“A Universal Need” — Gather, Inc.’s CEO Rachel Gildiner on her and Gather’s past, present, and future

by Samuel Milligan / March 15, 2023

Have you heard the news? At the end of April, Gather, Inc. CEO Rachel Gildiner will be adding a couple extra stops on the Red Line to her morning commute, as she becomes Hillel International’s Chief Engagement Officer. Before she heads out, we sat down with her and soon-to-be-interim CEO Jackie Zais to chat about Gather’s bright future, what has and hasn’t changed in the past 8.5 years, the universal need for relational engagement, and what they’ll miss about working with each other. Read the full interview below!

Rachel and Jackie together, smiling.

Samuel: Hi Rachel! It’s so nice to chat with you this morning. During your time at Gather, the organization grew from grassroots community-based project; to being a nonprofit focused on DC, then the entire DMV; to being a nonprofit with outposts in multiple metropolitan areas, employees working across every time zone, and training other organizations in the relational engagement principles that inspired that first community-based project.

What has allowed that growth to happen? What is the external need that has sustained and expanded this organization?

Rachel: I am a big fan of emergence. There’s an organic way that things grow in nature; that’s been a guiding principle for how Gather has grown. The goal was never to grow for the sake of growth. The goal has always been to continue to meet the emerging needs of young adults and the broader Jewish community through relational work. It’s been amazing to watch how Gather has continued to be in deep relationships with the people we’re trying to serve. 

By doing that, we’ve been able to identify those emerging needs and use our tried-and-true methodology – the relational approach of seeing the whole person, modeling deep listening, and inviting people to bring their holistic selves – to grow into that space. There’s no secret sauce other than modeling that work. Those relationships – with our community, with funders, with supporters, with colleagues –are a huge part of how we’ve been able to grow, build trust, and show our value.

Jackie and Rachel take a selfie in front of a powerpoint presentation on relational engagement.Samuel: What are you most proud about from your time with Gather?

Rachel: I’m most proud about the people who work at Gather, who believe in and live this relational methodology. I think that type of culture is really rare. I alone definitely did not do that; it was built by all the people who have worked here over the years.

Samuel: What have you learned over time through taking the principles of relational engagement and trying to authentically live those out, both inside and outside of Gather?

Rachel: I can distill it into three main learnings. One, even though we have traditionally focused on young adults in our DC and Bay Area work, this need for connection is universal. This is not just a young adult thing, or just about people who aren’t involved in Jewish life. People want and deserve to feel valued in community. They want and deserve to experience that sense of belonging. This practice is not about any one demographic; it is a universal need. 

Secondly, relational engagement can seem like an obvious thing to practice. I talk to people who say: We do this! This is so obvious! But what we’ve learned is that it’s not always obvious. We might say or think that communities are welcoming, but there’s a lot more room to really center people and that we, as Jewish communities, are not doing it as well as we think we are. 

The third learning is that change is hard. It is hard to fight against the flow of how things have always been done, to question, to put new ways of doing things in place. We can acknowledge and help each other understand that you don’t just snap your fingers and do things differently. It takes changing culture. It takes time. It takes communities of practice and shared language.

Samuel: What’s been most meaningful to you during your time with Gather?

Rachel: It’s not one moment. It is the many moments I’ve had to hear people’s real stories about their experience in Jewish community. I – and all of Gather – want to invite people to say things that are real, and true, and maybe have not been allowed to be said in other Jewish spaces. I carry all of those stories with me. It’s been 8.5 years of hearing from people about how Jewish community has served – and sometimes failed – them. That’s been a powerful part of this work.

Gather staff and Open Doors fellows pose together in ODF-branded sunglasses at an event.

Samuel: What are you most excited to watch happen next at Gather?

Rachel: I believe so deeply in Gather’s methodology. I know that this need for connection and meaning-making is not going anywhere. If anything, it’s only increasing. I’m so excited to watch the organization and everyone doing the work to continue to thrive and meet needs that we haven’t even identified yet. And, I’m really excited for Gather to find its next leader, someone who has a vision for the next era of this work. I will be rooting for them and cheering them on. I know that Gather has great things ahead. All that Gather is today is because of the vision of many people since its inception: the young adults who created it, the folks at GW Hillel who incubated it, the funders who invested in it, the staff who have worked to achieve its mission…this has been such a collective and relational process. This endeavor is so much bigger than any one person; it is a collective, shared vision of so many people over a long period of time.

Samuel: You mentioned the “next era of work” for Gather. What do you see in that next era? What’s the future of relational engagement in the Jewish world and beyond?

Rachel: I’m proud of the strategic plan that Gather has worked on over the past year. It outlines a bold vision for where relational work goes next. With the City model that we have – GatherDC and now GatherBay – I know that there are other cities for which that model is so ripe and aligned. I’m hopeful that Gather is not going to just be bicoastal, but that the Gather City model will exist in more cities over time. 

We’re also working with so many partners around the country who want to explore how a relational approach can help them maximize their impact and achieve their missions. There are opportunities to build networks and practices that help us learn what the future of relational engagement looks like in Federations, in JCCs, in synagogues. It will be up to the people leading and adopting relational engagement to figure out what the most useful parts of this methodology are and how they can specifically adopt it to their unique setting. 

Rachel, Jackie, and Rabbi Ilana stand together and smile indoors.

Samuel: How does it feel to step away from something you’ve been involved with for 8.5 years?

Rachel: “Bittersweet” is sometimes used too much…but it really does feel bittersweet. I am so proud of what we’ve built. I remind myself that Gather existed before me – a group of young adults in the community created Gather the Jews, and this incredible brand and group of assets and initiatives. That all existed before I started. And, I know that there will be a Gather after me. I am hopeful and confident that Gather has a bright future in its next evolution. I’m feeling personally sad. I’m going to miss the people. I’m going to miss the work. I’m going to miss being an integral, connected part of the local Jewish community. But I am really excited for Gather’s future – I’m holding both of those deep emotions, which is why it really does feel bittersweet.

Samuel: What are you most excited about for your next chapter with Hillel? 

Rachel: This move feels like a homecoming. My first job in DC was at Hillel International in 2007, piloting different ways to reach college students through peer-to-peer relational work. I was doing the seeds of what I’ve been able to bring to Gather. And so going back to Hillel feels like a homecoming. I know the people who are part of that movement are brilliant, creative, and work so hard every day serving students. I’m excited to go back to a movement that has helped shape who I am as a leader and to bring what I’ve learned over these past 8.5 years into the engagement work.

Jackie stands behind a table at a Gather event, fronted by a menorah, an orange sign, and plates of food. Samuel: Your long-time colleague, collaborator, and friend Jackie Zais is stepping in as interim CEO – What is Jackie bringing to the table for this role?

Jackie, faintly, from another room: Nothing!

Rachel: Jackie was the first person I hired to be part of Gather. I was alone for six months. It was very clear I needed a partner. I could not have known then that I was picking the most remarkable person that Gather needed, and who would become a dear friend and colleague and teacher of mine, honestly. Jackie has been leading this work and building this organization for eight years. She knows the ins and outs of the methodology. She’s a teacher of this work. She has deep relationships with the staff. She’s already been my co-captain in all of this. I have the utmost confidence and excitement in her leadership and her vision for how Gather continues to thrive in this transition time. I know that the legacy of Jackie’s work is so deeply infused in what Gather is today that, in many ways, it feels so natural for her to be stepping into this role. 

Samuel: What are you going to miss about working with her?

Rachel: Jackie’s the best. I’ll miss her thought partnership, her creativity, her fire, her impeccable taste in notebooks and pens, and our shared love for books and Thai food. Fortunately, neither of us are going anywhere geographically, so this relationship is only going to continue. 

Samuel: Jackie, thank you for joining us! You’ve been with Gather for 8 years. How has that time prepared you to step into this new position during a moment of transition?

Jackie: It’s been such an honor to be at Gather for eight years. It’s been amazing to grow and evolve with Gather. My first role was doing the newsletter, meeting people for coffee, making sure the website was running, leading the Happy Hours, and meeting with organizational partners. Being on the ground, practicing our methodology, and seeing our growth at every step of the journey has been an amazing opportunity both personally and professionally; it’s also set me up to support Gather as it goes through this change. Knowing that we have such an amazing team, having relationships and deep trust with the people in this organization, it makes me feel like we can weather any storm and that we are absolutely ready for this moment. 

Jackie hangs off a ladder inside a cabin at a Gather retreat. Samuel: You really have worn a lot of hats – you’ve been in the trenches at basically every level of Gather. How is all that experience going to inform how you approach your new role? How will it inform the search for the next person to fill that role? 

Jackie: First off, it’s kept me humble. I once sent the newsletter out saying “Purim Addition” instead of “Purim Edition.” So, because of that kind of experience, I’ve had the opportunity to see this work from every different angle. You should do every job and then hire someone who is better at that job than you. The level of talent that we’ve been able to recruit has given me so much trust. I can understand what everyone’s going through day-to-day, and also trust in their execution or their ability to come to me and say: Hey, Jackie, you’re wrong. Or hey, this is where we want to go. 

Every step of the way, the most important piece has always been relationships. As we think about the next person who could fill the role, there are a lot of exciting possibilities for who this person could be. But it needs to be someone who understands the power of relationships. I know that for every step of my journey at Gather, my success has been predicated on the strength of the relationships I’ve made. 

Jackie, Rachel, and GatherBay's Caroline sit together.

Samuel: What are you going to miss about working with Rachel?

Jackie: I show up to work every day and get to work with someone who loves me. As a person, as a professional. She’s someone who has mentored me and seen me grow. I want to know about her next tattoo, how her kids are doing, how her basketball team did. She wants to know how my intramural soccer team did. I get to show up to work with a great friend every day, and I will still have a great friend in my life, but I won’t get to show up to work with her. I’m so grateful for what I’ve learned from Rachel: her mentorship, her support. It means so much to me over the years, in the good moments and the bad moments. Part of the beauty of Gather, though, is that I’ve had those meaningful moments with everyone at Gather. Rachel leaving is such a bittersweet moment, but I’m so excited about the future of Gather and I’m deeply humbled by this opportunity and can’t wait to steward us through this moment of transition. Just like everyone else, I can’t wait to see where we’re going. 

Samuel: Rachel, are there any other big emotions or feelings that have come up as you’ve come to this moment in life?

Rachel: Gratitude. In a few ways. There’s this local artist I’ve been thinking about, Rella Kaplowitz. She created this one paper cutting of purple mountains – I love Colorado and the mountains, it’s my happy place, somewhere my family’s been going for years and I just feel so small and alive – and around the purple mountains is a prayer about gratitude, rejoicing, and blessings. It’s going to be hanging in my house in a few months, I hope. 

Then also, for years, I’ve had this mantra: I am Rachel, full of love. It’s been a driving force of how I want to live in the world. It’s also the first tattoo I ever got; I look at it every day and it reminds me who I want to be. So much of that idea is just gratitude, and remembering that every day is a gift. The fact that any of this – including Gather – exists, and that it has been my heart’s work for 8.5 years…I feel really blessed every day. 

Samuel: Last one: What three words would you use to describe the Gather community that you’ve been a part of?

Rachel: Curious. Brilliant. Caring. 

Jackie: Receptiveness. Ownership. Authenticity.

Jackie and Rachel pose together, smiling, in front of greenery.

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