Head of School
$400,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Multiple Locations, US
Semi-flexible schedule
In-person
full-time (40 hrs/week)
Long-term role

Head of School   $400,000 USD/year

Description

Elite education revolutionaries wanted: Can you transform demanding parents into fierce advocates for AI-powered learning?

We're seeking an exceptional leader with commanding presence to spearhead 2 Hour Learning's educational revolution. Our model replaces traditional 6-hour school days with 2 hours of AI-powered learning—a transformation that demands someone who can convert sophisticated skepticism into unwavering support.

This role requires a strategic communicator who thrives in high-stakes environments, someone who sees resistance as an opportunity to demonstrate value. You'll be the authoritative voice of our movement, equally effective in boardroom presentations, media interviews, and parent meetings. Your ability to maintain uncompromising standards while building advocacy movements will determine our success in reshaping education for the future.

What you will be doing

  • Command high-stakes presentations that convert sophisticated skeptics into vocal advocates
  • Build and activate networks of influential parent champions who drive our narrative
  • Design scalable systems that transform individual parent wins into compelling proof points
  • Implement sophisticated feedback mechanisms that identify parent concerns before they escalate
  • Lead critical media interactions and shape public narratives around our revolutionary approach
  • Create strategic opportunities to showcase our transformative educational impact

What you will NOT be doing

  • Managing traditional parent-teacher associations or conventional school committees
  • Organizing social events without clear strategic advocacy objectives
  • Compromising our educational model to accommodate influential parents
  • Taking reactive approaches to parent concerns instead of proactively shaping narratives

Key responsibilities

Transform our parent community into a powerful advocacy engine by building systematic approaches that scale parent champions across campuses while maintaining our uncompromising commitment to educational excellence.

Candidate requirements

  • Must be based in or willing to relocate to Austin, TX
  • 7+ years converting influential stakeholders into advocates (experience as Head of Customer Advocacy, Chief Communications Officer, Chief Development Officer, VP of Enterprise Sales, Director of Community Relations, or Change Management Consultant)
  • Exceptional executive presence with proven ability to command sophisticated audiences
  • Demonstrated success in high-stakes communications (media appearances, board presentations, crisis management)
  • Proven track record building and scaling advocacy communities from inception
  • Ability to uphold policies with powerful stakeholders while strengthening relationships
  • Deep conviction that educational transformation requires unwavering commitment to innovative methods

Meet a successful candidate

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Chris Hayes
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Applying for a role? Here’s what to expect.

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Chat-style
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STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
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STEP 5

Pass
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Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About the role

About Crossover

What you will learn

While we require your proven expertise in building influential communities and navigating complex stakeholder relationships, you'll apply these skills at the forefront of educational transformation. You'll pioneer how AI revolutionizes K-12 education, shape how parents and educators reimagine learning, and lead the most significant change in education delivery since the classroom's invention. You will write the definitive playbook for how forward-thinking schools build parent advocacy in the AI age.

Work examples

The potential impact of this role is best illustrated through what success will look like:

After a challenging meeting with an accomplished CEO parent questioning our unconventional schedule, you transform her from skeptic to champion. She now hosts dinner parties convincing other parents to embrace our approach, sharing concrete examples of her child's success.

When concerned parents start a discussion group about AI in education, you proactively create a compelling presentation incorporating success stories and research data. Your authoritative delivery transforms potential criticism into powerful advocacy, with parents routinely sharing your presentation with prospective families.

Your systematic approach to parent engagement builds networks of advocates across every grade level. When new families tour the school, they meet with current parents who articulately champion our model. Your advocacy systems are so effective that parents independently organize information sessions in their communities.

Most importantly, you transform parent concerns into opportunities to strengthen conviction in our model. Your executive presence means you're not just maintaining relationships—you're building a movement of parents who are betting their children's futures on our educational revolution.

Success means creating communities where parents become our most powerful advocates because they've witnessed the transformative potential of our approach. They champion our vision to their networks, drive growth across campuses, and partner with us to advance education.

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Why Crossover

School sucks. So we’re fixing it.

The education Olympics

The education Olympics

It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game. 

Salary without side gigs

Salary without side gigs

Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.

Skills make the grade

Skills make the grade

Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.

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