Giving Thanks for a Great Female Leader

By Deryn Pressman-Mashin

In the wake (or rather earthquake) of The Week That All Jewish Women Turned Invisible, I wanted to take a moment to appreciate that I may be among the few at this point in time – a woman, working under the leadership of a great woman, in an organization run almost entirely by women.

Currently, I am the Director of Community Engagement at a small Jewish day school outside of Boston. Prior to this, I was living in Israel serving as the Director of Registration of nonprofit focused on American Jews. The Israeli Executive Director was also the owner of a travel agency and ran this nonprofit offshoot because of what he called the “American Jewish Holocaust” (i.e. intermarriage – in his opinion). He often liked to make speeches about this “American Holocaust” to the staff, which almost always ended in team members (who I had spent weeks onboarding) quitting by the end of the day. When we had our weekly one-on-one meetings, he often lifted up his shirt to scratch his hairy belly in front of me, or put his feet on his desk right in front of my face, or asked when I was going to get married and make Jewish babies. He called me with “urgent matters” at all hours of the day and night and I could almost never finish a sentence without being interrupted by him.

Before that, I worked for a large hotel in Tennessee where my boss used to physically corner me in the office and make threats if I didn’t do exactly what he wanted. When we had big meetings with the senior leadership, he always claimed my work as his own. During my time in that job, I was once sent to HR to learn how to write letters and emails that were more feminine and less assertive, because a man had complained to my boss when I asked him why he had missed his project deadline and if he still intended to complete it (no joke).

A few years before that, during the wake of the recession, I was living in my car selling baseball tickets door to door and playing violin on the streets. And before that, as a young woman just out of college, I worked as an assistant at a law firm in Florida where the principal lawyer made me wear gloves to work because the sound of my “lady fingers” on the computer keyboard gave him a headache (seriously, no joke). Prior to my current job, I had never made more than $30,000 a year. Needless to say, I have grown thick skin and sometimes feel incredibly jaded. But this is exactly why I must tell the world that organizations and leaders who make you feel empowered do exist.

Amy Gold is the Head of School at the Arthur J. Epstein Hillel School, and though I did not come to the job with an extensive fundraising background, she was willing to take a chance on me. When I was hired, she was transparent about the salary, she made sure I was given a professional mentor, and she even arranged for me to dovetail with my predecessor for a year. I now have the opportunity to work alongside some rockstar women who lift each other up and empower each other on a daily basis.

Amy also helps me to work through my varying stages of imposter syndrome. As the Director of Community Engagement, I am responsible for a fundraising budget of over one million dollars, which includes our Annual Fund, our annual Gala, a major gifts program, a capital campaign, other small fundraisers, donor reports, and our alumni engagement program. I have both an MBA and an MA from Brandeis University and the Hornstein Program for Jewish Professional Leadership and a decade of leadership experience. But I also know that I am female, stand 4’11”, and have a young face (so they tell me). I have not once, not twice, but several times been asked if I am a student of our K-8 school by donors at various events. (Ouch!). I always wonder what donors think of me or if they take me seriously.

In 2016, I had the opportunity to interview the great Sheila Katz for a graduate paper I wrote, and for which I won the Hadassah-Brandeis Institute Graduate Student Prize for Outstanding Research on Jews and Gender in 2017. When asked what she thought a leader was supposed to look like, Sheila listed off many excellent qualities, but mentioned that she often had to take a senior executive with her to donor meetings in order to feel validated. As a female, one in her early 30’s with an extremely high position (and now CEO of NCJW!), she says she needs to be loud, really loud, exhibiting signs of self-awareness and self-management at every moment. I think about that conversation often.

We as women, no matter how hard it may seem, need to continue to fight to be enough, even if Michelle Obama says imposter syndrome never really goes away. According to this Leading Edge survey, approximately 70% of our sector’s workforce identifies as women, yet women represent only 30% of our CEOs. So it’s no wonder that women feel like no matter what they do and what they achieve, they are merely hiding their own inadequacy. I know that Amy Gold must sometimes have imposter syndrome of her own, as I believe all women do at some point or another, even though she never shows it.

Amy is a leader who leads by example – she would never ask someone to do something she wouldn’t do herself. She practices adaptive leadership and emotional intelligence. She inspires us all to be the best versions of ourselves, and for that, I am grateful. And while her gender itself does not unequivocally make her a good leader, her passion behind what she does, why she cares about Jewish education, and her life experiences that have led her to this point, are just some of the reasons why I am so lucky to have her as a leader, mentor, and friend. The best advice I can give to new Jewish professionals is to find themselves an organization under a great female leader. It makes all the difference.

Deryn Pressman-Mashin is the Director of Community Engagement at the Arthur J. Epstein Hillel School and holds and MBA/MA from Brandeis University. And while she believes Epstein Hillel School cares deeply about women’s empowerment, this article is entirely her own and was not in any way written on behalf of EHS.