12 Leadership Lessons from DocuSign CEO Dan Springer

by Jason Nazar

In Comparably’s ongoing series in partnership with Entrepreneur, If I Knew Then: , I host virtual fireside chats with high-profile CEOs of major brands from, Nextdoor and Blue Apron, to Waze and Warby Parker. As the host, I ask talented leaders to share some of the valuable lessons and practical career advice they learned during their career trajectory. These rare, candid insights into the lives of remarkable catalysts for success in the business world are accessible as a resource of inspiration for current and future entrepreneurs and are not to be missed. When CEOs get transparent, you can’t help but lean in.

For the latest episode, I sat down with Dan Springer, CEO of DocuSign, who leads thousands of employees globally, allowing DocuSign to modernize organizations by making every agreement 100 percent digital. Driving and growth in technology and the Software-as-a-Service (SaaS) industry exemplifies Springer’s executive leadership and experience for the past 25 years. Prior to DocuSign, the Harvard MBA graduate served as chairman and CEO at Responsys for a decade, where he revolutionized and grew the business from a private startup to a leading cross-channel global marketing automation platform — resulting in Oracle’s $1.6 billion purchase of Responsys in 2013.

As a veteran of , Springer holds honors as both the Bay Area’s Most Admired CEO and Best CEO. He is also a 2020 recipient of the Robert F. Kennedy Human Rights Ripple of Hope Award, sharing this accolade alongside top U.S. infectious disease expert, Dr. Anthony Fauci, as well as San Francisco 49ers Colin Kaepernick, for his leadership on social change during these trying times. , , Bono, and the late Representative John Lewis have also received this award, catapulting Springer into the company of greatness.

Among other topics, this conversation covers Springer’s origin story — from “winning the ovarian lottery” to attending the famous Lakeside High School with alumni such as Bill Gates and Paul Allen — laying the foundation for his early life before becoming a serial entrepreneur. Here are the 12 essential takeaways from our chat:

1. Successful business leaders don’t all come from the same mold 

Everyone has a different background and path in life; use that to propel you forward. Springer shares that he grew up with a single mom in an affluent suburb, which might have given him a chip on his shoulder in the early part of his career at McKinsey. However, he turned that initial insecurity into something positive by excelling and overachieving. Continue reading

Managing the COVID stress crisis with finesse, compassion

By: Tracey Ferstler

With the pandemic causing new anxieties, employers need to rethink their benefits to provide a better mix of tools for managing stress, burnout and depression.

Everyone faces stress in their life, but the ripple effect of COVID-19 has caused new sources of financial, social and physical stress that go far beyond the norm. These stressors are lasting and pervasive, piling up to the point where they pose a significant threat to employee well being if left ignored.

According to a new MetLife mental health study, employees say that their top stressors are financial issues (81%), job insecurity (77%), fear of catching the virus (60%) and social distancing (47%), followed by concerns about the presidential election, social justice issues and not having access to healthcare because of COVID-19. On top of this, separation of work/home life is increasingly blurring, especially for parents trying to juggle children at home.

Never before have employees had to cope with so much at one time, and never before have benefits programs been tested across the spectrum of holistic health, including physical, financial, mental and social health. Per the study, nine in 10 employers say their organization is not completely ready for a mental health crisis, although one in five say the United States is in crisis right now.

This is the perfect opportunity for employers to rethink their benefits approach to provide a better mix of tools for managing stress, burnout and depression. This will not only help employees become more resilient and productive, but will also improve long-term business recovery.

Start with understanding key stressors

Anxiety is at an all-time high, with 5.5 million employees saying they no longer feel mentally healthy and 38% of adults reporting symptoms of anxiety or depressive disorders, an increase of 27% since 2019 (pre-pandemic). In addition, 41% of employees say they feel stressed, burned out or depressed at work on a regular basis.

Financial stress is the No. 1 driver of overall mental health stress, up 29% since 2019. The biggest sources of financial stress rest in concerns about long-term savings and medical bills/expenses followed by fears about stock market volatility and retirement plans.

These concerns, combined with all the other top stressors listed above, are creating a workforce at the tipping point. This is compounded by the fact that not everyone can “self-diagnose” the warning signs of mental health. When asked, employees don’t always think they have a problem but say they have specific symptoms. Most employees report at least five key signs of burnout—such as feeling emotionally and physically drained—and at least five signs of depression, such as feeling tired, hopeless or unable to sleep.

Next, create an environment of support

As they plan for business recovery, 76% of employers say resilience is very important. Compared to least-resilient employees, those who are most resilient have better mental health, are more likely to be holistically well, and are less likely to be burned out or stressed.

To help return employees to good health, benefits plans should try to span every area of holistic health since financial, mental, physical and social health are interrelated. Organizational support tools can include effective tools like employee assistance programs that offer everything from financial consultations; to counseling for stress management, work/life and substance abuse; to childcare and legal support. Employees with EAP access show 17% more resilience than employees without EAPs.

Insurance programs (like life, disability, hospital indemnity, critical illness) may also help employees boost financial security.

It is one thing to offer the right mix of tools, yet quite another to create an open culture that makes mental health a priority. This culture also should build awareness about available resources, educate employees about the warning signs and remove the stigma of asking for help.

The ability of employers to manage the looming mental health crisis with finesse and compassion can only help drive loyalty, productivity and long-term success.

Source: Human Resource Executive

‘Be Human’: Marshall Goldsmith’s Best Leadership Advice Right Now

In any time but the current one, this is the last place Marshall Goldsmith, one of the most in-demand CEO coaches in the world and bestselling author of leadership classics like What Got You Here Won’t Get You There and Triggers, would be. Back in B.C.—Before Covid—Goldsmith was a legendary road warrior with 11 million frequent flier miles, tracking how many nights a year he was at home with his family, rather than vice versa, in the hopes of improving that KPI.

Yet, here he is, with a green screen behind him, chunky Sony earphones locked on snuggly, ready to talk from his home in Covid-subdued La Jolla, California. And, as you’d expect from someone who is obsessed with prepping leaders for change, he’s okay with it. “I’m a Buddhist,” he shrugs. “What is is, so you just make peace with what is and do the best you can and move on.”

This kind of equanimity takes work, of course. Lots of it. In the midst of crisis, Goldsmith is practicing what he preaches, meeting with a group of 50 or so high-performing people each weekend (virtually, of course), talking about issues, feelings—and fears. He’s working with his own coach, trying to improve his behaviors, checking in nightly on how he’s doing relative to expectations. And, more than anything else, he’s listening and trying to help his clients—many of whom are household names in global business—tackle a very, very tough time.

In a conversation with Chief Executive, Goldsmith, who will be the keynote speaker at our upcoming annual CEO Leadership Conference on November 5, talked about how Covid is disrupting his clients, what he’s counseling them and why this period of unparalleled change and challenge is an essential time to work on your own behavior and improve your emotional intelligence. The conversation was edited for length and clarity. Continue reading

Hiring in 2020 from your perspective

With the pandemic, the traditional face-to-face interview was suddenly replaced with video conferencing using tools such as Zoom, Skype and Go-to Meeting– leaving many in the interview space scrambling to figure out how to best assess candidates in an entirely new way.

Since everyone is adapting and learning in real time, we thought it would be helpful to crowd source ideas for improvement from our network of professionals. We can all benefit from understanding the challenges you have faced and the actions you have taken to foster improvement around interviewing.

Below are questions to consider. Please feel free to choose from them and/or contribute your own thoughts and insights.

For Hiring Managers

  • What steps have you taken to transition interviewing to a virtual environment?
  • What have you done to set the stage for professionalism in a virtual interview?
  • How have you conveyed the company culture when candidates don’t have the opportunity to see your office and meet your team?
  • How have you made it comfortable for candidates to be their best selves virtually, especially if they are unfamiliar with your conferencing tool of choice?
  • What have you learned by doing virtual interviews? What tips can you offer?

For Candidates

  • What steps have you taken to understand the company that you didn’t need to do for a face-to-face interview?
  • What tips on dressing can you offer to ensure you and your environment reflects a professional image?
  • What have you learned by doing virtual interviews? What tips can you offer?

Many thanks in advance for your contributions and please let us know if you would or would not like us to use your name in our published report.

Thank you in advance for your time and contribution to our blog. We will send you a link when we have compiled the results.

Please email us:

Larry Janis janis@issg.net

Jeff Bruckner bruckner@issg.net

Integrated Search Solutions Group

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Why Now Is the Perfect Time to Rethink Talent and Leadership

Startups and scaleups worldwide are facing a make-or-break moment with coronavirus, a health crisis with vast and unprecedented economic consequences. Each entrepreneur is in a unique situation, whether they’re well-funded, planning their next funding round or struggling through the uncertainty.

As a result, founders are turning to their VCs and mentors for support and conversations are, unsurprisingly, centred around cash. In the UK, while £81m has gone to startups that haven’t received investment previously, there’s been a 31 percent decrease in deal numbers compared to the same period last year—so it’s a pressing issue.

But cash alone only presents half the story. As startups seek advice on how to weather the storm and find positives in the situation, the conversation broadens. To survive this period of instability, growing businesses should look toward the key cornerstones of success: talent and leadership. After all, the best founders never waste a crisis and now is a good time for them to refocus.

The vision could be great, the founders innovative and cash readily available, but without strong leadership and world-class talent, businesses can’t continue to thrive in this climate. How to look after and manage teams during this time, as well as understanding what staff cuts to make and how, are important considerations that startups are looking to VCs for support and advice on.

A conservative approach. 

Any business plans that organisations had in place ahead of the pandemic are now likely to be irrelevant. Businesses need to start from scratch with a clear view of their burn rate and shouldn’t be afraid to rip up the rule book and abandon existing plans. Startups already doing this have looked to renegotiate their office rents, contracts with providers and suspended online advertising, for example.

Reducing such costs is sensible in a challenging fundraising environment. Deals have slowed down and the Pitchbook European VC Valuation Report points toward a decrease in early seed rounds. New investments certainly have stopped and great companies always get funding, but many investors are focusing on how to support their existing portfolio. The crisis isn’t over yet and, with further outbreaks still possible, now is the time to be conservative. Continue reading