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An entrepreneur is someone who gets motivated by the word ‘no’, With Amy Pressman, co-founder of Medallia

I remember interviewing a senior executive from one of Silicon Valley’s most successful tech companies. He described a really tough time…


I remember interviewing a senior executive from one of Silicon Valley’s most successful tech companies. He described a really tough time at a start-up with a candor I found refreshing. So I waited in great anticipation when I asked: “So what did you do?” “Are you kidding?” he answered. “I got the hell out of there.” I was so disappointed. This guy apparently believed the “drop out of college and become a billionaire overnight” Silicon Valley myth that starting a company is not that hard — and that even hardships or failures are just stepping stones to great success. He was an “I-just-play-one-on-TV” entrepreneur, not the real thing. True entrepreneurs get more motivated when things get tough… The quote that best captures the essence of entrepreneurship is one that resonated the first time I heard it and has helped keep me grounded ever since: “An entrepreneur is someone who gets motivated by the word ‘no’.”


I had the pleasure of interviewing Amy Pressman, the co-founder and current board member of Medallia, a high growth enterprise software company that is the leader in customer experience management software. Medallia arms companies to win through customer experience, powering the customer experiences of some of the world’s top brands including Bank of America, TDBank, Sam’s Club, Zurich, Farmers, IBM, Comcast, Generali, Best Western, Marriott, and Hilton. The company’s cloud platform enables companies to capture customer feedback everywhere the customer is (online, via mobile, in store, on the phone), understand it in real-time, and drive insights and action everywhere — from the C-suite to the frontline — to improve performance.


Thank you so much for doing this with us! What is your “backstory”?

I am hard to put in a box. In college, I couldn’t decide between the sciences or social sciences, changing majors multiple times. I joined the Peace Corps after university, then worked on Capitol Hill. I broke with tradition of my legislative aide colleagues, most of whom attended law school, to go to business school because I wanted to start a company. This was before it was a “hot” thing to do. Stanford only taught one entrepreneurship class when I was there.

I don’t fit the mold of a “typical” entrepreneur. I was a woman in my 30s with one child and another on the way when my co-founder and I started the company. I had a third child two years later. It was a rough ride; I knew many of the people who stocked the aisles at Safeway because I mostly shopped in the middle of the night.

I guess my backstory exemplifies that there is no typical backstory. You don’t have to be a twenty-something coding genius who dropped out of college to be an entrepreneur in Silicon Valley.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

One recent interesting story occurred in the last month. I was in a meeting with Global 2000 executives charged with improving their companies’ customer experience (CX). We were discussing a common best practice in CX, which is to have senior leaders communicate with customers regularly. Some might staff a call center, others might call back happy and unhappy customers. The point is to make it an ongoing practice for senior leaders to dialogue with customers.

What was so interesting to me was the reaction of many executives. One CMO, when told she would need to call customers, retorted “Over my dead body.” Another executive reluctantly agreed but required two hours of coaching before he felt confident enough to pick up the phone and talk to customers. It illustrated for me the drawbacks of size: when companies get big, the people who run them become unaccustomed to speaking regularly with customers. How can businesses make the right decisions when the leadership team is not in regular contact with customers?

What do you think makes your company stand out? Can you share a story?

What I find really cool about our software is that it helps transform companies in a way that is palpable to me as an end consumer. For example, not too long ago, I had a problem with my telco provider, which happens to be a Medallia customer. To be honest, I was dragging my feet on calling the company because interactions with telco call centers can be so frustrating. Plus I rarely have time to sit on interminable hold. Eventually, my service problem became so painful I couldn’t procrastinate any longer. When I finally called the company, a human being picked up in two rings, fixed my problem without needing to transfer me, and gave me his personal contact info — both over the phone and in a follow-up email — in case I had questions in the future.

Wow! Was that a telco I’d just dealt with?

This is a company that confronted its historical poor performance with customers, decided to change course, and embarked on a journey to become a customer experience leader. And I felt it as a customer. When you experience the impact of your own software personally — that’s powerful.


Are you working on any new or exciting projects now?

I am really excited about the work we’re doing with the Federal government, such as with the Department of Veterans Affairs. With our technology, veterans can now provide feedback to VA no matter where they are — at a VA medical facility, on the Vets.gov website, or through the VA contact center. VA employees get real-time access to the feedback, enabling them to not only identify and correct one-off and systemic problems, but also identify new sources of value for veterans. It’s exciting to serve this constituency, which embodies the ultimate in service to us.

What advice would you give to other CEOs or founders to help their employees to thrive?

If you want to help employees thrive, don’t focus on perks, being “hot,” or buzzwords. Instead, connect employees to the impact of their work.

Over the years, I’ve conducted thousands of interviews with entry-level people to senior executives and always ask: “What do you want to have achieved by the time you retire?” I have never heard anyone respond with an answer other than a variant of “to have impact.” No one wants to clock eight or more hours a day and feel like it doesn’t matter.

In my experience, a great way to help employees understand their impact is to connect them to customers. For example, when one company we work with decided to provide customer feedback to all employees, we hosted a series of panels with frontline employees to hear their reactions first-hand. Each person told a compelling story about increased engagement and motivation. One three-year veteran of the company, when asked what he learned from the customer feedback, gave an answer that still moves me: “I learned that people liked me.”

Connecting employees to their customers — and by extension to their impact — is a way to help them thrive.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

So many people have helped me — including all of my co-workers — that it’s hard to single one out. But I often go back to a piece of advice I received a long time ago, and in a totally different context, that has served me well as an entrepreneur.

When I gave birth to my first child, I was reluctant to leave the hospital. I worried about my lack of experience caring for newborns. On the day of my discharge a very strict older nurse beckoned me to her office.

“Amy, I can find no reason to keep you here any longer. I know you’re scared because this is all new to you but don’t be. Just listen to everyone: the stranger on the plane, your relatives, child-rearing experts, your pediatrician, everyone. Genuinely listen to it all — even when it’s conflicting — weigh it carefully, and then make your own decision.”

It’s great advice for entrepreneurs. You have to learn about new things all the time. The best way is to do what the nurse told me: swim in as much advice as possible. Talk to a lot of experts. Read a lot of books. Listen to a lot of podcasts. And then make the call. You have to trust yourself to either make a good decision or, if not, learn from it.

How have you used your success to bring goodness to the world?

I believe that all of us, no matter where we are in our life’s journey (and how successful — or unsuccessful– we are), should be striving to make the world a better place. I have been volunteering since I can remember: the Council on Aging in high school, the Big Brother/Big Sister organization in college, the Peace Corps post-college. I worked on Capitol Hill on issues related to the well-being of children and senior citizens. To be honest, for the past two decades, co-founding and growing a company while raising a family has consumed most of my excess energy. I do find time — occasionally — to volunteer with our company’s fabulous non-profit group, Medallia.org. The group hosts volunteer events at the company, connects employees to outside volunteering opportunities, and showcases employees’ philanthropic endeavors.

I also believe that creating “good in the world” should not be something you do in addition to your work — your work itself should add value to the world. I am fortunate that Medallia’s enterprise software, when implemented at companies, changes corporate cultures for the better. We have seen employees’ engagement go up significantly. As one woman told her boss, after her job shifted from fending off angry customers to solving customer problems, “my marriage got better.”

What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why. (Please share a story or example for each.)

  • You’re never done hiring. I remember, years ago, trying to fill the “last” vacancy on our management team. I confidently told a Board member: “Once I fill this position, I’ll be done with hiring.” I wasn’t naïve enough to think I’d be done forever, but I certainly thought I’d be done for a while. He laughed and said, “you’ll never be done hiring.” He was so right. It’s not just that you need more people as you grow, you also need different skill sets — even for the same role. Some people grow into new responsibilities as their roles evolve, but many do not. So you’re never done hiring.
  • Watch the trail of talent. A mentor of mine used to say, “your title makes you a manager, your people make you a leader.” I’ve found the biggest predictor of senior leaders’ success is whether they attract BOTH talented people with whom they’ve previously worked and new talent they didn’t know before. It’s a red flag when no one follows a leader or when the people who follow him or her aren’t particularly talented. It’s also a red flag when a leader can only hire people he or she already knows because it constrains the pool of potential candidates too much. The ability to attract talent broadly is a great proxy for the impact a leader is going to have.
  • Hold people accountable: This advice is so obvious that it feels ridiculous to raise. But some behaviors that served me well as an entrepreneur, like creative problem-solving, can undermine my ability to hold people accountable. For example, when someone comes to me with an issue, my instinct is to jump in and start brainstorming solutions with them, drawing on the same can-do, “let’s solve this” attitude that helped get our start-up off the ground. The problem is that when you start ideating solutions, you absolve the person responsible of full accountability. If the person executes on your suggestion, then it’s your idea, not his or hers. The person hasn’t fully owned it. I try to curb my desire to roll up my sleeves and jump in — but, to be honest, I don’t always succeed.
  • Tell stories: I was trained to prove my points with data. What I have learned is how important stories are, because stories move people. The death of Cecil the Lion, for example, did more for anti-poaching than any poaching statistic. I think storytelling is even more important today, when we are awash in numbers, metrics, and promises of a predict-the-future utopia: Big Data! AI! Predictive analytics! I am reminded of the power of stories at every company meeting. The customer stories are always the highlight, eclipsing any data we share.
  • Be grateful: The job is to solve problems constantly. Sometimes it can be difficult to remember what a privilege it is to be in that position. It is helpful to start the day practicing gratitude: for your customers, your co-workers, your opportunity.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to get people to believe in our government again. My dad, who was part of the “Greatest Generation”, fought in WWII and later worked on the space program. I grew up hearing about the power of our government to do great things: defeat the Nazis, land a man on the moon, etc.

In Silicon Valley, we reap the benefits of past government investments every day. Technology initiatives funded by the government led to the Internet, GPS, the first graphical web browser, Siri, and even Google — to name but a few.

One of the saddest aspects of the current environment is our collective disbelief in the effectiveness of government to do great things collectively that no individual can do alone. We face daunting challenges today, and the collective “we” that government signifies can help us tackle them — we just need to demand that government operate in an effective way that makes us believe.

I’ve had my share of faith-shattering encounters with government that leave me with a “are my tax dollars really paying for this?” despondence. But what if government agencies served citizens the way our most admired companies serve customers?

I am excited by the President’s Management Agenda to modernize government for the 21st century, which includes improving citizens’ experiences with federal services. But, ultimately, I believe the work to re-establish faith in government by demanding excellence from it is the responsibility of all of us, which requires a movement.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I remember interviewing a senior executive from one of Silicon Valley’s most successful tech companies. He described a really tough time at a start-up with a candor I found refreshing. So I waited in great anticipation when I asked: “So what did you do?” “Are you kidding?” he answered. “I got the hell out of there.”

I was so disappointed. This guy apparently believed the “drop out of college and become a billionaire overnight” Silicon Valley myth that starting a company is not that hard — and that even hardships or failures are just stepping stones to great success. He was an “I-just-play-one-on-TV” entrepreneur, not the real thing. True entrepreneurs get more motivated when things get tough…

The quote that best captures the essence of entrepreneurship is one that resonated the first time I heard it and has helped keep me grounded ever since: “An entrepreneur is someone who gets motivated by the word ‘no’.”

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this 🙂

I’d love to chat with any CEO who genuinely wants to make his or her company customer centric, not just pay lip service to customer centricity. At least two CEOs (whom I won’t mention) have recently made very public mea culpas for real missteps with customers that were heavily covered in the press. I believe those CEOs genuinely want to change their cultures. To them I say: call us. We can help you! Or, more accurately, we can enable your customers to help you and your employees to help you. We have the results at other companies to prove it.

Originally published at medium.com

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