DocuSign CEO: How to lead a pandemic darling, after the pandemic

DocuSign’s new CEO Allan Thygesen tells MT how he is reshaping the business for a post-pandemic future.

by Kate Magee
Last Updated: 02 Aug 2023
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If you held one of Google’s most high-profile roles, it would be understandable that joining a pandemic darling, once the crisis had passed, might not be a particularly attractive career move. But that’s the leap that Allan Thygesen made in October 2022 when he left his position leading Google’s $100 billion advertising business in North and South America, to become CEO of DocuSign, the Nasdaq-listed company that shot to fame for facilitating e-signatures.

DocuSign’s strong brand recognition is both a blessing and a curse. To be a sustainable business in the long-term, DocuSign needs to broaden its offer and shift perceptions that it is a one-trick pony. The company’s new focus is to help businesses throughout the “agreement process.” For example, it can now handle identity verification and management of a contract - from flagging when it is due for renewal, to helping companies comply with the terms of the agreement and extract value from the contract.

It’s a necessary move, because while DocuSign held a 75% share of the e-signature market last year according to Deloitte, its competitors like Adobe Sign and HelloSign from Dropbox are increasingly embedding one-time signatures into their already larger systems.

Thygesen’s brief is to lead DocuSign’s reset. MT met him on his recent trip to London, the first stop on a global roadshow where he is unveiling a series of new products that help with contract management. Of his challenge, he says: “We have fantastic customer affinity and familiarity. The flip side is, like every company that gets identified to one particular thing, it takes a lot to reset customer expectations and perceptions. I think that's our opportunity now, and that applies to the stock market as well. I think we're well on our way.”

Taking the leap


Thygesen’s time at Google was “magical” but he joined DocuSign for three reasons. The first was its simplicity - “it’s very rare to find a company that solves a unique pain point.”

Second was his belief the business had an engaged customer base and the ability to expand successfully. “The satisfaction ratings DocuSign gets for customers are off the charts compared to most enterprise software companies,” he says. He was personally a happy DocuSign user - Google is a big customer - and he sees a larger opportunity to expand across all agreement workflows, leading to a “huge potential addressable market.”

Third, he believed he could make a positive difference to the company and how it is run and was up for the challenge of “leading the new beginning for DocuSign”. “Some of the operational challenges the company had resetting post pandemic were problems I felt like I could help fix,” he says.

For example, DocuSign used to insist that every customer, no matter their size or need, had to talk to a sales rep. “That’s not very modern, right? If you just want to add another feature, you should be able to go on the website and do that,” he says. So he simplified the process. He is also ensuring his teams are working closely with its existing large partners like Microsoft, SAP and Google to further integrate DocuSign into their systems.

One of the criticisms of the pandemic darlings was they hadn’t thought enough about the long-term trajectory of their business, and got complacent that the additional demand would continue after the crisis subsided. “I won’t speak for others, but I think that's fair for us. We reset that. I've made some leadership team changes. We have a full, fantastic, team in place now across every function at multiple levels,” he says.

He’s also shifted focus, by moving resources from sales to product innovation, an attempt to correct the pandemic strategy. “When there's an external event like that, it creates so much extra demand it can suck all the oxygen out of the room. All the energy of the company goes into satisfying that enormous demand increase. So our innovation and product development velocity slowed down a little bit,” he says. Now, he is “reigniting the innovation roadmap” at a rapid pace. DocuSign used to release new products three times a year, now it is launching them every month.


No great expectations


DocuSign went public on the Nasdaq in 2018. In March 2020, its share price was $89.26. By September 2021, it had hit a peak of $306.74. But by March 2022, it was back to $72.69 and has remained around $51 for most of 2023.



DocuSign has enjoyed two quarters of growth that have beaten analysts’ expectations, but they remain concerned about its potential. Thygesen himself issued caution on its future results, telling analysts the company is seeing “a more moderate pipeline and cautious customer behaviour”, smaller deal sizes and lower volumes. The business is currently predicted to break even in 2025.

Thygesen understands why analysts have negative perceptions of the business, but he says: “We’re still in ‘show me’ mode with the stock market, and appropriately so. We need to ship all of our new products...I accept that challenge.”

A career of three parts

Thygesen’s career has gone through three distinct phases. His decade working for a big corporate in Google, gave him a sense of how to run a business at a “massive scale”. “DocuSign is a $2.5 billion plus company now. I’ve seen ten to a hundred times that size, so it does not make me feel uncomfortable,” he says.

Prior to Google, he was a VC for a decade. “The investor and VC mindset is very helpful,” he says, providing an advantage when dealing with financial markets. It taught him how to get up to speed quickly on new topics, to harness innovation and “pattern recognition of having seen business at different stages of maturity, and what matters at each stage.” It also gave him a good network.

He started his career as a serial entrepreneur in the start-up ecosystem, working for a range of different businesses. “I’m an entrepreneur at heart, so in a way, I’m coming back to my roots of working for a smaller, more entrepreneurial company,” he says.

It was in the start-up world that he probably faced his biggest career challenges, including the acquisition of his company by a company that later went bankrupt. But as he says. “You learn from these experiences. They’re painful but they’re not life or career ending.”

His predilection for change is a fundamental part of his leadership personality. “I don’t get too fazed by the short-term ups and downs. I don’t get too excited when things are going well or too depressed when things are challenging. I really focus on setting long-term direction and make sure that is a forward-looking not too incrementalist view.”

He believes rapid decision making is really important and has a strong team-orientation. “It's impossible to move quickly and navigate a flexible way if you don't have the team on board. I'm a pretty direct communicator - I don't think it'll be confusing where I stand. But I really want to hear everyone's opinions and to the greatest extent possible, make decisions that we agree on,” he says.

Holding leadership roles for decades has given Thygesen a front seat to the changing mores in management styles. While he says people have always valued empathy and authenticity, he says it’s even more at a premium now. “A sense of purpose is more important now than when I was entering the workforce. People expect a higher mission and to feel like they are contributing to society, not making a quick buck or short-term objectives. It’s incredibly important to connect the dots for employees and have them feel there is that higher purpose,” he says.

He also believes inclusivity is crucial. “There’s a more explicit recognition now that different backgrounds, collectively create. You're more representative of the customers you serve. You get better decisions because of the diversity of views and backgrounds,” he says.

He manages the pressure of the role by “trying not to look at the share price daily.”. “Obviously I care about it a lot in the long-run, but I’d drive myself crazy watching the day to day movements of the stock market,” he laughs.

He admits that despite running a team as big as DocuSign in his previous role at Google, “it does weigh a little differently being CEO.”But he takes a simple approach, “I enjoy leading teams and being on the field. But when I’m off, I try to be off. I’m reasonably good at switching contexts.” His family was with him on his trip, and after the event, he was heading to Copenhagen, where he grew up.

Future headwinds


One of the biggest discontinuities from a technology perspective is the rise of AI. Like many CEOs, Thygesen is positioning the company as a beneficiary of the AI boom, arguing it plays a large role in DocuSign’s new products. He believes AI is a “significant enabler and a huge net positive for us and the entire market” because “all the steps of the agreement process can be meaningfully enhanced with AI,” says Thygesen.

As well as expertise, DocuSign has “the largest contract repository of any company in the world, with six petabytes of contract data. We're already a trusted partner to enterprises around the world. We're going to uphold that trust and work specifically on behalf of each of them individually to help them write and negotiate better agreements. That's a fantastic opportunity,” he adds.

He is less clear about the macro economic climate. “Anybody who says they know exactly where the economy in the UK or the US is going is kidding themselves. You just have to be prepared for optionality and for agility and, as a public company CEO, we need to manage responsibly, so that in the event things get worse, you're well poised for that.”

But he adds, “I also want to make sure I don't sacrifice the long term growth potential of DocuSign. We are improving our operating income, but I don't want to run the business just for short term cash. I don't think that optimises value for any of the constituents in the long run. So that's the balance. You bring people along with that and in some cases, you may have to wait for them to see.”

His final piece of advice for other CEOs is that clarity of communication is perhaps the most important thing for leaders. “When you're moving up in your career, it's hard to fully appreciate just how important communication is. But when you start running larger teams, it's the only way to affect change,” he says.

“If you can be very clear so people know what you're thinking, where you're going and you do that in a transparent and engaging way, people will follow.”

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