Taming Payments Chaos with Tal Kirschenbaum of Ledge

Our Guest: Tal Kirschenbaum- A Strategic Leap into Payment Automation Excellence

Tal Kirschenbaum stands at the forefront of the Payments Automation revolution, with a distinguished career that bridges the worlds of finance and technology. Before embarking on the entrepreneurial journey that led to the founding of Ledge, Tal honed his skills and knowledge in several high-profile roles. His academic foundation was laid in accounting and economics, which he pursued as an undergraduate before advancing to obtain an MBA from the prestigious University of Chicago, specializing in finance. Tal’s early career saw him navigating the complex landscapes of corporate venture capital with Intel Capital and strategy consulting with the Boston Consulting Group, where he began to develop a keen insight into the transformative potential of technology in finance.

Transitioning into the tech industry, Tal’s path took an innovative turn as he joined Facebook, focusing on mergers and acquisitions at their Menlo Park campus. This role not only deepened his understanding of the tech ecosystem but also exposed him to the intricate dynamics of payment automation at a global scale. Following his tenure at Facebook, Tal ventured deeper into the payments space with Melio, a Bill.com competitor, where he played a pivotal role in automating accounts payable and receivable processes for SMBs. This experience was instrumental in shaping his vision for Ledge, highlighting the acute need for more efficient, automated financial operations that could serve businesses at scale.

At Ledge, Tal Kirschenbaum applies his extensive background in finance and technology to redefine the landscape of payment automation. Under his leadership, Ledge has emerged as a cutting-edge platform designed to alleviate the manual burden of payment processes and enhance financial teams’ efficiency and strategic capabilities. Tal’s vision for Ledge was born out of a recognition of the fragmented and inefficient infrastructure that businesses typically grapple with, from disjointed ERP systems to cumbersome reconciliation processes. By offering a unified and automated solution, Ledge aims to streamline financial operations, allowing finance teams to focus on strategic decision-making and growth. Tal’s contributions to the field of Payments Automation have not only positioned Ledge as a leader in fintech innovation but also underscored his role as a visionary entrepreneur dedicated to advancing the efficiency and capabilities of finance departments worldwide.

Episode Transcript

Tal Kirschenbaum: Historically, CFOs have been always the ones who’ve had to talk about the business’s performance. They were essentially the holders of the truth in a way. And I think many CFOs have been able to shift to actually being the true strategic advisors that many of them can be. I also think that’s why we continue to see so many CFOs replace CEOs once they depart. It is, I think, still even more so today, one of the most probable, likely candidates for replacing the CEO. And we continue to see that. And I think there’s a very good reason for that, especially with recent advancements.

Jacob Hollabaugh: Welcome to PayPal, the payments industry podcast. Each week, we’ll bring you in-depth conversations with leaders who are shaping the payments and fintech world, from payment processing to risk management, and from new technology to entirely new payment types. If you want to know what’s happening in the world of fintech and payments, you’re in the right place. Hello, everyone. Welcome to Pay Pod. I’m your host, Jacob Hollabaugh. And today on the show, we are going to be discussing automating your financial systems, how you can relieve your financial team of some of that manual payments burden, and simplify the complexity that can come at times and overwhelm at times those teams. Essentially, how to tame payments chaos, which is a tagline so good that I cannot possibly take credit for it as I did in fact, lift that straight from today’s guest, who I am very pleased to be joined by. I’ve got Tal Kirschenbaum, co-founder and CEO at Ledge with me, the company automating your financial operations on a mission to solve payments at scale. Tal, welcome to the show. Thank you so much for joining me today.

Tal Kirschenbaum: Thanks, Jacob. Thanks for having me. Great to be on.

Jacob Hollabaugh: Yes, and thank you for letting me steal that incredible tagline. It’s one of the best I’ve seen. So absolutely love that and had to weave it in there. Before we dive into Ledge itself, let’s do a little walk down memory lane. If you don’t mind, can you give us a little background on how you came to be in the payments space originally, and what drew you to working within this world?

Tal Kirschenbaum: Yeah, absolutely. So I’m a finance person, but also a geek. So I’ve always walked the line between those two different paths starting out in terms of my educational background. So studied accounting and economics as in undergrad and then went on to get an MBA from the University of Chicago, where I also specialize in finance. And in terms of my professional career. So always have been straddling that line between, again, finance and tech. I actually started out my career in corporate venture capital with Intel Capital, which is Intel’s in-house corporate venture capital arm, then did some strategy consulting for the Boston Consulting Group, spent some time with Facebook doing mergers and acquisitions for them and their Menlo Park campuses as part of the corporate development team, and then transitioned actually very deep into the payment space. I got to spend a few years with an accounts payable, accounts receivable automation solution company called Melio, which is a Bill.com competitor. Absolutely fantastic company. One way to think of it is essentially like Venmo for SMBs, for small businesses.

Jacob Hollabaugh: Yeah, very familiar with them around these parts, although I don’t think we’ve had anyone from Melio on to talk. So I’ll have to make a note about that to potentially bring someone from there on to the show. So then coming up on, I believe, two years ago now or just shy of two years ago now, if I’ve got my dates correct, you leave Melio to co-found Ledge. And as your website says, you and your co-founder Asaf have felt the pain of payments before. I liked seeing that. And that leads me to the kind of obvious question I ask a lot of founders, which is what was it that you either experienced that pain that you did experience, or what was it you saw missing in the market that you wanted to dramatically improve upon? That led to the idea in the ultimately the creation of Ledge.

Tal Kirschenbaum: Yeah, absolutely. So I have to say, that’s primarily thanks to my time at Melio, which as a payments company deals with a pretty complex and fragmented infrastructure spanning across its ERP system, its internal database, the banks that it works with, the different payment processors that support some of its payment flows as well, and what Melio had to do simply to serve its customer, as well as to operate as a business, which is to know what really happened with its payments in the narrow sense, and finances in the broader sense, is to try and pull together and bring together all those disparate, siloed data sources. Now, Melio, as a payments company, is quite savvy when it comes to payments, so it was able to invest quite heavily into developing a sort of an internal layer that does exactly that, which is bridging all those separate data sources together and make sense of what really happened with its payments. And again, business in the broadest sense. While Melio, though, had the benefit of being able to solve that challenge with its internal engineering resources, the problem is one that is not unique to payment companies. It is actually an unbelievably common one. So many companies will share that same type of infrastructure of a stack, really, if you will, that the finance team has to struggle with. Which is to say they have, of course, one or multiple different bank accounts. And that’s especially true in a world post-SVB going into stewardship world. And of course, the same goes for payment processors, which many companies use more than one. Of course, companies have to also deal with the data that they themselves generate, and at the end of the day, also make sure that their books are aligned with what really happened. And so they faced this exact same challenge that Melio faced. But unlike Melio, they simply do not have the internal know-how and capabilities to build a sort of. Of an engine internally that’s able to sort out the mess that having this very fragmented stack can cause.

Jacob Hollabaugh: So then that brings us to. Can you give the overview of how large, what the kind of current product offerings are and how you go about solving that pain point for these companies then?

Tal Kirschenbaum: So at the end of the day, what we do is we help finance and payments teams really audit their day-to-day processes, their most common ones. And this is true across a variety of things. So from cash flow reporting and providing visibility into current cash positions as well as projected cash flow into the future to reconcile Ledgering exception handling as well as reporting. And so we’re able to do all of that by actually plugging in and connecting, integrating with the company’s entire finance and data-related infrastructure, those same data sources that I’ve mentioned before, which if you think about it, it’s really anywhere that houses any transaction level data. We pull all that data in and we make sense of it all. We match it, we reconcile it, and we build additional capabilities. On top of this understanding what actually happened with the company’s finances.

Jacob Hollabaugh: The thing within the broader fintech world, and certainly within what you do within it. It’s it is a crowded market these days. That is one of the most common things that comes up on this show is just how far this industry and how far the relationship between tech and finance have come in the last decade, especially even going back further than that. And it is a really crowded market. And so I do always like to ask, how do you go about setting yourself apart from other similar solutions? Because there are similar solutions out there, whether they’re trying to do the entire scope of what you do or little parts of it. How do you guys go about setting yourself apart? What do you think really differentiates you from anyone else doing either a part of or trying to do all of what you guys do?

Tal Kirschenbaum: Great question. So really at the core of it, we view ourselves as being unbelievably finance sick, which is to say, we view finance leaders and finance teams as not just the ultimate beneficiaries of a solution like ours, but actually as the primary and often the sole stakeholder that we work with. And that’s a guiding principle of ours. And so what that means is that we have three core product pillars that we live by, and we build our product, but which are independence, and ease of use. And then, of course, something that actually needs to get the job done. So being able to be effective. And that’s a pretty important distinction across all those three pillars. Because if you think about if you think about independence, for example, what that means is that the product needs to be built in a way that it can just be used day to day by finance teams, but also implemented and configured by them and by them alone, without having to have finance teams rely heavily on R&D for implementation and configuration and then ongoing use. And that’s a pretty major distinction between how we tend to approach this same problem area to to some other solutions in the market.

Tal Kirschenbaum: Now, when you think of the second pillar, ease of use, what that means is that we need to have the finance team be able to get up and running really in a matter of hours or days, and that’s instead of months and even years as some finance oriented solutions can be, such as ERP systems and every kind of heavy old school treasury management solutions can be as well. And that also means that they use their experience needs to actually be something that’s pretty unique, I think for finance teams, especially with B2B solutions. And that is why it needs to be delightful. So it needs to be as close to a consumer-like experience as can be, and that is so that they can actually get the most out of the platform, and the system, and be able to use it repeatedly as part of their day-to-day workflows and processes. And lastly, of course, the product also needs to deliver against what finance teams need, and that is essentially an accurate, robust, scalable solution that is able to help them automate their day-to-day tasks.

Jacob Hollabaugh: Yeah, and obviously the last one is the most important because everything it does come down to, does it actually work? Does it actually do the job and do what you purported to do? But I love that you have those first two pillars, because it is something that has come up on the show before, and that I have a lot of thought about. Sometimes after these shows and after learning about different solutions and things, of think to myself, that does really sound great. But if I was in the role that had to in the company that’s bringing in a solution, I would be a little nervous that they came and dropped off a bag of tools and a tool set that I have no idea how to use, and that it’s going to cause more pain in the timeline of me learning how to use these things than it’s ever going to be able to come back to. On the benefit side of things, so I love hearing the approach of this needs to be able to come in and they can do anything they want with it. It is theirs, but they also can learn how to use that toolset very quickly and get to the benefits very quickly versus basically, we’ll re-educate you and redo everything you do for a year or so, and then it’ll all work for you. But no coming in and being able to make that quick and give them that autonomy.

Tal Kirschenbaum: That unique thing is actually, there’s that thing I think is not unique just to finance teams or unique in the payment space. But I think it’s an even greater issue and problem with actually both of those domains. And again, if you look at many of the kinds of traditional legacy solutions, that’s exactly how they are. That’s why I think for us, it was especially important to try and deliver a sort of an experience, a capability which is one that, to be frank, all of us as consumers, as users would expect, not even want but expect to get nowadays.

Jacob Hollabaugh: Yeah, absolutely. So I think you used the word cumbersome at one point, but you mentioned this tech stack gets a little out of control for different finance departments and different types of companies. And it’s been a few months back now, but you have shared and expanded on this LinkedIn blog post that I found really interesting and wanted to ask you about. The original post was from Waterborne with the headline the traditional CFO tech stack is broken, manual in Excel, addicted. And I’ve got two questions about this. You had some thoughts on why that came to be true and how we could fix it. Obviously, Ledge, being a part of this new generation of solutions that could tackle this problem. What do you think though, were the main factors that led to finance departments falling behind in the first place? As far as technological innovation, was this just the way that it had to be, that they were always going to be last in line to put together all of the tech innovation that came in different departments and different parts of the commercial world Or was there a version, if we went back, that they wouldn’t have fallen behind? What are your kind of thoughts on why how we ended up in the first place? With this tech stack so broken and in need of solutions like yours?

Tal Kirschenbaum: Yeah, absolutely. Again, I think that’s a great question. I think a lot of it is, and unfortunately somewhat unavoidable due to simply the nature of the profession. And so if you think about it, the finance people are trained to be conservative and careful in what they do. Oftentimes you’ll find that teams have this, I’d say really tendency to ensure that you first of all do no harm. That is the mentality. And that is one of the primary operating assumptions that you need to follow. But I think aside from that, there’s also simply inertia is an unbelievably strong force, I think, in life in general. And I think it’s especially true in a business setting and especially true again, for, finance teams, you have a certain way of doing things for decades, and it’s quite difficult to then bring about an active change into that. And I think this is a lot of what we’ve seen. When you combine that with the fact that older legacy solutions had very extended ramp-up periods, both in terms of implementation and then in terms of simply learning how to use these solutions. Then, of course, teams are pretty apprehensive about adopting newer tech.

Tal Kirschenbaum: We spoke about the fact that ERPs and Treasury management systems often have an implementation cycle of 12 plus months, and so obviously, I think finance teams would be a bit concerned about adopting any new technology, just given that they’re all probably wearing some battle scars still. And the last point may be, I think that historically, many of the solutions that were actually focused on helping finance teams do their job were ones that lacked independence, so lacked the ability that finance teams had to independently both implement, configure, and use those solutions. Oftentimes, they would have to rely on other functions, be it product engineering, or data BI. It really is quite broad, and whenever you have to rely on anyone outside of the team, then obviously you’ve got those dependencies. You see timelines extended and it’s just a reality of life. And so I think those reasons collectively were a major factor in contributing to finance teams really being left behind or overlooked, perhaps for quite some time. Although we’ve of course seen significant advancements across many other areas during that same time.

Jacob Hollabaugh: Certainly. And I think all of those are spot on. And the inertia point is super key if we use the word entrenched a lot within the world of finances. It’s the industry that’s been around literally forever, essentially. And a lot of the major players are and a lot of the major systems. Are so entrenched that it takes a lot to overcome the inertia of that big, entrenched behemoth that’s sitting there, getting anything to change, getting anything started, and even rolling down the hill towards progress and innovation can be quite the undertaking to do. Now, the other thing I wanted to ask in reference to that blog post is whether it used the terms Excel, addicted, and a similar sentiment. Actually, this topic is random and nerdy to my heart. I came of age at the time when Excel was having its absolute heyday around the early 20 tens. Around that time period when I was in college, I wasn’t in the finance department, but I was in the business school, and I remember my now wife competing in the Excel contest that was like a big deal in our business school. It was like a proud thing to not just be one of the best students in the finance or accounting department, but like, no, I won or like I went to regionals. There were tournaments for Excel. There still are.

Tal Kirschenbaum: It’s actually sports of sorts now. Global Excel championship, which is streamed live with many viewers. And yeah, I think people like you and I can definitely geek out on that, although some may find it weird, but I’m definitely in that camp.

Jacob Hollabaugh: Yeah, those people are. I’ve watched a little of it and they’re well beyond any of what my compadres were doing back in the day. They’ve taken it a long way. But as much as that is going on and I think we’ll stay because it’s its own kind of niche sport thing now. But Excel has gone from being the most powerful thing in the world of finance and accounting to because we’ve started to catch up in the world of bringing tech innovation to this industry. Excel is slowly but surely no longer like the one tool that can hopefully do what you need it to do. What do you think Excel’s legacy is going to end up being, and do you think software like it? Are other tools similar to it have a place still in this new generation? Or do you just think that’s last-generation technology and we’ve moved beyond the world of Excel?

Tal Kirschenbaum: I love the terms that he used as well. Excel addicted. I think that Excel has been the tool that can do everything and that people have used to do everything, and I think we’ll see a lot of that fade over time as we actually see more specialized, purposely designed tools, take additional functions and tasks and are able to handle them much better and more efficient way. But I do think that Excel, or perhaps tools like it will probably still have some space left to them. At the very least, we will probably see things like highly detailed and nuanced modeling, which I think Excel excels at or shines at. I’m sorry, had to make that pun. So I think we’ll continue to see people use Excel to do so, just because it really is a fantastic tool for that specific type of task. I think that if you look at various types of analyses, and profitability analyses for a product, you can easily see someone at a strategic finance function in a large corporation in continues to use Excel for the majority of their day-to-day work. So absolutely, I think we’ll continue to see Excel and other spreadsheet-like tools continue to be used, but I think we’ll start seeing pieces be carved out over time.

Jacob Hollabaugh: Now, the final couple of things I want to ask you about are some kind of recent news items and other trend-related questions in the industry, the first of which is pretty recent news for you in your team there at Ledge. I did see you got to ring the bell at Nasdaq and made a pretty prominent top 50 list recently. And so one, what was that experience like as someone a day trader at different times of my life and very invested in this industry, ringing the bell at Nasdaq seems like it’d be really cool thing to do. Did it live up to it? But then also, I’ve always wondered with the different top lists that you can make out there, things like that, how much does something like that actually drive, impact, or drive anything that’s going on behind the scenes as far as either validating for you internally that we’re on the right path, we’re doing we’re getting acknowledged by someone that what we’re doing is right. Does it help in the marketing kind of angles, things like that? What was that experience and what is an experience like that kind of mean for a company like Ledge?

Tal Kirschenbaum: Absolutely. Personally, thinking about the experience, you walk past the visitor center that Nasdaq has and while you’re getting ready to go into the studio, they still have actually CNBC’s Squawk Box being taped or rather shared live, filmed exactly within that same studio. So that’s obviously pretty cool. And then they flip it over very quickly over the course of about 15 minutes. And while you’re waiting outside, you see photos of previous notable IPOs such as you’ll see the Microsoft one with Bill Gates and the Amazon one with with Jeff Bezos. Of course, ringing the bell. So it’s a very cool experience. Obviously, I think the required caveat. Here is the current market conditions are such that there not that many proper IPOs, that Nasdaq actually has the ability to invite various types of companies to both market open and market close ceremonies. But it was still a very cool experience and definitely a memorable day. And in terms of what it means to the company in a broader sense. And of course, it’s always great to see and get any external validation to what we do and to the vision really, that we’re trying to bring about of, of really just helping us finance and payments teams significantly, I think, disrupt and adapt to what’s available to them today. And of course, it has some marketing-related benefits, and we have seen quite a nice uptick in terms of inbound traffic as well. But I think at the end of the day, we’re trying to stay pretty focused on what it is that that we’re building and doing, and mostly on the feedback that we get from the companies that we work with. That for us has and needs to remain the key thing.

Jacob Hollabaugh: That’s fantastic. Yeah, I think a good thing to stay focused on but still relish in that. It was a super cool experience and glad to hear that it lived up to what I would expect from the outside, that it would be that really cool experience. Now, one of the things obviously Ledge sets out to do is not just relieve finance teams of the burden of manual payments reconciliation, but help them have the tools to, as we’ve been discussing, drive efficiency, insight, and growth for the companies, take a much more active role, or have the ability in the toolset to take a much more active role, which echoes a topic that’s come up a few times in recent months on the show, as we’ve talked with a few different CFOs about the kind of changing role of the CFO. And really, it’s come up not with CFOs, just with CFOs, but with CTOs with kind of across C-suite positions, that the roles of different C-suite positions have changed a lot in over, really, the last couple of decades. But it’s really accelerated, like a lot of things in the last half, decade to decade or so, of much more driving, of business decision-making, coming from each portion of the company, rather than we all kind of report to the CEO that makes most of these decisions, that drives most of the change. And the CFO position is one that’s been chief among those. And again, we’ve talked about it with multiple recent CFOs on the show about my career, my role has dramatically changed for the better. They have both thoughts or for the more interesting to them. They both thought. Would you agree that a shift has taken place, and how have you seen within your career the role of a CFO or the role of the like lead financial team change within a big enterprise-level company?

Tal Kirschenbaum: Absolutely. I fully agree, I think, with that statement, and I think that all executives have benefited from the broad technological shift and advancements that have been taking place over decades, as you mentioned, and more so, of course, in more recent years, I think they’ve been able to more easily take care of manual, of course, repetitive tasks, such as simply getting informed as to what really happened with their part of the business and shift a lot of their focus to, as you mentioned, decision making and in a broader sense, being a true strategic value-added partner to the CEO. And of course, I’m sure CEOs have benefited from that as well because that is how you get leverage and how you’re able to do even more. Right. And I think for CFOs specifically, that’s absolutely right. They’ve benefited from this in an outsized way. I think that their transition has actually been even greater. Historically, CFOs have been always the ones who’ve had to talk about the business’s performance. They were essentially the holders of the truth, in a way. And I think many CFOs have been able to shift to actually being the true strategic advisors that many of them can be. And I also say, I also think that’s why we continue to see so many CFOs replace CEOs once they depart it is, I think, still even more so today, one of the most probable, likely candidates for replacing a CEO. And we continue to see that. And I think there’s very good reason for that, especially with recent advancements that we’ve seen and those that we will continue to see hopefully as well.

Jacob Hollabaugh: Yeah, the holders of truth that is really good and I’m going to have to steal that from you in the future as well. That’s really fantastic and lays it out so plainly too. Yeah that the role used to be long ago just like hand in the report. But that report literally had where they’re the only person actually looking at the true facts of what is happening in the country or the company, what’s coming in and out. And so it, you know, seems pretty obvious now in hindsight that the person who is, if you’re giving that report to someone and saying, here, take these facts and make a decision based on it, it would seem like you would want to ask the person who’s been poring over and studying those facts and that sheet and that data, the first person. You’d want to ask their opinions of. So we’ve gotten to that place now, and we have, throughout this conversation referenced, the word data has come up quite a bit, one that has not come up that I’ll end on here. The final topic is AI, which I’ve got to ask everyone on the show about these days, especially those working so heavily in kind of data management and kind of getting everyone in sync across a financial team. In your instance here, this was also a few months back, so bear with me as I jog your memory again. But you did a LinkedIn post where an AI tips post that was in conjunction with PwC. I think about some ways to use AI effectively and better evaluate AI providers now that they’re starting to be a plethora of options of who you could turn to for something like that. The one that stuck out was how AI is bet at its best when working with unstructured data. So could you define unstructured versus structured data for us, and then explain why dealing with unstructured data is one of AI’s best use cases, in your opinion?

Tal Kirschenbaum: Absolutely. So structured data, of course, references any data that follows a very well-structured or repetitive and preset schema and unstructured data is one that does not. And I think one of the places that we’re starting to see unstructured data be leveraged and utilized unbelievably effectively by AI tools, ChatGPT, and actually has to do with its ability to fill in the gaps and connect the dots. So by actually being able to pull from various unrelated, often real-time and up-to-date data sources, they’re actually able to build a much more complete picture of whatever it is that you’re now trying to solve, or a prompt that you’re trying to answer or fill. And so one example that comes to mind is, let’s say you need to make a connection between a business’s old and new name. That is something that is actually quite easy for AI tools to do. Again, given that, the connectivity that they have to a very broad set of data sources and this task, although it’s really is a pretty minor one, but actually, a fairly common one, which can bring a business down to a halt if you don’t have that ability to make that connection. I think is a pretty good example of a day-to-day challenge that probably teams have dealt with in the past, and now is something that should be easily solved. But again, there are many examples, and I’m actually pretty excited about both additional use cases that we’ve seen to date and ones that, of course, will come up in the future. And of course, we, as well leverage AI across different parts of the product to categorize transactions, for example, to help with modeling and projecting various things into the future as well.

Jacob Hollabaugh: Yeah. Fantastic stuff. Well, Tal, this has been a real pleasure for those listening who may want to learn more about Ledge or may want to get in touch with you and keep up with everything you and the company have going on. Where would be the best place for them to go to find you?

Tal Kirschenbaum: So I think a website which is ledge.co is a great place or a LinkedIn company profile as well. And yeah, I’d love to to be to connect with really any of the listeners or viewers.

Jacob Hollabaugh: We’ll link to those and more in the show notes below. Tal, thank you so much for your time and knowledge today. I’ve greatly enjoyed it and hope to speak again sometime soon.

Tal Kirschenbaum: Absolutely! Thank you so much for having me, Jacob. Really enjoyed the conversation.

Jacob Hollabaugh: If you enjoyed this episode and want to hear more, head on over to soarpay.com/podcast to subscribe on your podcast listening platform of choice. That’s soarpay.com/podcast.