Your Mission. Your Values. Your Story. Your Retention Plan.
Retention isn’t a conversation you have when a family is leaving. It’s a system of touchpoints you build long before that conversation becomes necessary.
At The Woods Academy in Bethesda, Maryland — a Catholic co-ed school serving age 3 through grade 8 in one of the most competitive private school markets in the country — Caitlyn Chalk has spent the last four years building exactly that system. This webinar is a look at what it actually contains.
Thirty-eight percent of enrolled families are actively looking at other schools at any given time. The schools that respond to that reality with a retention plan — not a reaction — are the ones that stay full.
The 80% You Don’t Know
Rob Kodama spent 28 years at a private Catholic school in Los Angeles, the last 20 as Director of Admissions and Enrollment Management. His framework for thinking about retention is simple and immediately useful.
Every school has a top 10%: super-engaged families who volunteer for everything, show up to every event, and won’t leave unless something drastic happens. Every school also has a bottom 10%: families who are chronically in difficulty, frequently in the office, and may leave regardless of what the school does. Those 20% are knowable. The challenge is the 80% in the middle.
The top 10% typically don’t leave your school unless something happens. Then you have the 10% that you already know might leave. So we know 20% of our school. The question is, how do we handle that 80%?
Rob Kodama, Director of Sales, Vidigami
Most schools don’t have a systematic way to know that 80%. They find out a family is leaving when a family is already leaving. By then, the work of retention is almost always too late.
From Curated to Authentic
When Caitlyn arrived at The Woods Academy, the school’s communications were built around polish. A monthly newsletter with long, curated stories about individual student projects. A social media presence built on professional photography. A Vidigami library that functioned more as a branded photo album than a living archive.
What shifted her thinking was listening. The school gathered two years of voice data — through a head of school search, marketing surveys, and focus groups — before building a new strategic plan. What parents said, consistently, was that they wanted to see what was actually happening. Not a finished product. The process. The moment.
Let’s not have posed photos. Let’s show them in action — building that robot in sixth grade science, and it being messy and fun.
Caitlyn Chalk, Director of Advancement, The Woods Academy
The school replaced the lengthy monthly newsletter with “WOW Now” — quick, grade-level Google Docs with short classroom updates and links directly into Vidigami. The shift wasn’t just tactical. It was philosophical: the most powerful retention tool the school had was also the simplest. Show families what their child’s day actually looks like.
I took a step back and said, how do people consume media? They’re not reading these lengthy emails or stories. They want short little updates.
Caitlyn Chalk, Director of Advancement, The Woods Academy
The Micro Level: What Actually Moved the Needle
The Woods Academy already had strong macro-level community: Friday Night Lights, the spring musical, the Christmas concert. What they were missing was the micro level — grade-level connections, parent-to-parent relationships, the smaller moments that make a family feel genuinely embedded in a community rather than adjacent to it.
What they built:
- Grade-level parent ambassadors running WhatsApp groups, organizing potluck dinners and community service projects for each grade
- Quarterly learning showcases — casual 30-minute classroom visits for parents, four times a year
- Positive feedback initiative — proactive notes home when a student does something well, not just when there’s a problem
- A “Did You Know?” section in the weekly Wednesday newsletter, remarketing school features to current families who may have forgotten why they chose the school
- A retention committee with a formal process: if a family is spotted at another school’s open house, a coordinated response begins immediately
It is more affordable to keep and retain a family than to attract new families. Gone are the days where you just sit there and say, oh, I just heard so-and-so’s leaving. Oh, well.
Caitlyn Chalk, Director of Advancement, The Woods Academy
- Monthly newsletter with lengthy curated stories — parents weren’t reading them
- Community events at the macro level only — no grade-level or micro touchpoints
- Teacher-parent communication mostly reactive — problems and behavior, not strengths
- No systematic way to know which families were at risk before they were already leaving
- Vidigami used as a polished photo album, not a real-time classroom window
- Trust between school and families eroded through years of disruption
- “WOW Now” classroom updates — short, grade-level, linked to Vidigami
- Grade-level parent ambassadors, potluck dinners, WhatsApp groups per grade
- Quarterly learning showcases bring parents into classrooms four times a year
- Proactive positive feedback notes sent home alongside academic updates
- Retention committee with a formal tracking process and coordinated response
- 108,000+ photos shared with fewer than 300 students
Photos as a Retention Signal
Rob describes something schools don’t typically think to track: photo count per student over time. The idea is straightforward. A family that’s engaged shows up in photos — at events, in classroom shots, on field trips. A family that’s quietly drifting shows up less. A declining photo count, across a semester, might be one of the earliest signals a school has that a family is losing connection.
If we don’t tell people what’s going on in that classroom, what’s going on on that field trip in a timely fashion, then it’s as if it didn’t happen — especially with these millennial parents.
Rob Kodama, Director of Sales, Vidigami
The inverse is also true. When a school shares photos consistently — when parents can open an app in the morning and see what happened in their child’s classroom yesterday — the relationship between school and family changes. Not because a single photo does anything on its own. But because the accumulation of those moments, over months and years, builds the kind of trust that makes re-enrollment feel obvious.
Watch the Full Webinar
Caitlyn Chalk and Rob Kodama walk through the full retention framework — including the admissions mission-fit process, the 10/80/10 model, the Woods Academy micro-level playbook, and Q&A with Catholic school leaders from across the country.
Full Webinar: Your Mission. Your Values. Your Story. Your Retention Plan.
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