Founding Head of Product - Medley

Workshop Venture Partners • Boston, MA

1d

About The Position

Medley Learning is developing AI solutions for classrooms, focusing on enhancing established pedagogical practices with high-quality content. Their primary product is a browser extension that provides customized reading and writing scaffolds for digital content, initially supporting multilingual learners and soon expanding to students with disabilities. The company is mission-driven, aiming to improve student participation, reduce teacher workload, and achieve better outcomes, with its approach grounded in research and currently used by over 20 districts across the U.S. Medley is led by CEO Brandon Cardet-Hernandez and backed by Workshop Ventures.
This role offers a unique opportunity to significantly influence product direction, company strategy, and organizational culture within a young, funded company. The ideal candidate will be a hands-on leader, capable of making detailed decisions while also serving as a strategic partner to the CEO in shaping Medley's product vision and long-term AI strategy for education. It is a 'player/coach' role, requiring direct involvement in writing specifications, conducting research, defining success metrics, making prioritization calls, and collaborating closely with engineering to ship products. While the initial phase will be hands-on, the role is expected to evolve into building and leading a product team. The company is currently a team of six, projected to grow to ten by summer, with pre-seed funding and strong demand, aiming to serve over 15,000 multilingual learners this school year.
In the coming year, Medley plans to extend its services to students with disabilities, a demographic, along with multilingual learners, that represents over 20% of U.S. K-12 students and has been historically underserved by edtech. This expansion will be approached deliberately, recognizing the distinct instructional needs, purchasing dynamics, compliance requirements, and the necessity of building trust within the special education community. Additionally, the role involves staying current with AI advancements, including model capabilities, safety practices, classroom use cases, district expectations, and the competitive landscape, and translating these insights into an ambitious and responsible product roadmap.

Requirements

• 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. You follow where AI capabilities are heading, but you care more about building useful, reliable, and responsible products than chasing novelty.
• 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, separate signal from noise, and help engineers, educators, executives, and district partners 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.

Nice To Haves

• 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.

Responsibilities

• Own Product Vision and Roadmap: Define and prioritize the roadmap, balancing student outcomes, teacher needs, and district priorities while maintaining a high-quality bar.
• Stay Close to the Classroom: Spend time with students, teachers, and district leaders to understand their needs and keep the product grounded in classroom reality.
• Lead the Expansion into Special Education: Build and sequence the special education roadmap to strengthen Medley’s core multilingual learner product.
• Ship with Engineering: Partner closely with Engineering to turn ideas into shipped features, building a delightful user experience and interface for both students and teachers.
• Define Product Metrics and Operating Cadence: Establish key product metrics and operating rhythms that guide decisions and scale a strong product organization.
• Build and Lead the Product Team: While the first year will be scrappy and hands-on, over time, you will build a product team that drives adoption, retention, and impact.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed