School Success Lead

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 company strategy, organizational culture, and how schools experience Medley. We are looking for someone who is excited to work directly with educators and district leaders, build trusted relationships, and help shape the foundation of Medley’s School Success function as we scale. You will be our first School Success Lead and one of the earliest members of the Medley team. This role sits at the center of implementation, customer partnership, and educational impact. You will work directly with schools to ensure teachers and leaders successfully adopt Medley and translate product usage into meaningful classroom outcomes. You are joining a small team that will grow meaningfully over the next year, with strong district demand, an expanding customer base, and plans to support thousands more multilingual learners in the coming school year. This role can also be an exciting opportunity for educators looking to transition into edtech. We believe some of the strongest candidates may come directly from schools and districts. What You’ll Do Build Trusted School Partnerships: Manage a portfolio of school and district partners, serving as a trusted thought partner to teachers, multilingual leaders, and administrators throughout onboarding and implementation. Facilitate High-Impact Implementation: Lead onboarding sessions, support educators during implementation, facilitate training, and ensure schools successfully adopt Medley in classrooms. Drive Usage and Educational Impact: Monitor engagement and implementation patterns, identify opportunities for support, and help schools translate product usage into meaningful outcomes for students. Create Systems that Scale: Build repeatable processes, documentation, and internal workflows that support a growing portfolio of partnerships and future team growth. Stay Close to the Classroom: Spend meaningful time with educators and school leaders to understand their challenges and ensure Medley remains grounded in classroom realities. Partner Across Teams: Work closely with Product and Engineering to surface customer insights, advocate for school needs, and help shape future product direction. Required Qualifications Deep Multilingual Education Expertise. You have meaningful experience supporting multilingual learners within K-12 schools. This could include experience as an ESL Specialist, ELD Specialist, Multilingual Coordinator, Multilingual Director, bilingual program leader, or similar role. Experience administering or closely supporting language proficiency assessments is strongly preferred. School Experience. You have spent 5+ years working in K-12 environments as a teacher, instructional leader, administrator, specialist, or similar role. You understand how schools operate and can quickly establish credibility with educators and leaders. Facilitation and Relationship Building. You know how to build trust across diverse stakeholders and feel comfortable facilitating conversations and sessions with adults. Organization and Systems Thinking. You naturally create structure, manage details effectively, and can stay organized across many moving pieces and relationships. Startup Orientation. You thrive in early-stage environments, embrace ambiguity, and enjoy rolling up your sleeves to solve problems. Preferred Backgrounds We are open to several paths, including: Former teachers or school leaders transitioning into their first edtech role Educators with deep multilingual learner expertise and implementation experience Customer Success or Implementation professionals with strong school-based backgrounds Professionals who have worked closely with district multilingual programs and instructional leaders Candidates with personal or professional multilingual experiences Multilingual candidates, former multilingual learners, or candidates with deep personal or professional experience in multilingual communities are especially encouraged to apply. Why Join Medley Medley is building products for multilingual learners and students with disabilities, populations that together represent more than 20% of U.S. K-12 students and have historically been underserved by edtech. You’ll join early, work directly with founders and help shape a product that improves access to learning for students nationwide. We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.