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Episode 37: Dan Springer

Leading with Humility and Humor

Janice Ellig, CEO and founder of Ellig Group, sits down with real leaders in this series of game-changing conversations, bespoke to fellow champions of change. Heralded by Bloomberg Businessweek as one of “The World’s Most Influential Headhunters,” Janice is often consulted for her expertise and commitment to gender parity, equity, inclusion, and diversity.

We are honored to present this month’s episode of Leadership Reimagined, “Leading with Humility and Humor” with Dan Springer, the Chief Executive Officer and director of DocuSign. Dan has nearly 30 years of executive leadership, driving innovation and hyper-growth across the Software-as-a-Service industry, and leading with humility.

Dan Springer speaks candidly about his journey as a full-time dad to CEO of DocuSign; transitioning a historically non-diverse executive leadership team to new levels of diversity; significant initiatives in reducing the carbon footprint; and what it means to manage one’s ego and its impact on employees.
Episode 37: Dan Springer
As Dan reflects on the everlasting impact of this pandemic, he shares his optimism when he states, “I think I am a better listener and more open to the insights around the innovative ways we can run our business and create the employment brand where people can come here and do the work of their lives.”

Prior to joining DocuSign in 2017, Dan served as Chairman and CEO of Responsys, Managing Director of Modem Media, CEO at Telleo, Chief Marketing Officer at NextCard, and began his career as a consultant with McKinsey & Company. Dan serves on the board of directors for DocuSign and UiPath.

It is our privilege to present this episode of Leadership Reimagined “Leading with Humility and Humor” with Dan Springer!

Leadership Reimagined is available on the following popular podcast stations:

Show Notes: Dan Springer

Dan Springer remembers a moment at the WFNY Breakfast of Corporate Champions that changed his perspective on board gender parity

It was actually Ken Frazier who prompted a seminal moment for me when we were talking about the excuses that people have for why they don’t drive more diversity. At one point he asked the question: “Why is it that someone needs to make the case for diversity? Who decided that homogeneity is the right answer?” I thought about it more and more, and I realized we’ve been thinking about this all wrong. We should be thinking broadly about all the different voices and perspectives we want, as opposed to assuming there’s some inherent risk in diversifying our boards. That was a catalyst for me to think more aggressively about how I would remake the DocuSign board and senior management team. 

Dan Springer on the importance of diversity in board search

When I joined DocuSign, there was a twelve person board, which was large, and we were still a private company, but it was Mary Meeker and eleven white dudes. It was pretty clear this wasn’t the right mix. But I had an interesting opportunity as we were going to prepare to go public. I knew that would be a natural way to drive some change on the board. There are only two people left on the board from that time, and it wasn’t as though there was a sudden dramatic overhaul, it was just a thoughtful transition. So as I’ve made the transition, I’ve made a point of adding women and people of color to the board. We now have nine members and of the outside eight directors plus myself, three are women and three are people of color. I don’t think that’s a finish line, but I think it’s good progress. But I’ve also added other white men onto the board in that time as well. It wasn’t an absolute rule that we could only add diversity. The key was to say “we’re going to have the best candidates, but we are going to ensure we have a diverse slate.” I think in the past, when the DocuSign board was being built, there hadn’t been an effort to have either people of color or women in that mix of candidates.

I think it’s really important for everyone to see that the board search is not just about the diversity effort. Diversity was one of the most important components we needed to add, but there was also other talent we needed to bring in, regardless of their gender or race, to have the talent we needed to lead the company going forward. 

Dan Springer on innovation in the Software as a Service sector

There’s a phenomenon that always strikes me when we look at new technologies and opportunities for innovation. I think in the short run, we sometimes overhype them. We say, “everything is going to change tomorrow,” and then of course, it doesn’t. But at the same time, I think we underestimate the dramatic nature of that change in the long term. Let’s take a consumer product like the iPhone. When the iPhone came out, I think everyone said, oh, the world is going to change within two or three years. There weren’t that many apps yet. At first, it was in a lot of ways just a heavier phone with poor internet service. But then when you get to ten years later, you say, “oh my gosh, smartphones have fundamentally changed the way we do so many things.” And in the software space, I think it’s the same thing. We’re a SaaS [software as a service] business here. Early on, people got all excited about the cloud. But people didn’t really change dramatically. Corporations didn’t move all of their information onto the cloud because they had concerns about security and reliability. But if you look out there today, there are very few, if any software companies using the old model anymore. They just don’t exist in terms of new businesses and almost all those that still use the old business model are transitioning to the cloud. The point is that you have to be patient. You have to spot the trends that really matter and then have the confidence to say, “I’m not going to get vindication on this new trend overnight, but if I’m putting my focus on the right bets and the right trends, I will definitely be rewarded over time.”

Dan Springer on lessons from the pandemic and carrying DocuSign into the post-pandemic era

One big learning experience is that we sent all the DocuSign employees home on March 2nd, 2020, and it kept working. We never thought company-wide WFH would work as smoothly as it has. So we’ve learned we can be flexible about giving people the opportunity to work from anywhere. It makes sense because our whole mission at DocuSign is to make it easier for companies to have the digital transformation that allows their team to work from anywhere. 

There’s another trend that I think might be even more important, which is the way we listen to our employees. As an example, I have town hall meetings next week and I’ve been doing a survey on some big issues. Some of the questions are about where people work and which jobs will require people to sometimes come into the office. This has led me, and I think many other leaders, to realize that there are certain things we just assume to be true, even though sometimes our employees might be telling us otherwise. But in our infinite wisdom based on our experience, we say, “no, we really know this to be true,” and it makes us less flexible. One of the most important takeaways for me is that I’m going to work on being a better listener.

Our growing comfort with meeting people over Zoom has unlocked the ability to see a lot more people a lot more efficiently. I think that is a fantastic innovation. In general, when I think about DocuSign, we’ve realized that there are a lot of interactions that we don’t need to have in person, particularly some larger group gatherings, and we’ll still have some, but we have a huge focus on ESG and our environmental impact. We’re a company that says if you don’t need to use paper, you don’t need to cut down trees. Going paperless is a huge focus of our DocuSign impact initiative. And yet we’ve realized that one of the biggest negative impacts we have on the environment is carbon emission from people flying around the world for internal meetings. So we’re dramatically revisiting the question of whether those meetings really need to be in person. 

Dan Springer on Agreement Cloud and DocuSign’s plans to harness emerging technologies

A specific example that’s relevant to DocuSign is the blockchain. As I mentioned earlier, with some of these trends, it may be that in the short run they don’t have a significant impact on our business, but in the long run, they’re going to have very significant impacts on how our customers really run their businesses. 

We’re quite excited about the overall Agreement Cloud vision. We talked about listening to our employees earlier, and I think it’s important to have that sort of humility as a management team when you’re leading a software company. In that vein, you also need to listen to your customers. Three or four years back, we started talking to our customers about their e-signature business. Clearly, e-signature is what brought DocuSign to the dance, and it’s a fantastic and very high ROI service. But what we heard our customers saying is, “before I am able to sign a document, that has to be generated, and then it needs to be routed around through a workflow, and then once I sign it, I need to manage those agreements. I need to have integrations with other software, so it links together to build my overall business system. And then I need to store those agreements someplace, and I need to be able to search those agreements to run my business better.” And so that’s really how we’ve thought about this overall piece. It’s not just the signature, it’s the generation of agreements before, it’s the actions you take once you have those agreements, and then managing that repository, so to speak. And that’s where you’re really going to see us focus. Our innovation roadmap for the next few years involves a lot of what we call signature plus. That includes things like notary services and enhanced ID verification, but also things like CLM or Contract Lifecycle Management. You manage that set of agreements in a repository and run advanced searches on them to really run your business better. 

Dan Springer’s advice for startups

I’m always sensitive about giving people advice around their businesses because, while I feel somewhat confident I’ve started to understand my own, I don’t want to be presumptuous. But there are certain principles that I think make a lot of sense. And the first one is, especially for software companies, you have to realize that today it’s about customer success orientation, particularly in the SaaS world, where people are not stuck with long term, embedded, on prem investments. We put a huge focus throughout our company on saying we all work in customer success, and when we measure our success as a business, the crucial question is, “are we really delivering success for our customers?”

The second thing is that there’s an unbelievable war for talent in tech right now. You have to figure out a way to make your love coming to work at your company. And one of the reasons we’ve had some very good success in Glassdoor ratings and internal surveys is that we’ve done two things right. First, we’ve shown employees that we’re really focused on investing in them in terms of their career development. And two, we’ve had a sense of purpose. As I mentioned before when we talked about environmental impact, people realize that DocuSign makes the world and the environment better by moving people away from paper and manual processes. At the same time, we have a huge investment in DocuSign Impact, which is where we do our philanthropic work. Primarily our focus is about getting our employees physically working in the communities that have been so good to us, and that makes people feel excited about working at DocuSign. 

The last piece, which has been the most special to me in my tenure here, is that when I go and meet somebody and they ask, “what do you do?” And I say, “I work for DocuSign,” most people have the reaction you had, which is, “I love DocuSign!” Then they usually tell us a story about how they signed on for a job or bought a home or some momentous thing in their life that DocuSign enabled or made easier. We call those “DocuLove stories.” It makes employees feel so good to know that not just our customers, but also the end users who aren’t even paying us, feel their lives are better because of the work we do. That’s what helps us win that war for talent.

Dan Springer on the sabbatical he took after completing the sale of Responsys

It was a very easy decision, and it was probably the best professional and definitely best personal decision I’ve ever made. I had, unfortunately, recently become a single father with two boys, and I was in a situation where I was not doing a great job being the CEO of a public company and a full time dad. So after the sale, I took the opportunity to focus on one instead of trying to do both and became a stay-at-home dad. I drove carpool and made breakfast every morning and did all those great things a parent can do if you have the time and the closeness. I was already a very close, pretty hands-on dad. But doing it full time was really special. I really value the relationships it allowed me to nurture with my sons, and I felt like I was doing the right job of launching them to hopefully turn out to be fine young men. I did not know that it would last that long. I didn’t make that plan. I just said I was going to do this until I thought it was done. I started when my younger boy was an 8th grader and continued until he was a senior and had figured out where he wanted to go to college. At that point I decided it was time. When the DocuSign opportunity came up, I asked my son, “hey, what do you think? If I get a job, I won’t be around as much.” And I can’t tell whether Robert said this because he really felt this way or because he was just trying to give me the flexibility, but he said, “dad, you’ve been crowding me a little bit. I wouldn’t mind a little space and you getting a job, it’s probably not a bad thing.” That made me comfortable going off and taking the job at DocuSign.

Dan Springer on how his family changed him as a leader

When I was at McKinsey, people used to talk about certain people who are very hard charging and maybe didn’t have all the EQ that others had. And then they had children, they had the gift of becoming a parent and sometimes it really changed them; it enabled them to see things differently. I know when I had children, it dramatically changed me because it gave me the opportunity to love someone more than I love myself.

When I was married to a stay-at-home mom and that support from a family standpoint, I probably took it for granted, but it was substantial, and it allowed me to focus on my career. When I tried doing both, I wasn’t that great at it. In fact, I was mediocre at best at each. So I had a lot more appreciation for the fact that some people are balancing so much more outside of the workplace than I was. And now when I look at people and I see sometimes people struggling and figuring out how to make it all work, I definitely think I have more empathy. It’s one of the reasons that right after I joined DocuSign, we put in place a family leave program and we now give six months off to new parents, whether they’re adopting a child or giving birth. And that’s whether it’s a mother or father. As long as they tell us they’re going to be focused on the child. We want them to have that bonding opportunity. But also that opportunity to say, “let me take a little break from the work pressure so I can really focus on being a great parent.” And then come back to work and ease back into a balanced environment. So I think that definitely is something that probably wouldn’t have been on my radar. It’s a little bit ironic, because I grew up with a single mom, the greatest mom in the world, who worked all the time. And I should have probably had more appreciation of how challenging that was for her to raise me and my brother in that setting. Now I have all that appreciation and empathy, but it’s often wasted on the young. 

When it comes to humility, I also learned a lot about the experience of being focused on other people full time. In the past, I’d always thought of myself as being focused on our customers and employees. But what really crystallized that understanding was taking on the job of helping these two boys blossom to the best of their ability. It’s just not about you when you have your parent hat on full time. 

I spent much of my life, I would say ambitious, and I defined a lot of that ambition around success in a very traditional corporate way of moving up the ladder. And I’m okay with that. I don’t have any sort of regrets about it. If I could do it all over again, I would have a lot more wisdom probably for what I learned and how I influenced people along the way. But I’m okay with that path. But now and looking forward, the biggest change from becoming a stay-at-home dad for a while is the satisfaction that I get is very different. What satisfies me professionally is watching the people around me blossom. And when I see people at DocuSign and look at their career trajectories and the opportunities we’ve created for people to do more and take on more and push themselves to become better leaders and better contributors to the company and drivers of our success for our customers. That is what amps me up. 

Dan Springer on his future career plans

At some point, Silicon Valley will tap me on the shoulder and say, “hey old man, make way for the young folks.” And I’ll be okay with that when it happens. But at this point in time, it’s a fun ride and I’m getting a lot of joy out of driving it. So I’m going to continue in this mode as long as they’ll have me. 

Dan Springer’s advice for aspiring leaders

One thing I think people should try to monitor – in their own leadership, and broadly, in life – is ego. I think a lot about the impact people have in the company when they put the focus on the company’s success versus their own. And I think it’s probably the single biggest lever that we can control. Between where I was at 24 and where I am today, there’s been a huge change. I wish I’d had the maturity, self-assurance, and self-confidence back then to say, “I’m all about the organization’s success and not so focused on my own.” So the counsel I would give to people is that if you want to be successful, you want to make your organization successful. And to make the organization successful, find a way to keep your focus on that and not on you, and it will come back in spades for your own success and development. Manage that ego to a point where you’re saying, “all my activity and all my focus is on driving the success of the organization.”

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Janice Reals Ellig

Chief Executive Officer

As the head of the Ellig Group, Janice is dedicated to increasing the placement of women and diverse candidates on corporate boards and in C-suites by 2025. Janice joined the legacy firm in 2000 and became Co-Chief Executive Officer in its transition to Chadick Ellig in 2007; she assumed sole ownership of the company as the Ellig Group in 2017 with a new focus on Reimagining Search. Prior to her career in executive search, Janice spent 20 years in corporate America at Pfizer, Citi and Ambac Financial Group, an IPO from Citibank, where she was responsible for Marketing, Human Resources, and Administration.

Heralded by Bloomberg Businessweek as one of “The World’s Most Influential Headhunters,” Janice is often consulted for her expertise and her commitment to gender parity, inclusion, and diversity. She frequently appears at speaking engagements and as a media guest, and she has penned multiple articles for outlets such as Directors & Boards, Directorship, Corporate Director, The Huffington Post, and Forbes.com. Janice also co-authored two books: Driving The Career Highway and What Every Successful Woman Knows, acknowledged by Bloomberg Businessweek as “the best of its genre.”

A tirelessly active member of the industry and champion of her causes, Janice is Founder of the Women’s Forum of New York’s Corporate Board Initiative and its signature event, Breakfast of Corporate Champions. Since 2011, Janice continues to spearhead this event to honor companies committed to board diversity and to encourage CEOs to sponsor board-ready women for the Women’s Forum database. (LINK: www.womensforumny.org).

Janice is personally committed to several NFP organizations: Board Director of the National YMCA and Past Chair of the YMCA Board of Greater New York; Trustee of the Actors Fund and Committee For Economic Development (CED); Incoming Chair, University of Iowa Foundation; Women’s Forum of New York Past President and Chair of the Corporate Board Initiative; member of the Steering Committee, US 30% Club and The Economic Club of New York.

In recognition for her many philanthropic activities, Janice received the University of Iowa Distinguished Alumni Award in 2011 and the Association of Executive Search Consultants (AESC) Eleanor Raynolds Award for Volunteerism in 2008. Named one of the “21 Leaders for the 21st Century” by Women’s eNews, she was also a recipient of the Channel 21 Award In Excellence for her contribution to “Excellence in the Economic Development for Women.”

“Listening to our clients’ needs, learning their business and understanding their culture is how we present the best talent and provide  a competitive advantage. We place candidates with the character, competencies, commitment, (intellectual) curiosity and courage to make a difference. Our goal is always to go beyond the expected and deliver valuable advice, measurable results and great talent!”

– Janice Reals Ellig

  • Champion of gender parity, diversity, and inclusion
  • Industry expert, speaker, and author
  • Founder of the Women’s Forum of New York’s Corporate Board Initiative
  • Committed board and committee member and philanthropist

T: (212) 688-8671 ext. 226
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