
Docusign’s Allan Thygesen says “not providing an AI service isn't really an option.”
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Neelai Patel
The world moves fast. Your workday even faster. Pitching products, drafting reports, analyzing data. Microsoft 365 Copilot is your AI assistant for work built into Word, Excel, PowerPoint, and other Microsoft 365 apps you use, helping you quickly write, analyze, create and summarize so you can cut through clutter and and clear a path to your best work. Learn more@Microsoft.com M365Copilot hello and welcome to Decoder. I'm Neelai Patel, editor in chief of the Verge, and Decoder is my show about big ideas and other problems. Today I'm talking with Alan Teigason, 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. 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. 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 dunks on Google in the mix, as you'll hear. Okay, Alan Teigason, CEO of DocuSign. Here we go. Alan Tigison, you are the CEO of DocuSign. Welcome to Decoder.
Alan Teigason
Thank you, Neil. Good to be here.
Neelai Patel
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 end product?
Alan Teigason
This morning.
Neelai Patel
This morning. What did you sign? Can you say?
Alan Teigason
I signed an agreement for our procurement team, but yesterday I signed your release form.
Neelai Patel
Very good. 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.
Alan Teigason
It's not great. I agree.
Neelai Patel
And DocuSign is a, is a weird one. It's in, 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, like use the product. Most people sort of experience DocuSign. How do you think about that split?
Alan Teigason
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, the counterparty, but they don't pay us anything. And so most people have experienced us that way. And then if you work at a company and organization that uses DocuSign, you may have experienced being on the, on the Sending side of approvals or other functionality.
Neelai Patel
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. 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, that the product range hasn't dramatically expanded in other ways.
Alan Teigason
How do you it's expanding now?
Neelai Patel
Well, sure, we'll come to that in the way that everyone's expanding right now. The chat bots 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? What's made it resilient in that way?
Alan Teigason
Well, yeah, so you're right. We are a little over 20 years old. And you know, the original idea was to help 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, 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 Doc Sign 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, okay, 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 front on core? 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 never gone beyond the marketing side of, 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, was a very meaningful value proposition. And it's a lot harder than it looks.
Neelai Patel
Can I let me ask you a Very existential question. First, you know, again, I, I, I, I assign DocuSigns that my signature in DocuSign has no relationship to my actual signature. Right? Like DocuSign just generates some cursive that says my name. What, what is a signature? And like in DocuSign's worldview, what is a signature?
Alan Teigason
I mean, signature to me is really identity and consent commingled, right? And the identity aspect that there's a lot of things we do to identify you, right? We, we obviously this thing comes to you in your email or you're on via SMS, or we have WhatsApp, we do all kinds of IP tracing and other things. And to validate that you are the intended, to say you're the signer, that you are the intended recipient. 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, could be a checkbox, could be a signing. It's almost less important. There's identity, 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.
Neelai Patel
Make that as reductive and simple as possible. It sounds like the service that you're providing to StockiSign is, you know who I am, you know who the other party of the agreement is. I hit the button and your database says, this person that we verified hit that button and they say agree. And then if, you know the contract comes into question, you can say, well, you definitely signed it. At the very least, maybe you disagree on the terms, but you definitely signed the contract. We're not going to argue about that. That implies, like, fundamentally a product is just a big database of identities and then a marking of consent. Is that how you think about it in like the most reductive way possible?
Alan Teigason
That's the aspect of the execution side. There's all the stuff that leads up to preparing a document for execution. And we have a lot of products there that you as a signer would not see, but that companies use to get documents ready for signing and to get them appropriate, approved internally to get them maybe customized for you. Let's Say I'm running a big sales team, let's say DocuSign sales team and I want to send an agreement to the decoder for you to be able to use DocuSign for your releases. I can automatically sort of mass customize a standard template using DocuSign's functionality that's embedded in Salesforce and other CRMs. So that's an example of the type of workflows that we do. We do that for hiring, we do that for procurement, we do that for new vendor onboarding. All those tools that lead up to that mag signature moment where it is I think about identity and consent, even.
Neelai Patel
That part where you're okay, we're going to generate a bunch of documents that's downstream of the first product which is right signing. The reason I ask about it in that reductive way is there's a lot of ways you could verify identity and mark consent. You have a lot of competitors. There is is DocuSigns sort of dominance market leadership. Is it based on just network effect that it exists? It's the one you can use, it's one everyone trusts and because so many people have already used it, it's the easiest thing to use.
Alan Teigason
Well, I do think that that network effect is very important and people choose DocuSign in part because they know that the recipients consumers mostly trust it. And so yeah, maybe if you're a giant bank and you have an existing relationship and you're sending something to a customer that's already yours, you know that matters a little less. But for most companies in the world, in most situations, all new customer onboarding, et cetera, that trust component is super important. Now to the other thing that was implied in your question which is well, what about identity and these alternative technologies for establishing identity? Well, you know, we could sort of see that coming, right. And so we, we worked on a federated identity strategy to give you all kinds of identity validation at different levels of risk. So you probably, we let people do knowledge bench authentication that's sort of on its way out, but that's answering those questions that you were probably remembering where did you live on the street 10 years ago? We do biometric based identification. So video or other we, you know, can link up with the, you know, the Apple and Google stu. We do risk based assessment. So we can fork you to which validation mechanisms. Right. We use the new digital IDs so in the US clear or ID me which is the government one that the IRS uses. In Europe, of course, many governments have a national digital ID same in Many other parts of the world and all the way up to a notary solution. We have online notaries. So whatever your the shoe say, risk assessment, whatever you feel is the appropriate trade off between convenience and security, we can give you all those solutions, turnkey in one platform and then at the end, most of the time you're also legally required to get a signature.
Neelai Patel
So when you think about that journey, right, who are your biggest customers? Is it just big banks? Is it mom and pops? How does that break down for you?
Alan Teigason
We're incredibly diversified, so we're used by, As I mentioned, 1.8 million companies. You know, by definition, if you have that many customers, most of them are going to be small. But we are used by over 95% of the Fortune 500 and equivalent in many other the international markets and then many midsize companies and then a huge long tail of small companies and no one company represent any meaningful share at all of our business. That said, our biggest customers tend to be banks or other large companies that have high volumes of high value agreements. You know, if you have agreements that matter and you, and you're entering to them in large volumes, you're very likely to be a DocuSign customer.
Neelai Patel
Is that the push for growth? And I do want to talk about your expansion into other kinds of products and services is part of that. You're just out of big customers. There's no more fish in the sea.
Alan Teigason
Well, we already have most large companies in the world as customers, but of course there's so much more we can do for them beyond the signing piece. And even the signing piece, we're certainly not done with that. Even the large banks who've been with us for a decade plus, but you go and audit them on how many of their agreements are actually automated and digitized and executed electronically. And it's 20, 30% because people take the biggest high value workflows and everything else is sort of left to the side. So we have a lot of opportunity. If we can make that more efficient and easy to do, we can close all of that gap as well as of course, provide this broader value in all other aspects of the agreement cycle.
Neelai Patel
Talk to me about that. So there's identity and signing, which I was very curious about because the notion that a signature represents many complex concepts underneath. I think most people don't ever spend time unpacking about it. So that's the first part. Then there's, okay, we're generating documents for signature. We might as well help draft the documents and prepare them and get them approved for that final step. I want to, I want to understand that a little bit. And then there's obviously your expansion into AI and other tools and other parts of the workflow. At what point do you run into Microsoft Word, right? Like where is the boundary of some of that, that work and like where are the boundaries of some of that opportunity?
Alan Teigason
Well, I mean we ran into Microsoft Word the day we got started, right. And Microsoft word is where 90 plus percent of legal documents get authored. That's the tool that most lawyers use. That's where documents are crafted and often negotiate redlined, you know, et cetera. So we've always been deeply integrated with Word and of course with, with Google as well and frankly with all of the tools that people use to, to do their jobs. So I mean we've had a 20 year partnership with Salesfor we were the first or second vendor on the app Exchange and deeply embedded in their flows. We do similar work with Workday and SAP and so on. So to your question about, you know, I don't think that we or Microsoft have ever thought about competing with each other like Microsoft. I mean I worked at Google for 12 years before taking this job. And so, you know, similar scale company and you take on the biggest, broadest opportunities in your office suites. And yeah, you might add more and more features to your office suite, but you don't want to add stuff that's sort of separate workflow or things that are too specific. You rely on your ecosystem for that. And that's what Google, Microsoft have done. So they'll both allow you to render a signature inside of a doc that you author in those packages. But no one thinks that's a substitute for DocuSign for all the reasons we've discussed. And so it just literally doesn't come up with customers. I've never heard anybody say, well maybe I could use Microsoft Word or Google. That has never happened in my three plus years here.
Neelai Patel
It's all of the steps leading up to you're going to experience DocuSign that are fascinating to me. So when you say help prepare a document for signature, there's the drafting, right? Microsoft Word. Honestly, Microsoft Word might be the reason I'm not a lawyer anymore. I was like, I just can't, I can't use this software anymore. There's a Microsoft Word of it. We're going to redline a bunch of stuff. We have the document from that point. What do you mean by prepare a document for signature? What are the services DocuSign provides?
Alan Teigason
Let's imagine most some Contracts are completely custom crafted, right? You know, maybe, but most, I think you're a lawyer, right? So you. Most documents, most contracts start with a template of some kind. Maybe it's a template for something really complex like an M and a agreement or something really simple like an NDA or anything in between. Could be a master service agreement between a company under that company or a license agreement. But they always have a template and then they tailor it. Some of that is done sort of legal tailoring. Right. You know, I'm going to have different limitation of liability. I want to have different payment terms. And some of it is just, should we say mass customization? I want to get the data about that customer and some things we've already negotiated. And I want that to flow automatically from whatever the system of record is. Could be salesforce, could be workday, could be SAP, could be whatever. And I want to populate that into the agreement. So this template that I have gets personalized, customized. And that's also what happens in consumer applications. You know, the forms that you get from Chase or Wells or, you know, they are, they are mass customized that way. And so that's essentially a data pool. So that's what I mean when I say customized or personalized, it's. It's taking a standard document. Now there are a lot of things that can flow from that. You know, let's say that you are a national employer, but you need to take into account employment laws in the 50 states. That would be an example of a customization that's a little bit more complicated. And of course that gets even worse. If you're a global employer and you have to do offer letters in 180 countries, that starts getting pretty complex. But there are rules. We have a system for applying those kinds of rules so that you can have global standards but still create documents that are tailored to local laws and customs.
Neelai Patel
This gets me right into the opportunity for AI broadly, which is you're starting to do some of the lawyering a little bit. Right. You're saying we're not going to hire the junior associate to figure out the local law. You can actually just programmatically make a contract that abides by the local law.
Alan Teigason
For that type of application. Correct. I think there are two big use cases for us. One is to make agreement workflows more efficient, sometimes just by automating them and sometimes by reimagining them. That's a huge part of what we do. And this mass customization is not a new thing that's been going on for a While it's sort of advanced mail merge. Right, so you said it.
Neelai Patel
I didn't want to say it.
Alan Teigason
You said is it is, it is. But look, it's really, it's really good and it saves a lot of time and it's, it, you know, a lot of companies live, live, live with that.
Neelai Patel
If I could start a business that was charging a premium on mail merge, I would do it too.
Alan Teigason
Oh my God. Yeah, managing people's address book would be another one that would be very valuable. No one has solved that. But anyway, so making workflows more efficient and now tackling all of the steps in the agreement process, that's part of, of, of what we're doing. And so we, we're tackling things like. Well, in payments we have a whole queuing system where a sales rep or procurement rep can trigger the sending of documents. Illegal. It can get an automatic first review. Then it gets assigned to a lawyer. The lawyer does a quick thing and everyone has real time status. That's an example of reimagining legal workflow which today is totally asynchronous. Email unpredictable, non transparent. That's one piece and I think that's what people have historically focused on with contract managed practice. And then the other piece is I'm going to take AI and I'm going to extract data out of the agreements to run my business better. That's something that was conceptually possible for, you know, historically, but it was just too heavy and hard to do with legacy LLMs. And now we can do that in a completely automated way. So I can go to people and say, hey, you have 5,000 agreements with me. Would you like to know what's in them? Let me highlight how these agreements deviate from agreements with peer. You know your company X is coming up for renewal in 90 days. How can I review that? How can I know what I should be renegotiating? I can give you that using AI automated right off the shelf. It leverages the fact that you already use DocuSign and you've already stored your agreements with us, uses modern AI and then adds of course some workflow and automation on top of.
Neelai Patel
We have to pause here for a short break. We'll be right back.
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15 days after rebate submission Qualify unlocked device credit Service port in 90 plus days with device ineligible carrier and timely redemption required. No cash access and Card expires in six months. Card issued by Sunrise Banks NA member FDIC welcome back. I'm talking with DocuSign CEO Alan Teigason about why exactly his company needs to be as big as it is. Let me take a beat here and just ask the decoder question so I have a better sense of the company itself. How is DocuSign structured? How many people is it, how they organized?
Alan Teigason
DocuSign has a little under 7,000 employees and you know, our structure has gone through some, some transformation. Historically I would say DocuSign was a, you know, ignoring the very early days of conceiving the product evolved into becoming a very sales centered company. Sales all most customers interfaced with DocuSign through sales. We had a very large sales team and that was sort of the most powerful function of the company. And things flows from there were optimized around that. When I joined and I very quickly realized we needed to completely reimagine our product roadmap. I really wanted to put product at the center of the company and say we're going to articulate a new product roadmap and things are going to flow from there. That's not to say that we're not taking lots of customer input. After all, we've got 20 years of experience working in agreements and millions of customers. But we want the product vision and the overall architecting of that to be the guiding light for then how we go to market, how we spend, etc. Second area that I focused on was historically marketing here worked in the service of sales. It was basically about creating qualified leads for sales. But I'm like, well customers, this is an electronic contracting product. They should be able to just come in and do whatever they want to do directly self serve to the greatest extent possible. You know, I came from Google where every advertiser, including people who spend a, you know, a billion dollar plus a year, places their own orders in the system. But at DocuSign we couldn't, couldn't do that. So that was another area. And really taking all the pieces of the company that worked on identifying, sourcing and bringing new customers on and combining them in one team. And the third area that I'm really pushing on is we've always felt like we needed to own the ball and when you have an iconic simple product then that that you maybe don't need partners as much. But now with this broader vision for agreement management, we really need partners to help us go to market and install and service the product. And so we're very focused on working with system integrators like the Deloitte Syn accentures of the world as well as distributors and resellers. Those are the big changes we've made.
Neelai Patel
I have to say 7,000 people is a shocking number. The last number I heard was actually 4,000, which was shocking. Then how are 7,000 people organized at Docusign? Is it sales and marketing? Is it product? How does that work?
Alan Teigason
Sales and marketing is the biggest area. We have about a thousand account executives that cover everything from SMB accounts all the way up to enterprises. We're not a small company. We do over 3 billion in revenue. Our revenue per employee is pretty much in the median of the SaaS businesses. So sales and marketing is the biggest function. And it's everything from pre sales to account executives to customer success people to help with implementation and support. Of course, product and engineering, we have about 1000 people in engineering, 1200 engineering proper and then there are product managers and designers and so on. I think if you look at the number of countries and the complexity of the regulatory and compliance environments we're in, that's a significant effort. And then now with iam, I pivoted. Pretty much all of the open investment dollars in the company in the last three years have been pivoted into this. So we've gotten much leaner on the sales and marketing side and we've gotten invested more heavily in product and engineering.
Neelai Patel
IAM is the AI product.
Alan Teigason
That's right.
Neelai Patel
When you think about shifting that investment focus and then something like self serve, you were at Google, you were at Google for I think 12 years, something like that. You've been the CEO of DocuSign since 2022. So you've been there a minute, three years. How did you think about changing Docusign? How was it organized before and then when you got there, how did you think? How do you work through? Okay, here's. I'm going to reorganize it for the opportunities I want to attack.
Alan Teigason
I think the low hanging fruit was help of the company pivot from just being a good machine for acquiring new Customers, but not necessarily an amazing retention machine. So focused on customer retention and customer success and adoption. I think we sort of took that a little for granted. That was one area. Second, getting us to be much more efficient, as I alluded to, whether it was through building out digital channels or just streamlining our sales and marketing efforts. So that was a big immediate push into the low hanging fruit things that were in my control early on. But the biggest change is really the product vision effort and pivoting the company to being product innovation led. And restarting the innovation engine of DocuSign Covid was a seminal event in the company's history. Not in a good way. I think everybody thinks DocuSign is a Covid darling and that must have been so great for us because everybody had to use this. And look, there was some of that temporarily, but if you look at the long run, it didn't change the sort of secular adoption trend of signing things electronically. But everybody literally fell asleep. If you're a sales rep and your revenue growth rate without much effort goes from 25% to 60%, you're in the order taking business. And on the engineering side, we didn't need to develop that much. You just need to keep the service running and scaling that. And so I think restarting that, hey, we can build something great, something new and reclaim that innovation mojo. That was, I think the most important transformation to DocuSign is still ongoing. But I mean the, the pace of product innovation and product release is completely different now. And we actually had to throttle the number of releases we were doing because there was so much. It was sort of starting to overwhelm our, our customers and our sales team. We have so much stuff.
Neelai Patel
Yeah.
Alan Teigason
And there's so many opportunities and that's an exciting place to be.
Neelai Patel
So was that your pitch when you, when you got the job? Very few people are going to ever interview to be the CEO of a multi billion dollar publicly traded company. What was, what was the pitch? I, I'm going to restart your product innovation.
Alan Teigason
It was a dual pitch. I said, look, what I know I can do is I can come in and make things much more efficient. And of course I use my digital marketing background from GO to make some suggestions on things that I thought we could do.
Neelai Patel
Did you make just like a killer deck?
Alan Teigason
You know, I didn't get time to make a killer deck. I mean, literally. I got a call from Headhunter on a Thursday night that the board wanted to meet with me for an hour and hear my thoughts on the future of DocuSign Saturday morning at 9 and I was working full time at that time. I had a big job at Google so I couldn't just take a day off. I suppose I could have, but I didn't. And so I basically had Thursday evening and Friday evening to prepare, you know, a short slide deck. And the reality in these kind of situations, nobody expects, you know, the super polished multimedia thing. What they really are focused on is what's, what are the thoughts, right? And you can use 10.4, that's fine. And so I was really focused on, look, I, I know I can make the company more efficient and I know there are, there's gold on the retention side. And I believe that the agreement problem is fundamentally unsolved, but that DocuSign is the best position to capture that opportunity. I mean we were a big DocuSign user at Google still is one of our largest customers. Huge E sign and contract lifecycle management was our advanced contract management project that enterprises use. And yet I knew we were in the earliest possible phase of transforming how agreements get done and that there was so much opportunity. And so I just articulated my confidence in that I knew enough that I couldn't, that it would be, I would lose credibility if I was too specific. So that took six to nine months to really say, okay, okay, that's fine at a 50,000 foot level. How do you get to the real vision of what's the singular thing we're going to do? I mean, just as an example of that, it's easy to talk about all the steps in the journey and I think people naturally gravitate towards the drafting and negotiating side of agreements because that's, it's almost like what's in movies. Of course, that's what lawyers do. But we actually started at the end, we said, look, the, the foundational piece of reimagining agreements is to have an intelligent repository, to have an intelligent, a place where all your agreements are stored and to be able to apply AI to that. So we can tell you what's in all your agreements, start comparing them and then ultimately close the loop to what happens under those agreements. So that's what we built.
Neelai Patel
Is that what you mean when you say the problem is fundamentally unsolved?
Alan Teigason
Well, that's part of, that's part of it. We've done, the way I would describe it is we've digitized the asset, right? We've taken what used to be an offline asset, we turned it into an electronic document and we move it around electronically mostly well, and then hopefully we execute them Electronically. And other than that, absolutely nothing has changed in fit for the last 50 years. In agreements they all other aspects of the workflow, they're just as inefficient, just as brittle, just as unpredictable. There's just as much time lost waiting for some somebody in the process. You don't even know who they are, what, what steps they're on. Once you've signed the agreements go to a deep dark place. It might as well be a physical filing cabinet a in a basement. In fact it's probably harder to find now than it used to be when it was in the filing cabinet. You know, now it's in some SharePoint drive or email inbox or who knows. And so bringing all that together and presenting that information in, in a way that you know is, is intelligent, bite sized, appropriate for the, for the Persona is incredibly valuable. I mean every CFO wants to know what are the top 10 contracts where we have leverage, we've things we've negotiated for that we're not getting every head of sal to know what are their top 10 renewals and what are the three things my rep should be renegotiating every procurement and you can just go down the list. It is an obvious pain point that no one has solved and so that's our opportunity. That was my pitch and I think, I think it was a good pitch and I think the story and I think the story is much better now than it was three years ago.
Neelai Patel
I want to get into that, I want to, I want to talk about how you were implementing that obviously as part of it. I want to talk about what it's working which is interesting. But I want to ask the other decoder question first. Obviously you're at Google for a long time. Google's decision making. Lots to say about decision making at Google. What's your framework for making decisions? What did you take from that experience and what do you do at DocuSign?
Alan Teigason
Look, I loved my time at Google. It's an amazing company and proud of the time I spent there and I've always special place in my heart. One thing I do not miss is the seven dimensional matrix of time to make decisions. So I really try to avoid that here and have much greater clarity about who owns the decision, who needs to be consulted and all those constitutional frameworks. But I'd say one thing that I took away from Google as a very positive lesson is my experience, and this is not limited to Google, but that the most effective leaders in tech can go super deep when they need to and they need to be willing to do that, you know, management is not floating up in the abstract, 50,000 foot above the problem and just admiring it and thinking you can just, you know, operate at that level. I think when hard decisions need to be made one way, doors, things that are complicated, you need to be able and willing to really dive into the details. And I've always prided myself on that. And I think that was. It's particularly important at a transformation moment because, you know, it needs more push from the top to get people to change. Right. People naturally want to do things super incrementally. It's not unique to any one company. That's just how people are. And so if you're trying to get more radical change, you need to push. And in order to push and not break everything, you need to get deep in the details. So when we were deciding on the early architecture and what the key launch pieces were going to be for intelligent agreement management, I was in, you know, daily whiteboarding sessions to help decide what that was going to be. You know, once we had set that direction, then you step back and you just let the team run. Then you maybe get to a decision point about, okay, well, how are we going to talk about it? How are we going to explain to people this newly reimagined DocuSign? That was a big moment of getting super deep in, into deciding how we were going to message this to the market, how we're going to relaunch the company effectively. And then you got to decide, well, how do we take all this capability and find the singular thing that we need to tell customers about to get them to try it and buy it? Because all software has 10x the functionality that people use, and finding that singular proposition is super important. So those are examples of things that I got much more deeply involved in and I think that is essential to being effective. But then you got to let go.
Neelai Patel
So let's talk about the technology here. It's iam, it's intelligent and great management. That's the new system. That's where the AI focus is going. You've talked about it already a little bit, right? You have this library of documents you've signed. You can extract intelligence from them. I got to say, I looked at the website just before we started talking and how are we marketing this thing? And a lot of it is DocuSign will tell you what's in the agreement you're signing. And all of my lawyer red flags just went off. You should not let the robot interpret the document for you. How. And one of the reasons is well, is DocuSign now responsible for the interpretation of this agreement?
Alan Teigason
Right.
Neelai Patel
If I sign this and you know the AI hallucinated an interpretation of this clause and then I'm mad, do I, do I get to, do I get to sue DocuSign?
Alan Teigason
We literally, I think the reason you're seeing that on the website is we literally just launched this for consumers last week. And so it's the most recent beliefs. It's not generally, wouldn't generally be the top thing, but right now it's newsworthy and things that are consumer facing tend to get more attention.
Neelai Patel
As you know, here you are in decoder.
Alan Teigason
With all that said, I mean look, we've had agreement summarization for a long time. We, we provide it internally to companies that, that prepare documents, that send documents and we wait a long time to launch it for consumers. Exactly. Because of some of the concerns that you raise. Right. We, we wanted to get to a high level of accuracy. We wanted to make sure that we could position this as something assistive but that we're not replacing a lawyer and you still need to get legal advice. But that people valued that sort of high level summary. And all of our, all of our very robust testing suggests that people have, are more comfortable and have greater confidence and that they at the same time understand that you know, when something's sensitive they need to get to a lawyer. So it's, look, it's a delicate, it's a delicate thing. Right. We want to, we want to be the place where that people trust the most for receiving and executing agreements. And so not providing an AI service isn't really an option. And at the same time you got to have a ton of guardrails to avoid putting yourself in position where people who claim that they relied on you or that you are acting as a lawyer.
Neelai Patel
Yeah, I'm just curious about the dynamic there. I was talking to a colleague of mine just before we started and I said they've got this new product. When I asked him about it and what she said to me was, oh, that makes sense. I already take the agreements and paste them in a chatgpt. Exactly what's happening. But in that case, right, you don't get to go in front of the judge or file the complaint or even send the threatening letter. Being like this is what chat GBT told me. The document I was signing says probably.
Alan Teigason
They'Re probably worried about that, whether they.
Neelai Patel
Might be worried about consumer's gonna do. But, but I think it was like that fact pattern is like, well that's your fault. Right. I signed that. I pushed the button. I indicated consent after having my identity verified in the database. Next to the summary is a different fact pattern. So what are the guardrails that you thought of? I mean, because it's going to happen, right. Someone's going to blame you for a mistake that they made or that the system made. What are the guardrails that made you comfortable with that or that made you think we're not liable at all?
Alan Teigason
There's two answers to that. I mean, they're sort of what got it comfortable legally. I think we got very comfortable that all the language of the scammers and how it was done graphic. And so it was fine. But I don't think that that's big question to me. It's more of a moral question. Right. Are you doing the right thing for the customers? Feel good about that. And we got to a place where there was no question in our mind that this was better for consumers and that to continue to uphold trust in our platform as a place to come and execute documents, that we were the best position to provide this kind of additional advice and context. In fact, it would be dereliction duty not to provide it and that we needed the best possible job we could to make sure that people understood that this was context. But if this is something that's really sensitive for them, they. They should get. They should get a lawyer. Of course they don't today.
Neelai Patel
Yeah.
Alan Teigason
So I think we're improving the situation both but for consumers, but also, by the way, for companies. And so that was our motivation. And it's impossible to eliminate. People are going to claim things. I think we're doing the right thing. And we felt like we were taking not just the necessary precaution from a legal perspective, but necessarily come from a company values and morals perspective. And this felt right. So that's how we got to it.
Neelai Patel
We need to break here for a quick minute. We'll be right back.
Host/Announcer
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Neelai Patel
It may not feel like it, but Trump's approval rating is some of the lowest in recorded history, and it's fallen to new lows in recent weeks as the nation reels from recent killings of two anti ICE protesters in Minnesota. But not everyone thinks he's failing. This week we're hearing from Trump voters. It is very unfortunate that it happened, but it's also unfortunate that the ICE is being blamed for like just murdering somebody who is just so innocent. Which isn't the case whatsoever. A they were provoked. B He got ran over and you know, it just. It's hard to tell what's real and what's not anymore.
Alan Teigason
He's delivered on virtually every promise he's made. The economy is booming right now. He closed the border. We're not getting any more legals in. That has been done. That was a major promise that's been done today.
Neelai Patel
Explained. Listen, wherever you get your podcast.
Alan Teigason
Welcome back.
Neelai Patel
I'm talking with DocuSign CEO Alan Teigason about the risks of AI in legal work work. The reason for me asking about liability and whether the system is going to be Wrong. Is that LLMs as a core foundational piece of technology still hallucinate. Right? This is the flaw with LLMs. You know, if you talk to any of the big AI CEOs, if you talk to Sundar Prachah, he will say it's also their feature. Right. The reason that they are creative is because they are effectively hallucinating.
Alan Teigason
And if we inbox that in, that's a creative repositioning.
Neelai Patel
But yeah, you said it, not me. This is the dance, right? You, you want an LLM that can do a bunch of creative writing, you need hallucinations. You want an LLM that's going to do legal analysis on a library of documents that maybe is 20 years old. You really don't want it to hallucinate. How are you constraining the LLM to make sure it does what you want it to do?
Alan Teigason
I mean, so if we pivot to the folks that use our document to use our tools to prepare documents, there are a lot of guardrails that we put in. I mean, we have a whole risk scoring thing. We of course benchmark you versus your existing templates or playbooks as they're often called inside of companies and highlight things that deviate from that. And this is true both for agreements that the company prepares themselves and for third party agreements that they receive from others. Because of course, most companies are takers of terms from other companies. Right. And so there's a lot of workflow there. We also don't fully automate flows. We, we put deliberately humans in the loop at key decision points and I think that will persist for a very long time. Companies are, are very averse to, to the, the risk of, of automation that's going rogue. I, I was, we talked about Google for a little while and there was a lot of efforts at automating the commerce process. And this is for buying toothpaste. And both consumers and retailers were very resistant. And even with all the new stuff, I think it's getting better. But I still think there'll be a lot of hesitancy and those are much lower stakes than agreements.
Neelai Patel
Put that into practice for me. Just with the products you're talking about.
Alan Teigason
Today.
Neelai Patel
I am a company. I've got 20 years of agreements in DocuSign. I want to know how my terms changed over time. And I asked DocuSign to generate that intelligence for me. What's the guarantee that it's not just hallucinating, that it doesn't go through the first five years in the rag process and then it just decides to get bored and makes up some contracts that never existed.
Alan Teigason
Look, I think the stakes and the opportunity for hallucination and an extraction scenario are far lower than in a drafting scenario.
Neelai Patel
But it's going to draft a report, right?
Alan Teigason
Yes. It'll highlight things. Well, I mean, you've got to link to the sources, you got to have all of that to sort of show your work and the logic of the decisioning. But look, there's no amount of automated decisioning that's ever going to be 100% perfect. I think we're getting to an extremely high level of accuracy. I mean, we have the largest agreement repository in the world. You know, when we got started, this is a very interesting story. So when we got started with iam, we, we have petabytes of agreements because of our signed product, but we did not license those agreements specifically for processing. And AI, you know, thought of that and I don't think people would have consented anyway. And so we said we're not going to use any of that data. We're only, we're going to require customers to, on A1, on one basis, consent to, you know, allow us to process individual agreements and we're going to put in product functionality so they can opt out at any time. So that meant that when we started, we only had access to public agreements is what the big LLMs have as well. And we had a very good level of accuracy in our extractions as rated by human eval. And then we turned the loose on actual agreements inside these companies and the accuracy felt 15 percentage points out of 100, that turns it from super useful, not perfect, but super useful. First drafts, first table type of thing to wow, I feel like I have to redo everything this thing does. And we've now worked our way back mostly to, to our original starting point and we think we can go much further. And that's because we now have 150 million private consented agreements in our AI and we're adding tens of millions every month, which is orders of magnitude bigger than anybody else. And these are all the complex private agreements that aren't generally publicly available. So I think we have a hidden huge AI advantage in accuracy that's not just. No one's ever going to get to 100. So it doesn't take away from your point that there could be cases where, you know, you need to have human eval and oversight. But I'm just saying we're going to be in a much better place to get to a place where you get the real productivity benefits because we can be much more accurate.
Neelai Patel
You're not training your own models. Right. It seems you're obviously using foundation models from other companies.
Alan Teigason
Yeah. So we started with OpenAI and GPT. We use Azure as our first public cloud provider. And since then we've added, you know, other frontier models. And so we score them against each other and use the best of the best. And it's. I mean, it's an incredible innovation pace and so. And capital investment that's going in. And the cost per token. Right. Is the cost per unit, if you will, has just been dropping precipitously. And so for a company like us, for whom that's a cost of goods, that's amazing.
Neelai Patel
Yeah.
Alan Teigason
I can now go to customers up to a pretty large size and see said, just give us one. It's. It's included in your price.
Neelai Patel
Tell me what the dynamics of the AI pricing per token. Because the idea that the prices are falling requires some amount of competition in the market. Right. It requires the ability for you to switch. Are you building your system so you can switch from model to model, or are the models different or differentiated enough?
Alan Teigason
We already have. And look, early on, you have to say GPT was, you know, head and shoulders ahead of other frontier models. And over time, so we started there, plus our internal models, and we had, you know, five years of experience in, in building and using AI models internally. Over time, it just became clear the Frontier LLMs were great. OpenAI in particular, and for a little while, they were kind of the only game in town. But now there are a lot of choices. We've got excellent results with Gemini, and so we are. And other models. And so we are. We have good range of choices. But even if you're with one vendor, the cost of processing an individual document has plummeted.
Neelai Patel
Yeah.
Alan Teigason
When we got started that summer of 23, I was very worried that we'd have to have this very complicated pricing structure tied to the number of agreements that you were uploading, because the cost to process them and reprocess them all the time for all these things people wanted to do was felt like it was going to be prohibitive. And now up to a fairly large company just included in your subscription, and it's a totally different game. I mean, it's like a factor of 100.
Neelai Patel
So do you think the models are interchangeable? I mean, you're talking about them all getting good and they're getting terrific.
Alan Teigason
I mean, I don't think they're perfectly interchangeable, but for our purposes, for the application, I mean, Obviously the models have different personalities in the consumer context. And for certain specific workflows like coding, there are some models that I think have some specific advantages. But for document extraction, we're able to get very good results with multiple models and multiple of the top frontier models and they are advancing at roughly similar rates.
Neelai Patel
This leads me to basically the bubble question, right? If you're saying we're delivering a bunch of value, but the cost of the models is so low that I'm just bundling into my existing subscription cost. Unless the customer is so big that they're using massive amounts of tokens, how do you expect the model companies to make any money? Right. Like that's a race to the bottom where if you're not charging additional margin, you're not going to pass any on to them. How do you expect that to reconcile?
Alan Teigason
I mean, look, I am obviously paying, writing a large check to money Google. So it's not that it's insignificant, it's just that the incremental.
Neelai Patel
Yeah.
Alan Teigason
Is value of an additional.
Neelai Patel
But you're getting more usage for the same dollar over time, right?
Alan Teigason
I'm getting more usage for the same dollar. And I, you know, we, look, they've gotten so much more efficient. The models have gotten better, the hardware has gotten better. The amount of capex that's gone in is now being replicated is, is incredible. And so I think some of that is sort of already in the water. But to your point, look, I, I think they will all, you know, add value in different ways. But I do think that the LLM models, it's, it's a highly competitive space and you got to add value above or below that. Right? And you can see that in the strategies. You know, OpenAI is now really doubling down on both their consumer and enterprise efforts. Google of course, has investments in the hardware side on the cloud stack. They use their AI for YouTube and ads and the other vendors, Anthropic is being incredibly successful with their coding product. And so you're seeing different strategies playing out for leveraging a strong position in the foundation model space.
Neelai Patel
Yeah, I'm curious about that because you have the perspective, right? You run a big enterprise software product, ChatGPT announced DOCU GPT and the idea that they're going to come and attack your moat, which is the database of identities, and that the float like that seems not a big threat. But I look at that big sweep that you just described and most of those companies, they think their money is in enterprise use, right? That's the first big set of customers it's big businesses with budgets that need to get more efficient and increase productivity. And maybe that's happening and maybe it's not right. I think that's still an open question.
Alan Teigason
It's starting to happen.
Neelai Patel
Yeah, something's happening, happening. And then you have the big consumer products. And so you see Google and Meta saying, well, we already have ad technology. Meta is going to move all of its stuff to GPUs and we're going to serve reels ads that way. And it doesn't matter how many GPUs we buy because it's already being monetized. Google's the same way. Then you have OpenAI, which announced an advertising product last week. Right. We're going to do ads in ChatGPT. Do you see a path forward? Like, I guess the question in relation to DocuSign is do you think that industry is stable enough for you to bet on in the long term as it works through all these machinations? Because this is the core technology of your growth. And then second, you have experience at Google, you have experience running an advertising business. How do you think that's going to go?
Alan Teigason
Okay, there were a lot of questions in there. Let's start with the. I think from a DocuSign perspective, so far it's all been goodness, right? It's dramatically expanded the value that we can deliver to customers, the scope of our services and in a way where we could leverage the R and D of others but preserve a really meaningful competitive advantage through our data, through our workflow, through our trust. And I think it's been a huge win. I am not, I mean, as you alluded to, I don't believe that the big LLM providers are going to provide agreement management solutions. I think they're going to look for others to build applications on top of their systems like we have. I suppose it's possible that there could be some of that capability that seeps into standard products as we saw with, you know, you can do it in a summary, et cetera. I feel like it's been amazing in opening up new, a much broader market opportunity for DocuSign and we are running as fast as we can to capitalize on that. And I think the cost dynamics so far have been super favorable to us and I frankly, I expect that to continue. In terms of the other part of your question on the ad side, I think it was always inevitable that OpenAI was going to get into the ads business. I think you can't really do a scaled consumer services play without advertising these days. And so it was just a matter of time before they got there. It'll be delicate to incorporate ads into a assistive AI experience, but look, it was delicate for Google to do that with paid search, but they did and I think that turned out to be a huge value unlock. So I think that prize is very significant and I actually think they're late in launching it. They should have done it earlier. I think the transformation of having all that context of the full journey you've been on and the ability to fully close the transaction potentially takes that kind of intentful activity to the next level. You can literally almost go through the entire, what used to be called the funnel, right? In one platform that's incredibly valuable. And so it's a big prize. And that's why I think OpenAI is investing and that's why Google is fighting hard and keep its position. And why Meta, I think, is well positioned. Why there are so many meta people at OpenAI. So I think it was always inevitable. We'll see how it shakes out. I don't have a moral issue with it. I think it needs to be done well.
Host/Announcer
Right.
Alan Teigason
I think it's, you know, I think you can say a lot of things about Google, but I think they did a pretty good job of keeping those walls pretty separate. And I saw that when I was there. And you've got to maintain the integrity of the results people are getting while incorporating advertising experiences that are accretive to the users. That's a difficult thing to do.
Neelai Patel
I was just at CS and you couldn't turn the corner without a marketing influencer jumping out of a bush and saying the funnel is dead because everyone has experienced everything randomly nowadays. That's a different podcast.
Alan Teigason
That's a different podcast.
Neelai Patel
Let me try to draw a connection between these two ideas and there's a reason I asked them together if you are looking at all the big model providers and they, they are saying our first opportunity is in enterprise and the enterprise customers are going to unlock a bunch of value and build products around that.
Alan Teigason
Are they actually saying that?
Neelai Patel
By and large, when I talk to.
Alan Teigason
These folks, it doesn't seem like what OpenAI and Meta and Google are doing. But I mean, well, I mean, meta.
Neelai Patel
Is I think, a unique one, maybe the exception that proves the rule because they have no enterprise business to speak of, so they have nothing else to say. Google, right?
Alan Teigason
I agree. There's a huge focus on enterprise and we're very focused on enterprise, of course.
Neelai Patel
So you see that and then I'm talking to you, you're building A scaled enterprise product product on the back of these models and you're saying they're almost interchangeable and the rates are dropping because I can go get pricing terms because I can just switch. That's one dynamic of pricing that's happening in the industry. Then next to it you have, well, what's the biggest prize in the history of the Internet? It's search advertising. OpenAI is going to attack that and we're going to take some of that share away from Google and Google's certainly going to defend its territory and Meta is going to do whatever Meta is going to do. That's where you would, would decommodify your models. Right. You would say ChatGPT is so much better. It's such a better consumer experience that you have no choice because all the users are here and that might be a zero sum game. Those things are pulling in wildly opposite directions in my view. Right. You have commodity models for enterprise which, where all the budgets are and then you have deeply specialized consumer experiences where you can layer in advertising and high rates. Can you bring those together? That's why I asked if the foundation seems stable because eventually one of those things is going to be more lucrative than the other and you might run out of enterprise model providers and you know, that industry might collapse down to one or two that charges high rates.
Alan Teigason
I think both are so large that you, the biggest players are going to go after both with very different teams. So obviously very familiar with Google. Right. And Google Cloud is a standalone operating unit inside of Google and operates quite separately and necessarily so. Right. In fact, I don't think Google Cloud could have become successful if it wasn't pulled away from the traditional consumer services and ad business at Google. And I think OpenAI is a smaller company but are going to need to replicate that very different MO and go to market. That comes in the ads business versus and the consumer side of the house versus the enterprise side. That's a lot to take on for a young company. It's an incredibly capable team and they a huge amount of IP and so. But that is a very ambitious undertaking to do both. And Tropic seems to have decided to focus exclusively on the enterprise and are really executing incredibly well and we're using their cloud code product and it's fantastic and so huge kudos to them. And then there'll be a host of other players that I think become either more enterprise or more consumer focused. But I think Google, Meta, OpenAI are probably the three that are trying to do both.
Neelai Patel
Are you structuring Your contracts with these vendors to be long term, short term, how do you think about that?
Alan Teigason
The contracts in that space tend to be relatively long term. We and they want three plus year commitment type deals. You can't, I mean, as much as people want to say, oh, I can just swap one for the other, that's not really how things work if you're doing enterprise deployments. So there's a significant investment in porting to a platform and the vendor of course wants to see the benefit of your growth and the upfront investment they're making and helping you come onto their platform. And so they're three plus year deals, sometimes longer.
Neelai Patel
When do you think you'll have a feature set that's so robust using these tools that you can actually charge a premium to all of your customers?
Alan Teigason
Well, we can't do that today. I mean we went from being a sign provider, we're charging a substantial premium for moving to this AI assisted suite because the value, and I can provide that value instantly. Right. You sign with DocuSign and I can turn on, I can give you AI insights into your agreements. Day one. In fact, we deploy our new products as fast as we deploy sync. We deploy in under 20 days, which is kind of unheard if you follow enterprise software, that's kind of unheard of, right? And frankly a lot of that is just human stuff because the product is ready. Day one. Our customer agreements right now average around 19 months in length, but they're longer with big customers and tend to be shorter with smaller customers. That's a typical pattern. I expect that our agreements will get longer over time, but we already charged a substantial premium for getting access to the AI features and customers have been and very willing to pay. We have over 25,000 customers live on this new AI platform in under 18 months.
Neelai Patel
So I'm always curious about that number, right? I hear these usage numbers from all the companies that deploy AI tools and underneath it is sort of the. Well, it just showed up one day and we're counting that person as an AI user, right? Like AI overviews are there, everyone loves them. And it's like, I don't know about that. Like they just started in my face whether I want them or not.
Alan Teigason
Fair enough.
Neelai Patel
Are you actually measuring happy customers using the tools because they want to or because the button is there and everyone just clicks flexit?
Alan Teigason
Both. I mean, look, we, we turn, we, we give you a license for, you know, however many users you, you want. And we obviously track, you know, what's consumption of that license. What are People doing, how often do they access the repository, how many searches they do and extractions they do, how many document sendings and ex document executions do they do? And we keep a very close eye on that as fundamental health metrics. So I think product adoption leads to renewal and retention. Right. And so we are very focused on that. And no, not everyone uses the AI features but we're seeing really robust usage and we're constantly looking for ways for more of the users discover what's possible. I mean this is one of the endemic problems, enterprise software. You build the stuff, but how do people actually figure out what's possible? And you know, the good news is we have something that has a near universal value prop and can be deployed easily and we can there all kinds of magic moments where, oh, did you know you could do this? We are, we're making that available so, you know, as you send a document or as you sign a document, hey, would you like a agreement somewhere? We'd like to know how this agreement appears. Hey, did you know that we have all of them and you can see all the stuff. Stuff. And that's, it's a new world, it's exciting.
Neelai Patel
I do love that the future of all software is some combination of like ultra smart clippy and tooltips. It's, it's, there's something there. Someone shouted a book on it. All right.
Alan Teigason
Hopefully we're providing more value than that. Yes.
Neelai Patel
You're an enterprise software CEO. You've come, you face the gauntlet. So I'm going to ask you the hardest question of all. You use your own tools. You start off by saying you use your own tools. What is your biggest frustration in with DocuSign and how would you fix it As a product, not as a. I.
Alan Teigason
Don'T, I don't think, I don't think our mobile experience is good enough. I would expect that everything should automatically flow, we should predict the next steps and you know, it all works. Obviously millions of People sign with DocuSign Daily so and often on their phones, but I think there's still some, some room for improvement there and so I'm pushing the team on that.
Neelai Patel
Well done. You actually answered the question. Most enterprise software CEOs don't. So I commend you for that. Alan, this has been great. Thank you so much for being on Decoder.
Alan Teigason
Thank you, Neil. I really appreciate you having me.
Neelai Patel
I'd like to thank Alan for taking the time to join Decoder today and thank you for listening. I hope you enjoyed it. If you'd like to let us know what you thought about this episode or really anything else. Drop us a line. You can email us atdecoder the verge.com we really do read all the emails. You can also hit me up directly on Threads or Bluestone sky. We're also on YouTube. You can watch full episodes at Decoder Pod. And we have a TikTok and an Instagram. They're at Decoder Pod as well. They're a lot of fun. If you like Dakota, please share it with your friends and subscribe where we get your podcast. If you really like the show, hit us with that five star review. Decoder is a production of the Verge and part of the Boxing Media Podcast Network. The show is produced by Kate Cox and Nick Statt. It's edited by Ursa Wright. Our editorial director is Kevin McShane. The Decoder Music is by Breakmaster Cylinder. We'll see you next time.
Episode: DocuSign's CEO on the dangers of trusting AI to read, and write, your contracts
Date: February 2, 2026
Guest: Alan Teigason, CEO of DocuSign
In this episode, Nilay Patel sits down with Alan Teigason, CEO of DocuSign, to discuss the company's approach to digitizing agreements, the journey from e-signatures to intelligent contract management, and the implications of introducing AI into high-stakes legal workflows. The conversation tackles trust, AI liability, how DocuSign is structured internally, and the evolving expectations for enterprise software.
The episode offers a candid look at DocuSign’s strategic direction and the ethical, legal, and practical challenges of using AI in mission-critical business software. Alan Teigason is forthcoming about both the opportunities and the limitations of AI, the lessons from Covid’s chaos, and even points out what still frustrates him about DocuSign’s user experience—an unusual moment of honesty from an enterprise leader.