Founding Head of Product

Role Description

This is a special opportunity to join a young company with momentum and funding, but early enough to have a tremendous impact on the product direction, company strategy, and organizational culture. We are looking for a hands-on leader who is eager to dig into critical, detailed decisions and, at the same time, can serve as a thought partner to the CEO, helping build Medley into a leader in the AI edtech space.

You will be one of the CEO’s closest partners in shaping Medley’s product vision, company direction, and long-term perspective on how AI should support learning in classrooms. This is a true player/coach role. You will:

• Write specs
• Run research
• Define success metrics
• Make hard prioritization calls
• Work closely with engineering to ship

Over time, you will build and lead the product team, but in the early days, you should be energized by doing the work yourself. You are joining a team of six that will grow to ten by summer, with fresh pre-seed funding, strong district demand, and a plan to serve more than 15,000 multilingual learners this school year.

In the coming year, Medley will extend its work to serve students with disabilities. Together, multilingual learners and students with disabilities represent more than 20% of U.S. K-12 students, and both groups have been historically underserved by edtech.

We are approaching special education deliberately. This is not simply a matter of repackaging our multilingual learner product for a new segment. Special education involves:

• Diverse instructional needs
• Distinct purchasing dynamics
• Compliance requirements
• A high bar for trust with districts, educators, students, and families

You will also help Medley stay ahead of the AI curve. That means:

• Tracking changes in model capabilities
• Monitoring safety practices
• Understanding classroom use cases
• Keeping up with district expectations
• Translating that signal into an ambitious and responsible roadmap

Qualifications

• Student and Teacher Empathy: Classroom reality isn't abstract to you. You've designed for or worked closely with kids, teachers, or educators.
• Product Craft: You have experience building and shipping products that users value. You can speak clearly about the tradeoffs you made and what you'd do differently now.
• AI-Native Product Judgment: You use AI fluently in your own work and have strong judgment about where it belongs in high-trust classroom environments.
• User Research Instincts: You know how to learn from teachers and students and turn what you hear into sharper roadmap choices.
• Clarity of Thought: You make ambiguity easier to navigate. You can write crisp specs, explain tradeoffs, and help others understand what matters and why.
• Commercial Orientation: You understand that strong K-12 product decisions must account for adoption, implementation, renewals, procurement, and stakeholder trust.
• Startup Orientation: You thrive in early-stage environments, embrace ambiguity, and stay hands-on even in senior roles.

Requirements

• Former teachers, school leaders, or education operators who transitioned into product and have developed strong product craft.
• Product leaders from edtech companies who have shipped instructional, student-facing, accessibility, or classroom workflow products.
• Product builders who have worked on AI-enabled products and understand how to balance speed, quality, safety, and trust.
• Product leaders from consumer or consumer-like companies who have shipped products that kids, families, or non-technical users choose to use regularly.
• Multilingual candidates, former multilingual learners, or candidates with deep personal or professional experience in multilingual communities are especially encouraged to apply.

Benefits

• Opportunity to shape product direction and company culture.
• Work in a mission-driven organization focused on educational outcomes.
• Join a growing team with strong district demand.

Company Description

Medley Learning is building the AI that teachers and districts actually want in their classrooms. We do this through a browser extension that wraps around all of a classroom’s existing digital content, adding reading and writing scaffolds customized to each student. Our approach is grounded in research-backed practices and is already being used by over 20 districts across the US.

Medley is led by CEO Brandon Cardet-Hernandez, a former multilingual learner who has worked across K-12 as a teacher, turnaround principal, policy advisor, and edtech leader. The company is backed by Workshop Ventures and advised by leading researchers.