STEPHANIE NEILL: Good morning everyone. I’m Stephanie, and I lead the Tax product here at Stripe. I want to say thanks for joining us today for this session. I think it’s going to be one of the most practical ones you’ll see during your time here at Sessions. All right. First, I’m going to kick us off with something that might sound like the start of a bad joke, but I swear it is an actual real question and I really would like you guys to respond from the audience. Okay? How many systems does it take to run revenue operations and close your books?

Did I hear 16? Right out the gate? Can anyone beat that? 10. Ten, okay. Okay. We’re still in double digits. All right, so that’s a lot. But I get it. I really do. There’s logic behind each and every one of those choices, by each and every one of the probably myriad of people who made them. You got to start with the billing tool, then you add a tax tool. Of course, you need revenue recognition, financial reporting, billing analytics. Actually, do you want to say the 16? But the list keeps going. So with every new tool, that’s another integration that you then have to maintain, and that’s another place where data can break. So it might feel easier to keep choosing the workaround or realistically accepting the set of workarounds that you inherited. Until there’s an audit or a board question or a failed reconciliation, that really forces your hand.

So you have to step back and you have to reconsider this whole system. So in our time together today, we’ll show you what it looks like to get ahead of that moment and we’ll show you the ROI that you get when you do.

So what are disconnected systems actually costing you? I speak with a lot of users like the folks in this room, actually. It’s the best part of my job. And I hear mostly three main challenges. The first we call operational drag. So even with AI transforming how teams work, data teams actually still spend upwards of 70% of their time cleaning data and reconciling data when systems aren’t connected. And then of course, finance teams are stuck reconciling across these systems instead of closing the books, which is obviously not the best use of their time. And engineers, they’re writing bailout code so that we can ship reliable numbers this month instead of actually building your product. So basically you have high-value people doing low-value work.

The second main challenge I hear is around compliance exposure. In 2025, we saw over 400 US tax rate changes and 190 new jurisdictions added just in the US alone across the indirect tax landscape. And then of course, globally we see e-invoicing mandates multiplying and they mean business. So if you’re like more than 80% of startups on Stripe who sell into 20+ markets, you’re going to need to take this stuff seriously. If your tax logic lives in a spreadsheet, it’s hard to keep up, especially when the rules are changing this fast.

And then the third main area is around unreliable reporting and analysis. So revenue data is in one system, taxes in another, customer data in a third, you have no single source of truth. It’s not surprising that 67% of organizations don’t trust their data for decision-making. So forecasting, reporting, and go-to-market decisions all slow down because nobody trusts these numbers.

So what do these problems mean in practice? They don’t show up as a convenient line item called “opportunity cost” or “growth we missed.” It’s the market that you didn’t enter. It’s the hire that you had to make to manage a process instead of building your product. The cost is real. It’s just hiding in plain sight.

And here’s what this has taught me. The cost of managing disconnected systems is higher than the cost of consolidating them, and that gap actually widens as you grow. So a centralized revenue stack isn’t just back-office optimization; it’s growth infrastructure. But don’t take my word for it. We’re going to talk to two leaders who tackled these exact challenges, and we’re going to hear what they learned along the way. Please welcome Cristina Cordova, COO at Linear; Tessa Barnett, VP of finance at Thinkific; and our panel host, Tyler Bryson, CRO of the Americas here at Stripe.

TYLER BRYSON: All right. Great. Well, thanks you guys for joining us today. I think you’re going to find this discussion really, really enlightening, but let’s get to know our panelists here for a second. Cristina, let’s start with you. Tell us about what you’re doing, I think, Linear.

CRISTINA CORDOVA: Yeah, sure. So I’m Cristina. I’m the COO at Linear. We are a product development system for teams and agents, so we primarily sell to people who build software, and we sell our product all over the world. We’ve experienced quite a bit of growth in the last couple of years with the rise of AI and agentic coding. And then we’re also expanding our team globally as well.

TYLER BRYSON: Fantastic. Okay, Tessa, tell us about the amazing things you’re doing at Thinkific.

TESSA BARNETT: Yeah. Hi, thanks for having me. I’m Tessa. I’m the VP of finance at Thinkific. We’re an online learning platform, so we sell globally to customers who are teaching their users or students or buyers how to learn something. And we’ve been on Stripe. We’ve used Billing for many years now, and more recently we’ve consolidated onto using the Revenue Recognition and Tax products. And my accent is from New Zealand, so you don’t need to worry. Spend any time wondering if it’s Australian.

TYLER BRYSON: We were all wondering. Yeah. Okay. So we’ve got two very different companies, but here’s what I love. They’re high growth and they’ve had to figure out how to run revenue operations while scaling so fast, which is exactly where we think many of you are probably in this room. It’s why you’re here. So let’s dive into some questions, if we could. So Cristina, I know Linear was on Stripe early, which is fantastic, but being on the platform and getting its full benefit and using it is maybe a different thing. What did it look like day to day when you started?

CRISTINA CORDOVA: Yeah, sure. So when I started at Linear, we actually were already on Stripe, which was great. We actually incorporated the company through Stripe Atlas originally, and then of course started using Stripe Billing to bill for our SaaS products. And initially we had, customers can pay what they want. It was like a dial when we were in beta and you could select what you wanted to pay for the product. By the time I got there, we’d obviously moved some of those users over to a more structured pricing plan, but there wasn’t necessarily any formal finance or operations component of the business. We outsourced all of our bookkeeping and accounting, so it was pretty hands off. We didn’t charge any of our customers for taxes, so we were eating all of that. We also had, I would say, a lot of manual download of data from Stripe and then upload to a third-party system to understand what was going on with revenue.

So it was very manual. And we were also starting to sell to enterprise customers at that time, but all of our reps were going into Stripe and creating their own invoices, sending them to customers, which as you can imagine, led to a lot of fat-fingering and things that were not done properly. So there was just a lot of making what you can from a company that at the time was 40 employees.

TYLER BRYSON: Well, I love you kind of giving that scrappiness view of everybody was just trying to figure it out and get to grow somehow. And I see some other people’s heads nodding out there that they may have been or been at similar stages, but was there a moment that you just said, “Oh no, we just can’t keep doing it this way.”

CRISTINA CORDOVA: Yeah. I mean, I think fairly early on, I wanted to actually roll out a price increase, which is never the fun thing to do as a COO. It’s like, we need to charge more and we need to migrate all of these customers from—

TYLER BRYSON: And charge for tax.

CRISTINA CORDOVA: Right. Yes. From these old plans to these new plans, and we’re going to charge for taxes at the same time. So that was a pretty big initiative, right? So of course, our default was to go to Stripe Tax. It had all the functionality for where our customers were at that point in time. And then at the same point, we also started to... a little bit of starting to unbundle some of our pricing in a lot of different ways, and Stripe fully supported that as well. And then we also started using products like Stripe Data Pipeline and taking all of our data and moving it into Snowflake. We hired a data person who could start putting that data in the context of some of our other product metrics and making those into kind of fully functional dashboards as well. So there was a lot that we did at that point to kind of get to a better place, but I think the initiative really started with saying like, “We’re not charging what we should for our customers.” And then that was kind of like a waterfall effect.

TYLER BRYSON: Drove. Drove it all. Great. Well, going from like, “Hey, let’s just figure this out,” to having a structured framework to deliver it is great. Tessa, what about you? Where were you feeling the pain?

TESSA BARNETT: Yeah, Thinkific really started to hit some real growth in 2019. And then in 2022, we built out a payments offering, and it was around that time that the volume and the complexity of the data really started to slow us down. We’re also a public company, so we need to have very accurate revenue and tax reporting and we need it quick. We want to stay lean and efficient on the finance team as we grow. So it was managing across three different tools. That was the challenge that we had Stripe for billing, Workday for revenue recognition and Avalara for sales tax. And it was just the amount of time that people would spend moving data between systems and reconciling that became unsustainable.

TYLER BRYSON: Just a ton of reconciliation going on all the time. Something breaks and it’s like, “We’re not working. We’re just trying to get there.” So what did you do about it with all these manual data transfers, what was the next step?

TESSA BARNETT: Yeah, we decided to consolidate onto Stripe and I wouldn’t say that was one decision. It was a phased approach. We did it incrementally. We started with Stripe Tax for the North American side of the payments business, and then we moved over and did Revenue Recognition, and then we went back and further expanded the tax offering globally. So that goal was just to kind of keep consolidating so that we can run quicker and have one source of truth.

TYLER BRYSON: Fantastic. I think what’s amazing is that two very real stories of where Stripe was involved, but you’re able to find new value and create more of a platform for managing your revenue. Okay. Let’s shift gears and talk about compliance. And Cristina, I’d like to talk a little bit more about, you had an audit, and what did that tax situation look like when you got to Linear?

CRISTINA CORDOVA: Yeah. So thankfully I did hire a finance person who really knew what they were doing, long history of accounting, those kinds of things. So I think for us, that obviously kicked off a lot of processes going into our Stripe settings and understanding like, okay, we have discounts showing up in certain ways, they should be showing up actually in different kinds of ways and how are we recognizing that revenue over the course of two-, three-year terms with some of our largest customers. And then on the tax side, a lot of things were not figured out at the beginning. Thankfully, for the vast majority of our customers, we had already been collecting addresses, so we didn’t have to go back to them and say, “Hey, actually we need to collect all of your addresses and you have to give them to this by this date or we’re going to potentially cut off services.” And that was just for like a very small percentage of customers, most of whom we had like personal relationships with.

So getting all of that data into Stripe and then sending one email notification out to all of our customers to say, “You may or may not be subject to tax in the future, but if you are, we will begin charging for it.” And I think people accept that it’s a normal way of life and—

TYLER BRYSON: They were wondering why you never asked.

CRISTINA CORDOVA: Right. And an understanding for it. And then separately, making sure that we’re also accounting for that in the right way, right? If there was like $9 in taxes on top of a $100 service, that $9 isn’t necessarily revenue, and making sure that we’re working to account for that in the right way. So yeah, in general, it was pretty straightforward, which was great.

TYLER BRYSON: Awesome. Okay. Tessa, you mentioned you were using Avalara and still are in some places, but what was that experience like? How’s it working now?

TESSA BARNETT: Yeah. And I can totally relate to the not having the tax piece figured out, Cristina. We began our sales tax journey on Avalara, and for us, the real challenge was that our engineers found it quite challenging to connect to and build with. So that was time-consuming. And then operationally on the finance side of the house, it just took a long time to, again, like be moving data between the two systems. So that was where we decided that this was not something that we wanted to have it in the one system.

TYLER BRYSON: Great. Great. Okay. So both of you had these gaps and I think it’s important for the room to hear that these really aren’t just edge cases. It’s just what happens when you’re moving so fast. Cristina, let’s get deeper into fixing it. What changed? How did you get tax set up in more detail?

CRISTINA CORDOVA: Yeah. Yeah. So I would say first obviously was the rollout of the addresses, collecting all of that information. And then our engineers were kind of working on the actual technical implementation. I think that took like no more than two weeks. So it was very, very straightforward. Now we’re getting notifications of like, “Okay, now you might be subject to taxes in this particular state or this particular country and we’re setting it up and rolling it out as we need to and as the business scales into new regions.” So it’s nice to just be kind of proactively notified when there’s more that we need to do as we’re scaling the business instead of being in this mode where we’re constantly wondering like, are we doing it right? Is it working properly? Are we compliant? And that working really smoothly with our finance team.

TYLER BRYSON: Great. So the proactive, “Hey, we’ve got somebody looking at this with us. We’re not alone.” What about you Tessa, when you made the switch to Stripe Tax, how’d it go?

TESSA BARNETT: Yeah. When Stripe released the tax functionality, I’d say we were cautiously excited or as excited as one can get about tax software. But our main concern was, is this going to be accurate? Avalara has always been a leader in the market, and Stripe Tax was new. So we tested it against Avalara’s tax rates. We worked pretty closely with the Stripe Tax research team to make sure that we had a really good understanding of how it was going to work for us. And then we had the confidence to move over, and the move was worth it.

TYLER BRYSON: Yeah. Great. I’m so glad to hear that. We had a little joke because there was this part of the script where I asked her this really cheesy question like, “Was it worth it?” So she just threw that in for me. Oh yeah. All right. Okay. So we had operations that have been, we’ve been able to tighten operations. We’ve got compliance in a better place, but now let’s talk about the piece that really ties it all together, reporting and data, reporting and data, because you fixed the engine, but there’s still an unlimited hunger to see what’s going on and kind of improve transparency. So let’s see, Tessa, I’ll start with you. How were you handling accounting and financial reporting? And you heard some people talk about 14, 15 systems. What was your story?

TESSA BARNETT: Yeah, for sure. We didn’t have 16, but we had a few, and it was challenging even just to manage those few. So I would say most people use their ERP for revenue recognition, in our case Workday, but the challenge was really that managing the integration from Stripe on the billing side into Workday for rev rec. And we would find that anytime we did something new or different in Stripe on the billing side, it would break or we’d have to figure out, is it doing it right? And that would slow us down and raise risk. Again, our revenue is our most important number. We need to have that accurate and quick. And we also didn’t want to be pulling engineers off to help us troubleshoot this integration. We wanted our engineers focused on the product. So that was where the challenges really arose for us.

TYLER BRYSON: And the speed to close?

TESSA BARNETT: Yeah, the speed to close. When we moved over to Stripe Tax, we slimmed it down from, we used to close revenue and receivables by day four, and now we close by midday on day one. So it’s great.

TYLER BRYSON: Awesome. Pretty important for a public company to be moving at that pace. Great. Okay. Let’s, Cristina, on your side, I know you’ve invested a lot in reporting to get this infrastructure in place. Tell us about your journey. What were you working with and what are you doing now?

CRISTINA CORDOVA: Yeah. So we had this previous Hevo integration that had a lot of data gaps within it. Stripe Data Pipeline now sends data in real time to Snowflake. And then we use Snowflake to get that data into our company metrics dashboard, combine it with other third-party data that we have. And then from there, we’re also doing a lot of like kind of cross-company data analysis where it makes sense. So as an example, with the pricing migration that we did, it was really great because a lot of our customers were not necessarily migrating to a new plan immediately when we rolled out new pricing, but were saying like, “I want to keep my plan until a year from now when my plan is supposed to renew, and then I will schedule that migration.” So being able to just like schedule pricing plan migrations and the context of like rolling out a lot of pricing updates was great.

And then we could also take that data back into our own internal systems and say, “Okay, how is the legacy migration doing? How many people are scheduled to move? How many people haven’t scheduled to move yet?” And have a good understanding like who are the customers we still need to go out there and kind of do some hand-to-hand combat with and make sure that they get moved over. So—

TYLER BRYSON: Especially when you’re trying to find that right price point, value point. Yeah, exactly. And making a lot of adjustments along the way and be able to reconcile that.

CRISTINA CORDOVA: Right. Yeah. Are people churning because of the pricing migration or is this like a quick flip of the switch and it doesn’t really make a difference for most of our customers? So that was really great to see. And then I think that provided a lot of like accuracy and visibility across the organization. And then just even in like the Billing dashboard, I think one of my biggest frustrations when I joined was that the dashboard wasn’t real time. So a lot of our revenue on the enterprise side closes at the end of the month, the last day of the month or the last day of the quarter. And so I was waiting for like three days to figure out, how did we actually do this month or this quarter. And now it’s real time, which has just been so delightful to kind of have a really good sense of—

TYLER BRYSON: Everybody’s asking you, “Where are we? Where are we?”

CRISTINA CORDOVA: Right I’ll be like, “I’ll get back to you in three days.” Yeah.

TYLER BRYSON: That’s really satisfying.

CRISTINA CORDOVA: So it’s really great to see all of it.

TYLER BRYSON: That’s awesome. Thank you for that. Okay. So you can see there’s just huge differences from one, just the way they’re operating, the compliance confidence, and then just being more adaptable to the real-time needs of the business with data. So we’ve covered a lot of the hard stuff. I’d love to get into some of the metrics of like, what have you unlocked beyond some of the areas we’ve talked about? And global expansion is an area that I would love to talk about. So Cristina, what’s getting easier for you?

CRISTINA CORDOVA: Yes. Well, we lived in a nice world when we sold to customers all over the world from the United States, but of course we started to realize that a lot of those customers, despite not necessarily being in the US, wanted to meet in person and that they would love for us to come to their offices and all over parts of the world. And a growing portion of our business was in EMEA. So we decided to open up a London office, hire a sales leader out there, and actually concentrate our sales team there as well, which is unusual for us because we’re also completely remote as a company. And so that also begged the question of like, okay, we need to set up a new entity, potentially transfer some people over from the US into this new office in London, hire some people from the country as well, and build that team out.

So we needed revenue to actually run through a new Stripe account that was associated with that new entity. And then obviously from there, it starts to get like, “Well, I have this one account over here and one account over here.” But I think also with Stripe Data Pipeline, making sure that all of that data can come to a single source of truth within our internal dashboards starts to become more and more important to understand how the business is operating in these separate regions. Obviously we have like tax and legal requirements that are kind of driving this new structure and way of operating, but Stripe’s platform makes it really easy to kind of connect different accounts to each other and kind of make that pretty manageable. And then we’re also starting to think ahead to APAC as well. So hiring our first rep out there, and then kind of giving more confidence to the plan because it’s worked pretty seamlessly in London.

TYLER BRYSON: Love it. Global by default, all of our businesses. So global expansion goes from this massive, scary thing. We didn’t even talk about the tax side of that, but to something that like, hey, this is a revenue driver. It’s revenue infrastructure that we’re building here. Okay. Tessa, what has the consolidation unlocked for Thinkific?

TESSA BARNETT: Yeah, I mean, we just move faster, which is a huge benefit when the company says, “Hey, we want to focus on this new jurisdiction,” or, “Hey, we want to do token-based pricing for this new AI feature.” Our accounting and billing team can go, “Yep, let’s go.” Which is just, we know we can operationalize it and that’s really great.

TYLER BRYSON: Fantastic. I love that. And then that’s not new engineering requests. It’s a billing team that’s enabled to go figure that out. Okay. Now, I know that some of you may be thinking, “Well, this is wonderful for Linear and Thinkific, but we’re not there yet, or we’re not sure we could handle that.” And that’s okay because actually everybody’s at a different stage. And I think one of the key themes or message that we want you to take away is that whatever stage that you’re at, Stripe can help you have a pathway to a more consolidated opportunity. But Tessa, I want to tackle one question that I think is on the minds of some of our customers and users. Going all in with Stripe versus multipoint solutions, was there some concern about single-vendor risk?

TESSA BARNETT: Yeah, definitely. We had concerns about moving everything onto one provider. We also had some question marks around the functionality and accuracy of the products, because at the time, both Stripe Tax and Revenue Recognition were fairly new. So we assessed that and for us, the benefits really outweighed that risk. The benefits of being able to move so much quicker, being able to actually do what we want to be able to do in the business made it worth it for us.

TYLER BRYSON: Great. So the risk of single-provider risk was offset by the greater return.

TESSA BARNETT: Yeah, definitely.

TYLER BRYSON: Okay. Awesome. That’s a really honest answer, and I appreciate you sharing that with the room. Cristina, last question. If there are some businesses out here in the room using just a few of Stripe’s capabilities today, any guidance based on your journey, what would you share?

CRISTINA CORDOVA: Yeah. First, I’d just say it makes sense to plan as early as you can. We had a good sense probably about six months to nine months ahead of time that we were going to open this office in London, that we were going to hire a team based there. So having conversations with finance and operations and accounting and making sure that you’re doing things to plan ahead for that. Sadly, like opening up a bank account in London is not as easy as opening up a bank account here in the US, even if you’re doing it with the same banker in a different region. So just some of these things just take a lot more time than you would anticipate. So like plan early for those things. Second, of course, just like find the right partner that you’re really able to scale with and has a good line of sight for what you need.

So one of the things that I’ve loved about working with Stripe is that you’re not in a situation where it feels like you’re constantly coming to Stripe and saying, “Do you have this? Do you have this?” And I feel like as soon as I think about the next stage of the business, it’s like, “Oh, we have that,” or, “It’s in beta,” or, “It’s coming.” With things like usage based billing, which are on our mind for the future and some new products that we’re doing or other things that are critical for the business going forward. So also just be communicative about what you need and make sure that you’re working with a partner that ultimately is going to be building alongside you and is working with customers who probably have a lot of similar needs as you do. And then lastly, while Stripe does... I try to put everything into Stripe, but I’m trying to consolidate as much as possible.

I’ve worked at other companies where maybe you take the enterprise business and you put it over here, and then it’s running separately. I want to centralize as much as possible and simplify for the company, but in order to do that, I think you realize that there are still integrations that you’re going to need, accounting and bookkeeping and lots of other things. So just thinking about the integrations that we need, we’re thinking about changing accounting platforms as an example. And it’s like, well, each one of these has to have a really robust Stripe integration and that’s like the default for anything that we might be selecting if we’re trying to move to maybe one of these new-age AI-powered bookkeeping and accounting systems to ensure that everything works really well together.

TYLER BRYSON: I love it. Just the planning and just having that view around the corner a little bit. That’s one of the reasons we were pushing so hard internally to get these roadmaps more publicly out to you so that all of you could have more confidence in the capabilities, the countries, and the markets that we’re going to be helping you get into. So I’d like to give a big round of applause to Cristina and Tessa for their insights.