Amy Pressman
Where it All Began With Female Leaders

Where it All Began with Amy Pressman

What do you and your company do?

Medallia helps companies become customer obsessed. Our software makes it easy for every employee in a company to understand what customers think and, based on that understanding, take action to improve the customer experience. Medallia is the leader in the growing SaaS (“Software-as-a-Service”) category of customer experience management, serving 100s of global companies including Bank of America, TDBank, Sam’s Club, IBM, Comcast, Generali, Best Western, Marriott, and Hilton. The company is headquartered in the Bay Area, has more than 1300 employees, and generated revenues of more than $250M in 2017. As co-founder, I’ve held many responsibilities over the years — from fundraising to talent acquisition to go-to-market to facilities (including taking out the trash). Currently, I’m focusing on evangelizing Customer Experience Management, the technology category Medallia leads.

What did you want to be when you grew up?

I had a different answer to that question almost every year of my childhood. The most perplexing was my “dentist” phase. Why I thought I wanted to look into people’s mouths for my career I will never know.

Share the story of a business you started as a kid. How old were you and how did it do? What did you learn?

Starting from when I was 8 or so, I looked for ways to sell. I sold candy for my friends in Camp Fire Girls, ran Kool-aid stands (it was a thing — my generation’s version of lemonade stands), held yard sales. In high school, I joined Junior Achievement and co-founded a company that produced and sold silk-screened greeting cards. We set up booths at local businesses and waited for customers to come to us. It didn’t work. We had to go to customers. We had to get out from behind our table, walk up to people, and start talking to them about cards. It was uncomfortable — but it worked. Basically, I learned that “build it and they will come” is not usually right. It’s more like “build it and then go out and get them.” You have to be ready to have many doors slammed in your face.

What advice would you give to your elementary school self?

I wish Carol Dweck’s book on Mindset had been around and that I had read it. I had too much of a fixed mindset and was too much of a perfectionist.

Who was your role model and/or mentor when you were a kid and how did that person influence you?

I didn’t have a role model or mentor. Most of the adults I knew were scientists or professors or doctors. I didn’t really know anyone in business.

Share a time that you failed and what you learned from it.

At the end of my freshman year in college, I had to choose a major. Some majors were open to everyone, others were selective and required an application. I applied to the two that were most appealing to me and got into both. The one I really wanted accepted everyone, the other was extremely selective. I chose the one I was less interested in because it was more “elite.” It was the dumbest decision I made in college. When I returned for my sophomore year, I tried — repeatedly — to switch to the major I really wanted, but the department refused to admit me. Ever. What I learned was: always follow your heart and DO NOT WORRY about what others think. Other people generally do not have to live with your decisions. You do.

Give one tip to a 10-year-old girl who is opening her first lemonade stand this weekend.

Signage. Maybe it’s the artist in me, but I have always been big on signage. Big, bold signs that people will remember — maybe with some humor or fun. When adults buy from a lemonade stand, they are doing so not to get a beverage, but to support a neighbor and, potentially, the next generation of entrepreneurs. So be entrepreneurial and do something creative — that buyers will remember — with how you advertise.


Did you enjoy our interview with Amy Pressman? Take a look at other interviews that we did with successful women entrepreneurs.

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