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Good morning everyone. I'm Stephanie,
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and I lead the Text product here at Stripe.
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I want to say thanks for joining us today for this session.
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I think it's going to be one of the most practical ones you'll see during your
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time here at Sessions. All right. First,
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I'm going to kick us off with something that might sound like the start of a bad
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joke,
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but I swear it is an actual real question and I really would like you guys to
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respond from the audience. Okay?
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How many systems does it take to run revenue operations and close your
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books? Did I hear 16?
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Right out the gate? Can anyone beat that? 10. Ten,
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OK. Okay. We're still in double digits. All right,
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so that's a lot. But I get it. I really do.
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There's logic behind each and every one of those choices,
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by each and every one of the probably myriad of people who made them.
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You got to start with the billing tool, then you add a tax tool. Of course,
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you need revenue recognition, financial reporting, billing analytics.
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Actually, do you want to say the 16?
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But the list keeps going. So with every new tool,
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that's another integration that you then have to maintain,
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and that's another place where data can break.
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So it might feel easier to keep choosing the workaround or realistically
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accepting the set of workarounds that you inherited.
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Until there's an audit or a board question or a failed reconciliation,
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that really forces your hand.
So you have to step back and you have to
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reconsider this whole system. So in our time together today,
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we'll show you what it looks like to get ahead of that moment and we'll show you
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the ROI that you get when you do.
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So what are disconnected systems actually costing you?
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I speak with a lot of users like the folks in this room, actually.
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It's the best part of my job. And I hear mostly three main challenges.
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The first we call operational drag.
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So even with AI transforming how teams work,
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data teams actually still spend upwards of 70% of their time cleaning
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data and reconciling data when systems aren't connected.
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And then of course,
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finance teams are stuck reconciling across these systems instead of closing the
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books, which is obviously not the best use of their time.
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And engineers,
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they're writing bailout code so that we can ship reliable numbers this month
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instead of actually building your product.
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So basically you have high-value people doing low-value work.
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The second main challenge I hear is around compliance exposure. In 2025,
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we saw over 400 US tax rate changes and 190 new
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jurisdictions added just in the US alone across the indirect
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tax landscape. And then of course,
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globally we see e-invoicing mandates multiplying and they mean business.
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So if you're like more than 80% of startups on Stripe
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who sell into 20+ markets, you're going to need to take this stuff seriously.
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If your tax logic lives in a spreadsheet, it's hard to keep up,
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especially when the rules are changing this fast.
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And then the third main area is around unreliable reporting and analysis.
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So revenue data is in one system, taxes in another, customer data in a third,
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you have no single source of truth.
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It's not surprising that 67% of organizations don't trust their data for
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decision-making. So forecasting, reporting,
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and go-to-market decisions all slow down because nobody trusts these numbers.
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So what do these problems mean in practice?
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They don't show up as a convenient line item called "opportunity cost" or
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"growth we missed." It's the market that you didn't enter.
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It's the hire that you had to make to manage a process instead of building your
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product. The cost is real. It's just hiding in plain sight.
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And here's what this has taught me.
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The cost of managing disconnected systems is higher than the cost of
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consolidating them, and that gap actually widens as you grow.
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So a centralized revenue stack isn't just back-office optimization;
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it's growth infrastructure. But don't take my word for it.
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We're going to talk to two leaders who tackled these exact challenges,
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and we're going to hear what they learned along the way.
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Please welcome Cristina Cordova, COO at Linear; Tessa Barnett,
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VP of finance at Thinkific; and our panel host, Tyler Bryson,
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CRO of the Americas here at Stripe.
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All right. Great. Well, thanks you guys for joining us today.
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I think you're going to find this discussion really, really enlightening,
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but let's get to know our panelists here for a second. Cristina,
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let's start with you. Tell us about what you're doing, I think, Linear.
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Yeah, sure. So I'm Cristina. I'm the COO at Linear.
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We are a product development system for teams and agents,
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so we primarily sell to people who build software,
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and we sell our product all over the world.
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We've experienced quite a bit of growth in the last couple of years with the
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rise of AI and agentic coding.
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And then we're also expanding our team globally as well.
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Fantastic. Okay, Tessa,
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tell us about the amazing things you're doing at Thinkific.
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Yeah. Hi, thanks for having me. I'm Tessa. I'm the VP of finance at Thinkific.
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We're an online learning platform,
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so we sell globally to customers who are teaching their users or
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students or buyers how to learn something.
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And we've been on Stripe. We've used Billing for many years now,
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and more recently we've consolidated onto using the Revenue Recognition and
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Tax products. And my accent is from New Zealand,
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so you don't need to worry. Spend any time wondering if it's Australian.
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We were all wondering. Yeah. Okay. So we've got two very different companies,
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but here's what I love.
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They're high growth and they've had to figure out how to run revenue operations
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while scaling so fast,
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which is exactly where we think many of you are probably in this room.
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It's why you're here. So let's dive into some questions, if we could.
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So Cristina, I know Linear was on Stripe early, which is fantastic,
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but being on the platform and getting its full benefit and using it is maybe a
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different thing. What did it look like day to day when you started?
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Yeah, sure. So when I started at Linear,
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we actually were already on Stripe, which was great.
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We actually incorporated the company through Stripe Atlas originally,
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and then of course started using Stripe Billing to bill for our SaaS
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products. And initially we had,
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customers can pay what they want.
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It was like a dial when we were in beta and you could select what you wanted to
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pay for the product. By the time I got there,
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we'd obviously moved some of those users over to a more structured
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pricing plan,
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but there wasn't necessarily any formal finance or operations
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component of the business. We outsourced all of our bookkeeping and accounting,
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so it was pretty hands off. We didn't charge any of our customers for taxes,
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so we were eating all of that. We also had, I would say,
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a lot of manual download of data from Stripe and then upload to
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a third-party system to understand what was going on with revenue.
So it was
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very manual.
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And we were also starting to sell to enterprise customers at that time,
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but all of our reps were going into Stripe and creating their own invoices,
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sending them to customers, which as you can imagine,
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led to a lot of fat-fingering and things that were not done properly.
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So there was just a lot of making what you can from a company
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that at the time was 40 employees.
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Well,
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I love you kind of giving that scrappiness view of everybody was just trying to
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figure it out and get to grow somehow.
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And I see some other people's heads nodding out there that they may have been or
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been at similar stages, but was there a moment that you just said, "Oh no,
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we just can't keep doing it this way.".
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Yeah. I mean, I think fairly early on,
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I wanted to actually roll out a price increase,
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which is never the fun thing to do as a COO. It's like,
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we need to charge more and we need to migrate all of these customers from-.
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And charge for tax.
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Right. Yes. From these old plans to these new plans,
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and we're going to charge for taxes at the same time.
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So that was a pretty big initiative, right? So of course,
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our default was to go to Stripe Tax.
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It had all the functionality for where our customers were at that point in time.
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And then at the same point, we also started to...
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a little bit of starting to unbundle some of our pricing in a lot of different
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ways, and Stripe fully supported that as well.
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And then we also started using products like Stripe Data Pipeline and taking all
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of our data and moving it into Snowflake.
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We hired a data person who could start putting that data in the context
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of some of our other product metrics and making those into kind of fully
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functional dashboards as well.
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So there was a lot that we did at that point to kind of get to a better place,
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but I think the initiative really started with saying like,
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"We're not charging what we should for our customers." And then that was kind of
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like a waterfall effect.
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Drove. Drove it all. Great. Well, going from like, "Hey,
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let's just figure this out," to having a structured
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framework to deliver it is great. Tessa, what about you?
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Where were you feeling the pain?
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Yeah, Thinkific really started to hit some real growth in 2019.
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And then in 2022, we built out a payments offering,
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and it was around that time that the volume and the complexity of the data
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really started to slow us down. We're also a public company,
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so we need to have very accurate revenue and tax reporting and
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we need it quick.
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We want to stay lean and efficient on the finance team as we grow.
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So it was managing across three different tools.
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That was the challenge that we had Stripe for billing,
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Workday for revenue recognition and Avalara for sales tax.
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And it was just the amount of time that people would spend moving data between
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systems and reconciling that became unsustainable.
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Just a ton of reconciliation going on all the time.
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Something breaks and it's like, "We're not working.
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We're just trying to get there." So what did you do about it with all
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these manual data transfers, what was the next step?
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Yeah,
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we decided to consolidate onto Stripe and I wouldn't say that was one decision.
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It was a phased approach. We did it incrementally.
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We started with Stripe Tax for the North American
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side of the payments business,
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and then we moved over and did Revenue Recognition,
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and then we went back and further expanded the tax offering globally.
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So that goal was just to kind of keep consolidating so that we can run quicker
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and have one source of truth.
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Fantastic.
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I think what's amazing is that two very real stories of where
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Stripe was involved,
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but you're able to find new value and create more of a platform for
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managing your revenue. Okay. Let's shift gears and talk about compliance.
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And Cristina, I'd like to talk a little bit more about, you had an audit,
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and what did that tax situation look like when you got to Linear?
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Yeah.
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So thankfully I did hire a finance person who really knew what they were doing,
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long history of accounting, those kinds of things.
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So I think for us,
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that obviously kicked off a lot of processes going into our Stripe settings and
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understanding like, OK,
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we have discounts showing up in certain ways,
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they should be showing up actually in different kinds of ways and how are we
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recognizing that revenue over the course of two-,
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three-year terms with some of our largest customers. And then on the tax side,
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a lot of things were not figured out at the beginning. Thankfully,
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for the vast majority of our customers,
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we had already been collecting addresses,
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so we didn't have to go back to them and say, "Hey, actually we need to
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collect all of your addresses and you have to give them to this by this date or
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we're going to potentially cut off services." And that was just for like a very
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small percentage of customers,
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most of whom we had like personal relationships with.
So getting all of that
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data into Stripe and then sending one email notification out to all of our
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customers to say, "You may or may not be subject to tax in the future,
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but if you are, we will begin charging for it.
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" And I think people accept that it's a normal way of life
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and-.
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They were wondering why you never asked.
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Right. And an understanding for it. And then separately,
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making sure that we're also accounting for that in the right way, right?
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If there was like $9 in taxes on top of a $100 service,
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that $9 isn't necessarily revenue,
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and making sure that we're working to account for that in the right way.
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So yeah, in general, it was pretty straightforward, which was great.
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Awesome. Okay. Tessa, you mentioned you were using Avalara,
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and still are in some places, but what was that experience like?
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How's it working now?
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Yeah. And I can totally relate to the not having the tax piece figured out,
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Cristina.
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We began our sales tax journey on Avalara and for us,
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the real challenge was that our engineers found it quite challenging
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to connect to and build with.
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So that was time-consuming.
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And then operationally on the finance side of the house,
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it just took a long time to, again, like be moving data between the two systems.
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So that was where we decided that this was not something that we wanted to have
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it in the one system.
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Great. Great. Okay.
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So both of you had these gaps and I think it's important for the room to hear
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that these really aren't just edge cases.
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It's just what happens when you're moving so fast. Cristina,
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let's get deeper into fixing it. What changed?
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How did you get tax set up in more detail?
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Yeah. Yeah.
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So I would say first obviously was the rollout of
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the addresses, collecting all of that information.
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And then our engineers were kind of working on the actual technical
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implementation. I think that took like no more than two weeks. So it was very,
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very straightforward. Now we're getting notifications of like, "OK,
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now you might be subject to taxes in this particular state
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or this particular country and we're setting it up and rolling it out as we need
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to and as the business scales into new regions." So it's nice to just be kind of
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proactively notified when there's more that we need to do as we're scaling the
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business instead of being in this mode where we're constantly wondering like,
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are we doing it right? Is it working properly? Are we compliant?
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And that working really smoothly with our finance team.
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Great. So the proactive, "Hey, we've got somebody looking at this with us.
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We're not alone." What about you Tessa, when you made the switch to Stripe Tax,
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how'd it go?
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Yeah. When Stripe released the tax functionality,
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I'd say we were cautiously excited or as excited as one can get about tax
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software. But our main concern was, is this going to be accurate?
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Avalara has always been a leader in the market, and Stripe Tax was new.
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So we tested it against Avalara's tax rates.
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We worked pretty closely with the Stripe Tax research team to
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make sure that we had a really good understanding of how it was going to work
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for us. And then we had the confidence to move over, and the move was worth it.
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Yeah. Great. I'm so glad to hear that.
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We had a little joke because there was this part of the script where I asked her
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this really cheesy question like, "Was it worth it?
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" So she just threw that in for me. Oh yeah. All right. Okay.
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So we had operations that have been, we've been able to tighten operations.
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We've got compliance in a better place,
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but now let's talk about the piece that really ties it all together,
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reporting and data, reporting and data, because you fixed the engine,
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but there's still an unlimited hunger to see what's going on and kind of improve
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transparency. So let's see, Tessa, I'll start with you.
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How were you handling accounting and financial reporting?
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And you heard some people talk about 14, 15 systems. What was your story?
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Yeah, for sure. We didn't have 16,
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but we had a few, and it was challenging even just to manage those few. So
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I would say most people use their ERP for revenue recognition,
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in our case Workday,
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but the challenge was really that managing the integration from
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Stripe on the billing side into Workday for rev rec.
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And we would find that anytime we did something new or different in Stripe on
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the billing side, it would break or we'd have to figure out,
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is it doing it right? And that would slow us down and raise risk.
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Again, our revenue is our most important number.
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We need to have that accurate and quick.
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And we also didn't want to be pulling engineers off to help us troubleshoot
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this integration. We wanted our engineers focused on the product.
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So that was where the challenges really arose for us.
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And the speed to close?
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Yeah, the speed to close. When we moved over to Stripe Tax,
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we slimmed it down from, we used to close revenue and receivables by day four,
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and now we close by midday on day one. So it's great.
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Awesome. Pretty important for a public company to be moving at that pace. Great.
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Okay. Let's, Cristina, on your side,
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I know you've invested a lot in reporting to get this infrastructure in place.
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Tell us about your journey.
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What were you working with and what are you doing now?
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Yeah.
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So we had this previous Hevo integration that had a lot of data gaps within it.
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Stripe Data Pipeline now sends data in real time to
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Snowflake.
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And then we use Snowflake to get that data into our company metrics
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dashboard, combine it with other third-party data that we have.
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And then from there,
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we're also doing a lot of like kind of cross-company data analysis where it
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makes sense. So as an example, with the pricing migration that we did,
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it was really great because a lot of our customers were not necessarily
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migrating to a new plan immediately when we rolled out new pricing,
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but were saying like, "I want to keep my plan until
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a year from now when my plan is supposed to renew,
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and then I will schedule that migration." So being able to just like schedule
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pricing plan migrations and the context of like rolling out a lot of pricing
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updates was great.
And then we could also take that data back into our own
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internal systems and say, "Okay, how is the legacy migration doing?
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How many people are scheduled to move?
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How many people haven't scheduled to move yet?" And have a good understanding
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like who are the customers we still need to go out there and kind of do some
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hand-to-hand combat with and make sure that they get moved over. So-.
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Especially when you're trying to find that right price point, value point. Yeah,
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exactly.
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And making a lot of adjustments along the way and be able to reconcile that.
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Right. Yeah.
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Are people churning because of the pricing migration or is this like a quick
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flip of the switch and it doesn't really make a difference for most of our
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customers? So that was really great to see.
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And then I think that provided a lot of like accuracy and visibility across the
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organization. And then just even in like the Billing dashboard,
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I think one of my biggest frustrations when I joined was that the dashboard
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wasn't real time.
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So a lot of our revenue on the enterprise side closes at the end of the month,
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the last day of the month or the last day of the quarter.
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And so I was waiting for like three days to figure out,
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how did we actually do this month or this quarter. And now it's real time,
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which has just been so delightful to kind of have a really good sense of-.
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Everybody's asking you, "Where are we? Where are we?".
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Right I'll be like, "I'll get back to you in three days." Yeah.
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That's really satisfying.
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So it's really great to see all of it.
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That's awesome. Thank you for that. Okay.
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So you can see there's just huge differences from one,
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just the way they're operating, the compliance confidence,
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and then just being more adaptable to the real-time needs of the business with
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data. So we've covered a lot of the hard stuff.
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I'd love to get into some of the metrics of like,
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what have you unlocked beyond some of the areas we've talked about?
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And global expansion is an area that I would love to talk about. So Cristina,
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what's getting easier for you?
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Yes. Well,
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we lived in a nice world when we sold to customers all over the world from the
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United States,
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but of course we started to realize that a lot of those customers,
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despite not necessarily being in the US,
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wanted to meet in person and that they would love for us to come to their
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offices and all over parts of the world.
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And a growing portion of our business was in EMEA.
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So we decided to open up a London office, hire a sales leader out there,
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and actually concentrate our sales team there as well,
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which is unusual for us because we're also completely remote as a company.
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And so that also begged the question of like, OK,
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we need to set up a new entity,
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potentially transfer some people over from the US into this new office in
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London, hire some people from the country as well,
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and build that team out.
So we needed revenue to actually run through a new
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Stripe account that was associated with that new entity.
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And then obviously from there, it starts to get like, "Well,
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I have this one account over here and one account over here." But I think also
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with Stripe Data Pipeline,
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making sure that all of that data can come to a single source of truth within
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our internal dashboards starts to become more and more important to
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understand how the business is operating in these separate regions.
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Obviously we have like tax and legal requirements that are kind of driving
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this new structure and way of operating,
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but Stripe's platform makes it really easy to kind of connect different accounts
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to each other and kind of make that pretty manageable.
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And then we're also starting to think ahead to APAC as well.
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So hiring our first rep out there,
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and then kind of giving more confidence to the plan
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because it's worked pretty seamlessly in London.
380
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Love it. Global by default, all of our businesses.
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So global expansion goes from this massive, scary thing.
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We didn't even talk about the tax side of that, but to something that like, hey,
383
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this is a revenue driver. It's revenue infrastructure that we're building here.
384
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Okay. Tessa, what has the consolidation unlocked for Thinkific?
385
00:24:06.880 --> 00:24:08.540
Yeah, I mean, we just move faster,
386
00:24:09.400 --> 00:24:13.280
which is a huge benefit when the company says, "Hey,
387
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we want to focus on this new jurisdiction," or, "Hey,
388
00:24:16.420 --> 00:24:21.180
we want to do token-based pricing for this new AI feature." Our
389
00:24:21.220 --> 00:24:23.140
accounting and billing team can go, "Yep,
390
00:24:23.240 --> 00:24:26.520
let's go." Which is just,
391
00:24:26.860 --> 00:24:29.980
we know we can operationalize it and that's really great.
392
00:24:30.560 --> 00:24:35.280
Fantastic. I love that. And then that's not new engineering requests.
393
00:24:35.360 --> 00:24:38.800
It's a billing team that enabled to go figure that out. Okay.
394
00:24:41.220 --> 00:24:42.920
Now, I know that some of you may be thinking, "Well,
395
00:24:43.040 --> 00:24:47.160
this is wonderful for Linear and Thinkific, but we're not there yet,
396
00:24:47.280 --> 00:24:50.500
or we're not sure we could handle that." And that's OK because actually
397
00:24:50.600 --> 00:24:51.980
everybody's at a different stage.
398
00:24:52.400 --> 00:24:56.780
And I think one of the key themes or message that we want you to take away is
399
00:24:56.820 --> 00:24:58.620
that whatever stage that you're at,
400
00:24:59.080 --> 00:25:03.740
Stripe can help you have a pathway to a more consolidated opportunity.
401
00:25:04.820 --> 00:25:05.220
But Tessa,
402
00:25:05.220 --> 00:25:08.760
I want to tackle one question that I think is on the minds of some of our
403
00:25:08.920 --> 00:25:09.940
customers and users.
404
00:25:11.060 --> 00:25:14.920
Going all in with Stripe versus multipoint solutions,
405
00:25:15.280 --> 00:25:19.320
was there some concern about single-vendor risk?
406
00:25:19.700 --> 00:25:20.533
Yeah, definitely.
407
00:25:21.700 --> 00:25:25.020
We had concerns about moving everything onto one provider.
408
00:25:26.000 --> 00:25:30.320
We also had some question marks around the functionality and
409
00:25:30.780 --> 00:25:34.520
accuracy of the products, because at the time,
410
00:25:34.580 --> 00:25:38.120
both Stripe Tax and Revenue Recognition were fairly new. So
411
00:25:39.880 --> 00:25:42.040
we assessed that and for us,
412
00:25:42.680 --> 00:25:45.240
the benefits really outweighed that risk.
413
00:25:45.960 --> 00:25:47.940
The benefits of being able to move so much quicker,
414
00:25:48.100 --> 00:25:51.460
being able to actually do what we want to be able to do in the business
415
00:25:53.700 --> 00:25:54.620
made it worth it for us.
416
00:25:55.460 --> 00:25:55.800
Great.
417
00:25:55.800 --> 00:26:00.740
So the risk of single-provider risk was offset by the greater
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return.
419
00:26:01.320 --> 00:26:02.040
Yeah, definitely.
420
00:26:02.040 --> 00:26:04.080
Okay. Awesome. That's a really honest answer,
421
00:26:04.140 --> 00:26:07.940
and I appreciate you sharing that with the room. Cristina, last question.
422
00:26:08.360 --> 00:26:11.440
If there are some businesses out here in the room using just a few of Stripe's
423
00:26:11.500 --> 00:26:15.840
capabilities today, any guidance based on your journey, what would you share?
424
00:26:16.280 --> 00:26:17.860
Yeah. First,
425
00:26:17.960 --> 00:26:21.720
I'd just say it makes sense to plan as early as you can.
426
00:26:23.060 --> 00:26:27.820
We had a good sense probably about six months to nine months ahead of time that
427
00:26:27.840 --> 00:26:30.820
we were going to open this office in London,
428
00:26:31.540 --> 00:26:34.000
that we were going to hire a team based there.
429
00:26:34.780 --> 00:26:39.320
So having conversations with finance and operations and accounting and making
430
00:26:39.340 --> 00:26:44.080
sure that you're doing things to plan ahead for that. Sadly,
431
00:26:44.240 --> 00:26:49.000
like opening up a bank account in London is not as easy as opening up
432
00:26:49.540 --> 00:26:53.760
a bank account here in the US, even if you're doing it with the same banker in
433
00:26:55.340 --> 00:26:56.160
a different region.
434
00:26:56.160 --> 00:26:59.400
So just some of these things just take a lot more time than you would
435
00:26:59.420 --> 00:27:03.960
anticipate. So like plan early for those things. Second,
436
00:27:04.320 --> 00:27:04.860
of course,
437
00:27:04.860 --> 00:27:09.720
just like find the right partner that you're really able to scale with and has a
438
00:27:09.780 --> 00:27:13.580
good line of sight for what you need.
So one of the things that I've loved about
439
00:27:13.600 --> 00:27:18.060
working with Stripe is that you're not in a situation where it feels like you're
440
00:27:18.180 --> 00:27:20.100
constantly coming to Stripe and saying, "Do you have this?
441
00:27:20.160 --> 00:27:24.640
Do you have this?" And I feel like as soon as I think about the next stage of
442
00:27:24.660 --> 00:27:28.600
the business, it's like, "Oh, we have that," or, "It's in beta," or,
443
00:27:28.600 --> 00:27:32.320
"It's coming." With things like usage based billing,
444
00:27:32.420 --> 00:27:37.240
which are on our mind for the future and some new products that we're doing or
445
00:27:37.560 --> 00:27:40.060
other things that are critical for the business going forward.
446
00:27:40.120 --> 00:27:44.480
So also just be communicative about what you need and make sure that you're
447
00:27:44.500 --> 00:27:49.360
working with a partner that ultimately is going to be building alongside you
448
00:27:49.560 --> 00:27:53.680
and is working with customers who probably have a lot of similar needs as you
449
00:27:53.720 --> 00:27:57.350
do. And then lastly, while Stripe does...
450
00:27:57.680 --> 00:27:58.900
I try to put everything into Stripe,
451
00:27:59.100 --> 00:28:03.280
but I'm trying to consolidate as much as possible.
I've worked at other
452
00:28:03.320 --> 00:28:07.140
companies where maybe you take the enterprise business and you put it over here,
453
00:28:07.320 --> 00:28:08.960
and then it's running separately.
454
00:28:09.200 --> 00:28:14.060
I want to centralize as much as possible and simplify for the company,
455
00:28:15.160 --> 00:28:16.320
but in order to do that,
456
00:28:16.440 --> 00:28:20.020
I think you realize that there are still integrations that you're going to need,
457
00:28:20.720 --> 00:28:23.380
accounting and bookkeeping and lots of other things.
458
00:28:24.280 --> 00:28:27.300
So just thinking about the integrations that we need,
459
00:28:27.940 --> 00:28:30.940
we're thinking about changing accounting platforms as an example. And it's like,
460
00:28:31.000 --> 00:28:31.800
well,
461
00:28:31.800 --> 00:28:35.180
each one of these has to have a really robust Stripe integration and that's like
462
00:28:35.380 --> 00:28:39.580
the default for anything that we might be selecting if we're trying to move to
463
00:28:39.620 --> 00:28:44.540
maybe one of these new-age AI-powered bookkeeping and accounting systems to
464
00:28:44.600 --> 00:28:46.140
ensure that everything works really well together.
465
00:28:46.560 --> 00:28:47.140
I love it.
466
00:28:47.140 --> 00:28:51.460
Just the planning and just having that view around the corner a little bit.
467
00:28:51.820 --> 00:28:54.980
That's one of the reasons we were pushing so hard internally to get these
468
00:28:55.040 --> 00:28:59.460
roadmaps more publicly out to you so that all of you could have more confidence
469
00:28:59.480 --> 00:29:01.060
in the capabilities, the countries,
470
00:29:01.100 --> 00:29:03.540
and the markets that we're going to be helping you get into.
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So I'd like to give a big round of applause to Cristina and Tessa
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for their insights.