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 Michelle in Finance based in San Francisco to learn more about her career.

What do you do at DocuSign? 

I’m the Vice President Corporate Controller and responsible for many aspects of our global accounting functions.

 What was your first job after school? 

I was an entry-level accountant at a large Wall Street brokerage.

How did you get that job? 

My first choice was to work at a large public accounting firm and get my CPA. But I was clueless, wasn’t prepared for the on-campus interviews and failed miserably.  Then, I got serious, bought some books on how to interview, and asked another student who got a job how he did it. I had one last chance when one more recruiter came to the college. They were only hiring one person, and I got the job. It was then I learned I could do things if I really set my mind to it.

Why accounting? 

Nobody in my family was a professional. My dad was an immigrant and mechanic who was adamant both his children go to college. And he saved money like crazy for us to do it. I loved Monopoly and was always the banker. I loved money, statistics, and baseball. Numbers were my thing.

 Tell us about a pivotal moment in your career that helped propel you to another level. 

The best choice I’ve made so far was to take a lesser job at a great company. I had wanted a manager role but decided it was a great company to work for, so I settled for a lesser role. After only six months, a manager position opened up. I told my boss I wanted that job, and to prove I could do it, would also manage my current job. To my surprise, he gave it to me. From there, I was able to accomplish many things.

How would you describe your career and the choices you’ve made? 

It was definitely not a straight path. I made many lateral moves to check boxes in each level of the pyramid, but always making sure to go in the right direction. I tried to diversify in many areas of finance, not get siloed and stretch myself to change jobs within the company every two or three years.

What tactics have helped you through challenges at work?  

When you get a new job, you have to put in a lot of time and hard work. Don’t just do your job, but dedicate yourself to mastering it and going the extra mile.

Have you had any important mentors? 

The best leaders, I’ve found, have the best teams. I had some very good managers, and I also try to learn from other leaders, incorporating their successful habits into my work.

Have you taken risks in your career? 

Transitioning into my gender as a woman was risky in certain ways, of course. In addition to that, I worked on Wall Street for two years and knew it wasn’t for me. In the 1980s, my brother encouraged me to move to Silicon Valley during the boom to realize my dream as a public accountant. Then I sold my house and accepted a big job in Amsterdam. That was a little scary. I didn’t realize what I was getting into and quickly figured out how much I didn’t know. But I learned fast.

Can you describe how it was to transition in your professional life? 

Well, I had to leave the large company that I worked at in Florida, where I was in a very senior position. My former boss would have been fine with it, but I felt the person who was my boss at the time wouldn’t have been, nor would others. I left the company and worked at a nonprofit as the head of finance, which was a good place to figure things out as I transitioned. When I was ready to step it up again, I couldn’t find a job. I had several interviews with companies where I’d meet first with HR, and then suddenly the CFO who I was scheduled to meet wasn’t available. It’s as if they thought my brain was removed because I had changed genders. I realized I wasn’t going to get what I wanted there, so I got in my car — literally only with some clothes — and drove to San Francisco. It was a big risk, particularly at this stage of my life. I had no job and was interviewing from a motel room.

How did you end up at DocuSign? 

The controller position here opened up and my brother, who also works here, encouraged me to apply. Everything clicked, everyone was so open, and I started three weeks later. It’s great to be at a company where I can just be me, do my job, and be a good colleague. Sure, there are times when a colleague whom I’ve had a phone relationship with meets me for the first time and there’s a moment of recognition. But then we move forward and get back to work. There are also funnier moments like when my brother will walk by and out of habit say, “Hi, Mike.” And I say hi right back before catching myself and realizing he was not talking to me! But it’s all good. I myself trip over pronouns, so I don’t get bent out of shape when others do. It’s new to a lot of us.

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

Have some goals in mind. Come to an interview with a plan that’s relevant to the job you’re looking at. Get a job in a company with growth prospects and a track record of treating their employees as their most important asset. You’ll find many opportunities to develop your career in those kind of companies.

Any specific tips on how to actually find a job? 

Network as much as possible. Don’t rely solely on job boards or recruiters, and be mindful of their motivations and the advice they give. Find successful people to trust through friends, relatives, alumni, professors, LinkedIn, etc.

If not this job, what would you be doing? 

I’d be a rock star. I’m living out that fantasy by doing karaoke. I’m very animated, and I look like “Michelle” but sound like “Michael”, my childhood name. Sometimes I change the words to reflect some transgender issues, and people love that I have the guts to go out and sing these songs.

Have you been driven by a larger purpose? 

What motivates me now is being somewhere where I can use my experience, contribute my skills, and be part of growing the business. That’s the most exciting type of job for me, and I wanted to get on that ride one more time — and be at place where I was accepted in my new gender role.

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