One evening during The Covenant Foundation’s 2016 Project Director’s retreat, Jewish music legend Elli Kranzler generated an infectious rhythm of joy in a room full of a few hundred Jewish educators.

Suddenly, Oren Massey rose from his front row seat and began dancing. He eventually led others into the spirit until at least half the crowd was winding its way through the aisles, hands clasped, in full hora-like celebration.

“That more or less defines my character more than anything else,” Massey said, laughing. “I’m a spiritual person, energized by, with and for people.

“A big part of me always wants to bring playfulness and fun into whatever setting I’m in, whether it’s a conference or synagogue or classroom. Fantasy and fun shouldn’t be exclusive to Jewish summer camp.”

So it is that in a career that so far includes leading tours in Israel and teaching in Jewish day schools, to heading a groundbreaking afterschool program and now serving as Director of Education at the Diller Teen Fellows program, he has nurtured environments pushing Jewish education to deep levels of meaning, impact and engagement.

Massey is a self-described “meta-thinker and strategist.” Focused on the educational process as well as human and relational development, he recognizes that theory, design, and practice are mutually supportive pillars in Jewish educational settings. And furthermore, that intensely deliberate and creative thought must be given to each to maximize learners’ experiences.  

“I’ve been fortunate to have an incredibly diverse array of professional opportunities and they have all been my testing grounds,” said Massey, who received The Covenant Foundation’s 2014 Pomegranate Prize for his vision and impact as an emerging Jewish educator.

“In every single one of my settings, no matter how deep I get into the trenches, I’m focused on the core of what we are doing, why we are doing it, what our vision is for it, and how we design best for it in a spirit of innovation, growth and lasting engagement.”

Massey received the Pomegranate Prize when he was Executive Director of Edah, an independent Jewish afterschool program in Berkeley, CA that by its very founding in 2010 and dramatic growth since has become a national model of what alternative Jewish education can look like for elementary-school age children.  

At Edah, Massey was committed to understanding and evaluating the success of the curriculum and programming, and as such, made sure to full engage on a daily basis with his students. He also focused on solidifying and advancing innovative pedagogies notable for their emphasis on experiential learning over more traditional and formal approaches, and elevating conversational Modern Hebrew as a bridge to lifelong Jewish identity and connection to Israel.  

“We were not accountable to synagogue standards or any educational norms,” he said, describing a purposeful, no-bounds atmosphere that bred experimentation and growth. “We were accountable only to our own standards of Jewish knowledge and Hebrew literacy.

“It was hyper-creative,” he added. “We were always brainstorming something different, more exciting and engaging than had ever been done before. We created an environment of a start-up with no limitations to bring fun and play to Jewish learning.”

Unsurprisingly, Massey is a fierce and unabashed advocate for Jewish experiential education and doesn’t hesitate to use his standing to call for its more widespread adoption by the educational community.

“Judaism is an experiential learning process in the practice of life,” he said. “You can take a class in Jewish history or halakhah or liturgy from the Middle Ages and find it interesting and do what you want with it, but Judaism is more than that. You have to live it.”

Rena Dorph, Edah’s Co-Founder and Board President, said Massey brought a unique set of leadership skills and passions to Edah and helped to fuel the program’s rapid growth and position it as a national model within Jewish education.

“Some leaders lead in a very top-down approach and from a 30,000-foot level,” she said. “What stands out about Oren is that he sits with people and pulls them in and engages them on a human level and a Jewish level.”

“He gets into the guts of methodologies with children and parents and makes it work in collaboration with staff. He shows what excellence looks like in real time.”

In 2015, Massey became Director of Education at the Diller Teen Fellows program, a year-long international leadership track for high school students to develop and deepen their connection to Jewish identity, Israel and the global Jewish community.

It is a position that doesn’t put him on the ground with program beneficiaries so much as it immerses him in the “mega strategist” role as he described his headspace there.  

Here, Massey has applied his passion, interest and talents in relational and personal development to clarify the program’s educational philosophy, mission and goals, and redesign and strengthen trainings for the program’s educators around the world.

During his tenure within the Pomegranate Prize program, Massey also set out to deepen his knowledge and practice within his spheres of Jewish educational leadership, specifically teacher training and mentorship, and experiential education. He joined the Mandel Teacher Educator Institute, a two-year program of the Jack, Joseph and Morton Mandel Foundation that works with “teachers of teachers” to design and implement creative professional development for Jewish educators.

He also took part in the Senior Educator’s Cohort of M² : The Institute for Experiential Jewish Education, a year-long program equipping and empowering Jewish educators to articulate, refine and sharpen their practice of experiential education.

“This was less theoretical in practice and more focused on the practical elements of the educational work that I do,” he said of the M² participation and exposure. “It was incredibly interesting to be enmeshed in this within a diverse cohort of educators from around the world.”

And it would surprise no one who saw Massey moved by the power of music at that 2016 Project Directors retreat to learn that he used a small amount of Prize resources to pay for guitar lessons. This, he said, to improve his own skills in leading Jewish song, and to deepen his own personal and professional passion and curiosity for nigun.

But receiving the Pomegranate Prize, Massey said, is invaluable not only for the resources, exposures and platform that it provides. Its real value, he said, was and is the recognition.

“To be so singled out with such appreciation and confidence not at the end of my career, but at the mid-way point, certainly gives me the motivational force and traction to continue to make whatever positive impact that I can.”

By H. Glenn Rosenkrantz, for The Covenant Foundation