Head of Learning
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Worldwide
Fully-remote
full-time (40 hrs/week)
Flexible schedule
Long-term role

Head of Learning   $200,000 USD/year

Description

You should pursue this position if you are an academic leader who prefers to design the system rather than critique it from the sidelines. Your subject-matter fluency enables you to recognize high-quality learning experiences, your rigor allows you to codify that recognition into rubrics and AI-driven quality mechanisms, and your pragmatism empowers you to respond quickly to imperfect data. Student improvement matters to you, and you accept being evaluated on that metric.

2 Hour Learning pursues an objective the broader software and education industries seldom undertake. Teachers, textbooks, and the familiar scaffolding of traditional instruction are absent from the product. AI serves as the operational foundation. In this capacity, you leverage it to produce and refine learning content, architect interventions, oversee quality standards, and advance the platform continuously. The tempo resembles high-performance technology, consulting, or finance more than traditional education, and the reward is direct accountability for student outcomes in your subject across multiple campuses.

This position centers on operating a function. You will construct AI-powered enhancements to the learning ecosystem, react to student-performance data with focused interventions, produce evidence-grounded decision records, and lead a team measured against explicit benchmarks tied to MAP, AP, SAT, and ISEE performance. You will also collaborate closely with product, engineering, and data science teams to shape platform priorities. It suits someone who gravitates toward AI, conducts analysis independently, delivers under uncertainty, and accepts full ownership of results. It will frustrate anyone who favors consensus-driven timelines, minimal accountability, or the security of established systems.

You will serve as a key leader within the academics organization, wielding genuine influence over your subject's performance and the evolution of the broader learning infrastructure. Your colleagues will depend on your standards, judgment, and capacity to translate student data into action. If that prospect feels energizing rather than daunting, you are likely the candidate this role is designed for.

What you will be doing

  • Learning Ecosystem Enhancements — AI-generated refinements to subject-specific K–12 learning experiences spanning content, adaptive pathways, and student interventions, shaped by student feedback, analytics, assessments, and coaching observations.
  • Data-Driven Academic Interventions — Focused intervention strategies for underperforming students or cohorts, guided by MAP, AP, SAT, ISEE, and comparable performance metrics.
  • Student Performance Decision Records — Repeatable, evidence-supported decisions that document actions taken to improve student performance, backed by dashboards, analytics, tickets, surveys, coaching interactions, and assessment results.
  • Learning Ecosystem Improvement Specs — Implementation-ready specifications for product, engineering, and data science enhancements, featuring problem definitions, supporting evidence, anticipated student impact, and acceptance criteria.

What you will NOT be doing

  • Repackaging traditional education in an AI wrapper. This isn't about replicating classroom instruction via screens – we're fundamentally reimagining learning from the ground up.
  • Analyzing data in isolation. You'll be expected to regularly engage with K-12 students, valuing their feedback as essential input from our paying customers.
  • Waiting for consensus to push boundaries. You'll champion a bold vision and rally others around data-driven results.
  • Sticking to conventional methods. You'll be free to experiment with innovative approaches to motivation, assessment, and instruction. 
  • Fearing AI's impact on education. Here, you'll harness AI as an exciting tool to revolutionize learning, not as a threat to be mitigated.

Key responsibilities

Drive innovation in AI-powered, teacher-less education to deliver exceptional student outcomes across multiple campuses. Blend data analytics with regular student engagement to continuously optimize our learning ecosystem, as measured by AP exam performance and MAP assessment growth.

Candidate requirements

  • Master's degree or higher in Educational Science, Learning Science, Psychology, Psychometrics, Instructional Design, or a related field
  • At least 5 years of experience in academic or EdTech leadership roles, with direct people management responsibility (hiring, performance evaluation, coaching, termination decisions)
  • Demonstrated experience using AI tools as part of day-to-day professional workflows, and willingness to rely on AI extensively to improve academic and operational outcomes.
  • Strong understanding of learning science principles, such as Cognitive Load Theory and Mayer's Multimedia Principles, and data-driven educational approaches

Meet a successful candidate

Watch Interview
Guilherme Colombo
Guilherme  |  VP Strategy & Operations
Brazil

Are you waiting for a shot at the big leagues? This VP of Strategy and Operations proved that he was ready for so much more when he aced Cro...

Meet Guilherme

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

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
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
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About the role

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.