The world of B2B subscriptions has changed a lot since companies like Salesforce first paved the way for what would become known as Software-as-a-Service. And while there are hundreds of marketing and sales-oriented SaaS products, it’s taken a lot longer for the subscription model to be fully embraced in the CFO’s office.

Randy Wootton has seen the evolution of SaaS and understands the changing role of the CFO better than most. He’s led businesses focused on sales and marketing solutions at companies like Salesforce, Microsoft, and Rocketfuel, but more recently took over the CEO role at Maxio, a leading provider of billing and financial operations solutions for B2B SaaS companies.

In this very rich and full conversation, we talk about why pricing and packaging of subscriptions is so hard, the power of a pricing council, and the changing role of the CFO in a SaaS world.

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Subscription Pricing, Metrics and the Changing Role of the CFO with Maxio’s Randy Wootton


The world of B2B subscriptions has changed a lot since companies like Salesforce first paved the way for what would become known as Software-as-a-Service. And while there are hundreds of marketing and sales-oriented SaaS products, it’s taken a lot longer for the subscription model to be fully embraced in the CFO’s office.

Randy Wootton has seen the evolution of SaaS and understands the changing role of the CFO better than most. He’s led businesses focused on sales and marketing solutions at companies like Salesforce, Microsoft, and Rocketfuel, but more recently took over the CEO role at Maxio, a leading provider of billing and financial operations solutions for B2B SaaS companies.

In this very rich and full conversation, we talk about why pricing and packaging of subscriptions is so hard, the power of a pricing council, and the changing role of the CFO in a SaaS world.


Robbie Baxter: Randy, welcome to the show.

Randy Wootton: Thank you. Glad to be here.

Robbie Baxter: Yeah, it’s great to have you. You’ve been in the world of B2B Software-as-a-Service for a long time. And I was hoping you could start by just walking us through your subscriptionography when your relationship with subscriptions started and how you’ve come to be the CEO of Maxio?

Randy Wootton: When I went to Salesforce, Marc Benioff was key to the whole, “Hey, we’re software in the cloud!” and mainstreaming the idea of SaaS, which I think has two components. Number one is how a software delivered and Number two is how is it paid for?

The legacy model was on-premises software (on-prem) and everyone built software or sold a bunch of software. I actually met with a group called T.S. I. A., Technology Services Industry Association, and a guy named Thomas Law, who wrote a book called B for B. He’s written seven books, but one book I found incredibly powerful. His whole mission, and they’ve been around for a while, has been helping companies move from an on-prem software model where you are maintaining it yourself, you’re buying the house versus renting it to the software delivered as a service. We called that web-based Active Server Pages (ASP) in the early days, which was we had a software that we delivered and people bought it and rented it like an apartment.

The other change was around the business model. And it was Bennioff who really championed this in terms of since you were renting the software, you could pay for it out of operating expenses rather than capital expenses. And so it reduced the overall cost upfront and amateurized it over time.

And that business model was radically new and different. Then the third part, in which I had grown up in services, and how did that manifest? Well, in a SaaS model where you’re renting the apartment, you expect to have a landlord who’s going to take care of things when they’re broken and that whole function around customer success was a new idea in terms of how do you get customers up and on the platform? How do you continue to deliver value so that they were new? Right. You haven’t sold the phone or the prepackaged software on-prem and walked away. Maybe you had a maintenance contract instead to get the value out of the contract. You had to work with the customers over time. So I think there were a couple of different elements that made SaaS very different, but it was what I started with from the very beginning of my career. So I didn’t know anything else other than SaaS. I mean, I went into SaaS deliberately because it was the business model of the internet, as you’ve written about in your books.

Robbie Baxter: Yeah, it’s great. we’ve talked quite a bit in the last couple of weeks and I’ve really enjoyed hearing about your journey that brought you to Maxio where you’re now the CEO, and your experience with Software-as-a-Service.

And with that second point that you just brought up, what does that do from a financial perspective? Going from capital expenditures (CapEx) to operating expenses (OpEx) and what does that mean for the office of the CFO.

Before we get into what and how the role of the CFO has evolved, I want to spend a little bit of time talking about how you align value with pricing and what kind of subscription is one step in that but I was interested in how you think about the best way to align value and pricing, thinking about growth from a sales-led perspective versus a product-led perspective, and just what changes as you try to get better at aligning the value that your organization provides with the way that you charge for it.

Randy Wootton: Yeah, that is a great question, Robbie. And I would say what was interesting for me about starting this company was that I didn’t start company but joined the company after the merger of two companies. I was having a conversation with my lead investor, Chelsea Stoner, who’s just brilliant and has been in the space for a super long time, incredibly successful. And we were chatting about pricing and packaging and she said, “Randy, across their portfolio, pricing and packaging is the most difficult exercise and it is the thing that few people bring experience with, and most early stage companies get wrong. And so I think your implied point is, how do you associate value and quality delivered with the price that you’re paying?

I think there are a couple of ways to think about it. When I was at Seismic, so I was CEO of another company called Percolate. We were a content marketing platform. We sold Seismic, which is a sales-enabling platform. The idea was how do you connect the production and distribution of content from marketing to sales to prospects and customers?

One of the interesting ways that we’re thinking about pricing in that specific space was, “Hey, we’re selling to the office of the Sales Leader CRO. There’s a price per seat that they’re probably willing to pay, and it’s not going to be 500 dollars per AE. And so then you’re competing with all the other software. So Salesforce, Gong and Clari and etc, everything in the sales tech stack. You’re competing for part of what is the amount of dollars that someone is willing to pay for technology broadly across SaaS businesses. We’ve seen that it’s about 2 percent of revenue that people are willing to spend or best in class in terms of spending on your SaaS software.

Robbie Baxter: Sorry, just to clarify 2% of your revenue on all SaaS software or just specifically for the sales stack?

Randy Wootton: No, internal software. So that’s across all functions, not including cost of goods sold (COGS). So you have software that you would be supporting like Amazon Web Services (AWS), and then you have other software that you’re using to just deploy your software. This is more about your marketing stack, your sales stack, your CFO stack in this case.And within that, you double click down on the sales in this specific example and say, “Okay, well, how much does that translate into percent of revenue you’re willing to spend on sales tech stack, how much does that translate into dollars per AE and then what’s the relative value that you’re offering versus Gong?” I’ll just tell you Gong commands an incredible price point in the world around sales enablement and conversational intelligence. So you’re trying to chip away at that and increase your price. One pricing strategy is understanding what is the willingness to pay and the budget that you’re competing with.

The other strategy around pricing, which I think is more modern now in the subscription business, you have different types of subscription businesses that you’re alluding to. One is sales-led where you’re doing a negotiated invoice, and obviously, a sales team is doing it. The price can come down to a combination of factors in terms of what are you charging for the platform? What are you charging for the modules? What are you charging for professional services? Each of those components, you should have some understanding of your ongoing cost to serve or ongoing cost to deliver so that you have a perspective on profitability and contribution margin. That’s one model.

Product-led growth is people coming to your site. They get a free trial. They sign up, they’re able to self-instantiate, and you have very little cost in terms of sales and customer success, so you can offer a lower-priced product as you move them from a freemium to a trial What we’re finding in the product-led growth model and across the cohort of customers that use that model is a usage-based pricing model where you identify a specific widget or some type of attribute that is associated with value for the customer and you charge based on that individual widget.

When I was at Avenue A, we did third-party ad serving. Third-party ad serving means that you would price based on the number of ads that you were serving. And so the value was associated directly with what you’re delivering. Think about it similarly to telephones or cellphones. Cellphone service used to be how much data did you consume? AI companies, modern AI companies now are charging based on number of attributes that are being rolled into the model. You can have different types of pricing strategy, and at its core, you’ve got to be able to demonstrate the value to the prospect or customer such that it makes sense on their side economically.

Robbie Baxter: Yeah, this is so interesting, and you’re bringing up several points that are important for our listeners to understand around the options they have with pricing. That pricing is based on the number of users or the volume of usage. If it’s about the volume of usage, what is the unique metric?

I think one of the reasons that you were talking about how SaaS products that are aligned with your actual cost of goods are in a different category because that ties directly to revenue. Suddenly, you have access to more budget if you’re in that category, versus being lumped in with all the internal SaaS stuff. For listeners, it’s really important to understand how your customer manages their budget and what they’re going to tether your pricing to. Are they going to price it against an outcome? Are they going to price it against, “I have this much money, and I’m going to allocate it equally?” But there are a lot of choices that people have, even in something as structured as a SaaS model, you’re not limited to seats. There are lots of different ways to think about it, and some of them are going to put you in a different category and maybe get you out of the fray a little bit.

You can have different types of pricing strategy, and at its core, you've got to be able to demonstrate the value to the prospect or customer such that it makes sense on their side. Share on X

Randy Wootton: Yeah, so to that point, like Maxio, one of the reasons I joined Maxio was that it has a different business model than the classic SaaS model, which is about seats, features, and divisions, meaning you expand a customer through either adding more seats, rolling out more features, so you get your add-on and your expansion, or your division hop.

You move over to another division within that customer. So customer growth—how do you run customer success plays? How do you run renewals? It is very standardized. That’s what I did at Salesforce, Microsoft, Avenue A, and Quanta, an advertising model; it was a little bit different. At Maxio, our pricing is based on percent revenue because we’re a billing and invoicing solution. The faster a customer grows, we have different tier-based pricing tied to their trailing 12 months of revenue. It’s different. It’s hard because, with customers who grow very quickly, they’re like, “Hey, I was spending $10,0000 with you last year, and now you’re charging me $60,000 based on my growth. Why should I pay that?” And you talk about all the value that we’re creating, the reporting, the insights, and the revenue recognition. It’s a different type of pricing model, almost like a usage model in that regard, because you’re tied to their revenue growth.

At Maxio, our pricing is based on percent revenue because we're a billing and invoicing solution. Share on X

It does come back to Chelsea’s point, having pricing and packaging as a capability that you are building once you get past that, 5 million-dollar threshold and you’re in a 10 million-dollar zone is absolutely critical. The other insight that I would offer is my background experience. I’m like, “Hey, if you don’t have pricing capability inside, you should go hire a consultant, and there are a bunch of pricing consulting firms out there that can help you do the market analysis to determine where you are in the market and your price point versus the competitors. They’ll go do a bunch of research with prospects and customers in terms of value and how to associate value. You create your zone, a possible agreement where you could price the people who are still willing to pay.” That market check is probably worth doing every 2 to 3 years.

Navigating Customer Growth: Maxio’s unique pricing model adapts to customer success and renewals tied to revenue growth. It’s not just a billing solution, it’s a strategic partnership in value creation and growth

We did that when I started because I didn’t understand the business model. I just wanted to understand where we were in our pricing structure and strategy. It was a little complicated. So we hired an external consultant and how we came out of that? I was like, “Oh gosh, we need to set up a pricing council.” Meaning every 90 days we’re going to get together and review our pricing and see how it’s working with different segments. See how our win rates are being affected by new pricing with new products. See how our churn rate is being affected as we roll out our new pricing. Across the board and SaaS, there’s been a 9 percent increase in price like Salesforce. Salesforce raised their prices in August and just said, “Tough. This is the way it is. We’ve launched a lot of bunch of features and you guys are going to have to pay more.” And you’re like, “Wait, what’s going on?” Anyway, my point was going to be, I made a proposal to the board, “Well, we should hire a pricing strategist.”

And it was super interesting. They said, “You know Randy, pricing is one of these things your core team, your customer success, sales team, product team need to have pricing as a muscle they build, and if you outsource it to a pricing guru, you lay it on a lot of bureaucracy without really building the capability as a muscle of the team. And I thought that was super interesting. So now we have a 90-day. We get together and we’ve already found some really interesting things in terms of how we segment our customers. This is the advertisement for Maxio. This is what Maxio lets you do. If you’re going to be SaaS in terms of understanding what’s happening in terms of your revenue, churn, and expansion by customer, by product, by segment, by region and you can look at that level of detail to say, “Hey, what are we going to do with our new pricing and packaging?” It’s one of the biggest levers you can pull and we’re doing it collectively as an executive team versus having a pricing specialist

Pricing is one of these things your core team, your customer success, sales team, and product team need to have pricing as a muscle they build, and if you outsource it to a pricing guru, you lay it on a lot of bureaucracy without really building the… Share on X

Robbie Baxter: Yeah, I love that. What I find really interesting is I haven’t heard any practitioners talk about a pricing council. I’ve heard several talk about bringing in pricing expertise as a one-time thing every year or two, which is great, but the importance of having pricing as a muscle and having it be a differentiator. Mark Stiving, who’s a pricing educator and consultant, talked about this, and Marco Bertini, who’s an author and a professor at both Harvard Business School and Esade in Europe, believes that always working on pricing against an ongoing outcome for the customer is the number one most important thing that a company should be doing. It’s fascinating to me to hear about your journey at Maxio and the fact that you’re continuing to iterate, evolve, and get smarter about what drives value and what drives the perception of value. Great lessons for everyone listening to think hard about what are your options. There are some pricing options that work great to get people on board. And there are some pricing options that work great to expand over time and to keep the relationship for the long term sort of trying to thread that needle.

Randy Wootton: Yeah, I think that’s right, Robbie. Two other quick stories. One was when I was at Salesforce, I was responsible for customer success products. So developing services as a product, marketing, and distributing them, so when you think about SaaS or software, you have the software that you buy, and what’s different than on-prem is that you used to pay implementation fees, and then as a provider, you would leave or you would charge a maintenance fee, an ongoing 15 to 25 percent maintenance fee for the on-prem model, as we were talking about earlier in the software subscription model, you have this ongoing relationship, and one of the things that we were trying to figure out at Salesforce was how could we better articulate package and sell services at different stages of the customer’s journey?

So they’re getting up. You probably pay for professional services and implementation. But what are the adoption services that you could charge for versus just giving away free. Data and insights, technical tests and architecture. Salesforce does this really well. I brought in your point, a pricing specialist. At Salesforce, we have a lot of money, so we could hire someone with an incredible background and experience who was a pricing expert for product and services pricing. So the the first type of consultant I was talking about was more like a market check Where they go out and do a bunch of surveys and they have a bunch of insights but having someone I brought on board to help us with deliberate packaging and pricing strategy, what pieces of capabilities could you put in different packages and price? It was really powerful.

Number two was the point you were making around value. Price is associated with a certain level of value. So, how do you articulate that value? That’s a messaging challenge and a positioning challenge, that’s an ROI total cost of ownership challenge. So we rolled out ROI calculators so that when we go into a sales cycle, we’re able to say, “Hey, this is how we think we can impact your organization in terms of efficiency and effectiveness. These are the assumptions in terms of cost savings, etc. And so this is why our price point is what it is because this is what we’re helping you with.” But you have to continually be able to articulate what is the value that you’re providing.

When Salesforce raised their prices by 9 percent, they said, “Look, here’s all the investments we’ve been making in the time that you’re benefiting.” It’s like retrofitting the roof on the apartment, rebuilding the foundation, or building out a jacuzzi, If you’re the tenant, you don’t necessarily see that value, but as the provider of that apartment, you need to continue to articulate that because you are making all those investments in engineering and restructuring your database so it’s faster, etc. And if you’re not doing a good job of that, then the pricing conversation turns into an arm wrestle around, “Well, I don’t want to pay an extra two bucks per head or whatever. I don’t need a roof. Why did you put a roof on?” This ongoing value realization has to be communicated through your customer success motion so that doesn’t become a surprise.

At the time of renewal when we’re trying to pull the pricing lever and everyone else, like all of our customers, are in a contracting environment with super intense pressure to control costs and like,” No, I can’t pay that.” And you don’t want to turn a renewal into a churn. I do think this pricing strategy, regular connections, and thinking about how you drive it with those new prospects as well at the time of renewal is critical.

Avoid the arm wrestle over a few bucks: Continuous value communication through customer success prevents surprises at renewal. In a cost-controlled environment, strategic pricing connections ensure renewals don’t turn into churn

Robbie Baxter: Yeah, great points. If you want to have a forever transaction with your customers, if you want them to stay forever, you have to build that relationship from the very beginning. And you have to communicate the value you’re providing and make sure it’s aligned with the ongoing outcome that the customer is hoping for. And I think your point about the role of post-sales of customer success is to find ways to communicate what value is something that’s often overlooked by organizations that maybe over-index on the initial sale on the transaction, rather than thinking about how do I justify the loyalty and the trust that actually leads to the renewal. And the other thing I just want to point out that I believe is that if you’re not sure if someone’s going to renew at the moment of renewal, you have not done your post-sales motion very well, you should know what’s going on with that customer leading up to the days of renewal rather than kind of being, I see companies that are sort of in a tizzy in the last whatever weeks before a renewal is expected because they haven’t really stayed on top of it and they don’t really know how the customer feels about how the cost has gone up, either because the customer is growing or because of an internal pricing change.

Ongoing value realization has to be communicated through your customer success motion so that doesn't become a surprise. Share on X

Randy Wootton: Yeah, that’s a great point, Robbie. Just going back to my Salesforce days, I think we had this brilliant data scientist and he had an enormous customer base. And what he was able to do was build an attrition predictor. And it came down to four factors in terms of how people were using the product, engaging with the services, etc, that he could do pretty accurate forecasting predictions to determine which customers were going to fall into which buckets.

Why this is so important is that at some point, you’re going to have too many customers for you to have one-to-one engagement through the post-implementation adoption cycle. So you’ve got to have a segmented customer success approach where you have your high-touch customers where you can afford to put either assigned or dedicated customer success resources against where they’re going to be meeting on a quarterly basis, doing health count checks, reviews, etc.,, understanding business problems, and matching strategic priorities. You should never be surprised at your highest segment.

The challenge is when you get to the medium and low segments where you’re doing web touch engagements, primarily through support, community webinars, learning. It’s super hard to know how a customer is feeling. You could do the Net Promoter Score definition (NPS). You can do some Customer Satisfaction (CSAT) surveys, but that’s where it’s critical that you have intelligence built into your product so that you know if your customers are using your product.

If you're not sure if someone's going to renew at the moment of renewal, you have not done your post-sales motion very well. Share on X

How many daily average users, monthly average users, and module adoption. What is the key trigger that you know people are getting more value out of your product versus if they’re pulling back. If we see a customer at Maxio that’s stopping invoicing, red alert should be going off in terms of the person’s not using our system to do invoicing. Well, that’s the core value. All the other stuff we offer in terms of revenue recognition reporting is tied to invoicing. If the invoices aren’t going out, we’re absolutely up the creek. But what’s so hard is doing customer success at scale. How do you figure out how to use system technology in today’s AI technology to be able to distinguish the customers that are at risk and then make decisions about who you’re going to go after? I think one of the other challenges we’ve had at Maxio is we love all of our customers. There are some small customers that set up, suck up an enormous amount of time and energy. We’re trying to move to a world where we’re embracing unit cost economics and we can look at each customer and say, “This is how much they cost to acquire, we need to get our payback on our cash. This is how much it costs to serve over time. Can we make money on this customer? Do we think they’re going to grow? And so it’s worth the investment we’re making.” If not, we have to be okay with them churning. Having that segmented-based approach, a deep understanding of customer profitability informs your customer success strategy and your renewal motion.

Robbie Baxter: Yeah. You’re talking about a lot of financial things, and it’s leading me to the next area of our conversation, which is the office of the CFO and what you’re doing with Maxio to help those CFOs deal with a changing role. You talk a lot about how the CFOs office is poised for disruption, much like what we’ve seen in marketing and customer success over the past 20 years. Can you talk a little bit about what a rise in SaaS in particular means for the CFO’s office and how that role needs to evolve?

Randy Wootton: I think it’s an enormous opportunity. As someone described it to me, with the types of data and technology that’s now available for CFOs, they can move from back-office compliance officers to front-office strategic advisors for CROs and CEOs. What I saw was those functions have been transformed by technology. The first company I was CEO of Rocket Fuel in 2012, they’d already been applying first-generation, real AI, predictive insights, build all their own data centers. We were cranking a billion different transactions a day, making decisions in less than a tenth of a millisecond, and providing enormous value using AI technology 10 years ago. The transformation of those functions, advertising, marketing, and sales, a lot of it has already happened. There’ll be continued opportunities. But as I looked for my next gig after selling Percolate to Seismic, I was like, “Was there a function that’s right for disruption based on similar ideas around data and technology?” So driving workflow automation, providing more efficiency and effectiveness, and the office of the CFO is one of those.

I think what you find is why has it taken so long. There are a couple of reasons. One is CFOs historically have been CF NOs, who have told other people they can’t buy new technology. And so they suck it out using old technology, which is Excel.

Robbie Baxter: They are really good at it.

Randy Wootton: Really good at both saying no and using Excel. The other thing that is super interesting about the profile of CFOs are experts, meaning you go to them for answers for them to feel confident in terms of providing those answers. They often want to build their own models. So every CFO I’ve hired has come into the business and said, “Oh, your model stinks. I’m going to rebuild it.” It’s a month-long process they’re going through. It’s about a 40-tab Excel sheet. They’ve got all these different components that they’re layering in, but they want to know every single cell and every single tab. There’s a resistance because a lot of CFOs come from big eight accounting firms, they start as accountants, they come in as a controller, and they have to be super precise, and they need to know the models, and they don’t know where all the cash is.

There’s this evolution of thinking in terms of moving from Excel thinking to a database mode thinking that is powered by technology and the other component is that CFOs want to draw a big wall around their technology from everybody else because they can’t have a Salesforce admin coming in and changing the value of an opportunity in the general ledger and screwing something up because at the end of the day, you got to pass the audit. You have this wall between systems that has prevented CFOs from embracing more of this financial operation optimization technology. Those changes I’m seeing in the strategic CFOs recognize this opportunity that they can use their data to help inform the market strategy. It’s the CFO using a technology like Maxio that is doing the reporting on our customer’s cohort analysis. The Annual Recurring Revenue (ARR) roll forward, the revenue depreciation, and the deferred revenue schedule. All of these different components come out of the CFOs office, and it’s sort of like an input into the forecasting process in the business model process, it’s going to be up to the future CFOs to embrace that and recognize that they have a seat at the table in terms of go-to market strategy, that front office motion versus just compliance, ensuring we pass the audit. I think it’s going to be in the next 15 to 20 years.

The other trend I think is happening which I went and presented at the American International CPA Association. I was fascinated to hear the number of people that are going into accounting is dramatically down over the last couple of years. The office of the CFO and accounting firms in general are going to need to figure out how to do an accountant’s job differently. They just can’t keep up with the demand. That is where technology services help. That’s where AI is going to help. You just can’t throw bodies at the problems because you can’t find the bodies. All the old CPAs are retiring and the young kids don’t want to do it.

Robbie Baxter: Yeah, I actually also spoke at the American Institute of Certified Public Accountants (AICPA) a few years ago and was very surprised that that was one of their biggest issues. The young people are moving into other areas, into tech. It is requiring the CFO office to find new ways to leverage themselves. The other thing that you bring up, which is so exciting for the marketers listening, is that many CFOs are finally engaging in a proactive yes-kind-of-way or what they say, the improv world. I’m taking a comedy class right now, you know, yes and right. Where a CFO can say, yes, we can do that and here’s a way to do it in a way that protects our business, even as we grow. It’s an alternative to the no, which kind of shuts down all creativity.

Randy Wootton: Yeah, the other thing which relatively new is the capabilities in the Financial planning and analysis (FP&A) space. So if you think about CFOs having two dimensions, they have their controller duties, where they’re producing the financial statements, they’re ensuring you got cash, understanding the cash forecasting, and getting you through the audit. The other side of the CFO Office is this FP&A space where you’re doing the financial planning analysis. It’s a very different skill set. You often end up with like, if you’re a PC-backed company, one of the analysts may roll into that or bankers who’ve done it. That’s kind of like modeling the future and there’s a lot of gray area and a lot of assumptions. Those also were Excel driven models.

Now what I would say is what you’re finding with some of the technology out there in FP&A, ones that we’re partnering with Giraffe, Basis, and Forecaster. You can take the data out of the historical billing invoicing data out of Maxio. You can roll it into one of those systems and people can start doing modeling. The key here is that they can isolate the different inputs so they can give the model for marketing to the marketing people. They give the model to the sales to the salesperson.The visibility to employee salaries, marketing spend, etc. All these things that might be confidential that you wouldn’t want the person in operations to see what’s happening in marketing.

The CFO via their FP&A person can now isolate those through a SaaS delivered solution, and then you can start doing some modeling and say, “Well, what happens if we increase churn here or attach in in this segment? How does that play out? We invest more marketing there. How does that play out in terms of our overall Customer Acquisition Cost (CAC) ratio?”

I think there’s one thing that’s enabling CFOs to be more strategic and be a yes future CFO officers is because they can run scenarios.

Robbie Baxter: Yeah. That’s great. It’s kind of like meta because you want to use Software-as-a-Service tools like Maxio to enable your subscription businesses to be more nimble and to give everybody in the organization access to all of the different functional areas, not just to the data because as we’ve all learned, data can be overwhelming, but access to models that actually help people make better decisions.

We’re almost out of time, but I’m hoping that you would be up for a speed round.

Randy Wootton: Sure!

Robbie Baxter: First subscription you ever had?

Randy Wootton: Oh my gosh. I have no idea. Like what would count as a subscription? Like is it a phone or a data plan?

Robbie Baxter: Sure. Fair enough.

Randy Wootton: It would be a cell phone where you paid tier base and overage, I think.

Robbie Baxter: Favorite subscription you have now that you’re paying for yourself?

Randy Wootton: Wouldn’t a subscription also be cable TV? Okay, so that would have been the first one. The one I pay for right now, I’ll give you two.

One is Strava. Which I love. It’s for the weekend warriors to go out and do their biking or running and you aggregate your results over the course of the year. You’re able to have friendly competition. I think it’s absolutely fabulous and it builds a community. It’s like social service for weekend warriors.

The other one, which isn’t as well known as called Carv. It’s for skiing and they have created pressure pads to go in your ski boots and then you can track your skiing capability over time through your phone. Why this is so revolutionary is that I’ve been skiing my entire life. I used to coach skiing. I’m not that good, but the hardest thing about skiing is you can’t see what goes on in the boot in terms of how pressure moves, balance, etc. And now these pressure pads in the boot, you’re getting real time feedback in terms of how your turns are going and your pressure on the outside edge versus the inside is.

So both of those, I pay for personally and just love them.

Robbie Baxter: Awesome. Well, we had the CRO of Strava on the show last year, for people who are interested in learning more about Strava. And I think I need to get Carv featured because that’s fascinating and the use of hardware and software to provide a service is something I’m very interested in. So great one.

Last question, best habit you picked up in the Navy?

Randy Wootton: It’s going to take more than a minute, but in the Navy, there’s a saying, “Lead follow, or get out of the way.” And what that means at some level is first, you got to start to learn how to be a follower and then the flip side of that is when you’re faced with the situation someone needs to be the leader. That is taking the lead on just making a decision or driving something over their finish line. And in the military, it’s just very clear, it’s not contentious to say, “Well, are you going to own this or am I going to own it?”

What I found in the civilian sector is that it was, “Lead, follow, let’s talk about it.” And I was like, “Why are we talking about it?” And at big companies like Microsoft, you’d have these ongoing conversations for months at a time. They’re like, “What is the decision, and who’s going to own the decision?” Everybody in big companies thinks they have the right to the veto. Well, I’m going to say no and I’m going to shut it down. Very few people are willing to step up and take accountability and say, “I got this, and I’m going to go do it.” Flip side of that is that in the corporate sector, as a teammate, you got to say, “Got it, you got it, and I am in.” Just agree and commit. I’m going to follow. I’m going to do everything I possibly can to make you successful.

Leadership Lessons from the Navy: “Lead, follow, or get out of the way” holds true in both military and civilian sectors

The other one is that in the military, you never have enough resources. And you’re in a combat situation, you got to make do. That’s very analogous to a startup environment, where you’re never going to have as many resources as you want. The plan you build is immediately going to blow up the day after it got approved and you got to be able to respond quickly with a smart group of people, figuring out what you can do with what you got.

Robbie Baxter: Oh, fantastic. Randy Wootton, thank you so much for being on Subscription Stories. I learned a lot.

Randy Wootton: My pleasure.

That was Randy Wootton, CEO of Maxio. For more about Randy, go to or check out The SaaS Expert Voices Podcast, which he hosts, and where I was a recent guest myself. And for more about Subscription Stories, as well as a transcript of my conversation with Randy, go to

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About Randy Wootton


Randy Wootton, the CEO of Maxio is a multiple-time B2B SaaS CEO.

However, his current role is unique in that within six months of taking on the role, the existing company which was the combination of two well-known companies (SaaS Optics and Chargify) decided to rebrand as Maxio and doing this during the great SaaS market correction started in the 2H-22.


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