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On the Road with Alumni Support
October 28, 2024

If you come looking for Jen Glassmeyer or David Maia around the City Academy campus during the school year, you will probably want to make an appointment. As Director of Alumni and Community Partnerships and Assistant Director of Alumni Partnerships, respectively, they spend their days crisscrossing St. Louis to meet with 107 City Academy alumni currently in secondary schools. With 26 different schools on their roster, and a goal of meeting with each alumni at least four times a year, their schedules are packed, their mileage is high, and their dedication to City Academy’s mission is unwavering.

On the Move for Alumni

The school visits program, coordinated by Glassmeyer and Maia, is designed to maintain and strengthen the relationships City Academy has built with its alumni, ensuring they continue to receive support as they navigate new educational environments. “It’s about building and maintaining community,” says Glassmeyer. “We want them to know that City Academy is still their place.” This commitment to community is one of the program’s three main goals, alongside providing academic and social-emotional support, and ensuring students have trusted adults on campus to turn to.

The visits themselves are a blend of planned check-ins and spontaneous adjustments based on the needs of each student. “A lot of what we do is person-centered and individualized,” Glassmeyer says. “You might plan o discuss grades or summer plans, but then something happens in a class that day, and you find yourself processing that with them instead.” The focus is always on ensuring the alumni are “good,” as Glassmeyer puts it, and supporting them with whatever challenges arise, whether they are academic, social, or personal.

Maia, who joined the team full-time in 2022 after completing his social work practicum at City Academy in 2021, echoes Glassmeyer’s sentiments. “We’re here to show them that City Academy is still part of their community and support system,” he says. “We want to see how their transition is going in these new spaces, help with goal-setting, and offer social-emotional support if they’re dealing with challenges at school.”

Logistics and Challenges

Coordinating the visits involves a delicate balance of logistics, flexibility, and a lot of driving. Jen and David split the alumni between them — Jen handles the girls, and David the boys, from 7th through 12th grade. Their days are a mix of meetings at schools, follow-ups with counselors, and in some cases Zoom check-ins when in-person meetings aren’t feasible.

Secondary Schools Map
City Academy’s Alumni Team covers 514 sq. miles.

“We try to be as unintrusive as possible,” says Maia. “We work around their schedules, avoiding core subjects and trying to meet during study halls or advisories.” This approach not only respects the students’ academic commitments, but also allows Glassmeyer and Maia to connect with them in a way that feels supportive rather than burdensome.

However, the logistics are complex. With schools spread across the city and beyond — including some as far out as Illinois — planning efficient routes is a challenge. “I think I put about 3,000 miles on my car over the course of the school year,” Maia recalls. At schools with several alumni, he’ll try to schedule multiple visits in one trip, which can often mean working out of the school library in between visits. Glassmeyer enjoys working from parks or libraries between visits — her favorites? Millennium Park in Creve Couer and the St. Louis County Library – Thornhill Branch.

Building Relationships, One Visit at a Time

The success of the school visits program is measured not just by the number of visits or miles driven, but
by the depth of the relationships formed with the alumni. “It’s always cool when they start texting and sharing exciting news with us,” Glassmeyer says, “or when they ask us to write letters of recommendation for scholarships, jobs, or leadership positions. It shows we’ve done what we’re supposed to do — we’ve built that relationship — they know they can count on us.”

David Maia visits with alumni at Saint Louis Priory School
David Maia meets with Jon-Paul Mitchon at Saint Louis Priory School. “I enjoy the conversation and checking in,” Jon-Paul says. “I feel the alumni team has prepared me well for my future goals.”

For Maia, the evolution of these relationships is one of the most rewarding aspects of the job. “So much of the first year is spent building trust and consistency,” he says. “Once that relationship is in place, we can really get into the weeds — what works for them as individuals, how we can best support them, what their interests and goals are.” Over time, these relationships grow from surface-level check-ins to deeply personal connections that allow for tailored, holistic support.

Both Glassmeyer and Maia emphasize the importance of starting this relationship-building early, even before students graduate from City Academy. “We try to be as engaged in the building as possible,” David explains. “When we’re not doing visits, we’re here, getting to know the current students so that by the time they transition to secondary school, they already trust us.” That’s why between school visits and planning time in the office for other alumni programs, you’ll often find Glassmeyer engaging with students and parents at the front desk, or Maia out playing basketball at recess or enjoying lunch with 6th graders in the cafeteria.

Success Stories

Success in the school visits program isn’t always easy to quantify. While grades and academic progress are tracked, much of the impact is seen in more qualitative ways — through the comfort and confidence students feel in their new environments, the connections they build, and the personal growth they experience.

Glassmeyer and Maia have no shortage of success stories. Glassmeyer recounts helping a student prepare for her first job interview, working on her resume, and coaching her through the process. “Helping somebody get their first job is really cool,” she says. Another time, she recalls helping a student navigate the complexities of transitioning from a small, familiar environment to a larger, more diverse school. “It’s about building that confidence,” she explains, “so they can navigate these new spaces successfully.”

For Whitney Gross (CA ‘21), finding her place after City Academy was challenging, but the support
she received from the Alumni Team made all the difference. “I just wanted to feel comfortable and at home, like City Academy had always made me feel,” she says. “But with the access and opportunity Strive and Ms. Jen provided, I was reminded that my being or thinking differently shouldn’t have to be concealed or changed, but expressed and heard. I learned to contribute to the diversity in your environment, not just based on your race or religion, but based on your mindset, knowledge, and creativity.”

Maia shares a story about a student who struggled with organization. “They were doing well in classes but were getting feedback about losing homework assignments and not being able to find tests from earlier in the year,” he says. After dedicating several visits to the issue, David helped the student develop a color-coding system and other organizational strategies that made a significant difference. “It was nice to take that weight off their shoulders,” he says.

Looking Ahead: Continuing the Committment

As Glassmeyer and Maia look to the future, they see the school visits program continuing to evolve, adapting to the changing needs of City Academy alumni and the educational landscape. Both do their best to keep up with current trends and issues facing students through workshops, professional newsletters, and even some helpful advice from family. “I’m fortunate that I have a sister who’s in 12th grade,” Maia said. “I think talking to her helps me stay in the loop about the college application process, especially with all the recent changes to the FAFSA (Free Application for Federal Student Aid).”

At its core, the school visits program will always be about relationships — about being present, listening, and providing the right support at the right time. “It’s less about ‘This is what we need from you’ and more about ‘What’s your goal? How do we help you get there?’” Maia says. “Each student is different, and we’re here to fill in those gaps as much as possible.”

Whether alumni are navigating a new school, applying for college, or starting their first job, Glassmeyer and Maia are there, ensuring that the City Academy community continues to thrive, one visit at a time.