Youth Movement Sweeping Westchester Day Schools

A few months ago, Shalom Hartman Institute of North America’s Yehudah Kurtzer created a stir in Jewish institutional circles by critiquing the community’s graying leadership, lack of succession planning and reluctance to hire younger executives.

While Kurtzer’s observations may well be the rule, Westchester’s Jewish day school scene is a striking exception. This fall three Westchester schools are welcoming brand-new heads, all of them under 44:

Rabbi Joshua Lookstein, 43, at Westchester Day School, a centrist Orthodox nursery through eighth-grade school in Mamaroneck.

Michael Kay, 33, at Solomon Schechter of Westchester, a Conservative K-12 school with campuses in Hartsdale and White Plains.

Rabbi Rami Strosberg, 32, at Westchester Torah Academy (WTA), a startup centrist Orthodox elementary school in New Rochelle with a lower-tuition, “blended learning” model.

In addition to their youth, the three new heads have a lot in common. All are day school graduates and have participated in the Day School Leadership Training Institute, a program run out of the Jewish Theological Seminary. All three are newcomers to Westchester County and are parents of small children.

Indeed, while their schools may technically be rivals — particularly WTA and Westchester Day, which both cater to a similar demographic — the new heads are friendly with each other and say they are eager to work collaboratively when possible. Coincidentally, both Kay and Rabbi Lookstein are longtime associates of Rabbi Strosberg — Kay and Strosberg were one year apart as students at Albany’s Bet Shraga Hebrew Academy of the Capital District, a Conservative day school, and Rabbi Lookstein was Strosberg’s adviser in the Orthodox Union’s NCSY youth group. Rabbi Lookstein, a drummer, has also played music with Rabbi Strosberg, who sings and plays multiple instruments.

None is particularly concerned that his youth will pose a challenge. Kay, whose most recent job was upper school principal at the Charles E. Smith Jewish Day School in Rockville, Md., said he has experience “conducting myself in a way so that [age] is not an issue. I don’t anticipate it will be a concern.”

As for Rabbi Strosberg, heading a school at age 32 is hardly a jump, considering that he took his first head-of-school job at age 27 at his alma mater in Albany, where many of his former teachers reported to him.

“I don’t think I’m the youngest head of school anymore,” he said.

Rabbi Joshua Lookstein

In Modern Orthodox circles, Rabbi Joshua Lookstein’s last name is virtually synonymous with the Upper East Side’s Ramaz School and Congregation Kehilath Jeshurun. In fact, Rabbi Lookstein, the son of Rabbi Haskel Lookstein, was referred to in a recent JTA article as the “scion of the family that founded and leads Ramaz.”

A Ramaz grad, he also taught there for several years, while serving as assistant rabbi at KJ. Ten years ago, instead of continuing at Ramaz and KJ, as many people expected, he left to become executive director of the S. Daniel Abraham Foundation, later moving to UJA-Federation of New York where he was a major gifts officer, leading its Day School Challenge Fund and coordinating its King David Society.

Given the strong family ties to Ramaz, how does it feel to be working in a different school? “It’s definitely an adjustment,” he told The Jewish Week, noting that “I drank the Ramaz Kool-Aid, and I share my father’s pride in Ramaz graduates and everything Ramaz.”

However, he said, Westchester Day School — which sends many of its graduates on to Ramaz for high school — is also a “place with real history” and “a real commitment to academic excellence.” The two schools share the “values of Modern Orthodoxy, religious Zionism and a commitment to the Jewish people,” he added.

Not only is Rabbi Lookstein leaving the familiarity of Ramaz, but also the cocoon of Manhattan, where he has spent his entire life, even his college years (at Yeshiva University). Suburban life “takes getting used to,” he acknowledged, noting that “I did joke in my letter to colleagues when I was leaving that instead of hiring a live-in nanny, we’d be hiring a live-in superintendent and turning our garage into a 24-hour CVS.”

While he misses being able to walk out of his apartment door and see people waiting for the elevator, he emphasized that his new community “has been incredibly welcoming.”

Founded in 1948, Westchester Day has, in recent years, faced increased competition from SAR Academy in Riverdale and, now, the new lower-tuition WTA. Asked about these challenges, Rabbi Lookstein said, “Our goal is to be the best version of Westchester Day School that we can be and not to spend time focusing on the competition … SAR is a fantastic school, and we’re learning from them and from all the great schools in the area, including WTA.”

Rabbi Rami Strosberg

Expect to hear a lot of music coming out of Westchester Torah Academy. A longtime member of Shlock Rock, a band that adapts pop song lyrics to teach about Jewish concepts, Rabbi Rami Strosberg sings and plays the saxophone, piano and guitar.

“Teaching Torah through music is what I do,” he added, noting that when he was head of Bet Shraga, “one of the highlights of the week was an oneg we would have on Friday afternoons, when the kids would come in and sing. … I’m very passionate about using music to build school culture.”

An Albany native, Rabbi Strosberg said he is excited about starting a new school and working with his “amazing leadership team”: a director of business and a director of curriculum.

“I feel blessed by this opportunity and feel like I’ve had a huge amount of support from different leaders, rabbis, teachers and mentors.”

The rabbi’s two older children (a third is still an infant) will attend WTA, which is opening with 63 students in pre-K through first grade.

“Being the founding head of a school is an opportunity of a lifetime,” he said, but added “It’s hard to talk about it knowing I don’t yet have a relationship with all the kids. Give me a few weeks with them, and then I’ll feel like I’m the principal of the school. School to me is the kids.”

Michael Kay

While Rabbi Strosberg will be WTA’s first-ever head, his onetime schoolmate Michael Kay faces a very different challenge at Schechter Westchester: stepping into an established school and replacing a popular longtime head. Elliot Spiegel, Kay’s predecessor and now Schechter’s “headmaster emeritus,” ran the Conservative day school for 33 years, growing it from a 150-student elementary school to a K-12 institution with over 850 students on two campuses.

“He really built it,” Kay said, adding that the “challenge is for me to navigate between those elements of the community who are accustomed to tradition and those sectors who are looking for change right way. I’m trying to find that balance.”

Asked what changes he might implement, Kay said it is “premature to start discussing specifics.” However, noting that “parents who choose our school choose from among such an excellent variety of options at all price points,” he said it is important for the school to offer “a diversity of opportunities.”

“We need to make sure we are staying on the cutting edge of excellence in academics, Judaics, the arts and athletics,” he said.

Kay will also oversee the hiring of a lower school principal to replace Rabbi Shira Leibowitz, who after 13 years in that post has accepted a job as head of Solomon Schechter School of Queens. (An interim principal is serving this year.)

The search process for a new principal “gives everyone in the community the chance to have input and coalesce around the vision of what we want the lower school to look like,” Kay said.

A Harvard graduate, Kay has a doctorate in educational leadership and Jewish studies from New York University, where he wrote his dissertation on leadership and community building in pluralistic Jewish high schools.

While Schechter is officially Conservative and not pluralistic, Kay said his research is still applicable because the Westchester school “caters to a population with a broad range of ideologies both within and outside the Conservative movement.”

“One of the most important skills we can teach students in the 21st century is the skill of engaging with diversity,” he said.

What challenges does he see moving forward?

“The world is changing so quickly, and that presents a challenge for educators,” he said. “One of the purposes of education is to prepare students for careers, but 50 percent of high school students will end up in careers that don’t currently exist … We don’t know what they will be doing, but we do know what kind of skills they will need: being able to work collaboratively in teams, having facility with technology, critical thinking and being able to analyze a text. All those are skills that bridge the gap between general studies and Jewish studies.”

julie.inthemix@gmail.com