The Motley Fool Interviews DocuSign CEO Allan Thygesen

In this podcast, Motley Fool co-founder and CEO Tom Gardner, Motley Fool Chief Investment Officer Andy Cross, and contributor Toby Bordelon talk with DocuSign CEO Allan Thygesen about opportunity, innovation, and the business of DocuSign.

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A full transcript is below.

This podcast was recorded on Oct. 12, 2025.

Alan Thygesen: I've worked for 40 years. The pace of change right now in every aspect in our product innovation in our go-to-market, in our packaging and pricing, we just discussed in how we market, how people discover us. I mean, all of that is just changing at a rate that is exhausting and exhilarating at the same time.

Mac Greer: That was DocuSign CEO Alan Thygesen. I'm Motley Fool producer Mac Greer. Now, DocuSign provides e-signature solutions and other contract management tools. We recently had a chance to talk with Alan Thygesen about opportunity, innovation, and the business of DocuSign.

Tom Gardner: Hello, fools. Tom Gardner here with our Chief Investment Officer, Andy Cross and Toby Bordeloon, and we're so excited to be able to spend this time with the CEO of DocuSign, a Molly Fool recommendation, ticker symbol DOCU, and the CEO is Alan Thygesen and Alan, thank you so much for being here with us today.

Alan Thygesen: It's a pleasure to be with you, Tom. Thanks.

Tom Gardner: Of course, this is a standard opening question for you that everybody thinks historically of DocuSign as a signature company. Let's talk about all that it does now with AI workflows and just get right into it in terms of the end-to-end workflow opportunities of the company.

Alan Thygesen: Fantastic. Yes. Well, I'm sure many of the listeners have signed with DocuSign over the years, either in a personal or professional context. Look, that's an amazing starting point. We are involved in the perhaps, most important moment of the journey that an agreement goes through. That was part of what attracted me to the company three years ago was that position and affinity. But as you said, there's a lot more to agreements than the execution moment. DocuSign had that general idea for a while that we could go upstream from people executing documents to mass customizing documents, maybe to identifying the parties, and so on. But we've never really put it together end-to-end in an agreement management suite. That's what we've done. We launched that in June of last year. Literally every stage of the agreement journey from creating the agreement, negotiating it, managing all the internal approvals, pre-filling the agreements, executing them, and then managing them once they're executed and figuring out what you might want to renegotiate or figuring out how you're doing in your contracts or where you have exposure. All of that is available. Much of it AI-enabled, which I'm sure we'll get into. We call it intelligent agreement management, and it's been fun. It's been a revitalization of the company. I think we've rediscovered our innovation Mojo and benefiting from, as I said, at the beginning, from already being a trusted partner with the signing product. That's a nice starting point.

Tom Gardner: Two follow-ups for me and then I'll let the real great interviewers get in the mix. When you reenergize a company in terms of awakening its desire to innovate, what are the top two or three things that you think are essential to that transformation, the process of getting those muscles working again?

Alan Thygesen: The first thing is, look, you have to have the right leaders and so I attracted some great folks that combined with some of the amazing talent we had here could be leading that effort. I think we had to articulate a compelling vision, a mission that felt worthwhile and that honored what we had done before, but represented the opportunity, and sometimes it's better to be lucky than good. I joined in October '22, and GPT 3.5 launched a month later and I had some idea what was going to happen with AI, but obviously that's worked out incredibly well for us. Then lastly, I think you got to set some immediate goals that allows people to feel like they can be successful. We set this goal of launching the first part of the suite and in particular launching our intelligent repository. Basically, a place to store all your agreements that uses AI to extract all the essential data out of them. We agreed on that in August of '22, and we launched a Beta by the end of January the following year. I don't think anybody in product engineering thought that that was possible or good idea. I think once we did it, it was such a can-do moment for the company and it was so exciting. It became the heart of our launch, and then we relaunched the company in a big way and gradually got all the teams involved through the sales and support teams. I think the whole company has rallied around that mission and a sense that the transformation is now possible. The other chic had a bold vision, but you also got to show them how they can get there and having those early proof points was super important.

Tom Gardner: I'm going from the forest level right down to the pine cone with this follow-up in a very unprofessional interview format. But how is the suite priced now? What has changed in pricing with the addition of all these features?

Alan Thygesen: You'll not be surprised to hear that it's gotten more complicated. I mean, historically, the way DocuSign has been priced is we sell our electronic signature product in a batches of envelopes basis. The envelope is basically a collection of documents that are sent for signing. That was a good proxy for value. Didn't capture how important the document was, but it was a nice simple model that everybody could understand and that allowed us to scale up. Well, that obviously doesn't work anymore, given that we're now doing this much broader range of workflows that's not necessarily related to agreement volume and the value depends on which parts of the suite that you use and maybe how large your library is. We've evolved because you got to keep it simple enough that we sell to companies of all sizes. We're not just enterprise company. We sell to 100-person companies, even to two-person real estate offices and everywhere in between, so it needed to be simple to start, so we used a seat-bat model with some thresholds for the size of your library. Now we're rolling out more complicated or complex model that is a platform plus various features that can turn on and where we attempt to capture some sense of the value that we're delivering and that the customer would feel good about paying for. But to be honest with you, it's evolving as we speak, because all these AI features, what you really want is to align your pricing with the value that you deliver. It's just so hard to find those proxymetric that are objective and that you and the customer can agree on and then it has to be simple enough that they can understand it going in and that we can explain it to them in a relatively short conversation. I don't think we've nailed that yet, but we're getting there. But we started with something relatively simple with c+ and then we're evolving toward more platform pricing with tokens for different types of value.

Tom Gardner: It's never really felt great as an analogy going to you, Andy, but we're building the plane as we fly it. We've all heard it before. Maybe we don't want to actually visualize that. That probably doesn't feel great. But with the tooling, all the new tooling, all the upgrades, you have to be able to keep transforming yourself, and that means the value you're creating is going to shift, and it's going to be a fluid environment.

Alan Thygesen: I've worked for 40 years. The pace of change right now in every aspect in our product innovation, in our go-to-market, in our packaging and pricing, we just discussed and how we market and how people discover us. I mean, all of that is just changing at a rate that is exhausting and exhilarating at the same time.

Andy Cross: I want to have a follow-up on that because you talked about some of the sales restructuring and reorganization. We've been hearing this from a lot of different software companies. I think this is part of this conversation about things moving so fast and being able to articulate your value prop. Talk a little bit about what encouraged you to change or what forced you maybe to rethink the sales organization and what change did you actually implement throughout the year?

Alan Thygesen: I think to start, DocuSign was historically a direct sales company, and to a fairly extreme extent. I mentioned earlier how we have customers of all sizes. Unless you were buying the absolute most simple bundle we offered, you were basically told to talk to a seller. We had sellers that had hundreds of accounts, sellers that had a smaller number of larger accounts. But basically, everybody was assigned to a salesperson. Eighty five percent of the company's revenue was managed by the direct sales team. When I came in, my first observation was, wait a minute. We're a digital contracting product. You should be able to digitally transact with us in a more robust way. We worked on that and made a lot of progress on that. Now you can order all the products and upgrade as you see fit. But the second part is, as our product roadmap changed from this point solution that everybody understood well and that many people were able to implement by themselves without any external help to this broader agreement management solution, what we needed both on the sales front and on the post sale side changed, because we're now selling a solution, a platform that others can even add on top of, that's just very different kettle of fish. We've been doing a lot of enablement, which is a fancy word for training your sales team, as well as upgrading and select places to get people who are more familiar with that motion. We're leaning much more heavily on partners now. Historically, there wasn't a need for a partner to be involved in selling signing, but with this new platform, we need the delots to the world and their counterparts regionally and in specific industries to do more work with us. They're very interested, but we have to learn to dance with them and do a better job of that. Those are some of the changes on the sales side. Then the support side, of course, again, sign was a simple, singular product, and it was a fairly transactional support model. People would call or email it's a problem and we could usually solve it over the phone. That way. Now it's a much richer processes. You got to consult with people on how to use the AI, how to get their data in the right place, and how they might want to change their workflows. Those are all more robust things. Some of those are things that a classic enterprise software brand that would have done before and some of it is specific to AI. This notion of building models with customers that didn't really happen before. That's new.

Tom Gardner: Let's randomly leap forward 12 years and ask ourselves, has DocuSign replaced law firms? Have we moved beyond just the management of the actual workflow to a lot of the negotiation? The whole process of coming to agreement can be automated.

Alan Thygesen: No, I don't think so. Let me say a couple of things. First of all, I think you will absolutely see automation of some lower-level legal work activity today. Things like you could imagine an automated negotiation of an NDA. I don't think that's super futuristic. I think that's mostly possible with tech today and since there's not that much risk in most cases, I think we'll see some of that. You can imagine agent-type onboarding of new vendors and new clients. But I think that's not really, I think, why people retain law firms. Yes, they do do some of that work today, and so some of that work will go away. But the reality is that legal is one of the most under-resourced functions in any company. It's one of the reasons why everybody always complains that legal is a bottleneck. There's so much headroom, I think, to take those repetitive but manual tasks and automate them. I think on the more complex judgment where there's meaningful amount of risk involved. Sure, the AI will do a lot of pre-processing and will serve it up to humans, but you'll still have human review for an extended period of time, no opinion. Now, I think it's very scary to try to forecast what's happening in 12 years. That was your time frame?

Tom Gardner: You meant 12 months. If we had said 12 years, how long time is that 1995? Obviously, we know the pace has picked up so much. It's really interesting to think how planning happens. Your answer to that suggests that my second question, which is more of an idea, I wanted to play out and have you shoot it down. You've already shot it down. But would we ever think about renaming our company from DocuSign to Docu Flow?

Alan Thygesen: We had that discussion because we went through a significant rebranding exercise holistically, not just about the name, but about our look and feel and what we were trying to communicate about the brand when we were getting ready to launch Intelligen review and management. I said to the team, look, I was willing to consider anything but change in the name. Look, if you've got a name like ours that's instantly recognizable and has very positive generally affinity, I think the bar is incredibly high to mess with that. We have over 1.5 billion individual profiles that have executed the document, the DocuSign. We have over 1.7 million monthly paying customers that pay us for our services. I mean, those are very large numbers. I can't even imagine the media plan and the effort that it would take to meaningfully substitute that if you tried to change the name. Yes, I did have people who suggested that, and of course, it does tie us back to sign, but-.

Tom Gardner: They and I were dismissed from your company.

Alan Thygesen: I'm sorry, but I don't think that would be a good idea.

Andy Cross: You've been focused on bottoms-up, innovating. You've been talking about this, you've done that. Talk to us a little bit about the product development, the innovation, engine if you maybe peel back the curtain a little bit for us at DocuSign without getting too much into the weeds. But just curious how you think about motivation, your team, and just the release schedule, how quickly you trying to innovate these days.

Alan Thygesen: DocuSign was COVID darling, where we were growing very nicely before COVID and then we have all this demand pull forward from COVID. Then when that receded, it was a hard reset. Some use cases fell away and customers had pre-bought and bought more than they needed. It was pretty tough reset, and that affected all parts of the company. Think one of the things that's a hidden cost of that automatic demand is that it's not just your salespeople who fall asleep and forget how to sell your product engineering organization. Well, as long as I keep the lights on, I can do what I want. I think we lost some DNA. It wasn't as much of a focus on shipping and moving the needle from innovation perspective. As we discussed earlier, I think we setting the bar, articulating a new vision, explain to people that they were empowered to go and innovate and suggest ideas, raising expectations on release velocity. We were doing a couple of releases a year, and now we're shipping much more frequently. All those things are little things that you do. You give people better tools to get their work done faster. All those things have helped speed up productivity. We're in a much better place. I still would like to move faster. I'm impatient by nature, and I think particularly in today's environment, you need to be impatient. You can't be looking at yourself or how you are doing compared to how you were doing 2-3 years ago. You got to be looking at how fast are the cutting-edge companies going, and they are going very fast.

Tom Gardner: Do you see any threats on the AI front in terms of being a threat to your business, allowing competitors perhaps to come in and more easily compete with what you're doing?

Alan Thygesen: Let me put it this way. I think what it unlocks for us and for the category is such a massive leap forward. For historic documents, agreements have been done flat files. They might as well have been in a physical filing cabinet. Everybody had this PDF stored somewhere, if they could even find it, and I didn't know what was in it and they had no tools for managing that. AI really transforms that. That's an unlock not just for us but for everybody, but then the fact that we start in this position of having all this understanding of agreement structure and being involved in so many steps of agreement workflow and having the distribution to all these companies. Look, you got to worry, as we talked about earlier, about some smart start of coming up with some killer functionality that you hadn't thought of or can't replicate, but I feel it's been a blessing and just a giant opportunity for us and I'm just very fortunate to be leading DocuSign this time.

Tom Gardner: Alan Thygesen, CEO of DocuSign, thank you for spending time with us. We enjoyed every minute of it. Obviously, we've been following DocuSign since its IPO, all the way through and so excited about what you're creating there with your team and all DocuSigners. Are we DocuSigners when we come to work?

Toby Bordeloon: We are.

Tom Gardner: We're DocuSigners. In the way that Jensen Wong is working to bring us new technologies, you're working to bring us investment returns, and we thank you just as much as we thank Jensen. Thank you for the time and best of luck.

Toby Bordeloon: Thank you. It was really great to chat with you guys. We should have.

Mac Greer: As always, people on the program may have interest in the stocks they talk about and the Motley Fool may have formal recommendations for or against, don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley Fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. For the Motley Fool Money team, I'm Mac Greer. Thanks for listening, and we will see you tomorrow.

Andy Cross has positions in Docusign. Mac Greer has no position in any of the stocks mentioned. Toby Bordelon has positions in Docusign and has the following options: short January 2026 $60 puts on Docusign. Tom Gardner has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Docusign. The Motley Fool has a disclosure policy.