Heather Jassy will be the first to tell you that there’s no such thing as a right (or wrong) path. By the time she started working at the e-commerce site Etsy, she had been a practicing therapist and a bookstore owner. Now a senior vice president, Jassy, 41, helps Etsy manifest its values in every aspect of its businesses.
What was your childhood like?
I grew up in the South—in Texas, Tennessee, Georgia, and Alabama. My father is a minister. We always had people staying at our house who were going through something difficult. My parents started an adult literacy center in our town and ran a community food bank.
Right out of college, you owned and ran a bookstore.
The owners of this place were ready to retire, but they wanted to keep it open for the community [in Birmingham], and they gifted it to me. It was a dream come true.
What was it like jumping into that?
It quickly makes you aware of what you’re good at and what you’re not good at. I loved marketing and planning events in the space. The part I didn’t love was the operations—things like inventory management. It was a really hard job. I worked 12 hours a day.
After six years, you had to shut down.
It wasn’t sustainable financially. I probably kept it open a year longer than I should have, but I felt tremendous responsibility to the community—and I was personally attached.
What happened next?
I spent some time going back to school in art and teaching yoga. When I thought about the bookstore, what I missed most was the feeling of community. All day, people would come into the shop and talk to me about their lives and problems.
So it makes sense that you went back to school to become a therapist.
Also I had had a therapist who had really influenced my life.
After about five years, you changed careers again.
A friend offered me a job at an e-commerce start-up, and that was appealing. When it became clear that the company was not going to grow, I applied for a job developing Etsy’s Hudson, New York, office [in 2011]. It sounded a little like running an independent bookstore.
What are some of the things you handle in your current role?
My job is to make sure that Etsy continues to be a leader in making business a positive force in the world. I’m leading my team to put processes in place throughout the company that will support us to make business decisions in accordance with our values and will allow us to share our learnings with other companies and the public.
What’s a leadership lesson that you’ve learned?
Plants have to be in the right windowsill to thrive. I always think about that when it comes to getting people into the right jobs. We also need to create the right conditions for people.
How has it been moving from one work culture to another?
It took me a while to start expressing opinions more. One of the bigger things that I’ve learned is to find the right balance between planning and leaving enough space for accidents and discoveries. Learning how to be both kind and direct is something that I think everyone struggles with.
What does your typical morning look like?
I know it’s appalling, but I get up at 4 A.M. I meditate. I sometimes do yoga. I like to sit outside and watch the sun rise. I putter around. I have to have a cup of coffee before I talk to anyone. When my husband and daughter get up, I’ve already had a bit of a day.
What difference does meditation make?
I’m more likely to notice I’m feeling a certain way or notice things I’m avoiding. When I miss out on busy days, I really feel a difference.
What’s your life like outside of work?
My husband, John, is a therapist, and my daughter, Georgia, is 5½, going on 45. We try not to be incredibly scheduled on weekends. We spend a lot of time outside and with friends. My husband does the cooking during the week, and I cook on the weekends.
Any parting words?
We can put a lot of pressure on ourselves to make perfect decisions, but there are very few experiences that are wasted: When your intuition tells you something is compelling, trust it.