Tom Gonser, Founder of DocuSign: Q&A with SaaScribe

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Things are never as bad or as good as you think they are. And if you keep that in mind, really bad things can happen and really good things can happen. If you just keep your head and keep going, you can do anything. Nothing succeeds like persistence. I mean, you’ll get there if you keep going.


Tom Gonser Founded DocuSign in 2003 and as DocuSign’s Founder and Chief Strategy Officer, has helped the company become a global leader in SaaS based electronic signature and Digital Transaction Management. How? In part by building a world class team, an ethos of constant innovation spurred by a healthy paranoia and true passion and belief in what he does, that makes Tom feel like he hasn’t worked a day in 25 years.

Tom spoke with SaaScribe on The SaaS Revolution Show Podcast and shared some great insights with us,  available to listen to now on iTunes and Soundcloud. This article is the published transcript lightly edited as a Q&A:


Tom, Your Known as the Father of e-signature, are you also now the Father of Digital Transaction Management?

I think if you were to tailor that a little bit, when we started the company, we actually brought e-Signature to the cloud. So, Father of e-Signature I would be much older, because that’s been around for quite a while.
But SaaS-based electronic signature, clearly we pioneered that. And clearly as that’s evolved into Digital Transaction Management, I think we’re pioneering in that area as well.

Why did you start DocuSign?

Well, it was one of those things that was an obvious missing part. Back in 2003 when we got started, an electronic signature process required a hugely complicated set of tools. So the model, in effect, was broken in that I had to have some specialized software, you had to have some specialized software. I needed to encrypt a file and then send it off in an email to you and you would then decrypt it, try to figure out how that works. You could apply your signature and then encrypt it again and send it back to me.
Lots of problems in that model, the biggest one is the complexity of having the right software and being able to encrypt and decrypt as a normal human being. And the other is you’re basically still using email. You’re distributing a file off. You have no idea where it is. There’s really no control in that model.
And so we turn it inside out. Let’s put everything in the cloud. We can hide all the complexity of encryption and all the muckity-muck that makes all this stuff secure and you just need a browser.
And it was one of those things that once we figured out that that’s really the model that would work it was inevitable. It was like one of those things we’ve got to do this.

When you started DocuSign in 2003, were you a single founder?

Yeah. Actually my story is kind of interesting. I started several companies. My last company was a company called NetUPDATE. We managed mortgage transaction information, so documents, etc., but not signing.
And at the end of my time at NetUPDATE when the market collapsed in 2000 and everything went down, we decided to have that company focus directly on just loan origination. I wanted to do more.
So when I left the company, we’d actually purchased some assets prior. Around sort of digital signature technology. I was already looking at it, and said let’s do this new model. And I literally was going to stand up a server and sort of run it myself for a while. But as we started talking to customers it became obvious this was a much, much bigger deal.
And so it got started just because it was one of those things that needed to be done. As soon as it looked that big then you start pulling a bigger team together, bigger, bigger, bigger. And we are where we are today.

How many people are at DocuSign today?

About 1500.

Do you Still consider yourselves a startup?

Well, I think we behave that way. We’re continually innovating and we’re continually pushing the needle. The market is probably between 3-5% penetrated globally so there’s still most of the market yet to go. So I think it’s important that we are continually being aggressive in terms of moving the needle and inventing.
We are by far the largest player in this market, but my market leader of 3% does not mean you’re successful yet. So we behave like a startup still.

Is it hard to maintain startup culture as you scale so fast in terms of hiring?

It is. It’s definitely something we have to focus on. So we do some things specifically to make sure we maintain that creativity in that startup environment. We do a number of hackathons, for example. Or our engineers get together and sky’s the limit. And the stuff they come up with is fantastic. And we roll that into our product roadmap as much as we possibly can. So everybody can have a good idea.
We’re fairly distributed at 1500 people, too. I mean, we’ve got offices all around the world from Australia to Israel to Sao Paolo, Brazil, U.S., U.K., etc. So 1500 is not that big a company when you’re that distributed.

You mentioned NetUPDATE earlier. Is DocuSign therefore your second startup?

More like four or five.

But by far the largest, this is the largest market that we’ve ever tried to take on. It’s one of those things when we got started we thought we were just creating a signature. If we can make a signature happen in a browser that would be great. It turns out that as you start unravelling that, initially customers said, “That’s great. You got me a signature.” But it turns out that’s not really the problem. The problem is we have all these business processes we didn’t automate because we needed a signature. So we really need you to provide us a platform to automate a business process including the signature.
So it keeps growing, keeps growing, and keeps growing. Today, we’re expanding into the DTM space and starting to connect to things that are peripheral to the transaction, like payments, for example. You think about many, many documents and business transactions are talking about some sort of payment. So being able to marry the transaction of agreeing to make a payment and the payment itself is a very exciting surface area.

Before becoming a Founder/entrepreneur, you were seemingly climbing the corporate ladder, working at Apple, AT&T, Wildfire. Did you always know that you were going to be an entrepreneur and start your own company one day?

Yeah. When I was a kid I did a bunch of stuff like this. When I was in college I started a sailboard company with a buddy of mine. And so I’ve always had sort of the bend to say, “Let’s do it,” and if no one’s doing it, “Let’s do it ourselves.”
But when you get into sort of your real career, 23 years old and now you’re in the workforce, I went into big business and I learned a lot. I had an incredible time at Apple, an incredible time at McCaw and AT&T. But all the time I was there I still had sort of the back of my mind, ‘I kind of like to go do something on my own’. And not because I want to be my own boss or anything. Just because I like the ability to point the ship in a certain direction you want to go and then go there.

I think its interesting to see at what stage Entrepreneurs actually start. As to whether you’re an entrepreneur building lemonade stands and go straight into building your own business from School. Or whether you work for 10 years and gain some experience and then start your own company.
So I guess everyone has a different path but perhaps they always maybe know deep down that they have that entrepreneurial gene as such.

Yeah. I would say for me it was very useful to have the corporate experience. I learned a lot in those environments that’s invaluable.

To be successful, do you have to do something that you love?

Oh, I think so. I don’t actually think I’ve worked in the last 25 years because I think about when I get up in the morning, what would I rather do today? And the funny thing is what I’d rather do is exactly what I’m doing, because obviously if you start a company, you chose to. So that’s what you’d rather do.

Have you ever had days where you think, “Oh, this is such hard work. Why am I doing this?” Or is everyday like, “No, I absolutely love doing this,” and “this is what I want to do”?

I would never say that every day is a walk in the park. I mean, there’s not just days but weeks and months where you wonder if you’ve made a mistake, you wonder if gosh, this is a lot harder than I thought it was going to be or something changes in the environment that really makes it tough. But I guess I kind of like that challenge. I kind of like the puzzle ahead of you that says this is something that’s almost an impossible thing to solve. And while you’re in the process of solving it, it’s a little bit terrifying. But when you actually solve it, you look back, it’s incredibly gratifying to know that you kept your wits about you, you continue to move forward.
I’d like to say things are never as bad or as good as you think they are. And if you keep that in mind, really bad things can happen and really good things can happen. If you just keep your head and keep going, you can do anything. Nothing succeeds like persistence. I mean, you’ll get there if you keep going.

Who are the people that have inspired Tom Gonser throughout your career?

Oh, there’s been a lot of people that I’ve worked with. I think my father has inspired me quite a bit. He ran the American Bar Association and sort of brought technology to the legal profession in the early days.
I’ve worked with some great people at Apple who were sales leaders and technical leaders. Jean Louis Gassée at Apple in the early days had a quote that I thought was pretty cool. He said, “We won’t be done improving on the Macintosh until you can’t tell you’re using it,” which was kind of an interesting concept from a user experience perspective. Which I think user experience is very important.
But the notion that you would perfect a product to the point that you can’t tell you’re using it was always kind of interesting to me.

Moving from the people that have inspired you throughout your career to your peers in the SaaS industry today.Who do you see as the most inspirational or visionary leaders within the SaaS industry in your opinion and why? 

I think there’s some amazing businesses being built, and there’s a list way too long to mention everybody.
I think Aaron Levie at Box has done some amazing stuff in a very complicated marketplace, pushing through an IPO, etc. He’s done a pretty good job there.
I think Drew over at Dropbox has done some amazing things there. The thing I think that I really, really respect about Dropbox is their focus on keeping things simple and not biting into the temptation to just add features because that’s what a lot of people want to do. And I think because they’ve done that, they’ve built an amazing platform.
And then I think also if you look at what Satya’s doing in Microsoft, we’ve been trying to partner with Microsoft I’d say 6 years. And since he came on board there and really changed that culture, I think Microsoft’s just sort of been reinvigorated and they partner incredibly well now as opposed to what they were years ago.
So there’s a lot of people in a lot of different levels doing some amazing things.

I understand you’ve described yourself as a paranoid person. Is it good to be paranoid and do only the paranoid survive?

Well, I hope they survive because I’m paranoid.
I guess my perspective is we invented this stuff and people followed. And so if we’ve invented it it’s perfectly possible that someone else could invent something.
So I think it’s important for us especially in a category leadership position that if something is going to disrupt us, it better be us. So to that point, it’s a little bit paranoid but I think you always have to be looking forward to see where are the threat factors in your environment and you should probably spend some energy looking at that.
In our case, for example, we’re playing with some of the Bitcoin technology. Actually Blockchain, I should say specifically, because that’s a potential threat factor to what we’re doing. Right now it’s really an alternative cryptographic function. It’s not apparent that it has a play or not but I believe it’s the edge of something bigger. And so in that case, we spend some time and energy looking at it, trying to see how it applies to business transactions and digital transaction management.

What’s your advice to SaaS professionals that aspire to be the next Tom Gonser and maybe create the next DocuSign, although obviously not THE next DocuSign?

Well, I think you mentioned it earlier. I think having a passion about something. I want you to have that idea or see that business problem that hasn’t been solved or isn’t being solved correctly, if you’re really passionate about it that’s a very important starting point. You have to believe in it, I think. You have to believe in it to stick with it. You have to believe in it to sell it, etc.
And I think it’s important to find the right team around you. The first thing is convince 2 or 3 other people that that’s such a great idea or such a good thing to do that not only would you say it’s great but you’d quit your job and work for free to push the envelope.
And if you can find a small team of people that you can kind of be on the same page about an idea like that and be passionate, I would say nothing could stop you. A great idea and a great team together, you can get funded, you can build it, you can make it happen.

Aside from DocuSign, what are your favourite productivity apps?

Well, I was just using a bunch of different apps. I was just actually demonstrating a Google Translate app. We were just travelling around Europe, how useful that was. Being able to ask a question and have it pop out in another language is pretty amazing.

But if you looked at my iPhone I have way too many apps and they cycle quite a bit.
But I think Periscope is pretty cool right now. Obviously the main, Twitter, etc., obviously cool.
But I play with new stuff and I probably go through apps faster than other people do. I kind of tee them up and see if they work, and if they don’t I dump them.
I think Periscope is pretty cool. What else do I use? Probably too much time on LinkedIn and Twitter.

Will DocuSign be ringing the IPO bell this year?

You know, that’s funny. People ask us that all the time. And of course you never comment on stuff like that beforehand. I would say that…
Well, another way that people ask that is, “What’s your exit strategy?” which I always think is funny. Because my exit strategy means to me when am I leaving. And I’m not doing that.
So we see a public market as a funding strategy. We just raised quite a bit of money. We don’t really need any money right now. And it depends on the need for capital and the attractiveness of the public markets as a source of capital. But it’s really just a funding event. It’s not an endpoint.
So we haven’t commented on that, we haven’t announced anything.


Tom Gonser spoke with Alex Theuma on The SaaS Revolution Show Podcast, which you can subscribe to on iTunes here

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