Catherine Courage, SVP at DocuSign, Newfoundland Native and Sports-Lover   

What would it be to go from the icy, ocean-surrounded enclave of Newfoundland to the sun-soaked skies of San Francisco?  Catherine Courage, an SVP at DocuSign, knows about that scenario; she is a “Newfie” (as natives call themselves), but after getting her undergraduate and graduate degrees in Canada,  packed up and moved to SF, wanting to see “what all the Silicon Valley fuss was about.”

She now works in the Customer Experience division at Bay Area-based DocuSign, which has raised $443 million in funding since its founding in 2003, and now has a “unicorn” valuation.  Prior to her work there, she spent six years at Citrix, where she was also the vice president of product design, and was a founding member of the experience team at Salesforce.com.

On the personal side, she says she is a dog-lover, that she overcame her shyness to be able to shine in the corporate sphere, and gives big props to her mother and three aunts, all of whom earned  PhD’s (!), for their inspiration. She notes also that she loves being able to “enjoy nature year-round” in her adopted state of California – far from Newfoundland’s polar winds — and to that end, participates all kinds of sports.

Can you tell the readers a little bit about yourself?
I’m a senior software executive living and working in San Francisco.  I’m lucky to have a great job at DocuSign where I can focus on delivering outstanding products and service experiences to our customers. Outside of work, I’m passionate about great food, the outdoors and endurance sports. I live in city with my husband Ian and our rescue Cassie-Dog. You’ll often find the three of us at the beach enjoying life.

What does a day in your shoes typically look like?
In general, I tend to spend most of my days in discussions reviewing existing projects and plans to help the team push forward and remove any issues or blockers.  I really enjoy getting out and spending time with customers, so many days you’ll find me immersed in their world. I also enjoy speaking at conferences and industry events on customer experience.

What 2-3 things do you do to prepare yourself before work, and is there anything you try to accomplish every day?
I like to try and get into the office an hour before my first meeting. This gives me some time to think about the key things I need to accomplish for the day. I also like to start my day by reading my daily FastCo Design email. It is positive, fun and inspires me.  It sets a good tone for the day.

What is your breakfast of choice?
During the week I eat a Power Bar, fruit and a Vitamin Water. During the weekend I love to indulge in brunch; I love a classic American breakfast of eggs, bacon and toast!

What are your tips for staying energized and motivated? 
Work is very important and I spend a lot of time focused on it, but not at the cost of the things I love. I love the outdoors and physical activity. I strongly believe that making my alternative passions a priority helps me be better at my job. It allows me to clear my head and decompress. I often solve some of my toughest problems when I am out for a run, bike or a swim.

What is your favorite part about your job?
Working to make the great products and DocuSign even better. It’s especially fun to think about the future. I love sketching and prototyping ideas of where we want to take the product next, how can we delight our customers, and add greater value. There is nothing better than getting to dream and deliver the next big idea.

What and who inspires you at work?
A major driver in joining DocuSign was the people. I am inspired by our CEO, Keith Krach, and the leadership team who are setting a great vision; also the team with whom I work who strive to make that vision a reality. It’s a great group of talented, passionate, and driven people. I also love our customer stories — what we call DocuStories. These are the moments where a customer shares the great experience they had with our product, and they make me proud, and inspire me to do my best work.

Do you have a ‘Power Outfit’ that you wear for a big meeting or important work event?
Not really. But I tend to wear black, white and gray. I don’t want what I am wearing to distract, and believe in being comfortable.

How does your culture/background influence your work?
By nature, I am a curious person and I like to ask questions. Psychology and the study of human behavior was a great way to channel that curiosity. It makes me a fit for design and experience,  because I am always seeking to gain the customer’s perspective.

What is your favorite leisure activity after a stressful work week?
One of the benefits of living in San Francisco is that you can enjoy nature year-round. I love to hike, run, and bike. I love taking my dog to the beach.

I am also to be very commitment- oriented.  So if I plan to volunteer on a board, complete on a triathlon or have Thursday dinner with a friend, I’ll be there.  If I don’t think I can do something, I’ll say no. Learning to turn things down is an important skill. Too often people take on more than they can handle because they want to please someone — and then it’s impossible to maintain any sort of balance and worse, you can end up doing a bunch of things poorly.

How many times have you changed your career direction?
As a child, I thought I would be a veterinarian — until I realized I faint at the sight of blood!  I had a lot of uncertainly when in college, but picked classes that I enjoyed.

After graduating from the University of Toronto with a master’s in applied sciences, I became curious about technology, and wanted to see what all the Silicon Valley “fuss” was about.  The thought of moving to California and working in tech was scary — but the opportunity was also thrilling, and I used my excitement to overcome my fear.  So, I packed my bags and moved to California. It’s been fifteen years now, and it was one of the best decisions I ever made.

What has been your biggest obstacle in your career and how did you overcome it?
Early in my career, I was shy and quiet; I often would feel uncomfortable speaking up in a large room, especially if there were people more senior or experienced than me. I quickly learned that if I have good ideas to contribute — and learned to use my voice.

What are your most steadfast ‘don’ts’ rules regarding work and the workplace, and what are your most cherished ‘do’s’?  

Don’t’s:

• • • Don’t make assumptions; ask good questions to ensure you understand your co-workers, the project, etc.
    • Don’t take things personally.

Do’s:

• • • Do have respect, integrity and humility. Treat people well, and try to understand their perspective; if you believe that people have good intentions, you will do your best work.

What are the most important qualities of a good leader?
I really think this quote from Jack Welch sums it up: “Before you are a leader, success is all about growing yourself. When you become a leader, success is all about growing others.”  It’s important to hire great people, and let them shine.

What are the unforgettable traits of role models who have inspired you most?
I was very lucky to be surrounded by a group of great female leaders from birth: my mother is one of four sisters, and she completed her PhD while raising three children — and her three younger sisters also each completed a doctorate degree!  I grew up with great role models who showed me I could do anything I wanted. I watched them work hard and earn their accomplishments. And I was always driven to be successful like them.

How have mentors impacted your personal and professional development?
This question makes me reflect back on my first mentor… I had recently arrived in Silicon Valley, fresh from grad school, and my manager presented me with the opportunity to have a mentor. Believe it or not, I was actually a little insulted. I thought, “I know it all! What do I need a mentor for? I already have a manager, I don’t need a second one.”

I quickly changed my tune after my first conversation with Joe, my new mentor. I realized this was something very different. My mentor was someone with whom I could have very open and candid conversations with about my skills, ambitions, workplace politics, and whatever was on my mind. No matter what I said, I knew I would not be judged, and our conversations were always in the strictest confidence. My relationship with Joe, now going on more than fifteen years, has been one of the most valuable both professionally and personally.

What are three questions you like to ask during an interview to know if the candidate (or job) is the right fit?

Ensuring they have the correct experience is absolutely critical — plus I always like to ask:

• • • “Why are you interested in the role?” I want understand their motivation.
    • “What is their proudest accomplishment?” I like understanding how they define and measure success
    • I also want to know what questions they have for me. I want a candidate that has done some homework. Questions demonstrate their interest and understanding.

What advice would you give to women starting their careers?
I’ve always believed in the importance of owning your career. Often women work hard and wait for things to happen. Instead you have to be looking forward, seeking opportunities and challenges regardless of industry.

Also, make sure you’re learning from people in roles that you find interesting, and be proactive about finding out where you need to grow and improve. Join committees, lead projects and initiatives; as more people become familiar with your strengths and capabilities, you’ll have more supporters and advisors to help you advance.

What book would you recommend for women just starting their career?
Lean In is a really great book. I shied away from reading it for a while because it felt like there was a lot of hype around it, but when a trusted friend gave it to me, I decided to give it a try. I love that it was filled with real stories and experiences that felt real and relevant. In fact, I encouraged several male colleagues to read it, and they all gave it a thumbs-up!

 What is your favorite quote you try and live by?
“Stay hungry. Stay foolish.”  Steve Jobs’ Stanford University commencement address has become legendary, and for good reason. The speech ended with the quote, “Stay hungry. Stay foolish.” from The Whole Earth Catalog. This quote has stuck with me and are great words to live by; sometimes we get set in our ways and take everything too seriously. I believe you have to find the things that you love and that motivate you, open yourself to new possibilities, and have a great time along the way.