Thirty Minute Mentors Podcast Transcript: DocuSign CEO Allan Thygesen

I recently interviewed DocuSign CEO Allan Thygesen on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam Mendler: Our guest today is the leader of a multibillion-dollar technology company. Alan TigersOn is the CEO of DocuSign, the market leader in facilitating e-signature, serving hundreds of millions of users across more than 180 countries. Alan, thank you for joining us.

Allan Thygesen: Thank you for having me.

Adam Mendler: You grew up in Denmark and you studied econ at the University of Copenhagen before moving to the US. To go to Stanford for business school. Can you take listeners back to your early days? What experiences and lessons shape your worldview and shape the trajectory of your success?

Allan Thygesen: I have a strong sense of fairness and equal opportunity that I think is rooted in my parents and from having grown up in Denmark, and I bring that to how I lead. Denmark is also a very open economy, so a significant part of GDP, about a third is imports or exports. And so that means that you can't really compete with scale companies just by shipping inside the country. So I worked for a medical manufacturer that shipped products globally. And so my first job I saw that 98% export, and I think I've always had a very global view of business as a result. I came to the US. In 86 to go to business school. I hadn't planned on staying, but I loved it here.

Allan Thygesen: Met my wife in business school, and we decided to get married and settle in the Bay Area. So that's how I started my career in Silicon Valley.

Adam Mendler: And over the course of your career, you've worked for a number of different technology companies before becoming a managing director at Carlisle, where you spent seven and a half years. From Carlisle, you went to Google and ultimately led a 100 billion dollar plus business within Google. What were the keys to rising within your career, and what can anyone do to rise within their career?

Allan Thygesen: I had three phases to my career you sort of alluded to. I started working in Silicon Valley for smaller tech companies and loved it. And I think I learned a lot from being able to operate in a very entrepreneurial environment, take a variety of different roles, lots of chances. When you do that, you have to have more than one at-bat because the survival ODS are not 100. And so I took away from that whole experience of focusing on the horizon and not getting too excited when things are going well and not getting too depressed when they aren't. Then, as you said, I was a VC for almost a decade. If you're at all a curious person, I think that's a fantastic job. I think I really developed my ability to network and get up to speed quickly on different topics and have a mindset to sort of understand how you approach scaled businesses very differently from things that are maybe in the growth phase and things that are really at a very early stage. I came to Google in late 2010, and really initially my thinking on Google was it was sort of my rehab program. I'd been a VC for a decade and I was ready to come back to being an operator, and people will offer me pretty decent jobs, but they were looking at me, you've been a VC for ten years, can you still play? I was like, going to Google might be a good way to demonstrate that I still have some operating chops and see things from a very different perspective than the startup ecosystem that I had really spent my entire career in. And then it turned out to be just so much better than I ever could have expected. I got a chance to reboot and run a business that is really core to Google, which is Google sells ads to companies of all sizes, including small companies, and had been the first scale player to do that, but hadn't really paid much attention to that business. And as a result, they were sort of in relative atrophy. And so that was an amazing opportunity to take something that was already at size and grow it very rapidly. And so that we went from eight to 40 billion in five years. Those are billions, not millions, which just was incredible. And then I got a chance to run this larger pool, which is our business in North and South America, which is about half of Google's advertising revenue, a little under half of Google's revenue. And as you yeah, that scale was insane and it was a fantastic experience. The breadth of relationships Google has with clients, because the ads business is the primary monetization engine. All of the various partnerships that we would have, it was with a media company across YouTube and the Android store. Other things would tend to be coordinated by my teams. And so you got to participate in discussions, drive discussions that were incredibly complex and super important to all the large companies that we dealt with. Of course very important to Google. I also had a chance to get involved in our public policy efforts, which incredibly important for society, and if you're interested at all in that, having an opportunity to actually contribute there was super important. So I love my time at Google, still have so many friends and such affinity for that company. I'm very grateful for twelve years I've spent there.

Adam Mendler: Alan, as you're walking listeners through your career journey, your career trajectory, I'm pulling out some insights that I want to dive into. But before I do, I want to ask you, what do you believe were the keys to rising within your career? And what do you believe anyone listening to this conversation can do to rise within their career?

Allan Thygesen: Yeah, a couple of things. I think I was always very open-minded. I think fundamentally you can't over-plan. I think it's very easy and you get career advice and you lay out your master plan and I don't think that life works that way. I think you have to have a long-term sense of what you'd like to accomplish, but you also have to be opportunistic. I would never have planned to go to Google. Obviously having spent my entire career in the startup ecosystem, I would never have planned to become a VC because I was on the startup side. But those opportunities arose and then you got to walk through that door, even if it's a little outside your comfort zone.

Allan Thygesen: Being resilient is very important. Yeah, I had several failures at various points in my career. One of my startups got bought by a company, then filed the bankruptcy. That wasn't very fun. When I left Carlisle, I briefly tried to start my own fund with a friend and colleague who had a similar entrepreneurial background. And we started that effort in August, September of 2008, which was literally a month before the major financial crisis. And the last thing anybody wanted to invest in was two guys who hadn't worked together before and had a new venture fund. So I think you just sort of resiliency and focusing on the rise is very important.

Allan Thygesen: I have been very fortunate to have a great network of people that I've worked with who've helped me, that I've helped. And that network really comes into play later in your career and you just cannot know who it's going to be. And so you have to be nice to people. I see a lot of people forget that and do things that are not in your narrow self-interest in the short term and maintain relationships. Another thing that people don't do enough. So as an example, I had worked with my last company when I was in that series of startups we took public and the CEO of that company was a woman named Maggie Wilder. We worked very closely together for three years from 1998 to 2000. It's a long time ago.

Allan Thygesen: And then I saw the news that DocuSign was changing its CEO in June of 2022. So 22 years later. But I'd stayed in touch with Maggie and I saw she was chair and had stepped in as interim CEO. And so I sent her an email that day saying, I'm very happy at Google, but if you're looking for a permanent CEO, DocuSign, that's something that might be interested in. And that's how it happened.

Adam Mendler: Wow. The power of relationships.

Allan Thygesen: Power of relationships and showing a little bit of initiative and putting yourself a little bit out there. I've had some success and had things coming at me and so on, but that doesn't mean that ends.

Adam Mendler: I love it. You shared a lot of great lessons there the importance of being open-minded, being open-minded to new opportunities, different opportunities, not being afraid to push your comfort zone recognizing that there are going to be ups, there are going to be downs. There is no linear path to success. The path that I described, the trajectory that I described, you worked for these companies. Then you went to Carlisle where you had this great success. And then you went to Google where you had this great success. Now you're the CEO of DocuSign that overlooks the reality, which is that there are a lot of bumps along the way and significant bumps. And you described a couple of them.

Adam Mendler: How do you respond to those bumps? Are they terminal or are they bumps that you bounce back from? That's a huge part of it. And then the last piece you described, which you mentioned earlier on as you described, a key takeaway from your time working as a VC, the power of networking. And I want to know if you could dive more deeply into that topic. A lot of people listening to this conversation might be very astute networkers, trying to understand how can I be even better. But a lot of people listening might feel like networking is something I know I should do, I know is important, but is outside of my comfort zone, is not necessarily something that comes easily to me, comes naturally to me. What advice do you have to those two audiences as to how to become more effective at networking? Something that is so important to all of us and something that, as you just shared, has been a game changer in your career?

Allan Thygesen: Part of it is the label is not great. I think to a lot of people, including myself, networking sounds a little overly intentional, plan, maybe even a little greasy and something that is peripheral to your current job. And I think the way you should reframe it is it's about learning. And if you're a lifelong learner, the best way to learn is from other people. And you should make sure that you are constantly connected to and engaged with interesting people. And as you meet interesting people along the way, maintain those relationships and then you'll have more and more sources of learning and connection and that is networking. I think networking has a marketing problem. I mean, there are some people who respond very favorably to the concept, but for a lot of people it feels like I'm putting myself out there or this is a very salesy thing and it has this riff of I'm going to cocktail parties and collecting as many business cards that I have.

Allan Thygesen: That is not, in my opinion, very effective. What you do is you try to build relationships. You try to really have a reason for engaging with people and try to be open-minded about what you can learn from them and what they can learn from you and how you can help them. And I think that will then come back to you over time. It's not a linear relationship. It's not perfectly predictable, but the accumulation of that becomes very meaningful. I think, in terms of staying in touch, that's a lot about intentionality. People underestimate how much of a network they already have.

Allan Thygesen: When I travel, I really try to connect with people that I have established connections with, whether it's just for a drink. I really combine my personal life and work life with people that I enjoy. And it's interesting how a few people do that. So the last area would probably be how do you find people that you don't already know and that you want to get to? And again, I think being very careful about making sure you think about what's in it for the other person. I get a ton of unsolicited LinkedIn messages as an example. That is not networking, that's spam. But if you think about, okay, who do I know that knows this person? And why is it worthwhile for them to introduce me? And why is it worthwhile for this person to get to know me? And how do I make it a win for everybody who's involved? Then I think you'll have a lot more success, and you may be surprised at how many people you can actually get to, how many people that will have a good interest in hearing from you. And people, by the way, like helping.

Allan Thygesen: They like being asked questions. So lean to that.

Adam Mendler: Alan, you shared a lot of really important insights, the power of seeing things through the lens of others. How would you like to receive tons and tons of unsolicited LinkedIn messages? Probably not going to enjoy it all that much. So do you want to be the one sending it out now? There's an argument to be made, and I make this argument where we live in an environment where these are just the rules of the road. But the reality is you're going to be a lot more effective if you can add value, if you can position yourself in a way where before the relationship even commences, you're giving to someone rather than taking from someone. I love the way that you framed networking. So often we think of networking as something that forces us to get out and get out of our comfort zone and have to do something. But the way you framed it around lifelong learning, around bettering yourself, around growing, around improving, and through my interviews with hundreds of the most successful leaders, one of the commonalities that I've observed is the most successful leaders, the most successful people are lifelong learners. The most successful leaders, the most successful people have a desire to continually grow, see every single person around them, regardless of who that person is, regardless of what that person's title is, what that person's vocation is, where they meet that person as an opportunity to grow.

Adam Mendler: And that's the mindset that you have. That's the mindset that every single one of us should have.

Allan Thygesen: That's well said. I agree with that.

Adam Mendler: What do you believe are the key characteristics of a great leader and what can anyone do to become a better leader?

Allan Thygesen: I think some of the key principles for me is look, you got to be decisive but you also have to be flexible. But the decision part is super important. Organizations get into stasis when no decisions are being made and that's actually, I think in almost all cases even worse than making a bad decision. Most decisions are reversible but waiting for a decision is just a loss. And so trying to make decisions quickly and then adapt to new information and evolving if you have to and not being afraid to say you made a mistake and do something different, I think that's very important. And of course, the pressure to act that way goes up when there's rapid change externally. So during the pandemic for example, I think it was essential to make decisions very quickly and decisively. I've talked about this a little bit, but keeping your eye on the horizon.

Allan Thygesen: I think your job as a leader is in part to keep people focused on the long-term goals and not on the day-to-day Gyrations. And my experience is the smaller the company, the more entrepreneurial, more growth-oriented the venture, the higher the highs, the lower the lows. And a lot of people get caught up in those short-term durations. But really getting people focused on what are we trying to achieve in the long run and are we making progress towards that and how everybody else reacts in the market? That is important. It's important context but it's not the end game. I think third, communication. I think effective communication is the most important skill for a leader. You are directing typically a large number of people and they will proceed based on how you say now that can be a little paralyzing if you get overly conscious of that.

Allan Thygesen: So you also don't want to lose authenticity and immediacy but being really clear and being transparent, I'm a pretty direct person and I tend to be pretty clear about where I want to go and what decisions we're making now versus later. And I think that transparency is super important. And lastly, I think engagement, you have to bring people along and engage them in the process. If you're just running out in front and you're not bringing people with you, you will not be successful. Another way of saying execution beats strategy for breakfast, right? And I think execution only happens if everybody else follows and communication becomes more and more important. The more senior you get, the larger team you have, the more there's a premium on communication.

Adam Mendler: One of the key areas you've been laser-focused on since becoming CEO of DocuSign is innovation. You've shifted resources from sales to product innovation. You've been personally invested in what you call reigniting the innovation roadmap. How can leaders drive innovation?

Allan Thygesen: Yeah, that's a tricky one. Because I think innovation by its essence is organic and bottoms up. And so what can the leader do? A lot of innovation is about creating an environment in which people can pose things and setting up some broad parameters for what you'd consider innovation. And so we've had several efforts of that here over the last year, and I think we really have honed in on and sharpened on what do we want to be when we grow up? And then the details of how you get there, I think are much better left to the teams because I'm not going to be able to sit and decide how should our storage solution work or how should the mobile UI for this or that work. That should be left to the experts and they'll come up with amazing things that you could have never dreamt of. So I think your role is both to encourage and facilitate organic, bottoms-up innovation and to set some overall direction for what's important and what would constitute success. And then obviously, there's resourcing. And I felt we were under-resourced in product and in our internal systems, and probably a little over-resourced in our sales area where we had opportunities to get efficiency from allowing people to self-serve on our website and product and using partners more. And so, as you said, I shifted some resources from those functions into product so that we could go faster because sometimes you just don't have enough people for the job.

Allan Thygesen: And that was my feeling.

Adam Mendler: There's the resourcing component, there's the component of it, which involves setting the tone, creating the right climate, creating the right culture. You spent more than a decade as a senior leader at Google, a company synonymous with great culture, known for its ability to recruit and retain top talent. How can leaders build winning organizational cultures? How can leaders build organizations that attract and retain top talent?

Allan Thygesen: Yeah, well, I'll tell you an interesting story about that because I think people misunderstand the innovation concept a lot. And I saw that a lot at Google because of course everybody would come visit us and say, please tell us, how do we make our organizations more innovative? And it comes back to the point I made earlier that a lot of more mature organizations tend to be very rigid and operationalized and siloed, and that unfortunately, doesn't really enable innovation and it doesn't attract people who want to innovate. If you want innovation, then you have to give people the freedom to try and fail. And so one of the most important things, I think, with innovation is to build a culture where at least up to some level, there's an ability for teams to self-direct and innovate. And then at some point, they'll have to say, attract resources from the broader company and you'll have to call things. But I remember at Google, I've been there a few months and I found three separate projects doing roughly the same thing and you go, obviously that's not a great use of corporate resources. You might at first say, well, why would you have these duplicate teams? And I think it had happened organically because there were different teams who were coming at the problem from different sides and saw this problem and started working on it. And then over time we consolidated those efforts and brought some of the best of the different teams together.

Allan Thygesen: But if you squelch it at inception, you're not going to get any innovation. I think that's a super important point. Innovation also isn't about just over-resourcing. You got to have relatively small teams, you've got to have a sense of constraint that tends to be what produces some of the best results and a sense of urgency. I think commercial innovation is not a research lab. You don't get to go for five years without ever shipping anything. Either you get to something interesting and exciting that proves your thesis that you've declared upfront. You're not reinventing what the goals were after the fact or you don't.

Allan Thygesen: And one of the hard decisions that CEOs have to make is which projects should we not do? Because lots of projects have ongoing funding and staffing because at some point they were deemed important. So one of the ways to secure innovation is stop the projects that are consuming resources, bandwidth and diverting us from the things that are most important, including funding.

Adam Mendler: Innovation, what a leader needs is a mix of both patience and urgency. And it sounds conflicting. And how do you have that? On the one hand, you need to have this deep patience and on the other hand, you need to have this deep urgency. How do you do that?

Allan Thygesen:

You have to know when to be patient when to be urgent. I think there is a fundamental tension because certain tasks need some amount of space, like particularly, I think, early innovation and trialing. You need to have some patience. At the same time, once you're starting to scale a business or a go-to-market function, then I think applying pretty rigorous metrics and are you succeeding against those or not. And being pretty impatient, I think is both a healthy dynamic and appropriate because there's just a lot of information in that signal and a lot of people will want to ignore those. They'll want to restate what we were trying to achieve so they can just continue doing what they're doing. And I am a pretty analytical person and I like to see the data and try to understand the impact, not just whether you're surfing or being hurt by trends that were not controllable by you.

Adam Mendler: And I think it ultimately comes down to the first thing you said when I asked you about the key characteristics of great leaders, which is great leaders know how and when to make decisions. Sometimes you need to act with urgency. Sometimes you need to act with patience, and it's the job of a leader to understand which situation you're in. Exactly what do you look for in the people who you hire and what are your best tips on the topic of hiring?

Allan Thygesen: Yeah, I think for a senior leader, let's say somebody who would report to me, I do look for a demonstrated track record of success. Right. By the point that you get to run an organization with many hundreds or thousands of employees, there needs to be some evidence. I look for an open mindset. Are you a learner to our point earlier? I look for perseverance. Have you demonstrated perseverance? Because it's not always going to be easy. I look for can you lie high and low? By which I mean can you be a high-level framer and communicator of what the strategy is and get people to follow that? But can you dig into the detail when necessary? It's not the job of a very senior executive to run every little thing, but if you don't have the ability to dig in and go deep when necessary, then I don't think you can be effective. It's certainly true in a tech company.

Allan Thygesen: So I look for that. I look for ability, and I really a desire to collaborate and engage with others. No one is an island. I think you got to have that. So those are all the things I look for and how I look for them. To be honest with you, I don't fully trust myself interviewing. I like people. I want to like them.

Allan Thygesen: There are obviously some people that come across very poorly in interviews, but I tend to want to engage and see the best in people. And so knowing that about myself, I'm very rigorous about checking. And I'm fortunate to have a big network now. And so I can usually get a very informed opinion from people that I trust about individuals. And I put a lot of weight on that. Not the references that the candidate provides, but ones I can get to. People come to me with candidates and they say, we want to hire this person and say, okay, well, let's just do a little check-in here. Have you checked with this person, this person, this person? And that may make things a little bit more laborious.

Allan Thygesen: I always prefer to make those calls myself, and I expect my teams to do the same. So just because somebody has an impressive resume, a lot of people can claim things. I want to hear what they actually do. Did they have the impact? Did they have the personality? When you get very senior people, they can usually handle an interview pretty well.

Adam Mendler: And it comes right back to the power of building a strong network. The more people you know, the more likely it is that you're going to know the person who you're interviewing or you're going to know someone who knows the person who you're interviewing and you're going to know, hey, is this person a winner or is this person a loser? Should I hire this person? Should I not hire this person? You're going to have a much closer line to that answer. One of the first things you shared in our conversation was an early lesson you learned growing up in Denmark, coming to the US. Immersing yourself in global business. Today, you lead a global business. You have customers across more than 180 countries. What advice do you have for leaders on how to lead globally, how to lead across a wide variety of countries?

Allan Thygesen: First of all, we're not nearly global enough. I know we're in 180 countries, but 26% of our revenue probably should be 50, right? I feel a great sense of urgency to grow our international business. It is growing communically faster than our domestic business, and it should, and it'd be a huge growth diver for us. The US. Market is so big and so large and so attractive that if you're a US company, it's very easy to get overly focused on serving it. But I think for most companies, ultimately you should, and you probably will have to expand your business internationally. And we are an international business, I would say we're not fully global. We're working on that very intently. Right now, I'm investing in particular in our business in Japan, Germany, to scale up our presence there. Those are markets where we're at a much earlier stage of evolution in the signature space than we are in the US. And so the big opportunity, but more broadly on international, I think that 80 plus percent of what you do can and should become. So that's where I start that. Look, you want to build a gold business. It's not sustainable to build a separate product for every country or to have a completely distinctive value proposition in every company or AMA every country or different go-to market. With that said, that 20% tailoring is essential to your success. And that could be about product. Tweaks could be, let's say, in our business in Germany, things like privacy and security are more important to customers than they are here. And it's a core part of the conversation from day one. In Japan, you need things localized for local customs and laws. And I could go on. So you want to do that from a product perspective. Then there's the go-to-market side. In some countries, people expect to buy directly from the supplier that is us. But for most companies and in most countries, you need to use local distribution or amplify your go-to-market with local distribution. Whether you are like we are, a BP company and you maybe sell through local resellers or partners, or if you're in a consumer business, maybe you partner through local retailers. And I think really understanding how to manage the go to market, so to speak, of your business differently in different. Countries while getting the benefit of global scale and best practices that is incredibly essential to being successful. I just want to note, I think historically, when everything was direct sales and there was no such things, global media platforms that you could use to do digital marketing, for example, I think that balance was perhaps 60 40. I think it has been skewing. And despite all that you read about deglobalization and so on, from a company perspective, if you want to go to market globally, you need to think about everything that can be globally, central, standardized, best practice. You want to do that way, and then you want to make sure that the remaining pieces, that you don't drop those, and that you appear as local as possible. We just put an office in Munich and we're hiring German lawyers and German accountants and German support people. We have some of those already in other locations, but we want to really make sure that our German customers see us as not a German company then one that's very attuned to the local market investing there.

Adam Mendler: Alan, what can anyone listening to this conversation do to become more successful personally and professionally?

Allan Thygesen: I think being open-minded, being direct, being fair, engaging others without anticipation of immediate reward, paying it forward, building your network, but not in a way that's crass and transactional, but based on mutual interest and learning, those are all important. One thing we haven't discussed. I think people err often on the side of either wanting to move across functions too quickly, like a lot of young people today, six months out of college, they want to drop the first job they have and go on to advise the CEO. It's not really realistic. You should become master of your domain and really good at your job, and then you can look at other functions. And then the even more common error is the opposite one where, okay, I've been an engineer or salesperson for five or ten years, and now all I see are jobs that are exactly just the straight-up progression from that job. And that's very narrowing. And if you want to be a leader or CEO someday, you need to have a much broader skill set and portfolio. And the only way to do that is to seek out opportunities where maybe you take half a step backwards, but you're talented. You're going to progress so much faster in those other roles, and then over time, you become so much more valuable and ambidextrous right, you can do so many different things. I've, at various times, run practically every function. The only function I haven't managed myself is engineering. Not an engineer, although I certainly worked with engineers now for 30-plus years. But product, sales, marketing, finance, investments, all of those functions that I've run personally. And so I have a good sense of what those jobs entail and the perspectives that come with them. I think a lot of people have an over, really functional view, and they get stove-piped, and then they tap out as a result.

Adam Mendler: Alan, thank you for all the great advice, and thank you for being a part of Thirty Minutes Mentors.

Allan Thygesen: Oh, it's my pleasure. Really fun.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally-recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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