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Pincushion Hill Montessori: where we began

CommunityExpanding Minds TeamAugust 28, 20263 min read
Pincushion Hill Montessori: where we began

Every company has a first customer. Ours came before the company did. Pincushion Hill Montessori School has been teaching young children in Ashland, Massachusetts since 1962. Everything in this platform was used there first.

A school in Ashland since 1962

Pincushion Hill began on September 6, 1962, on an acre of organic farmland at 30 Green Street. The farmland is still part of the school. So is the original idea, that academic learning and real time outdoors belong in the same day.

Today it is one of New England's oldest independent Montessori schools, serving children from 18 months through kindergarten across its toddler, Children's House and kindergarten programs, with morning and after school childcare and a summer camp. Class sizes are small on purpose. A toddler classroom runs nine children with two teachers, and the mixed-age model means older children help the younger ones, which is not a staffing trick but the method working the way it is supposed to.

Running a school like that well takes more than good teaching. Enrollment has to stay healthy. Parents have to trust how you talk to them. And a hundred small tasks have to get handled quietly, every single day.

The software came out of the front office

Expanding Minds was not built by a software company that looked at private schools and saw a market. It was built by the people who run Pincushion Hill, in response to problems they had that week.

That is an unusual origin for school software, and it shows up in small places. Tour availability works the way a school actually sets tour availability, in windows around the school day rather than open slots on a calendar. The admissions FAQ exists because families kept asking the same handful of questions. Very little here had to be imagined, because all of it was already being done by hand somewhere.

In 2026, Pincushion Hill moved its public website and its front office onto the platform those habits turned into.

The tangle most schools are living with

Most schools we talk to are holding things together with a spreadsheet in one place, a group chat in another, a website an outside vendor manages, and a paper register at the front desk. It works fine, right up until the day it doesn't, and by then nobody remembers where anything lives.

The cost is rarely dramatic. It is a tour request that lands in someone's personal inbox on a Saturday. It is the same family entered twice, slightly differently, in two systems that will never talk to each other. It is a blog that went quiet in March because the person who kept it going had a harder job to do that month.

What Pincushion runs today

Anyone can go and look, which is the point. Their site is a custom-branded website on the school's own domain, and every page a visitor sees is edited by the school's own team from one admin portal.

A family that wants to visit picks a date and time from real availability and gets a confirmation without anyone at the school touching it. Open house signups work the same way. Inquiries arrive in one inbox instead of four. Programs, faculty, the calendar, and the admissions FAQ are all pages the team edits directly, with no developer on call and no ticket to file.

That is a shorter list than most platforms advertise. It is also the list a front office actually reaches for on a Tuesday morning.

A young company with an old school behind it

Everything we ship is used by real teachers and real families before it reaches anyone else, because the school is still there, still running, and still has opinions about it.

If your school is ready to trade the tangle of tools for one system that just works, we'd love to hear from you.