work in order to help to break down some of the silos and really make some of those processes much smoother.
AD: So let's start at Salesforce. That's a company that grew both organically through very strong sales driven culture, as well as inorganically through lots of acquisitions. I can imagine from an accounting point of view, you got a lot of different terms and conditions, a lot of different types of software delivery. Describe a little bit of kind of what that was like.
JK: Absolutely. It was one of those moments where the moment that you think you've caught your breath, another acquisition is announced. And we were a SaaS company. The revenue was ratable easy, as some would think. And then we bought MuleSoft. MuleSoft is on premise. Then came Slack, which had a component that was consumption. You know, Tableau was in the mix, and they were coming one after the other with very different folks who were involved. Where there are different accounting teams, different sales teams, the ability to put everything on one piece of paper didn't come together. That true integration for a long time. So while that's happening, all of the backend processes continue to change, and we were just trying to hold it together enough in order to make it all flow.
AD: So, Jane, I'm reminded of what one CFO client described to me, having gone through a similar kind of high growth/hypergrowth experience, saying it was like riding a tiger with a broken tooth. Share a little bit about what it was like inside of Salesforce with the combination of hyper growth or strong growth, plus the acquisitions.
JK: That's a that's quite a metaphor and quite a visual. Whenever you're moving so fast that you can't hang on. It feels like you're out of control. It feels like you don't know what's going to happen the next day. Now, some of the most intelligent humans, absolute professionals, folks who know what they're doing, we're being made to feel at times like they did not know where we were going. There's danger in that from the perspective of things get missed, things get messed up in one way or another, whether that be from a numbers perspective, from a process perspective and all you're trying to do is get the numbers, get them right, make sure that things are reported properly, the things that are important. The trouble is, from a day to day, you don't always know what's important, right? So you have sales teams asking questions and you know how sales teams can be. The questions can range from the most minute and small to the most theoretical. Never ask right. And you don't know what you're going to get at the same time. You have your accounting teams on the back end just trying to get it materially correct. And I do mean materially. We had so much fun during this time, but it was some of the hardest moments in my career as a result of just having to get it done. Once it got done, we all took a breath and lo and behold, something else came down the pike, right? But that's the nature of the rocket ship that is Salesforce. I am so proud to have been there during that time.
AD: Revenue accounting is one of those areas where you get it right. You get a nice two 3% increase in your comp and a little bonus, you get it wrong and you lose your job.
JK: Yeah.
AD: How much does finance have an opportunity to kind of lead the way in terms of looking forward in terms of business models, pricing models. He talked about the experience, seeing a shift from what was relatively simple subscription business to subscriptions usage. A lot of complexity happened in a relatively short period of time. How can finance help the rest of the business see that that's probably going to come?
JK: You need to be a storyteller. This is something that I talk about all the time. There is a core number of people at every company who understand the revenue. They understand the financials. They understand how deals scale and come together to form whatever that monthly, quarterly, annual number result is. They don't share that knowledge, or they don't have time to share that knowledge or nobody's listening. But the moment that you can let the folks on the product side, on the sell side, on the go-to-market side, marketing, or if marketing understands how the deals come together and how revenue is recognized, you can start making choices as to how you deliver the message from a from an individual, a perspective. If you can make that connection, it becomes really, really powerful. Again, sales doesn't need to understand what Graham does. Neither does marketing, neither does product. But if you understand the key tenets, but you can't go in there and start talking about ASC 606 and start throwing out paragraphs. You've got to find that shared language with our friends and all of those other pieces of the organization. And the moment that that light goes on and that light absolutely will go on, you will see changes that are immediate. The trouble that you've had, potentially, as a revenue accounting team will start to dissipate, because all of a sudden, the front end knows exactly what it is that you need and what you cannot do.
AD: Quote-to-cash is one of those areas where everyone in the organization may be feeling or seeing the friction that exists within the process, and yet it's so hard internally to find a champion and to find someone who wants to stand up and fix the problems that everyone sees. You talked earlier about some of the storytelling and how that's helpful in terms of getting momentum to get things done. What are some of the stories? What are some of the examples that you saw from the past that were useful in getting people to move and getting collective focus around quote-to-cash?
JK: Having done so much work with our sales teams, there is often a misconception that they are not heard. There are a lot of them. They are running disparate deals. The back-end teams are not listening. The backend teams are trying to just get it done in whatever way that they can, and sales is banging against that door, just trying to be heard. The moment that you sit down with some sales leaders and say, what are you hearing? What is it? I find that the group that has the most to win, to gain or lose from the perspective of order-to-cash becoming better is absolutely the sales team because the difference between 12 clicks to set up a quote or 72 or 35 makes all the difference in the world.
AD: So how do you balance the investment decisions? Finance likes to hold on to the general ledger is the primary gatekeeper to the general ledger in a good way. And yet there's so much opportunity and innovation that's taking place around the edges.
JK: What is the situation with the company today and where do you think it's going in the next 12, 24, 36 months? What's important? Is it the new go-to-market. Is it the new SKU? Is it the fact that you're not getting enough cash in the door? It's very simply bang for your buck. And the person who makes that decision needs to be not the CFO, not the CTO, everybody together.
AD: That being said, the argument for investing in quote-to-cash—is it increasing revenue? Is it increasing profitability?
JK: I actually think it has everything to do with the top line. It's the flywheel of the sales team. It's moving fast. It's moving in an agile way. It is getting things done and going on to the next deal. Order-to-cash is the vehicle. If you don't have that vehicle that's running smoothly and purring along the road, you will have a flywheel that is just having trouble getting started and the momentum is going to hit harder and harder to get to be trusted by the CFO, the CEO, etc. Like you're saying, it is a complete black box and sometimes you can't have a black box because you have to explain exactly where it is.
AD: Looking back, what's one piece of advice that you would give to your peers in an organization? That's a sales driven organization, and yet where you've got to have good controls over the numbers?
JK: Yeah, this is a publicly traded company, right? You've got SOX, you've got financial statements, controls all over the place. Don't say no. The piece of advice would be don't say no. Figure out what it is that will actually move the needle without completely breaking the back end. It is not easy, but once you have the front of the business, understand that you are not just a machine of now that you are a team that says, let's figure this out. Make sure I understand your language. You make sure to understand mine and we figure it out together. They come to you earlier with problems. They come to you earlier with solutions, and you actually end up having a productive conversation versus overhearing, as I did once. Hey, we just got to get through RevRec. We just got to get through accounting. We are not a hurdle to be jumping over. The true amazingness of the order-to-cash at a company like Salesforce, at a company like PagerDuty is the expertise of the people. And if you don't get that going, you don't have much. So piece of advice, don't say no, but back it up with everything that I just talked about. It's all about overcommunication and it's all about expertise.
AD: So companies that are going through strong growth, particularly tech companies, typically are going through multiple iterations of their back office. What advice would you give or what are the conditions in which you say it's time to replace what we've got, or time to rethink the systems that we've been relying on? We see organizations holding on to inadequate tools, inadequate processes for too long because it's just easier to hold on and try to stretch it and it's kind of in the nature of finance and accountants. Right?
JK: And the reason for that is finance, accounting, operations will do whatever it needs to do to get the job done. There's a lot of pride in finishing on time and doing it right. So the moment that you're saying, hey, we're going to rip this out, there is a moment of, well, wait a minute, how are we going to keep this particular boat afloat? In my experience, it is really, really important to say, do you have a situation where you have a tipping point of something going wrong, or is this a scalability question? If something is really going wrong, something has fallen through. Something is not reconciling. You have a potential SOX issue. It becomes very easy to say, time out, we're going to stop. We're going to stop. We need to rip it out. That's the easy one. The much harder one, especially as the company is growing very, very fast, is to say we're going to slow down your deals. We're going to slow down the back end. We're going to have more conversations with our auditors. We're going to just slow down. That costs money. That costs a CV, that costs a ton of money to implement. And time and resource—
AD: Capitalization.
JK: It absolutely does. So the only way to know when to do this and when to do this, right, and it should be led by accounting, it should be led by finance, but you have to get sales product sales ops, deal desk legal and all of the other parts and pieces of the organization on board. Once you understand that, everybody is on the same page, that the next iteration of a company is based on us having a much stronger order-to-cash system. You can have the freedom to make that change. What you cannot have at the same time is somebody in finance, somebody on the accounting side saying, I need to do X and then doing it without setting all of those expectations in a painstaking, explicit way.
AD: So your argument is this should be driven by finance—finance and accounting and not IT? Why is it uniquely Finance and not IT that should be driving this?
JK: Yeah, and I am fully biased. Just for the record, completely and utterly biased on this topic. It is all about seeing what's important and what's key for a publicly traded company. It's SOX. It's financial statement line items. It is those basic things. If you have a restatement of the financials, none of it matters. Your stock's going to tank, bad things are going to happen, people are going to get fired. Period. Right? So if you start with folks who understand that particular piece of it that have that at the top of mind all the time, as well as the risk tolerance and the entire thing, you end up then widening that aperture and saying, okay, now bring in product, bring and go-to-market, bringing sales ops and all of these other teams and say, what is it that you need from an order-to-cash system? And then you reflect on every request that's coming from all of these other teams with the understanding of. But the numbers need to be right. The numbers always need to be right in the very beginning of this evaluation process, because it always starts with that. That seems to be the most important piece of it is choosing a vendor, figuring out the when and the why. You end up hearing from all of these folks and understanding what the resources tradeoffs might need to be, where you need to put more people, where you need to put more money, where you need to put in more time. Because this is going to affect the entirety of the roadmap from a product perspective, especially if you're dealing with changes on the billing side, right? Monetization, using consumption versus whatever it might be, whereas you had ratable before. It is really key to keep front and center SOX and financial statements and then have that open mind. I find and again, super biased, but I find that the longer finance is kept out of the loop or they're not leading. The more trouble you're going to have down the road, when eventually the CFO is going to come to you and say, isn't this going to be a problem? And then you have to rework, you have to go backwards, you have to retool and absolutely nobody wants that.
AD: We've talked a lot about finance. You've talked about the importance of engaging with sales. One of the things you haven't mentioned that much, if at all, is the role of IT. Where do you see the role of it in terms of helping to inform and drive potentially the quote-to-cash process and improvements to quote-to-cash?
JK: Absolutely critical. Absolutely critical. I find that IT – I have a preference for IT not leading. I want finance to lead, but it should be used as a piece of the puzzle that allows for finance to be very open with its goals, its business goals. Right? The business requirements. And putting all of that together is very easy for a finance person to do. But at no time in my in my opinion, any way should a finance person say I need you to do X, Y and Z with the architecture. That's where you get into trouble. It has this broad view of not just today's architecture of a particular company, but where that architecture is developing to and where it's going. So the moment that you say I need business requirements X, Y, and Z, IT business applications will say, okay, that's great. Here's what we think we need to do. I hear you. Let's do this and then try it. Right. You don't want finance to search or solve in any way, shape or form for anything. It is related, but the work of the finance teams to make sure that business applications are really and truly understands. I find that that relationship is the thing that made me most successful at PagerDuty. It was a very open one. It was one where we were able to say, you know what? I didn't understand what you just said because, by the way, and I, a professional and a finance professional should not understand each other all the time. Right. But furthering out those pieces, I think, is exactly where success happens because you don't end up with rework on the back end.
AD: What are some of the unique challenges for finance when you're working inside of an engineering driven technology company?
JK: How much time you got? Because we speak such different languages. Getting somebody on the engineering side to see why prioritization needs to be a certain way is very difficult. They are focused very appropriately so on making sure things are running smoothly, that the product is going out the door, that the features are on time because they do not see the back end necessarily of the finance team. Oh, by the way, the finance team is has a bunch of pieces of tape and some gum, and they'll work the extra hours to just figure it out. The engineering team doesn't see all of that effort right. So in their mind, again, in my very humble experience, they are seeing what they what they are focuses and they are laser focused on it to take away some of that attention to an internal tool is very difficult because it is not fancy, it is not sexy, it is not bright, but it is absolutely critical to making sure that the organization actually runs.
AD: Let's step back for a minute. When you joined PagerDuty, you had the opportunity to see across all of the cash. Presumably you face the age-old challenge of are you going to take kind of a best of breed approach, cobble together whatever you have at hand, make more make improvements as you go? Kind of point by point. Do you take an overarching approach and say, we're going to try to get everything within one platform? How did you think about that problem and where did you land?
JK: Yeah. You end up with a question of how much money, how much resource, how much times of the humans who are doing the actual work that becomes the driver. It was very important for me to understand what the actual flow was. Right? Where could we have potential errors, potential issues with data, handoffs, etc.? When I came in, we were starting to put in RevRec. We had Zuora billing from 2017 implementation and then we were adding Zuora Rev Pro. That was a no brainer. We could not stay in spreadsheets. Right? That's the easy one right? And the team did a phenomenal job making sure that things all came together right. And that's the admin. That's my senior manager on the technical accounting side. And that gave me trust that at least that piece of it was solid. Right. And then we started looking at some of the other pieces to see what else we could move. But to have those key pieces together was extremely important from a trust perspective, etc. I find that you've got to be at the right place at the right time to rip something out or double down on it, because PagerDuty was in such a mode of changing and shifting and truly shoring up the order-to-cash flow simply because the business was moving in a different direction. I had the opportunity to make some, to make some changes, to add some things, etc. and we’ve made as many of the improvements as we possibly could.
AD: It's a journey.
JK: It's a journey. It's complex. You don't want to mess it up. I will say, like you said earlier accountants get that 2 to 3% raise, but if you have a misstatement, you're going to get fired. If you don't get this right, it will be a career limiting item. And so you want to be careful, but you want to move fast enough. While finance drives that particular piece of the transformation, there are so many dependencies and so many dotted lines to all over the organization that right place, right time. But then when you do have that opportunity, you have got to put everything else down and you've got to drive it because the same people who are doing the day-to-day work are the ones who are going to be doing the implementation on the actual new system and making sure that everybody else understands that everything has to stop. You can't have new SKUs, you can't have this, that, and the other. This becomes the only thing that people are working on, while the same time keeping the lights on as a manager, as somebody who does not have hands on keyboards. This was my job. The key was to make sure expectations are all in the same place, and everybody understands what we're doing together, because the faster we finish it, the faster we can start reaping rewards and go back to much more engaging and higher value work.
AD: So one of the things that we see consistently in failed or some I've what's called the semi failed implementations is inadequate staffing of projects. What do you do? Because there's a tendency within finance to say, “well, I can just work a little harder. We can stretch the team a little bit more. We can do this ourselves.” How do you avoid that temptation and make sure that it's staffed adequately, that the team isn't overworked and it gets done on time?
JK: Absolutely. I have so much respect for the work ethic of all of the accountants and all of the folks underneath that. On the operations side, I truly have seen it multiple places. It’s incredible. But sometimes we want to do it ourselves. The trick is, and this is something that we're all working on, myself included. When you burn out, you're no good to the company anymore. So to have that conversation of when you need help, please come to me. We have budget. We have an opportunity to bring in somebody else. Weigh that, of course, against having to teach somebody the entirety of your system. Right. And it all depends on at that point it becomes very granular and very specific. It's all about the people who you're bringing into the fold. If you can get the right engineer, if you can get the right consultant, if you can get the right person who understands your business, your systems, and is actually actively listening. Hugely helpful. But if you bring in somebody who is just going to give you the platonic ideal of slides, it is not useful. So I think it just depends. I think you're going to stretch your team any time you do this. Without question. Stretching is okay. Breaking? Much less so. And again, it depends on the individuals involved. And again, I've been so impressed with the ability of folks in my world to get this done.
AD: Let’s nut it out. What are the three unique business benefits that you saw based on your investments in quote-to-cash?
JK: We decommissioned a large number of extremely complicated Excel spreadsheets. We toned down and removed a number of giant risks to the financial statements, and we made our people be able to do high value work, as opposed to double and triple checking Excel functions. If we were to. If you were to give me two more—
AD: Sure.
JK: I would say better engagement. And from the sales perspective, quicker deals, more complicated deals, easier.
AD: Finance in particular, if you look at accounting as a as a degree and area of study, we're not graduating enough accountants today, and there's a real dearth of accounting graduates that are out there to finance majors. What advice would you give to an organization that's trying to scale the finance function, given the lack of new people graduating into the field or the fact people go work for the audit firms, etc.? How do you find talent today? How do you hold on to talent? How do you scale it up again?
JK: How much time do you have? I actually sit on the advisory board of the accounting department at Case Western Reserve University. This is a question that, as a board, we are talking about every single meeting, the staff, the faculty, the directors at Case Western are doing everything that they possibly can. It's a pipeline problem at the end of the day, right? Kids these days do not necessarily understand how they can apply an accounting degree. So you start there. You start with mentorship. You start with talking to sophomores and juniors. You start saying, hey, it's not just about making sure that you understand the debits and credits. You've got to let them know that you tell stories, the skill set, communication, understanding and the debits of credits. Yes. And the technical accounting piece all come together. The true value in an accounting degree, to me, is the fact that you can tie together numbers on a page with what actually happened during the quarter. That is absolutely invaluable to any C-suite executive who is talking to investors or analysts or whoever it may be. So to me, it is all about showing those students what this looks like and what the job actually is. In addition to that, I do think that the big four have done a great job of setting up some really valuable training.
AD: In closing, Jane, what advice would you give to your former self looking forward saying, what do you need to do in terms of accelerating your career, acquiring the right skills, getting the job done right. What advice would you give?
JK: As a true accountant, when I was younger, I would put my head down and I would work and it would make me myopic. It would make me see a very small piece of the organization. The piece of advice would be go talk to other groups when you're young. Talk to other senior analysts or managers. What do you do on a daily basis? How are you? What do you need? What kind of skill sets? How can I help you? By the way, how can you help me? Start making those connections, start making those decisions. Because again, as you rise up the ranks, it is not actually about being able to work a 60, 70, 80, 90 hour week. That's not what it's about. It's about bringing value and the way that you bring value is by making those connections. Helping folks catch issues up front and earlier, earlier and basically stopping some of the errors that will inevitably happen on the back end.
AD: Jane, thanks so much for the insights today. That was really good.
Thank you for listening to The Margin. If you have questions about today's episode, or if you'd like to schedule a consultation with an MGI analyst, reach out to us at insights@mgiresearch.com. You can also reach us on LinkedIn, Facebook and X, and you can find out more information about our research and advisory work at MGIresearch.com. Until next time.