Decoder with Nilay Patel
Docusign's CEO on the dangers of trusting AI to read, and write, your contracts
02 Feb 2026
Chapter 1: What insights does Allan Thygesen share about DocuSign's workforce?
Do you ever look back on something you posted on the internet and think, well, that was cringe?
Yeah, I mean, I look back at that stuff and I'm just like, it's so emblematic of the era. And it's also just like, why did I think this would age well, like in the slightest?
This week on Explain It To Me from Vox, what to do with your online regret. New episodes on Sundays, wherever you get your podcasts.
Hello, and welcome to Decoder. I'm Neil Apatow, Editor-in-Chief of The Verge, and Decoder is my show about big ideas and other problems. Today, I'm talking with Alan Tiegason, the CEO of DocuSign. You know, DocuSign, the platform where you sign things online. 7,000 people work there, which is one of those facts you see fly around sometimes that has always felt like perfect Decoder bait.
Chapter 2: How has AI influenced DocuSign's product roadmap?
What are those people doing? And what kind of a product roadmap does a company like DocuSign even need? I always assumed that I would never find out the answers to these questions, because most enterprise software CEOs do not like being on Decoder. That's because most enterprise software is terrible, and they don't actually use their own products, so they have a hard time answering my questions.
So I was pretty happy when Alan agreed to come on the show, and told me that he'd actually used DocuSign himself just that morning. From there, we talked about what DocuSign's platform actually is, how it's expanding, and of course, how all of those employees are structured.
Alan's only been the CEO of DocuSign for three years, so he has a lot of interesting perspective on where the company was, the changes he wanted to make, and where he thinks this is all going. Of course, that brought us to AI.
Alan and I spent a lot of time talking about the idea that DocuSign should summarize contracts for people before they sign them, and who is responsible if the AI gets that interpretation wrong. We also spent a while talking about how DocuSign's customers actually generate the kinds of documents that get signed and how automating that process with AI does and does not work.
Chapter 3: What challenges does DocuSign face with AI contract interpretation?
You'll hear Alan point out that a lot of this looks like a fancy mail merge, which was at least refreshingly down to earth in the context of an AI conversation. Of course, I also asked Alan which parts of his enterprise software were bad and how he'd improve them. And he actually answered the question, which might be a first for an enterprise software CEO. This is a good one.
There's even a couple of dunks on Google in the mix, as you'll hear. OK. Alan Tiegason, CEO of DocuSign. Here we go. Alan Tigason, you are the CEO of DocuSign. Welcome to Decoder.
Chapter 4: How does DocuSign ensure contract accuracy with AI?
Thank you, Eli. Good to be here. I'm excited to talk to you. I always love it when an enterprise software CEO comes on the show. Most of your competitors in enterprise software are very reticent to show up and answer the first question. When was the last time you used your own product? This morning. This morning. What did you sign? Can you say?
Chapter 5: What role does customer feedback play in DocuSign's product development?
I signed an agreement for our procurement team, but yesterday I signed your release form. It's the most important question, I think, for enterprise software CEOs because the experience of using enterprise software is, I would say, on the whole, pretty dicey. It's not great. I agree. And DocuSign is a weird one. It's in the background of everything all the time. Most people don't use it.
I think like a lot of lawyers, maybe procurement teams use the product. Most people sort of experience DocuSign. How do you think about that split?
Chapter 6: How is DocuSign structured to support its growth?
I mean, it is sort of a two-sided network, right? So we sell to businesses and other organizations that want to send documents for signature, prepare them and send them. So that's been historically our business. And then consumers or other companies sign documents. They're the counterparty, but they don't pay us anything. And so most people have experienced this that way.
And then if you work at a company, an organization that uses DocuSign, you may have experienced that. being on the sending side of approvals or other functionality. That business is really interesting to me. DocuSign as a company is interesting, most notably because it's been an independent company for 20-some years.
Chapter 7: What strategies does DocuSign employ for customer retention?
It's a public company. From what I experience, again, as somebody who just experiences DocuSign, it's just there. It's just in the background of almost every kind of thing I do. But it's shocking to me that it hasn't been acquired or people haven't tried to acquire DocuSign The product range hasn't dramatically expanded in other ways. It's expanding now. Sure, what comes next?
And the way that everyone's expanding, right? Now the chatbots are going to do all the work for us. But how do you think about the fact that it has been effectively one product experience all this time?
Chapter 8: What future developments are planned for DocuSign's AI capabilities?
What's made it resilient in that way? Well, yeah, so you're right. We are a little over 20 years old. And, you know, the original idea was to help companies and individuals sign agreements online. And at the beginning, no one thought that was a good idea. Not regulators, not companies, not consumers.
And so there was a tremendous amount of trust building across those three constituencies that happened over time. But as you said, over time, we became trusted for a variety of transactions. And now it's sort of in the water across companies of all sizes and functions. Look, we did come up with a great idea. And when you have a good idea, you want to run with it.
And I think DocSign has done a really good job of that. With that said, I mean, part of my goal joining about three years ago was to say, OK, that's an amazing foundation. And we're privileged that people have positive associations that we're used by. 1.8 million companies. What do we do for Encore? How do we broaden the platform?
And the company, I mean, we've had some ideas on that for a while, thinking about the entire agreement journey, but we'd never really put it all together. We'd never gone beyond the marketing side of identifying that problem to actually delivering solutions that could solve it. And I think that's what we're doing now. And so that's very exciting. But the signature piece is a foundation.
That is the most pivotal moment in the life cycle of an agreement. It's a very high value, a high stress moment for many people. And making that simple and delightful was a very meaningful value proposition. And it's a lot harder than it looks. Let me ask you a very existential question first. Mm-hmm. Again, I assign DocuSigns. My signature in DocuSign has no relationship to my actual signature.
The DocuSign just generates some cursive that says my name. What is a signature? In DocuSign's worldview, what is a signature? Signature to me is really identity and consent commingled. And the identity aspect, there's a lot of things we do to identify you. Obviously, this thing comes to you in your email or via SMS or via WhatsApp.
We do all kinds of IP tracing and other things to validate that you are the intended, let's say you're the signer, that you are the intended recipient. And that whole trail is then auditable and can be used in a court of law. So it's a perfect substitute for a wet signature that you might otherwise have done. In practically all cases.
There are a few in the US that are still requiring you to sign something in person, but we've done a pretty good job over time getting to a place where it's felt that that's super secure. And from the consent perspective, I mean, you're right. It could be a dot, it could be a checkbox, it could be a signing. It's almost less important.
There are some personal expression aspects of it, but it's the identity piece that's the most important, and then the fact that you take a step that indicates consent. Just to make that as reductive and simple as possible, it sounds like the service that you're providing is DocuSign is you know who I am. You know who the other part of the agreement is.
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