On today's episode of Roll Call, Brian and Josh welcome Keith Krass, Vice President of Partnerships and Global Strategy at Veracross, for a real-world look at how technology has shifted inside independent schools over the last decade. What used to be a "necessary evil" has become central to operations, student safety, and decision-making — and the people leading technology are increasingly becoming true campus leaders.

The conversation gets practical fast: cloud vs. on-prem, risk and resiliency, the critical importance of multi-factor authentication, and why schools still struggle with silos — not just between systems, but between people. Keith also breaks down why institutional research is emerging in K–12, and why schools that don't learn to use their data to ask better questions may fall behind.

Show notes:

00:00 — Welcome + Keith Krass introduction

00:54 - Keith's background: educators, coaching, student development

03:00 - Biggest shifts in independent schools over the last decade (tech's role)

03:25 - Two buckets: cutting-edge schools vs. bare-minimum tech adoption

04:30 - "Outside the solar system to the sun": tech becomes central

05:13 - Cloud vs. on-prem: how the nature of work changed

06:45 - Risk & resiliency: fire, breach, backups, and operational continuity

07:33 - Cloud interdependence + the "expert team" tradeoff

08:27 - The false sense of control + why schools need the "why" explained

09:25 - Data ownership: the questions schools should ask vendors

10:01 - Data hostage stories + why access matters when switching systems

10:30 - The shift from IT director to CTO-level leadership in schools

12:17 - Tech's connection to student safety + thriving through data

13:50 - Tech leaders moving into head roles + why that pathway is growing

27:38 - Lightning round: AI hype, MFA security win, deepfakes, phones, and change management

Learn more about Veracross: https://www.veracross.com/

This episode is sponsored by REACH Boarding

This episode is sponsored by REACH Boarding, an award-winning, feature-rich boarding school management tool used by over 400 schools in five continents to manage risk, increase efficiency, and improve communication in boarding school management.

To learn more about REACH Boarding, its features and integrations, visit www.reachboarding.com

Empowering the Future of Independent Education & Boarding School Management

Thanks for tuning into this week's episode of Roll Call, don't forget to share your favorite episodes with your colleagues on social media to help us spread the word and help more education professionals stay at the forefront of independent education and boarding school management techniques to empower the future of the education environment.

On today's episode of Roll Call, Brian and Josh sit down with Melissa Cassel, Dean of Students at Walnut Hill School for the Arts, to talk about what it really means to support teenagers in a place where school isn't just academics — it's a double curriculum of rigorous classes and intense artistic training, all inside a 24/7 boarding environment.

Melissa shares how she landed at Walnut Hill almost by accident… and why she stayed for 28 years: the job keeps changing, the students keep evolving, and the best part is watching young people become more confident, resilient, and fully themselves. She breaks down what a "normal day" actually looks like for a student (it's a marathon), why the arts are more than career prep, and how artistic training teaches skills most adults still struggle with — accepting critique, taking risks, making mistakes, and trying again.

The conversation also tackles bigger questions: how to help parents take the leap, what's changed in young artists over the last decade (hello, perfectionism and fear of failure), what grit looks like when your "instrument" is your body or voice, and why the future of arts education is shifting toward impact and global connection — not just technical excellence.

This is a thoughtful, human conversation for school leaders, boarding professionals, and parents who want their children to be more than high-performing… they want them to be whole.

Show notes:

00:00 – Introducing Melissa Cassel

01:23 – 28 years as Dean: how the job (and expectations) have changed

03:32 – A day in the life at Walnut Hill: the "double curriculum" reality

07:20 – Defending the arts: transferable skills, identity, and being "whole people"

10:08 – The tipping point for parents: "Your kid will be seen here"

12:57 – What's changed in young artists: perfectionism, fear of failure, learning through

mistakes

16:07 – What grit looks like when you're constantly judged as the instrument

19:05 – Why boarding makes the arts different: empathy, community, and processing in real

time

22:38 – Structure vs creativity: adjusting rules, accountability, and independence

32:52 – Where arts education is going next + Lightning Round

Learn more about Walnut Hill and Melissa Cassel: https://www.walnuthillarts.org/about/leadership

This episode is sponsored by REACH Boarding

This episode is sponsored by REACH Boarding, an award-winning, feature-rich boarding school management tool used by over 400 schools in five continents to manage risk, increase efficiency, and improve communication in boarding school management.

To learn more about REACH Boarding, its features and integrations, visit www.reachboarding.com

Empowering the Future of Independent Education & Boarding School Management

Thanks for tuning into this week's episode of Roll Call, don't forget to share your favorite episodes with your colleagues on social media to help us spread the word and help more education professionals stay at the forefront of independent education and boarding school management techniques to empower the future of the education environment.

On today's episode of Roll Call, Brian and Josh welcome Rob DiMartino, co-founder and Chief Evangelist at Finalsite, to unpack a truth school leaders are feeling in real time: your digital presence isn't marketing anymore — it's your first campus visit.

Rob breaks down how independent schools can honor tradition without living in the rearview mirror, and why the strongest brands aren't built on slogans like "small classes" and "great community" (because everyone says that). Instead, schools win by getting unapologetically clear on their pillars of value, telling human stories that create trust, and designing a digital journey that helps families actually feel the experience before they ever book a tour.

The conversation also gets practical — from why "digital-first rebrands" have flipped the traditional order of branding, to the canaries in the coal mine leaders should watch for (data silos, too many vendors, weak engagement cadence), and how to audit your strategy through Rob's simple framework: Purpose, People, Platforms, Process.

This is a must-listen for heads of school, admissions, marketing, and advancement teams who want to grow enrollment, improve retention, and build community by owning their story — authentically.

Show notes:

00:00 - Introduction to Rob DiMartino

03:25 - Tradition vs. innovation: honoring history without living in the past

07:19 - Brand vs. engagement: why relevance matters more than slogans

10:11 - Breaking the "small classes & great community" messaging trap

12:10 - Turning student outcomes into authentic digital storytelling

15:19 - Mission fit, admissions pressure, and the retention risk schools ignore

21:11 - Why schools shifted from agencies to owning their digital platforms

29:01 - Auditing your digital strategy: Purpose, People, Platforms, Process

31:31 - AI, demographics, and protecting a school's true value proposition

37:09 - Lightning Round

Learn more about Finalsite and Rob DiMartino: https://www.finalsite.com/

This episode is sponsored by REACH Boarding

This episode is sponsored by REACH Boarding, an award-winning, feature-rich boarding school management tool used by over 400 schools in five continents to manage risk, increase efficiency, and improve communication in boarding school management.

To learn more about REACH Boarding, its features and integrations, visit www.reachboarding.com

Empowering the Future of Independent Education & Boarding School Management

Thanks for tuning into this week's episode of Roll Call, don't forget to share your favorite episodes with your colleagues on social media to help us spread the word and help more education professionals stay at the forefront of independent education and boarding school management techniques to empower the future of the education environment.