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Client Story

How Woodside Priory Replaced Friction With Trust and Accelerated Recommitment

April 8, 2026

Set against` the redwoods of Portola Valley on a 50-acre campus, Woodside Priory welcomes day and boarding students into a learning community just minutes from Stanford and Silicon Valley.

Rooted in the 1,500-year-old tradition of Catholic Benedictine education, the Priory is shaped by five core values: individuality, community, integrity, hospitality, and spirituality. These values are the lens through which every operational decision is evaluated. And for Kirk Gossman, Director of Enrollment Management, that lens revealed something that had to change.

When the Application Becomes the Barrier

Before evaluating any platform, Gossman had watched what financial aid applications were costing families.

"Families were spending multiple hours trying to complete their financial aid application, and sometimes they ended up abandoning it altogether. We missed out on some great kids because they didn't feel like they could complete the process."

“Our previous system thought about the data and not how a school gets the data," he explained.

"Financial aid is a very sensitive topic to begin with," Gossman shared. "Then you add complexity and frustration in getting the information across, and it's a recipe that leaves everybody feeling bad."

A Framework for Confident Awarding

Switching to Clarity changed both the experience for families and the rigor behind every award decision.

"Often, under-resourced families don't have access to a computer, so the ability to apply through their phone in under 20 minutes — that's a game changer for everybody."

For Woodside Priory, Clarity surfaced patterns that had been hidden under outdated practices. "I inherited some back-of-the-napkin calculations that were happening for financial aid that didn't always equate to a fair and equitable allocation of funds," he shared.

"With Clarity, we have a framework. We know when we're making the decision versus having someone else’s calculation make the decision for us,” Gossman said.

"I've definitely seen a greater allocation of funds and an ability to have an understanding of where our dollars are going that wasn't clear before.”

When Values Drive the Technology

After three years with Clarity Financial Aid, Gossman turned his attention to the school's contract and billing products, and found the same friction, but with higher stakes for trust.

“As each year passed, our previous system became more restrictive and fees got added for everything. It would automatically enroll our families into things that they didn't agree to and then charge us to unenroll them,” Gossman shared.

"One of the five values that shape our community is integrity. Our previous system was lacking integrity, and didn't feel good,” he continued.

The operational cost was substantial too. The business office printed and manually entered 430 contracts into a separate billing system.

"This is oftentimes the very first interaction we're having with new families, and the experience we were offering them was subpar."

Reducing Friction to Accelerate Recommitment

The first year on Clarity's Contracts and Billing produced results Gossman didn't expect to see so quickly.

"Our re-enrollment rate at deadline in prior years averaged around 58%. This year at deadline, we were at 91%."

New family enrollment told the same story. "We just completed our new family enrollment, and we have eight families that haven't completed the payment side," he shared. "Before, it would have been at least 30."

The reasons, Gossman believes, are structural. "It’s easier for everyone. Families do everything in one system, and there's no more hunting around or waiting for communication from the school to complete what you need to complete."

The internal handoffs that used to consume hours of coordination have largely disappeared. 

"I've maybe had two conversations with our business office after the enrollment deadline because it's just clean. Everybody knows what the other one is doing, and people are paying on time."

For a school with a boarding program drawing students from around the world, Clarity's tax verification has extended that ease internationally. "The ability to verify non-US-based records within the platform is a game changer."

A Partner That Keeps Earning the Relationship

For Gossman, the consistency of partnership has reinforced his decision to choose Clarity.

"A lot of products are built with the school in mind, but they forget about the end user, or vice versa. Clarity has always been able to hold both perspectives in mind at once and optimize the product for both groups.” 

"I feel taken care of," Gossman shared, "and I know that my families do as well."

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