Founding Head of Product - Medley at Workshop Ventures

ABOUT MEDLEY LEARNING Medley Learning is building the AI that teachers and districts actually want in their classrooms – not generating lots of new, low-quality AI slop, but instead making it easier to implement established, strong pedagogy with high-quality content. 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. We’ve begun by supporting multilingual learners, and will expand to serve students with disabilities next year. The result is that all learners can access the same instructional materials, and teachers save hours and hours of prep. We are a mission-driven organization. In addition to building a thriving company, we are focused on enabling stronger student participation, reducing teacher burden, and achieving better outcomes in classrooms tasked with meeting increasingly diverse needs. 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. THE OPPORTUNITY 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, and 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, and 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, safety practices, classroom use cases, district expectations, and the competitive landscape, then translating that signal into an ambitious and responsible roadmap. WHAT YOU'LL DO - 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. REQUIRED 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. 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. PREFERRED BACKGROUNDS We are open to several paths, including: - 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. We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.