Career Lessons from the Last Frontier: Courage, Community, Creativity

By Kirsten Wolberg, Chief Technology and Operations Officer, DocuSign

I grew up in Alaska in the ‘70s, so I know a few things about pioneering. At that time, the motto on Alaska license plates was “the last frontier” and the landscape certainly lived up to the billing. It was a wild and untamed place.

Truth be told, I hated living in Alaska. It was too cold, too small and too unrefined for a girl with big dreams. What I didn’t appreciate at the time is that a childhood full of literal pioneering would give me three of the most important tools I would need later to be a successful tech pioneer in Silicon Valley: courage, community and creativity.

Courage

Pioneering by definition means trying things that have never been tried before, braving new trails and conquering the unknown. As a child, I was fearless; I didn’t know any differently. I was surrounded by people who inherently ignored risk and saw only rewards. 

When I left home for college, I landed in Los Angeles, completely unequipped for life in a city that big. I heard new languages spoken on the street, saw homeless people for the first time and had my mind blown by the mass of humanity that surrounded me at every turn. It was overwhelming. There was a definite temptation to retreat to what I knew. In fact, that is what most of my high school peers did—after one semester away, they went home for good. But not me. The courageous pioneer in me was determined to make the most of this opportunity in a new territory. 

College led me to a career in financial services and technology. In this world, being a smart, outspoken and ambitious woman was not only new for me, it was new for all of the men in my office as well. I studied them intently and I learned what it took for them to be successful. I started dressing like a man, swearing like a man, being aggressive like a man. To some extent, it worked. More accurately, it worked until it didn’t. 

All that courage and male behavior modeling worked until I rose high enough in the corporate ranks to become a threat to the men, who feared I might take their job or even become their boss. I got advice to “tone it down” and “work on my sharp elbows.” After years of fighting this feedback, I realized that what got me here wasn’t going to get me to where I wanted to go next. I needed to change my tactics or change my location. 

It took courage, but I did both.  I left banking for technology. I moved from Los Angeles to Silicon Valley. I also stopped trying to become someone else and embraced my authentic self. 

The best part of this story is that it worked then and it is still working now. Better yet, I believe my courage in some way has created a new path for women and a new model for success. 

Community

I think many people from my generation have an image of the entrepreneur as a lone inventor in a dark basement or a cold garage. This loner tinkers for weeks, months, even years until finally arriving at a eureka moment.  

Alaskans understand from a very early age that if you are going to be a pioneer, you shouldn’t try to make it alone—your life depends on the community. The smart pioneers stick together.  They help the community no matter what because they know that someday they will be the one who needs help. The only way to stay alive against the harshest landscapes is to leverage the skills and power of the community to solve new problems.

In Alaska, if your car breaks down and you pull over on the side of the road, here’s what happens: The car behind you pulls over too. Regardless of what that person has going on, they’ll stop to help you. The same goes with the next car, the car after that and so on. Everyone joins the effort until the broken-down car is back on the road or a tow truck has been dispatched. 

What happens in LA when someone breaks down on the side of the road? Absolutely no one stops to help. People barely glance in the direction of the troubled car. They might even honk (or worse) to show frustration that the breakdown is inconvenient for them.

Entrepreneurs who set out to change the world understand the power of community and often draw on the wisdom and talent of their communities to succeed. 

It wasn’t just Bill Gates who created Microsoft—it was Bill Gates and Paul Allen hustling and collaborating with the community. Salesforce is not a $10 billion company today because of Marc Benioff, but rather the collective brilliance of Marc’s marketing, Dave Mollenhoff’s cloud architecture, Parker Harris and Frank Dominguez’s application development. Benioff even leveraged his relationship with Steve Jobs for mentorship and guidance during the difficult early years. Salesforce is a technology pioneer because of the Silicon Valley community.  

As the tech industry continues to grow in other emerging areas, communities need to rally together to support the success of the collective, not just the individual or the company.  

 Creativity

Growing up in Alaska, summer days were endless. We didn’t have camps or classes to keep us occupied. Our parents usually threw us out of the house in the morning and told us not to come back until dinner. It was during these long, empty days that I learned how essential creativity is. 

I remember one day with particular vividness. My mom ushered me outside and gave me a new toy: a box of dry raspberry Jell-O. It doesn’t matter that it was Jell-O. What matters is that a standard household item completely ignited my play. My imagination took over—the Jell-O transformed into medicine for my make-believe hospital, face paint for my monster mash, fake blood for a staged bike crash. No matter what I had already imagined, I could always come up with something new. With a little creativity, that box of Jell-O turned an empty summer day into more fun than a ticket to Disneyland.

I took that creativity from childhood to companies like Salesforce, PayPal and now DocuSign—all technology pioneers—where I saw the power of innovation translating to real value in the marketplace. These companies have incorporated creativity into their culture. They build it into every process, screen for it in every hire and measure success by the new ways they’ve imagined to encourage customers’ passion for the platform.  

With the support of these innovative cultures, my imagination from childhood play grew into customer-focused professional curiosity, a drive to never stop asking “what if?” questions. It’s not enough to just make electronic signatures. What if we could automate the entire agreement process? What if we could make it touchless, frictionless and smart? What if we could make it possible for customers to prepare, sign, act on and manage agreements on a single platform? Imagine the implications of a process like that. Imagine what else we could do.

These questions fuel the DocuSign team. The creative minds here spark new questions every day that drive our company and our product forward. There are thousands more that our customers will help us discover. This is not the creativity of the future, it’s the creativity of today and it’s up to innovative companies to find a way to harness employee creativity to build something new and valuable. 

Maybe we should all ask the next candidate what they would do with a box of Jell-O? 

Blaze your own trail

Take it from this Alaskan explorer, pioneering success has three elements: courage, community and creativity. With courage, you can charter new territory while being your authentic self. With the power of your community, you can solve every problem while still looking out for the good of the whole. With a culture driven by creativity, you will innovate by ensuring that the same spark is in the DNA of every person you hire and every product you build. 

This is the path that I’ve taken so far and it’s gotten me to the right destination. Now, I want to give you the map that I’ve been making so you can get where you need to go too.