Crossover

Head of Learning, 2 Hour Learning (Remote) - $200,000/year USD

Administration

Milan, Italy

Pubblicato: 29/04/2026

Heltid

Scade il 28/06/2026

Descrizione del lavoro

This role is for professionals ready to deploy AI at scale to redefine what students can achieve.


2 Hour Learning has built AI into the foundation of everything we do. We have reconstructed the learning model from first principles, integrating AI and breakthroughs in learning science to transcend the limitations of the conventional school day. The outcome? Students who consistently exceed expectations.


Our results speak for themselves: learners on our platform routinely earn 4s and 5s on five or more AP exams, post growth exceeding two years on annual MAP assessments, and surpass their own perceived limits. If you are driven by the prospect of delivering transformative outcomes at scale, 2 Hour Learning offers that opportunity.


In this position, you will function as the lead designer of our groundbreaking learning ecosystem for a dedicated school model spanning multiple campuses. Guided by an uncompromising focus on student success, you will leverage the full capabilities of AI to design hyper-personalized learning pathways tailored to each student's distinct needs, interests, and goals.


The role combines strategic data analysis with direct student interaction. You will examine learning analytics in depth, extracting critical insights that fuel exponential progress. Yet your work will extend beyond data review—you will engage directly with students to grasp their experiences, obstacles, and victories. This direct engagement will inform your identification of the precise motivational and pedagogical tactics needed to break through achievement barriers across all campuses.


You will lead a team of learning engineers, data scientists, and instructional designers tasked with executing your vision. Most importantly, you will advocate relentlessly for students, ensuring every decision, innovation, and strategy prioritizes their learning outcomes.


This represents a rare opportunity to apply AI to education in ways that fundamentally reshape what is achievable. Equipped with advanced learning analytics, the capacity to test pedagogical ideas at scale, and organizational support to challenge convention, you will pioneer new approaches daily.


The scope is expansive, the resources exceptional, and the mission essential. At 2 Hour Learning, we deploy AI not merely to improve grades—we aim to unlock human potential in full, all without relying on traditional classroom teachers.


If you are prepared to apply the most transformative technology of this era to the most foundational element of society, this is your opportunity. Bold vision, disciplined execution, and total commitment to student outcomes are essential. Those comfortable with the status quo should look elsewhere.


Join us at the forefront of the AI revolution in education. Together, we will not only influence the future of learning—we will build it.


Learn more about 2 Hour Learning at our website [https://2hourlearning.com/] and on the Future of Education Instagram page [https://www.instagram.com/futureof\_education/]. To see our model in action, visit Alpha [https://alpha.school/].


**What You Will Be Doing**

- Designing and iterating an AI-powered learning ecosystem that demonstrably exceeds traditional education outcomes, validated by concrete improvements in student performance metrics
- Interacting directly with students via virtual channels to capture their learning experiences, obstacles, and achievements, and translating these insights into ecosystem enhancements
- Analyzing platform data to identify actionable patterns and create high-leverage academic interventions grounded in AI/ML, learning science, and motivational research
- Fostering a culture of rigorous experimentation and evidence-driven decision-making, using data to unlock breakthrough improvements in student growth
- Collaborating with platform engineering, data science, and design functions to convert academic insights and student input into product refinements

**What You Won’t Be Doing**

- Wrapping traditional teaching models in AI technology. This role is not about digitizing classroom methods—we are rebuilding learning from foundational principles.
- Working with data alone. Regular engagement with K-12 students is expected, and their feedback will be treated as critical input from our primary customers.
- Seeking broad agreement before advancing bold ideas. You will drive a clear vision and build support through demonstrated, data-backed outcomes.
- Adhering to established educational norms. You will have the freedom to test unconventional strategies for motivation, assessment, and instruction.
- Viewing AI as a risk to education. In this role, you will embrace AI as a powerful enabler of learning transformation, not a challenge to be managed.

**Head Of Learning Key Responsibilities**
Lead the advancement of AI-powered, teacher-less education to achieve outstanding student results across multiple campuses. Integrate data analysis with ongoing student interaction to refine our learning ecosystem continuously, with success measured by AP exam scores and MAP assessment growth.


**Basic Requirements**

- Master's degree or higher in Educational Science, Learning Science, Psychology, Psychometrics, Instructional Design, or a related field
- Leadership experience in education or EdTech
- Experience applying AI technologies in an educational or professional context
- Experience designing and implementing AI systems for tasks such as content generation, data analysis, or adaptive learning
- Strong understanding of learning science principles and data-driven educational approaches
- Proven ability to communicate complex educational and technical concepts to diverse audiences
- Experience leading cross-functional teams and managing complex projects

**About 2 Hour Learning**
Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.


**With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.**
They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.


**2 Hour Learning is reprogramming learning for the AI era.**
**Here’s How They’re Fixing It.**
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!


**Working with us**
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.


Crossover Job Code: LJ-4549-IT-Milan-HeadofLearning.009

Länk för att ansöka: https://it.linkedin.com/jobs/view/head-of-learning-2-hour-learning-remote-$200-000-year-usd-at-crossover-4406935094

Dettagli del lavoro

Data di pubblicazione

29/04/2026

Località

Milan, Italy

Data di scadenza

28/06/2026

Livello di esperienza

Medelnivå

Lavoro da remoto

Helt Distansarbete

Luogo di lavoro

Milan, Lombardy

Metodo di candidatura

Website

Candidature

47

Azienda inserzionista

category

Administration

Località

Milan, Italy

Sede dell’azienda

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