Lean Into Leadership: Amy Silverstein

Since joining the firm as chief financial officer two years ago, Amy has played a critical role in Prophet’s growth trajectory. I’ve been fortunate to develop a great partnership with her— partially because we work hard to show the ROI of our marketing efforts, but if I’m being honest, it’s really because Amy is a leader that cares deeply about the firm and its people. She’s a wonderful mentor— always willing to listen, share ideas, guidance and advice. Numbers fill her day, but she spends a lot of her time on people, empathy and leadership. I cannot imagine Prophet without her. 

Amanda Nizzere: What’s your go-to productivity hack?  

Amy Silverstein: It’s very simple. Most of my day is dedicated to my family and to work; and in all honesty, I feel very blessed to have both and wouldn’t have it any other way. To kick start my day, I try to carve out 30 minutes each morning for a quick workout—a run outside or some yoga. A little “me” time before getting the kids up and off to school changes my entire outlook and enables me to focus and bring my most productive self to the job. 

AN: Who has influenced you most when it comes to how you approach your work?  

AS: Earlier in my career, I struggled with maintaining boundaries and balance between work and family. Everything felt urgent, everything felt critical and everything required perfect execution and delivery. To say I was tough on myself is an understatement.  

But a dear colleague of mine shared one simple truth. He said, “We make cornflakes here. We aren’t saving lives.” He wasn’t diminishing the importance of our work; in fact, he too was very hardworking and gave much of himself to his career and the success of our firm. But he went on to explain that while we should take pride in the work we do, we need to also take pride in what we contribute to our personal lives, to our family lives. We need to make sure that we give the best of ourselves to those who depend on us and love us at home, just as we try to bring the best of ourselves to work, too. I keep the word “cornflakes” close to mind always now, and while I may not always get the balance right, I am always trying.  

“We need to make sure that we give the best of ourselves to those who depend on us and love us at home, just as we try to bring the best of ourselves to work, too.”

AN: What’s the worst job you’ve ever had, and what did you learn from it?  

AS: I was working at a not-to-be-mentioned investment banking firm very early in my career and had been pulling all-nighters for 2-3 days prepping for a board presentation with a key client. I was sick as a dog, but I somehow managed to get the presentation done.  

When I walked into the office of my managing director to deliver the final deck, he looked at me and said, “Don’t you dare come into my office. I don’t want to catch whatever it is you have. Drop it at the door.” It was at that moment I learned the importance of prioritizing a supportive and positive culture when choosing a job. I left shortly after that interaction.  

AN: What’s a mistake you made early on in your career, and what did you learn from it?  

AS: When I first started in investment banking, I didn’t have the same depth of accounting acumen that some of my colleagues had. The mistake I made was allowing myself to lean into Imposter Syndrome. It delayed my ability to own my role, learn what I needed to and shine.  

Luckily, I had strong mentors who saw what I brought to the table. They taught me that it was ok to not have all the answers and to not be able to do everything right out of the box. They taught me to not be afraid to ask questions or ask for guidance, and to recognize that we all, even at the most senior levels, have things to learn, areas to improve to grow ourselves and our contributions.   

AN: What energizes you at work?  

AS: There are two things that energize me every day at work. First, I love that I am learning and growing every day, that I am challenged with complex problems to solve and able to contribute value on a regular basis.  

Second, I love the amazing team I work with. They are bright and talented and bring incredible expertise, intelligence and thoughtfulness to their work. Not only are they curious people who are always looking for new ways to learn and grow, but they are also exceptional human beings—kind, compassionate and a joy to spend time with. Can you tell I feel very lucky?   

AN: If you could snap your fingers and become an expert in something, what would it be?  

AS: I would love to be a sommelier. I have a deep passion for great food and wine, and over the years have become a pretty good cook. But other than knowing what wines I enjoy, I really do not have much knowledge about wine—what vintages and regions produce the best of certain types, etc. And I don’t know how to best pair wine with food. I would love to be an expert in that! 

AN: If you could write a book about your life, what would the title be and why? 

AS: It would be titled, “To be Content.” I spent my young adult years and through my 30s always striving for more and more. I never took a step back to realize how blessed I truly was with all I had, and rather was always focusing on what I didn’t have, what I still wanted (whether it was children, further advancement with my work, wealth, etc.). As many people will tell you, the “Aha” moment does present as you get older, and I have found my last decade or so truly fulfilling as I have come to appreciate the smallest to biggest joys in my life. I am content and so genuinely appreciative of all I have.  

“I spent my young adult years and through my 30s always striving for more and more. I never took a step back to realize how blessed I truly was with all I had.”

AN: What’s one thing most people don’t know about you?  

AS: Before I had my children, I was incredibly adventurous. I have flown a few Cessnas, sky-dived in Rotorua New Zealand, whitewater rafted level 5-6 rapids in the Victoria Falls in South Africa, to name a few. I was fearless and willing to try any adventure (except bungee jumping) that came before me. Once I had kids, however, my courageous side faded away. I’m sadly now so afraid of heights I can barely walk to the top of a lighthouse without grasping onto the handrails for dear life. My children do not believe my tales of adventure!   

About the Series 

Throughout my career, I have been fascinated with the building blocks of leadership, from motivation, coaching and communication to mentorship, empathy, inspiration and more. Unraveling and understanding what makes a strong and impactful leader tick can help each of us implement new strategies to grow as individuals and leaders ourselves. Over the years, I’ve listened to podcasts, read books, attended conferences and listened to TED Talks about various leadership topics, but some of the most impactful lessons and pieces of advice I’ve learned have been from those around me—my mentors, colleagues and industry peers—which led me to create this interview series. I invite you to join me as I interview various leaders in my network to share new tools and wise advice from them that you may just want to add to your own leadership toolbox. 


Amy is Prophet’s chief financial officer and a member of its executive committee, with a tenured career running financial departments at large agencies. People go to her to discuss ideas and strategies as wide-ranging as how to advance the growth trajectory of the organization, how to analyze and assess the ROI of potential investment opportunities, how to secure necessary funding for new growth investment ideas and how to negotiate the gnarliest of contracts, among other things. Want to learn more about Amy or have another question? Reach out directly here