From Chalkboards to Checkbooks: How Jess Gartner Is Rewriting EdTech

In this episode of Capital Class , host Adam Giery sits down with Jess Gartner, founder of Allovue and current Vice President at PowerSchool, for an unfiltered conversation on the intersection of education, finance, and entrepreneurship. Jess shares her remarkable journey from classroom teacher to edtech trailblazer, driven by a relentless curiosity about one fundamental question: how are school resources allocated, and are we truly funding equity? The episode begins with Jess recounting her early days as a Baltimore City schoolteacher, where she quickly discovered the stark reality of underfunded classrooms. That experience sparked a decade-long mission to reimagine K–12 finance systems—culminating in the launch of Allovue and its eventual acquisition by PowerSchool in 2024. Jess and Adam explore the often overlooked complexities of school budgeting, the unsung heroism of district CFOs, and the emotional toll of entrepreneurship. With candor and conviction, Jess reflects on burnout, resilience, and the hard choices behind building a mission-driven company. She also unpacks why federal COVID-era funding didn’t transform education as some hoped and how we must reframe the conversation about what schools are expected to deliver. Key Moments 04:46 Solving the Student Achievement Gap 09:07 Evolving Role of Modern Schools 13:37 Teachers Subsidizing Classroom Resources 16:32 Public Sector Budget Efficiency 19:10 Balancing Extremes in Business 21:25 Embracing EdTech in Education 27:29 "Deep Problem Understanding through Interviews" 28:25 Understanding Data Gaps in Education 33:44 "Building Amidst Financial Constraints" 36:30 Entrepreneurial Vision and Persistence 39:52 School Budget Scrutiny Surges 41:44 Temporary Emergency School Funds Usage 46:26 Founder Reflects on Life Journey 48:38 Prioritizing Team and Mission Values 54:12 "Leading with Integrity and Resilience" 57:08 "Desert Sands: Otherworldly Experience" 59:04 "Capital Class Podcast Sign-off" Connect with Jess Gartner LinkedIn: Website:

You can listen to From Chalkboards to Checkbooks: How Jess Gartner Is Rewriting EdTech online on Radio and Podcast. Open the player on this page to stream the available audio.

From Chalkboards to Checkbooks: How Jess Gartner Is Rewriting EdTech is an episode from Capital Class by Adam Giery.

This episode is 59:37 long.

This episode was published on Jun 5, 2025.

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