Lindsey joined Milton Gottesman Jewish Day School as Chief Advancement Officer in October 2022. Prior to MILTON, she spent nearly ten years at Georgetown Day School, driving major gift efforts and strengthening the culture of philanthropy while growing revenue year over year and exceeding budgeted goals. Over time, her role expanded to leading the development team, with a focus on annual giving, major gifts, alumni engagement and development operations. Lindsey was a critical member of the team executing the $52,000,000 One GDS Campaign which exceeded its goal by $2,000,000. She also acted as a thought and action partner to the Head of School, Board of Trustees and school leadership on philanthropic partnerships and overall institutional advancement.

Prior to GDS, Lindsey served as Deputy Chief Leadership Officer for Americans Elect, an effort to hold a national online primary for a bipartisan presidential ticket. In that role, she developed and executed strategies for leadership and philanthropic partnerships, raising more than $38 million in a national campaign and stewarding a National Board of Directors and a 130-member Board of Advisors. Lindsey has a BA in anthropology from Washington University in St. Louis.

Engaging Parents of Alumni

I can still remember the day I discovered my passion for engaging parents of alumni. I was in the chorus room of my prior school, which had been transformed for a kickoff meeting of the Parents of Alumni and Grandparents Division of our $50M capital campaign. Even though some people in the room had known each other for decades, to break the ice we asked, “What brought you to the school?” It’s a simple question, one we fundraisers use every day, sometimes multiple times a day, and one for which there are myriad answers.

I can still see Richard’s face in my mind as he talked about the importance of community and how he stays involved because, with three kids moving through a PK-12 school, it was his family’s anchor, social circle and gravitational force for more than 25 years. He and his fellow parents, some of whom were in the room, had navigated loss, celebrated countless simchas and the trials and tribulations of raising kids together. Though his kids graduated in the 80s and 90s, he and his peers had been through a lot together and continued to be friends all these years later.

He talked about how, with the benefit of hindsight and perspective, he could see the real “product” of his investment in his kids’ education in how they are living their lives as adults. He relished in sharing how prepared they were to navigate college life. When you’re not mired in the everyday minutiae of raising a family and navigating school life (“Did you remember it’s spirit day? Did you sign the field trip permission slip? Are the health forms in?“) you can see the bigger picture.

So, how do you capitalize on that good will? On the fond memories, deep connective tissue and passion for your school? Engaging parents of alumni can be good for your bottom line; they are often in a strong financial position to invest in your mission, and they can be fantastic advocates for your school, incredible storytellers and keepers of institutional knowledge. At Milton, we’re only one generation away from our founding families, and I’ve relished opportunities to connect and learn about the school’s origins and early days to better understand the culture and ethos of a school where I’m still new.

Here are some strategies to engage parents of alumni in the life of your school today.


Create unique events and engagement opportunities just for parents of alumni. At my last school, we hosted an annual Cocktails and Conversation event each May for them. It was often held in someone’s home and included a host committee from different generations to build attendance. This was a school without a spring gala; this event was one of the most well attended events of the year.

At Milton, we had great parent turnout for our Purim Ball this year, but lower than expected from parents of alumni, so we decided that next year, we’re going to engage a larger committee to strengthen turnout for next year.

If you have an alumni reunion weekend, think of ways to bring in parents of alumni. Host a multigenerational brunch, or even something as simple as a playground afternoon playdate.

Many former trustees fall into this category. Plan an annual “special insiders” event for former trustees. If you have an annual state of the school meeting or if you’re releasing a strategic plan, this is a great way to give former trustees a sneak preview. Get more bang for your buck by combining this with a major donor event, since there is a lot of overlap in those groups. Be willing to get vulnerable with them and share what keeps your school leaders up at night; they remember other hard times and will be able to bring perspective and hope through challenges.


Get together with parents of alumni in a small group or 1:1 meetings. Ask for their advice on how to engage with their peers and with alumni, and they’ll become more invested in your success. Remember that their experience is colored by not only their child’s experience as a student, but what their child’s alumni experience is like.

If you’re starting a capital campaign, or even within your annual campaign, activate a parents of alumni committee to solicit support, open doors and identify prospects.

Think about opportunities for multigenerational get-togethers. Whether you have a robust group of legacy families or your numbers are growing incrementally each year, this is a group deeply invested in your school. Once you have a critical mass, develop programs to engage alumni parents who are also grandparents; cut out the middleman of the current parents. It’s a win-win.

Engage alumni parents as admissions ambassadors, again tapping into their networks and their desire to be advocates for the school and cheerleaders for your mission.

Low-Hanging Fruit

Start a Parents of Alumni Newsletter. Show what’s going on in your school and invite the opportunity to reflect or feel nostalgic without asking for money. At Milton, we have broad distribution for our weekly newsletter, and it’s a great way to keep parents of alumni and other constituencies connected to the life of the school.

Highlight parents of alumni in your annual report or regular newsletters with a “Why I Give” story.

Segment your annual appeal. Play on nostalgia and use it as an opportunity to ask for advice on what would work well. Engage a committee for your annual fund, if you have a cohort who is willing to be more involved. People give to people, and that’s especially true with this constituency. 

Key Takeaways

  • What can you do now or plan to use in the next year?
  • Think about the generational cohorts you want to engage. Who are the leaders in each? Who can help open doors to others?
  • Include profiles of alumni parents in your next newsletter as a stewardship touchpoint.
  • Add an event just for parents of alumni to your calendar for next year, or find a way to bring in former trustees, parents of alumni or legacy families into an existing event.