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21 Questions with Shara Mendelson - Founder of Plum Benefits

21 Questions with Shara Mendelson - Founder of Plum Benefits

Shara Mendelson founded Plum Benefits in 1998. Under her leadership, the company established relationships with 20,000 corporations and their HR departments to give over 5 million employees exclusive discount and access offers to live entertainment events, including Broadway shows, sporting events, attractions and family events. Shara grew the business organically through cash flow until the company’s sale in 2011 to The Shubert Organization, the parent company of Telecharge. She began her career at Grey Advertising in account services after graduating from Middlebury College. 

Shara now serves on a number of boards and was recently profiled in the New York Times.




1. What would the headline of your biography be?

"Go For It"


2. What is your mission / goal in life?

To connect with people, have many stages/ experiences and always be passionate.


3. What do you love to do?

I love to help people reach their potential and see their dreams come true - I am a teacher and mentor at heart. I love to meet new people and see new things – this includes travel, entertaining and taking random classes. I also love to be outside; running, hiking, anything that includes movement outdoors.


4. What were your “aha” moments - when you realized you were exceptional at something?

My aha moments were not about being exceptional, but rather about realizing that I could dream big and make my own path. Some examples: Having earned extra credits, I was able to leave college for three semesters to travel and still graduate on time with my class. When my career was not proving meaningful, I started exploring and came up with the idea for Plum Benefits.


5. What keeps you up at night?

As a child the thought of my father dying; issues with an employee or a client when I was leading the company; and now my nephews and niece. I worry about people!


6. What historical / business figure do you most identify with?

No one in particular, but I am always inspired by stories of overcoming adversity. People who fought for freedoms, those who made it out of poverty, the kid who keeps going despite no one believing in him.


7. What is the trait you most want to improve in yourself?

Responding rather than reacting. To break down and slow down. This ability literally impacts everything. - Deal making, personal relationships, savoring life. I have been working on this for a long time and will continue to strive to improve.


8. What are your unique talents?

I have the ability to listen and understand people at their core. Also I have the ability to draw connections between seemingly unrelated things.


9. Have you had to change your career path? 

I don’t really think about career in a traditional way. I never bought into the A then B then C mentality in anything in life. The path may not be straight, but if you are listening well to yourself and others, you can find the right opportunities at the right time. In a certain way, you are always in transition, yet always stable with this mindset. 


10. Which brands / businesses do you admire the most?

I am completely moved by Tony Hsieh’s mission with Zappos. I truly appreciate social good models such as Toms and DonorsChoose. Also, I am inspired by brands that are telling stories to truly connect with something meaningful. Dove, Chipotle and Pantene are some recent examples.


11. What was your career plan when you were young(er)?

Thinking about this makes me smile. I was raised in a competitive school system where tracked career paths were the norm. Go to an Ivy, head to Wall Street, get your MBA and so on. I tried very hard in many ways to succeed within that structure when I was a child and, despite superficial success, it just wasn’t me. It was only when I started accepting myself that I jumped off the track and started paving my own road. Hence why entrepreneurial environments are a great match.


12. What is your greatest career regret?

Possibly not selling my company earlier and using the lessons I learned from the first to build a second in the same amount of time.


13. What was your favorite job?

I had one traditional job before starting Plum Benefits. It was not my favorite!


14. Which talent would you most like to have?

Maybe it’s all those years with Broadway and sports clients, or perhaps it’s my alter ego wanting to be in the spotlight, but I sometimes fantasize about being able to sing or play tennis well enough that people might actually want to watch me. In reality, I am happy being behind the scenes.


15. What do you consider your greatest achievement?

Plum Benefits from start to finish was as a whole is my most obvious achievement. It all culminated during the sales process when meeting with my executive team to relay the imminent deal, each one proactively reacted by saying how happy they were for me, commenting on how hard I had worked and how much I deserved the outcome. It was shocking because I had come overly prepared to discuss how they would be impacted and what their outcomes would be from the exit. It was beyond rewarding and made me realize that those relationships were the most fulfilling “achievement”.


16. How do you define success?

Listening to your gut, developing dreams and going for it!


17. What do you regard as the lowest depth of misery?

Not having loving relationships and not having meaningful work.


18. Do you care about money?

I do not believe that money is my first motivating factor. However, I do appreciate it as a reward following results. I know how lucky I am to have a comfortable life.


19. What is your defining characteristic?

I am always trying to improve. I may not be the most talented but I will work my ass off to learn and grow.


20. Who are your favorite business writers / bloggers / people?

Seth Godin and Tony Hsieh amongst others.


21. Who is your hero in real life?

My dad. He dreamed big and never gave up hope, even as a child being raised in a Displaced Persons camp in post war Germany. He worked hard, made it to NYU Stern, found happiness and success in his work. He met my mom at 25 and was committed to her and his children and put family above everything. He was always growing and encouraged us to try new things and live big.



How difficult did you find it to convince yourself to make the major leaps in your career? 

I always find the process of figuring out what's next, the transition period, trying. But after much introspection, journaling and discussion with mentors, once I decide what I truly want, it gets easier. There's no need to convince me once I realize my goal... Then it's 100% "go for it!

21 Career Questions with Lindsey Kittredge - Co-Founder + Exec. Dir. / Shooting Touch

21 Career Questions with Lindsey Kittredge - Co-Founder + Exec. Dir. / Shooting Touch