The future of SaaS billing: Maxio’s CEO on AI integration and leadership strategies

0:01You're alone. You're the only person who can't quit and blame it on the CEO. If the company doesn't go well, right, the investors blame the CEO, employees that leave can blame the CEO, the executives can blame the CEO, but you're the CEO. And at the end of the day, the buck stops with you. And so I think that is the attraction of it and the terrifying aspect of it. And so how do people mitigate that? Or what have I found in my life? What do I tell people? I think there's four things you should do. Welcome to the SaaS Revolution Show, a podcast by SaaS. Here we interview SaaS founders from around the world who've been there and done that.

0:37They share the ins and outs of how they built their businesses, their operations, their path for securing investment and more. Our mission with the podcast is to help you, the founder, learn how to scale your SaaS, maintain your well-being and navigate the complexities of this ever-changing industry. I'm your host, Alex Dima, and together we'll explore the good, the bad and the ugly in the journey to SaaS success. Okay, welcome back to the SaaS Revolution Show. I am your host, Alex Sumia, CEO, founder of SaaStock and general partner of BackFuture Ventures. Delighted today to be joined by Randy Witton, who's the CEO at Maxio.

1:13How are you doing, Randy? Doing great, Alex. I'm looking forward to the conversation. Yeah, likewise. I was just mentioning before we were recording that I was in the U.S. ahead of SaaStock USA, went to Austin. I was kind of thinking, I was doing a bunch of meetings out there and was thinking without looking that you know an added benefit of being there last week would be just getting a bit of sunshine that the UK hadn't had for for several months as it's been a very long winter and then I got really surprised by the weather report and the this well the cold weather that overcame Austin and it wasn't wasn't as expected I know that's quite unusual for a place like Texas but really really caught me by surprise but I'm now back in the UK a little bit warmer and I know the sun is shining in Austin again.

2:01So my timing was pretty bad and unfortunate, I think. Oh no. Is it, is it cold, dark and wet in the UK right now? Well, it is. I mean, it's like, it is, it feels like spring is coming, but it is still wet. It is, it is cold, but it's kind of bearable. I think the winter jackets can be ditched, but I was, I packed for Austin for t-shirts and shorts and I was going to get, you know, a top-up of the tan because my skin hasn't seen sunshine for a long time. None of that happened, but it was still a good trip, and it was always good to be back in Austin. Well, we'll be excited to have you back. I think you're coming in May, is that right, when Sassock?

2:39That's right. Yeah, mid-May, 12th to the 14th, back, so we'll be back pretty soon. Excited, the third edition of Sassock USA. Maxio are going to be there, which I'm excited about. So not too far for you guys to travel, and should be a great event in a great city. So excited for that. Yeah, and I pretty much guarantee you're going to have sunshine and you'll have your t-shirts and you'll get your tan in May. Yeah, we actually, the first ever Sasso USA was end of May and it was getting too hot at that point. So we moved it to mid-May and it's just a little bit cooler, but still great weather. So we should be good.

3:17We should be good. Randy, I always love to start the podcast, getting to know guests a little bit better so our audience gets to know you a little bit better. So we'll start with that. Who is Randy Wooten? You asked me that earlier, and I'm having this existential anxiety about who I am. I would say, you know, husband, father, two boys, which gives me, you know, like joy each and every day. Professionally, I'd break my career into three stages. One, I was in the military for 12 years as a bombardier navigator and A6 intruders. A lot of fun, got to travel the world. I tell people I used to make history, and now I send emails.

3:52But it was a really cool experience. I was over in the Persian Gulf twice and met great people and got to do really cool things. And it was an awesome time. I then transitioned to the corporate sector. And the next 10 years was really just kind of marching up the corporate ladder, working hard, trying to figure out which function I wanted to be in and which type of company, which type of situation I was interested in. I had the good fortune to work at great companies like Microsoft and Salesforce, but I also did a couple of startups. And then in 2015, I had my first opportunity to join the executive suite, and I've been CRO, a CEO, a chief strategy officer over the last 10 years.

4:33So it's my third gig as CEO. Hopefully, I'll get this one right. The other two were incredibly interesting, really hard, and I feel fortunate for how they resolved in a couple of transactions and excited about what the people were able to do and the technology in our customers as we sold those companies. And now I'm at Maxio trying to see what we can do here. Amazing. Thanks for sharing that. And I wasn't aware of some of that background, so it's super interesting. We'll get back to probably some of the hard things about being a CEO a little bit later because it is obviously very hard. I mean, you're in the CEO seat at the moment, but you mentioned you're a CRO, I think Chief Strategy Officer, CEO.

5:19Is there a preference? Is it, well, I'm in the CEO seat and that's my preference, that's my calling? Well, I don't know if it was my calling. I would tell you if I hearkened back to the time I was in the military, I went to the Naval Academy, and part of the intention was, well, I thought I'd be a captain of a ship or a captain of a squadron or if I was really fortunate, maybe become an admiral. And so there was this ambition, even from an early age, to be a leader, to, at the end of the day, have the seat in the center and see if you could do it. And so I think as I transitioned into the corporate sector, that desire, that ambition started to transition as well to saying, oh, well, maybe I could be a CEO at some point.

5:57I never thought it would happen necessarily, but it was fortunate, as everyone is, to have a confluence of luck and opportunity and lots of people supporting me. And once you get to be the CEO, I had one of my mentors tell me, it's kind of like crossing the Rubicon. You never really go back. You're not going to go back to be a CRO or chief strategy officer if you have the opportunity to be CEO. And I think part of it is the CEO job, it's very hard. I mean, there's no preparation for it until you actually are in the seat, as you know, Alex, right? Like it's just a very different dynamic. The upside is you get to spend time with every function.

6:34Like I tell people I fall in love with each function. And in my three roles, I've run every function. I've run engineering. I've run product. I've run finance. Now people could argue I wasn't doing very well. But the opportunity to get to know those functions and the nuances and the dynamics, just it keeps the job super interesting. And then you're really in the middle of the nexus of all information and doing pattern matching, trying to understand what are the priorities and how to help make the tradeoffs and what's the strategy. And so there's an enormous amount of responsibility. And at the same time, there's an enormous amount of reward and joy in terms of helping a group of people move forward into an uncharted space or area of technology and define something that was never there before.

7:19And granted, it's due to the hard work of the people on the front lines. But as a CEO, you get the opportunity to help chart that course. And so, yeah, I don't know if I was born for it, but it's something that I've definitely enjoyed doing. I'm super grateful. I've had a couple of shots at it because I think with each time you get another chance to sit in the seat, you learn new things and you apply lessons from your last run. And with Maxio, you've been in the seat a couple of years now? Two, three years? About two and a half years. Two and a half years. And Maxio is the coming together of Chargify and SAS Optics, who are two SAS billing companies' products, both really kind of well-known.

7:58I think Battery Ventures came in, did a growth equity around 150 million, something like that. That's right order of magnitude in 2021. Yeah. And what can you share? I mean, you've been there two and a half years, so I guess wasn't there immediately after the coming together. But from the time that you've been there, and maybe just the experience in general, a little bit broader about, let's say, two competitors coming together, sort of merging the benefits of this. It might be sort of interesting for the listeners. Certainly, I can recall conversations, let's say, at SaaS Europe, like two competitors sitting at the same dinner table at SaaS Society.

8:39And so, should we merge this sort of conversation? We'd love to get a bit of your experience there. Yeah, so I would say first thing is I describe myself as a professional CEO. What I mean by that is I'm not smart enough to be a founder. I don't have the big ideas that are going to change the world. I come in to a company that something's not working. It's usually at the growth stage. And my background experience, to your earlier point, is I've tended to be a go-to-market guy. So sales, service, and marketing. How do you define a category? How do you define a compelling positioning of messaging?

9:10And how do you drive the strategy going forward? And so for different situations, investors usually are looking for someone to help take the company and pivot it. So with Maxio, similarly in 2022, they hadn't gotten as much traction as they had wanted with the MOE, the merger of equals, and wanted some new blood to come in. And so that's why I joined. And we can talk about how I approach that more broadly. But what I would say, what I really liked about the merger, one was I had been a customer of SaaS Optics at my last company, Percolate, and it changed my life, literally changed my life in terms of how I and the CFO ran the business, how we raised money, how we managed investors.

9:50So I was super familiar with the SaaS Optics value prop, and they were invoicing with RevRec and reporting. I was less familiar with Chargify, though I had known of them by reputation. Both brands had been in the market for 12 years prior to the acquisition and had great brand equity, about 1 ,000 customers each. And so strong, north of 10 million, so had made it to scale. And so bringing those two companies together was really interesting. The investment thesis was less about competition because Chargify was really focused on the low end of the market. So small customers and more of competing like the stripes of the world, more of like when a company moves from payments to billings for the first time, a PLG motion.

10:35And so when talking to the battery folks and the executive team, when they brought the two together, they felt like it was very complimentary. So SaaS Optics gained this access to high-velocity billing, usage-based billing, which they didn't have. They were more invoicing. and similarly, Chargify got access to this red rack and reporting, which is what their customers was talking about. So it really was this less of a competitive takeout and more of this interesting synergy in the space. And at the same time, there were some great competitors in the marketplace that were doing stuff. And so I think both of them saw it as an opportunity to not just catch up to the market, but to define the next wave of the evolution of billing.

11:16So Alex, to your point, like sitting around a SaaS society, I think you've really got to be clear about, are we complimentary or is it a competitive takeout? Both are viable strategies, but very different, I think, in how you approach the investment thesis and how you build the company post-close. And I'd love to learn, you mentioned how you approached it when you came in, how you've approached being the CEO of now this combined force, which is Maxio, and maybe some lessons learned over the, a couple of lessons learned over the last two and a half years. Oh, gosh, Alex, how long do you have? I've got lots of lessons learned.

11:51It's just one of those we should be sitting at dinner and having some wine. Yeah, we can do that in Austin, but we'll do the 10-minute version. The short version is I think that every CEO, and I'm not the first person to say this, but you should have sort of an operating system model in your head. And I'll give you a couple of books that we can throw in the show notes. One of my favorite is Galbraith's Designing Dynamic Organizations. And he talks about establishing a strategy, articulating the structure, but then getting clear about roles and responsibilities, process systems and tools, and then incentives to drive that.

12:25And if you think about that as a system, like every organization that you're involved in, small team to large organization is going to have those different components. And so you have to be thinking systemically about the situation that you're walking into and then start to think about where are we struggling? Are we struggling with the revenue architecture? Are we struggling with the team? Are we struggling with the process and systems? Are we struggling with the category? And so you start to identify the problems. Then I think you come in with a, and this is some of the benefit from having been at the larger companies like where Microsoft used to do MBOs.

12:56At Salesforce, Mark Benioff has a V2 mom process, what I would call a company operating system. So what's your company operating system? How do you lock down in terms of here's our vision, here's our values, this is what we need to accomplish over the next 18 months, here's your OKRs, objectives and key results, and here's a scorecard. If you have an operating system in place, you can start to then enact change because when you're trying to get people to step into this new world, they hold on to what was legacy. And so you have to create a new vision. I obviously called it One Maxio. So what does it mean to be One Maxio?

13:29What's the vision for the company? What's our strategy of bringing these two things together? And it takes a while. And so I think the CEO's job is really to help define that vision of the future and then inspire, try to get people to step into it and be in a new place. I think the other advantage you have coming in as a CEO to this type of MOE or an acquisition or company is you get to kind of turn the chapter onto this next phase. And I'm coming in only, my only motivation is to do what's best for the combined entity. So it's not like, oh, this is the way we used to do it at Chargify. this is the way we used to do it at SAS Optics.

14:07Now there's a one maxio way. And so I think that articulation and inserting an operating system, being sensitive to the overall system that you're operating within are some of the approaches. The other thing, last thing, and then we'll get to some of the lessons learned, is I do think being clear with the board, even before you start, about what the remit is and what success looks like in the first 90 days. And so I always have a 90-day plan. There's a great book, now I'm forgetting about it, First 90 Days. First 90 Days, I forget the author. But that person has this great construct. There are like five conversations you want to be having with the board or with your boss if you're not the CEO.

14:47But it helps frame over a short period of time what are the quick wins you're going to go after, what are the things you're going to explore, what are the key questions you need to keep thinking about. And it has a time frame around it that you come back after 90 days and report out and say, look, I came in, these were a set of things I was thinking, guess what? Some of these are right, some of these are wrong, and oh, here's some new things I need to be thinking about. So I think that real focus and default to action and executing within a construct of 90 days is very helpful. And you've obviously just spoken about the importance of having a system, you know, thinking about like the first 90 days, speaking about or working with the various different departments as, you know, something you love as a CEO.

15:33If we look at like this week, right, and I don't know if you have a typical week, but in general, as a CEO, where are you spending your time? Like, so how much time, you know, across departments or just with the leadership team on strategy, looking at, you know, the bird's eye view, meeting customers, sales, et cetera. We'd love to just know what that looks like. Yeah. And, you know, it's a great question, Alex. And I would actually encourage every CEO to track their time because I think there is you have this idea of where you're spending your time or where you want to be spending your time. And then there's a reality of where you actually spent your time.

16:08And now I'm fortunate. I have an EA that is able to schedule. So when we align and say, hey, I want to spend 30 percent of my time with customers or partners, she's able to take that and sort of manage the meetings. Otherwise, you know, create space for those types of things. And then every week she provides a review of where did I actually spend my time. And we talk about next week, or really it's like the next two weeks, in terms of what does it look like. And, you know, am I meeting with enough customers? Are I meeting with enough partners? And, you know, board prep, et cetera. We just did a year-end review in terms of the full year from 2024.

16:43How did it play out in terms of the amount of time I spent of those different categories that you identified? And what I found was I was spending less proactive time with customers. I was spending a lot of reactive time with customers when things weren't working because then you get pulled in. But what I was missing was more of the, hey, let's take the strategy that we've been working on and validate it with our top customers. And so as we think about this year and the operating plan and, you know, I've just been working with my chief product officer about how do we get more, it sounds stupid, but more customer focus.

17:19But how do we set up a customer advisory board? How do we use events like yours and have dinners where we're not just, you know, meeting and greeting, but we're actually having substantive conversations about what's going on with the industry, what they like from competition to really have more of the external listening poise. So I think that's an area where I haven't spent as much time. And honestly, Alex, it's just because, you know, there's so much stuff that pops each and every day that I get consumed. And the important, maybe the urgent, hopefully it's important. Sometimes it's not important.

17:50And that's where I really need to, at the end of the day, think about, gosh, where did my time and life energy get sucked? Because all we have is 24 hours. The most precious commodity we have as CEOs is our time and attention. Where do we put it? And so I think it's hard, unless you're deliberate and have someone who can help act as a buffer, so an EA, to block time and space to have the important, not urgent conversations. Yeah, I mean, I resonate with this, and I'm sure many listeners do. And I think maybe just a relevant example, in my case, I had a virtual assistant, probably up until just before summer of last year.

18:32we then parted ways and I was spending a lot of my time last year because it was a tough environment you know focus on sales and customers and then as we got towards the end of the year and trying to balance it out a little bit more a bit more on strategy thinking about you know the next 12 24 months and effectively just managing my time it all of a sudden became chaos. And then I'm also doing, like found myself doing a whole bunch of admin tasks, which are really time consuming, but really not moving the dial for the business, right? So I am now just signing a contract, getting a virtual assistant back in, where initially the aim and the sort of result will be that I'm buying back 40 hours of my time a month, which is pretty significant and it could actually even be more um and so i can spend time on you know the things that that matter the things that i enjoy don't suck my energy you know just have a better idea of what what's going on um so yeah i i i've learned the hard way of like not having that function the virtual assistant or executive assistant uh and the impact that it's had and perhaps just how exhausting it can be without one right um and it can be very cost effective and from a virtual assistant perspective you know it's not a lot of money right so uh hoping and i'm sure it will work out this time and uh i'll i'll buy back my time and and spend a lot more in the areas that i need to uh as a business so uh so if you're thinking about should i have as a ceo should i have an ea or va i would certainly look into it and look at where you're spending your time because it can be a very crucial hire.

20:20And if people are interested in that, please have them reach out to me. I'm a small investor in a company called Doxa, which does business outsourcing based in the Philippines. And that's what they offer is lots of different roles, but the Philippines economy is primarily like a BPO economy. And I have this wonderful EA who I feel bad she works my hour so it's her through her night um but she's great super attention you know very very detail oriented attention to detail uh is great with follow-up english is if not the first language it's they all speak it in native english great communicators through through email and so i i don't even and with all the technology we have today it's it's like she's next door so um it really is wonderful and i recommend it to anyone and happy to provide introductions or you just find it online.

21:11I mean, there are other ones that do it, but I just, I know the CEO, they're high integrity. They pay their people well, offer benefits. And so I think it's a wonderful, wonderful organization. Awesome. Awesome. And Randy, it wouldn't be a podcast in 2025 without talking about AI. How, I guess, two part question, how have you been thinking about AI as a CEO and the strategy and how it's going to impact the business. But then also relative to billing, what are your thoughts around that and the future of SaaS billing and subscription billing with AI? Yeah, well, I think there's probably three dimensions to AI that we talk about.

21:55One is what are you doing to just play with AI and get better and smarter? And I think a lot of us are using ChatGPT or something along those lines. I found that to be an incredible augmented intelligence in terms of when I write notes to the company, I run it through. When I was writing my operating plan this year, I'd run it through and have it tighten up and draw more connections. It was fabulous. I've been working on this paper, which we'll talk a little bit about adaptive billing, and I was in dialogue with ChatGPT. So just really augmented my own ability to think and move quickly with ideas.

22:26Be careful when you ask it to cite sources. It makes up sources. so there were Gartner reports it was referencing that I couldn't find and it was really really funny I kept saying and now really is this a you know report can you point to it and so anyways I think it's that's why I think of it as augmented intelligence it's not going to replace you but it's there you can be in dialogue with it I think there's another dimension to how are you taking advantage of the AI that's being available made available through every company is trying to figure out how to create more efficiency and effectiveness.

22:59One thing we've done is we've rolled out AI chat for support, like many people, and that's allowed us to scale the support organization. We are starting with AI SDRs. We're doing stuff with marketing where we're building entire campaigns. And I've challenged the entire team over the last year to go find how can you not just use AI to get better as an individual, but how can you use AI to get better in your function? I think what will happen, Alex, is that the VCs going forward are going to expect you to have an AI efficiency gain. And I've seen slides going around amongst my CEO friends that it's upwards of like 30 % of what they're expecting, meaning you're going to have to drive 30 % more efficiency cost per FTE as well as ARR per FTE going forward.

23:49And all the other companies are going to do it. So if you aren't encouraging your teams to be working and adopting this new technology, you're going to fall behind. We had last year an AI challenge, and I kind of thought it was goofy. But I was really impressed. And when we sat down at the end of the year and I asked each executive to walk through how they had used AI, it wasn't, you know, I thought maybe 40 or 50 percent of the teams would have been using it. A hundred percent had been using it. A hundred percent. Now, some to greater effect than others, but 100 % had been experimenting with AI tools.

24:23And I think that's the future. So this year at our company, Kickoff, we have four challenges, much like most people. We need new business. We've got to retain customers. We need to come up with new innovation. And we had people join the team that they were most interested in, which business problem they wanted to engage on. And the assumption was they were going to work together cross-functionally and come up with some way to use AI to address this problem. And we're going to work on that all half, and then we're going to do a readout and a celebration at the end of the half. So how do you as a CEO and executive team inculcate this value of experimentation with AI within your organization?

25:01So that's how I think like two dimensions of AI. The third dimension of AI is what you're pointing to is what at your core as a company can you do with AI to impact the industry you're in. And I think, Alex, it really is important to understand, do you have a system of record? Do you have data that is unique? If you do, then you can layer in an intelligence layer on top of it and start to do things like benchmarking and forecasting and your data. We have over 2 ,000 customers. We collect the data anonymously. We publish the results in this thing we call the Maxio Institute Growth Report. You've probably seen it where we give a view of what's happening in the private markets.

25:44Again, we can put the link to the show notes. But all of that's a manual grind right now because of the way our database is structured. We're moving forward with refactoring our database and aggregating the data. We're going to move into a data lake, data pipeline. And so we are doing all this plumbing work as a company so that we can get into the AI space, the augmented intelligence move from workflow automation to an intelligence engine. The challenge is there's a bunch of companies that have started in the last two years that are AI first and they're out of the gate, you know, and their database is right for the, you know, their vector databases and they're using Python and all this stuff that you need to be really successful that we're wrestling with tech debt to get there.

26:27We know we have to get there. We're moving as fast as we can, but people aren't paying for it right now. It's you got to make a bet on it going forward. So how does that play out? I think that all the money in VC right now is going to AI. Now there's kind of chat wrappers, there's true AI, there's infrastructure, but all the money in the VC is going into AI. Number two is I think AI companies are wrestling with how do they monetize their solution? You see this with open AI. They have three different types of tokens and they charge differently for it because the costs are real. Well, at least until DeepSeek came out and said, hey, we built our model for$6 million.