YouSaid · the spoken record

Dan Springer

lines on the record: 79
first: 2026-02-02
most recent: 2026-02-02
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“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 it all works. Obviously, millions of people signed the document daily and often on their phones. But I think there's still some room for improvement there. And so I'm pushing the team on that.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Hopefully, we're providing more value than that. 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 started off by saying you use your own tools. What is your biggest frustration with DocuSign and how would you fix it? As a product, not as a...”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 to discover what's possible. I mean, this is one of the endemic problems enterprise software. You build this stuff, but how do people actually figure out what's possible? And the good news is we have something that has a near universal value prop and can be deployed easily and we can keep there are all kinds of magic moments where, oh, did you know you could do this? We're making that available. So as you send a document or as you sign a document, hey, would you like an agreement somewhere? Oh, how this agreement repairs. Hey, did you know that we have all of them and you can see all this stuff? And that's the new world. It's exciting.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I mean, look, we turn, we give you a license for however many users you want. We obviously track 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 document executions do they do. And we keep a very close eye on that as for a fundamental health metrics. So I think”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I expect that our agreements will get longer over time. But we already charge a substantial premium for getting access to the AI features, and customers have been very willing to pay. We have over 25,000 customers live on this new AI platform in under 18 months.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 assistant suite because the value, I mean, and I can provide that value instantly, right? You signed with OcuSign and I can turn on and I can give you AI insights into your agreements day one. In fact, we deploy new products as fast as we deploy signals. 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 are 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.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“The contracts of 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 deployment. So there's a significant investment in pointing 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 multi- they're three plus year deals sometimes longer.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Incredibly well and were using their clog code product and it's fantastic and so huge kudos to them and then there'll be a host of other players that you know 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.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I think both are so large that 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 of Google. And I think OpenAI is a smaller company, but again, I 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 incredibly capable team and they have a huge amount of IP. And so, but that is a very ambitious undertaking to do both. Entropic seems to have decided to focus exclusively on the enterprise and really execute.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Course, so you see that, and then I'm talking to you. You're building a scaled enterprise 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 the Meta is going to do whatever Meta's going to do. That's where you would.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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, right? I think it's... 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 got to maintain the integrity of the results people are getting while incorporating advertising experiences that are accretive to the users It's a difficult thing to do.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 think 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 his position and why Meta I think is well positioned, why there are so many. Meta people at OpenI.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“You know, you can do it on a summary, etc. I feel like it's been amazing in opening up 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 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 system AI.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“It's going to go. Okay, there were a lot of questions in there. Let's start with, 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 ID 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”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I'm getting more usage for the same dollar. And 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 incredible. And so I think some of that is sort of already in the water. But to your point, look, I think they will all add value in different ways. But I do think that the LLM models, it's a highly competitive space and you got to add value above or below that. And you can see that in the strategies, OpenAI is now really doubling down on both their consumer and enterprise efforts. Google, of course, has investments on the hardware side, on the cloud stack. They use their AI for YouTube and ads and the other vendors entropic is being incredibly successful with their coding product. And so you're seeing different”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I mean, I don't think they're perfectly interchangeable, but for our purposes, for the applications, I mean, obviously the models have different personalities in the consumer context and for certain specific workflows, like coding, there's 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.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 felt like was going to be prohibitive. And now up to a fairly large company, it just included in your subscription. It's a totally different game. I mean, it's like a factor of a hundred.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“We already have. And look, early on, you have to say GPT was head and shoulders ahead of other frontier models. And over time, so we started there plus our internal models and we had five years of experience 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 have good arrangement of choices. But even if you're with one vendor, the cost of processing an individual document has plummeted.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Tell me about 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? Are the models different or differentiated enough?”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so we started with OpenAI and GPT. We use Azure as our first public cloud provider. And since then, we've added other frontier models. And so we score them against each other and use the best of the best. And it's an incredible innovation pace. And capital investment that's going in and the cost per token, 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. I can now go to customers up to a pretty large size and say, let's give us one agreement. It's included in your price.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 our original starting point, and we think we can go much further. That's because we now have 150 million private consented agreements in RAI. 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 and accuracy. That's not just, you know, 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 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.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“We have petabytes of agreements because of our signed product, but we did not license those agreements specifically for processing an AI. No one thought of that and don't think people would have consented anyway. And so we said we're not going to use any of that data. We're going to require customers to on a one-on-one basis consent to 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, which 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 fell 15 percentage points. Out of a hundred.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Yes, it'll show you a link to the sources, you've 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. When we got started, this is a very interesting story. So when we got started with I am.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Deliberately humans in the loop at key decision points. And I think that will persist for a very long time. Companies are very averse to the risk of automation that's going rogue. We talked about Google for a little while. There was a lot of efforts of 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 will be a lot of hesitancy and those are much lower stakes than agreements.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I mean, so if we pivot to the folks that use our document, use our tools to prepare documents, there are a lot of guardrails that we put in. 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 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 and so there's a lot of workflow there we also don't fully automate flows we put”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“They don't today. So I think we're improving the situation, both for consumers, but also, by the way, for companies. And so that was our motivation. And it's impossible to eliminate people who 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 necessary come from a company values and walls perspective. This felt right. So that's how we got to it.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 and disclaimers and how it was done graphically and so it was fine. But I don't think that that's the big question. To me, it's more of a moral question, right? Are you doing the right thing for the customers to 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 comment execute documents that we were the best positioned 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 the people understood that this was context. But if this is something that's really sensitive for them, they should get a lawyer.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“They might be worried about it. But I think it was like that fact pattern is like, well, that's your fault, right? I sign 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?”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Look at a delicate thing, right? We want to be the place 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.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“You are a Dakota. With all that said, I mean, look, we've had agreement summarization for a long time. We provide it internally to companies that prepare documents, that send documents. We wait a long time to launch it for consumers exactly because of some of the concerns that you raised, right? 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 very robust testing suggests that people have more comfortable and greater confidence and that they at the same time understand that when something's sensitive, they need to get to a lawyer. So it's...”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 release. It's not generally, wouldn't generally be the top thing, but right now it's newsworthy and things that our consumer facing tend to get more attention, as you know.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“So let's talk about the technology here. It's intelligent ingredient 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 I 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 like went off. Like you should not let the robot interpret the document for you. And one of the reasons is, well, as DocuSign now responsible for the interpretation of this agreement, right? If I sign this. And, you know, the AI hallucinated an interpretation of this clause. And then I'm mad. Do I get to sue document?”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“What the key launch pieces were going to be for intelligent management. I was in 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 of 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 function people use and finding that singular proposition is super important. So those are examples.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Go super deep when they need to. And they need to be willing to do that. Management does not floating up in the abstract 50,000 foot above the problem and just admiring it and thinking you can just 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's particularly important at a transformation moment because 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 anyone company. That's just how people are. And so if you're trying to get more radical change, you need to push 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,”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Look, I loved my time in Google. It's an amazing company and I'm proud of the time I spent there and I've always had a special place in my heart. One thing I do not miss is the seven-dimensional matrix of big 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 constitution frameworks. But I'd say one thing that Took away from Google's very positive lesson my experience, and this is not limited to Google, but that the most effective leaders in tech”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“And I think It was three years ago. I want to get into that. I want to talk about how you were implementing that, obviously, as part of it. I want to talk about whether it's working, which is interesting. But I want to ask the other Dakota question first. Obviously, you're at Google for a long time. Google's decision making, lots to say about decision making at Google.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“me negotiating 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 better it was three years ago I want to get into that”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 somebody in the process. You don't even know who they are, 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 in a basement. In fact, it's probably harder to find now than it used to be when it was in the filing cabinet. Now it's on some SharePoint drive or email inbox or who knows. And so bringing all that together and presenting that information in a way that is intelligent, bite-sized, appropriate for the persona is incredibly valuable. I mean, every CFO wants to know what are the top 10 contracts where we have leverage, things we've negotiated for that we're not getting. Every head of sales wants to know what are their top 10 renewals and what are the three things my rep should be.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Well, that's part of 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 via email. And then hopefully we execute them electronically. And other than that, absolutely nothing has changed for the last 50 years in agreements.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 almost like what's in movies. Of course, that's what lawyers do. But we actually started at the end. We said, look, the foundational piece of reimagining agreements is to have an intelligent repository, to have 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 where we build.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“Look, I know I can make the company more efficient. I know there's gold on their attention 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 one of our largest customers. Huge eSign 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 that a 50,000 foot level, how do you...”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“You know, I didn't get time to make a killer deck. I mean, literally, I got a call from a headhunter on 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 at a big job at Google. And so I couldn't just take a day off, man. I suppose I could have, but I didn't. And so I basically had Thursday evening and Friday evening to prepare a short slide deck. But the reality in these kinds of situations, nobody expects the super polished multimedia thing, but they really are focused on is with what are the thoughts, right? And you can use 10 point where you want. That's fine. And so I was really focused on”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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. Of course, I use my digital marketing background from Google to make some suggestions on things that I thought we could do.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 the pitch? I'm going to restart your product innovation.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“You're in the auto-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 that Docsan is still ongoing. But, I mean, 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 customers and our sales teams. We have so much stuff. There's so many opportunities. And that's an exciting place to be.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“It must have been so great for us because everybody had to use us. And look, there was some of that temporarily, but if you look at the long run, it didn't change the 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%.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“I think the low hanging fruit was helping 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 and a 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 at DocuSign. COVID was a seminal event in the company's history, not in a good way. I think everybody thinks of DocuSon as a COVID darling.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“When you think about shifting that investment focus and then something like self serve, you work at Google, you were at Google for, I think, 12 years and like that. You even the CO document since 2022. So you've been there a minute”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT
“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 got invested more heavily in product and engineering.”
2026-02-02 · Decoder with Nilay Patel · Docusign's CEO on the dangers of trusting AI to read, and write, your contracts · IDENTIFIED FROM THE TRANSCRIPT