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: https://www.linkedin.com/in/jessgartner

Website: https://www.jessgartner.com/