The Exit Interview: Jennifer Bails
TransitionsJennifer Bails

The Exit Interview: Jennifer Bails

Strategic thinker and voice for substantive Jewish education reflects on years at Community Day School

Jennifer Bails, left, is shadowed by Community Day School student Lucy Brown. Photo courtesy of Community Day School
Jennifer Bails, left, is shadowed by Community Day School student Lucy Brown. Photo courtesy of Community Day School

Since 2014, Jennifer Bails has been a sounding board, strategic thinker and compelling voice at Community Day School. After a decade of helping the institution navigate communal and national challenges, Bails is leaving her role as director of marketing and communications.

Before exiting the senior leadership position on June 30, Bails spoke with the Chronicle about her time at CDS, the line between parent and professional and why a substantive Jewish education is important.

This interview has been edited for length and clarity.

Can you tell me a little about your responsibilities at CDS?

Sure. I’m responsible for leading, planning and directing all strategies for marketing communications with the goals of raising the school’s visibility, advancing the brand of CDS, supporting fundraising, admissions and messaging to both internal and external stakeholders.

What are some projects you’ve worked on?

Newsletters, brochures, press releases, materials for events, web copy, email marketing, social media, digital and print ads and school merchandise.

Tell me what brought you to CDS.

My older daughter started here in kindergarten and my younger daughter was in the very first pre-K early childhood class at CDS, so I was an invested parent at the school. I had been doing freelance writing and editing for a number of years for universities, hospitals and foundations, and, when this position opened, I saw the need within the school. Through conversations with Avi Munro (CDS’ head of school) I just felt like it would be a really good fit and partnership, and that I could make a difference in a place that was important and meaningful for my children and my family.

What’s it like working in a way that not only immediately impacts your family but so many others as well?

I think for the most part I’ve done a good job establishing healthy boundaries for my parent and professional role. It can be complicated, as a lot of Jewish professionals know, to work in the community and be part of the community, to work at a Jewish institution and be part of that institution. That said, you have that extra investment — like this matters for your children, for people that you care about, for the community that you care about — and I think that makes the
work even more meaningful.

Every generation faces its own challenges, but recent years have presented young people with numerous devastating events. Whether it was the Pittsburgh synagogue shooting, COVID-19 pandemic or a “national youth mental health crisis” as declared by the U.S. Surgeon General, what’s it been like working through these experiences?

They’ve fundamentally shifted my job. Starting on Oct. 27, 2018, nothing has been the same since. We’ve gone from one crisis to another crisis. We’re sort of emerging from that and still feeling its after-effects in ways that I don’t think we’ll begin to know for a long time.

Can you identify some takeaways?

The year of the shooting was a dark and daunting place for the community as a whole and for the school. But I feel it was an affirmation about the important work our teachers are doing every day — and why it matters. I saw the strength of the community and the relationships that I’ve built, so I’m grateful for that. I think that heading into the pandemic my background was in science and public health, so that positioned me to be able to help communicate clearly and effectively through COVID. It definitely was all-consuming and all-encompassing, but I feel very proud of how the school was able to pivot, how our educators put kids first above their own fears and how we all sort of banded together to make it work.

Why do you think you’ve been able to succeed and what would it take for others to do the same?

I feel very grateful that I worked for a leader — Avi — that really understood the value of this role. I never had to advocate for why I exist, why it’s important. There has to be buy-in at that level, of understanding why this role is so important. And then I think it’s really finding that person who’s so dedicated to your mission and is on the same page with your leadership team. That partnership is really key.

Munro recently announced that after two decades as head of school, she’s retiring next year. What can the community expect moving forward?

The institutional advancement team is going to be really strong, really focused in helping bring CDS into the next era. We’re coming at it from a position of strength. I’m excited to see what’s going to happen and to offer whatever support I can as an alumni parent and a past employee.

Whether it’s at CDS or in other settings, what advice do you have for those who also want to be change agents?

I think it takes a lot of careful listening. I think I spent my first year here just building relationships, asking “How can I help,” “What can I do,” — just trying to be of service to people. After you build a level of trust, and you listen carefully, you learn that a decision ultimately has to be made for what’s best for the school. We need to speak with a unified voice, so while we can all disagree behind closed doors at a leadership level, when it comes to communicating at-large we all need to be on the same page. This is something that I never took lightly. I tried really hard to professionalize the way we communicate to both our internal audiences and the broader community.

As you mentioned, your role required developing meaningful relationships within school and externally. What does the community need to know about the cause you and your colleagues care about so deeply?

The future of Jewish Pittsburgh, and the future of the Jewish community, is fundamentally tied to Jewish day schools. There is no other place where you can get 24/7/365 Jewish education for your children that is so integrated into the life of the family. Jewish day schools help children understand who they are before sending them off into the world empowered to view themselves, to live a Jewish life of their own choosing — of their own making. This education and experience gives children the knowledge that they need to begin to see that life for their own family and their own future. It’s fundamental for the community to invest in Jewish day schools. It really lays the groundwork for the future of our community.

Your heart is in this work. Why leave and what comes next?

It is not a decision that I took lightly. It took a lot of personal work and reflection to build these relationships and to make this decision. I’m approaching what comes next with the same kind of intentionality. I don’t have a grand life plan yet. I’m trying to stay open to the universe.

Thanks for all the work you’ve done for the community.

My pleasure. A lot of times with change comes growth. It’s an exciting chapter for CDS, and it’s important for the community to continue supporting the school and to continue investing in the excellence of its Jewish professionals. I’m really excited about what’s coming. PJC

Adam Reinherz can be reached at

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