Our “DocuSign UP Career” blog series places the spotlight on employees who tell us about their first job (how they landed it, why they chose it) and key moments in their career that lead to greater learning or career momentum. At DocuSign, we believe in the next generation of leaders and want to help them get on the right career trajectory. That’s why we started DocuSign UP (University Program).  

This week we sat down with Michael in HR based in Seattle to learn more about his career.  

What was your first job after school? 

My first job was building houses. I also ran a company that did catering for concerts and films. I met almost every band that came to Seattle during the late 80s — Madonna, Motley Crue, U2, etc., and worked on movie sets.   

 How did you get that job? 

I wasn’t a very good carpenter and decided to go back to school. While in school, I met someone who needed my help one night at a concert. She liked my work so much that she asked me to be the operations manager for her business. Over the next two years, I ran that company.  

Is it related to the work you do today? And what did you learn? 

Absolutely! If you can keep people like Madonna happy, then everyone else is relatively easy. It taught me how to operate in a high-stress environment. I learned how to negotiate and make immediate decisions, how to adjust constantly in a rapidly changing environment. In movies, filming can happen anytime, anywhere in a 24-hour period. You had to plan, but be willing to adjust. Those lessons very much relate to working with the people and cultural challenges companies like DocuSign face.  

Tell us about a pivotal moment in your career. 

After graduate school I was hired (with no formal HR experience) to be an HR generalist and in the first three months, I knew I loved it. I couldn’t believe I was getting paid to this kind of work. I would have done the job for free. The work was so dynamic, and I got to do a little bit of everything. On any given day, I could be neck deep in spreadsheets, making numbers balance, working on a predictability model around staffing, and dealing with complicated human relations issues. So, I decided I would pursue a career in HR, but didn’t know how to do that. One day I saw a job posting for VP of Human Resources at NBC Sports (which looked like a great gig!) and I carried that job description around for seven years. It was something to aspire to, and a blueprint for how to get there. I educated myself as much as I could, raised my hand for projects, I took on roles to continuously expand my skill set.  I focused not on my titles, but on what I could learn, and what roles could stretch my thinking and enable me to be an effective HR leader and make an impact.   

How would you describe your career?  Linear or more like a jungle gym? 

Definitely a jungle gym, as I took roles across different companies. The beauty of being in HR is that you can do it in any industry — public, private, factories, corporate, basically anywhere with people. In each place, I was able to get new experiences, build a level of capability, and learn how to solve problems in different environments.   

 At what point did you discover your limitations? 

There were times when I didn’t buy into what I was doing – there’s only so much you can do selling carbonated sugar water, for instance – and couldn’t imagine doing it for the rest of my life. The world is changing fast every day, and that’s part of the continuous learning approach.  The key is to balance being relentlessly self-critical, but also grateful for what you have and where you are today. 

 Have you ever faced a setback in your career?  

Yes, often there is no real blueprint for complex people challenges in a global environment, so I’ve had a lot of learning opportunities, and likely will have many more. I’ve learned quickly in those different scenarios.  There’s only one job in my life that I regret taking, and I left because the environment was so negative. It was just the wrong fit.  But mistakes do not define who we are, just what we need to learn.   

Did you have any important mentors in your life?  

I’ve am fortunate to have many strong mentors in my life today. One mentor said to me 20 years ago; “Michael, you care a lot about what others think of you, but really we just don’t think of you that much.” It was a valuable lesson. It gave me perspective to not take myself so seriously.   

What advice would you give a college junior or senior breaking into the job market? 

First, never stop learning. The world is changing fast, and what you know now can soon be obsolete. Second, create change and make an impact. Focus on how to solve problems. I went through different industries where the situations were so radically different. I couldn’t rely on what I knew, but had to learn how to solve problems to be successful.    

Any specific tips on how to find a job or organize a job search? 

Network, network, network. Knowing someone can open up opportunities. Even a small level of familiarity can make a difference whether you get an interview or not. 

If you weren’t in this job, what would you be doing? 

Other than playing in the NBA or being a race car driver? I’d probably teach full-time. I love teaching and helping students grow.   

Interested in working at DocuSign? Check out our open positions.