Key Takeaways
- Integrated day and boarding attendance for full-student visibility
- Faculty engagement improved across academic and residential teams
- Improved communication between faculty, students, and parents
- Reduced duplicated data entry between Blackbaud and Orah
Background
Cheshire Academy is a boarding and day school located in Connecticut, serving approximately 375 students from over 30 countries. About 200 of these students are boarders, making the balance between residential and day school operations essential.
Jennifer Guarino, Director of Residential Life, has been with the school through Orah’s evolution from its early days as a boarding-only tool to its current use across both boarding and day programs.
“We started with Orah when it was still Boardingware,” Jennifer shared. “It worked well for boarding, but this year we took a big step forward and started using it for day school attendance too.”
From Fragmented Systems to a Unified Approach
Previously, Cheshire Academy used Blackbaud for day school attendance while Orah managed boarding check-ins. This dual-system approach created friction.
“Faculty were bouncing between platforms, and parents were confused,” said Jennifer. “You’d get attendance from one system during the day, then have to manually track evening attendance in another.”
This wasn’t just an operational challenge. It created blind spots when tracking student patterns.
“Sometimes we’d miss the full picture,” Jennifer explained. “A student might be missing morning classes regularly, but unless you pieced together data manually, you wouldn’t spot it until it became a bigger issue.”
The decision to integrate day and boarding attendance into Orah aimed to solve this and improve transparency for both staff and families.
Real-Time Student Visibility Strengthens Communication and Support
Integrating Orah school-wide made an immediate difference.
“The biggest win is the full student profile,” said Jennifer. “Now, whether you're a teacher, advisor, or dorm parent, you see the whole picture—not just part of it.”
The change improved communication internally as well. Academic faculty, who don’t live on campus, now have visibility into boarding notes, enabling them to better understand and support students.
“It’s made our advisory program stronger,” Jennifer explained. “Now teachers know if a student was struggling emotionally the night before and can respond more sensitively in class the next day.”
For parents, the integration improved engagement, although Jennifer noted there’s still room for growth.
“Our parents want more details in the app—specific absences, infractions, and the context behind them,” she said. “When we have that, it’ll make parent conversations much smoother and reinforce trust.”
Lessons Learned and Looking Ahead
Jennifer shared candidly about the learning curve involved in making the shift.
“Training was key,” she said. “We did summer training, optional tutorials, and still needed lots of one-on-one troubleshooting during the first few months.”
Her advice to other schools considering integration: take the time upfront to design the system holistically.
“If we could do it again, I’d recommend starting by aligning boarding and day school needs from day one. Build a structure that works across both areas instead of trying to patch two systems together.”
Jennifer also sees potential for Orah’s communication tools to reduce the school’s reliance on platforms like Microsoft Teams.
“We want to eventually centralize everything—attendance, notes, passes, and communication—in one place,” she said. “That would make it even easier for students and faculty to stay connected.”
Final Thoughts: A More Connected and Supportive School Community
“We are all about teaching the whole student,” Jennifer said. “Having one system where everyone is on the same page—boarding, day school, parents, faculty—helps us do that.”
For other schools considering Orah, Jennifer’s advice is simple: “Plan carefully, train your people, and be patient. The payoff is worth it.”
