Hire Ground

Former co-host Josh Czupryk returns to Hire Ground to check in on the education hiring market. He compared October job postings from 2024, 2025, and 2026, then asked chief people officers what was behind the numbers.

Here’s what he found. There are fewer open principal roles, which is good news for schools, though some of that drop comes from networks switching to pooled listings. Talent and development staff are staying in their roles longer. Operations and finance vacancies are rising as private-sector pay pulls that talent away. Early-career roles now make up 38% of charter postings, up from 32%, as organizations rebuild their bench.

Christina and Josh also talk about why Gen Z isn’t joining mission-driven pipelines the way earlier generations did, where AI helps and where it doesn’t, and how to protect student and staff data. Then they take on the question every hiring manager asks: when should you launch a search? Josh shares when job seekers are actually looking. Christina explains why Edgility Search now coaches fall clients to plan for finalists in February.

Ben Kornell has been a teacher, school leader, school board member, edtech CEO, and investor. He calls it a “lily pad journey” instead of a career ladder. He co-founded Edtech Insiders and invests through the Common Sense Growth Fund, so he talks with more education founders and operators than almost anyone.

Ben and Christina cover where AI is ready for schools today. Ben gives it a green light for operations, yellow for teacher tools, and red for anything student-facing. They also get into why behavior change, not the technology, is the hard part of any new tool, and why slow, steady growth beats the hockey stick in education.

Then they turn to talent. Ben explains which roles are merging into one, why so many chief of staff jobs are set up to fail, and what changes when your own team can build what you used to buy. He also offers a caution on student data privacy for a new generation of teacher-builders.

Learn more about Ben: benkornell.com
Edtech Insiders: edtechinsiders.org/podcast

Most nonprofit mergers happen because one organization is failing. Dr. Arun Ramanathan has led the other kind: strategic mergers between financially strong organizations looking to scale their impact.

Arun is CEO of PowerMyLearning, a national nonprofit reimagining how kids learn math. He previously led Pivot Learning through its merger with CORE and later UnboundEd, served as executive director of Education Trust–West, and was Chief Student Services Officer at San Diego Unified. He's also stepped into leadership after founders more than once.

In this conversation, Arun and Christina discuss:

• Why every part of the education ecosystem - from districts to policy shops to edtech - has its own culture and language, and why new leaders have to learn it fast.
• What nonprofit boards and CEOs miss about M&A, and why revenue thresholds matter for things like federal grants and government relations capacity.
• How PowerMyLearning used AI to transcribe and analyze young children's mathematical speech, a problem researchers have worked on for 25 years.
• Why transparency, privacy, and accuracy will separate AI edtech that lasts from AI edtech that gets banned.

Diane Tavenner has done the thing most founders talk about and few do well: she built something, grew it, and handed it off cleanly. Then she started over.

Diane co-founded Summit Public Schools, scaled it from one high school into a network across California and Washington, transitioned it to a successor, and is now CEO of Futre, a platform helping young people figure out what comes next. She joins Christina for a conversation that moves across all three chapters — leaving well, scaling well, and building for a generation whose expectations have shifted.

On succession:

• Why her board set a bar instead of hunting for a unicorn — and how that avoided the internal-candidate-versus-national-search trap that poisons so many processes
• The eight-month side-by-side onboarding and offboarding plan she built with her successor
• The outgoing leader's real last job: doing the hard, yucky things so the next CEO doesn't have to

On scale:

• What stays non-negotiable at every size, and what has to change
• Personalized learning plans for everyone — and why the "where do you see yourself" conversation should be bigger than someone's job
• Why engineering teams and teams of teachers have more in common than she expected, and why mission comes free in education but has to be built deliberately in a company

On what young people actually want:

• The two questions they ask first: what does it pay, and will this job still exist in ten years
• Why they're thinking about a good life, not a career — and Diane's invitation to leaders who find that framing uncomfortable
• Northeastern's co-ops, Minerva, and why apprenticeships still aren't a realistic pathway at scale

Find Futre at futre.me (yes, it's missing a vowel).

"Either you hired the wrong CEO, or you need to take a step back as a board."

Irene Shih has sat on both sides of the governance table, as Board Member and CEO, and she's direct about what each one owes the other. She's the Founding CEO of Pave HER Way, a new nonprofit empowering women and girls facing systemic barriers. Before that, she built Minds Matter Bay Area from the founding up so she's just lived both halves of the founder story: the leaving and the starting again.

What we get into:

• The founder's real problem isn't scarcity, it's abundance — too many good ideas, too many willing hands, and the discipline to pick three
• Why culture, not documentation, is what a successor actually inherits
• Irene's mother: an immigrant who took odd jobs, went to teach at a local Chinese school, and became an award-winning educator rewriting curriculum across Northern California
• Christina's mother: told she couldn't get a PhD with a child, and what happened when she said "we'll try it"
• Meeting people where they are — Irene's approach to developing talent, and why coaching has to feel like an offering
• How Irene will know at the twelve-month mark whether Pave Her Way is working

Season 1 Finale: Lessons from the Hiring Season — and What's Next for Hire Ground

Season 1 of Hire Ground started last August and ran the full length of the hiring season. In this finale, Christina Greenberg and Josh Czupryk close it out with the takeaways that actually stuck.

It's also a transition episode. Josh is stepping back as a regular host to finish his dissertation, handing day-to-day hosting to Christina and the Edgility Search team. He'll be back as a guest whenever he can pull himself away from coding qualitative interviews.

Before they sign off, they trade the season's most useful lessons:

• Run your search like a real estate listing. A messy hiring process signals that you're messy at your best and candidates read "days on market" the same way buyers do. Priority deadlines create real urgency and keep people moving.
• Timing beats a head start. This year's data was clear: searches launched in January and February ran the cleanest and drew the strongest pools, while roles posted before Thanksgiving mostly meant spinning wheels and multiple slates. Pre-source in the fall, but launch with intention.
• Negotiate the whole pie, not just salary. Post the range (it's the law in over 20 states, and it's the right thing to do), benchmark against what people actually earn rather than what gets posted, and coach candidates to name their one or two highest-leverage asks instead of stacking six. And once you've shaken on it, honor it. Walking back a deal is the fastest way to burn the credibility you'll need on Day One.

New episodes are back in your feed later this summer.

The Education System has a consistency problem. In this episode of Hire Ground, Christina Greenberg and Josh Czupryk sit down with a true titan of the field: Michael Moore. With a career spanning 52 years—from the classroom to the superintendent’s office to national leadership strategy—Moore has seen every initiative, reform movement, and pendulum swing the industry has produced.

What emerges from this conversation isn't a simple trip down memory lane. Instead, it is a clear-eyed interrogation of why K12 leadership feels more fragile today than at any point in the last half-century. Moore and Greenberg dive into the "hard math" of sustainability and the structural crises currently threatening the teacher pipeline.

In this episode, we explore:

• The Principalship Paradox: Moore contends that campus-level leadership has become so complex that even a seasoned superintendent might struggle to run a single building today. We discuss the new "policy storm" of social media, family dynamics, and shifting student needs that have fundamentally redefined the role.
• The Evolution of "Grow Your Own": How leadership development is moving away from structured, technocratic programs toward more organic, community-rooted pathways that prioritize relational trust.
• Austerity and its Aftermath: A look at the "policy storms" facing current districts. Moore offers a cautionary tale from the 2008 downturn, questioning whether districts are currently repeating the painful mistake of eliminating recruiting functions exactly when they need them most.
• AI vs. The Human Element: Is AI a near-term panacea for the teacher shortage, or simply a tool to reduce adult workload? Moore weighs in on where technology ends and the irreplaceable skill of a teacher begins.
• The 30% Pay Gap: We look at the rational barriers preventing talent from entering the profession and the "headcount math" required to actually move the needle on teacher compensation.

Michael Moore’s perspective is rare: he is a veteran who refuses to be cynical. He argues that the field’s deepest problem isn’t a lack of good ideas—it is a chronic failure to stay committed to them. This episode is a must-listen for any K12 talent professional looking for a reminder that while the work is harder than ever, we already have the map; we just have to stay the course.

Listen now and join the conversation on how we can finally start sticking with what works.

Brent Bushey has visited enough schools to know the difference between one that's working and one that isn't — and he says you can feel it before you see it. In this conversation, he shares what that feeling is made of, why the way we talk about teacher burnout may actually be making things worse, and what school leaders can do right now, inside whatever constraints they're working in, to build something worth staying for.

The K-12 world is changing faster than anyone can plan for, and the leaders who will thrive are those who can stay nimble without losing sight of what matters most: kids. In this episode, Christina sits down with Caitrin Wright, CEO of Silicon Schools Fund, to explore what great school leadership looks like at a moment when the pace of change is exponential.

From the emergence of differentiated teacher roles to a potential renaissance of social entrepreneurship in education, Caitrin shares the bright spots she's seeing across the country, and what they mean for how we hire, develop, and think about talent in K-12 today.

In this episode, host Josh Czupryk sits down with Dacia Toll, co-founder and co-CEO of CourseMojo, to explore what it really takes to lead schools effectively in a post-COVID world. From rethinking how we hire and retain talent to leveraging technology for better student outcomes, Dacia shares hard-won insights from decades at the forefront of education leadership — and a fresh vision for what's possible.