Head of School Success

Workshop Venture Partners • Boston, MA

11d

About The Position

Medley is a software solution that fosters inclusive, rigorous classrooms. Medley allows a classroom of diverse learners to all access the same grade-level content, with scaffolds designed specifically for multilingual learners and students with disabilities. Teachers control what supports are provided, but Medley does the time-consuming work of scaffolding to match each student's needs. This is AI done right: not creating lots of new low-quality content, but instead adding just-right supports to existing grade-level content. After a successful spring pilot, Medley is now being used by dozens of schools. We designed Medley to ultimately support the more than 5 million multilingual learners in U.S. schools, and our early pilots are validating that trajectory and are expanding to support students with disabilities, ultimately helping more than 20% of U.S. K–12 students. Learn more at medleylearning.com . We're proud to have the support of Workshop Ventures, a venture studio building and investing in startups in climate and education. Medley is guided by leading advisors including Eleanor Laurans (SimpliSafe co-founder, former CFO of Boston Public Schools), Dr. Margo Gottlieb (WIDA co-founder), Dr. Timothy Boals (WIDA co-founder), and district ML leaders who are actively shaping our pedagogical strategy. Join Medley Learning as Head of School Success at a pivotal growth moment: Join a company with momentum, leadership and funding Working product actively used in multiple districts Strong early demand and a growing pipeline of paying customers Deep partnerships with multilingual education thought leaders Backed by Workshop Ventures with both funding and also hands-on support from proven entrepreneurs As a member of the founding team, embrace an entrepreneurial opportunity to shape the direction of the company Build the School Success function and team from the ground up Work with the founding team to build culture, systems and processes that translate into a high performing growth team You'll be an architect and operator who designs scalable systems, drives engagement, while working directly with school and district partners to ensure they succeed with Medley Learning. In this role, you’ll build the foundation for growth and a high-performing team, ensuring that Medley's innovative product translates into measurable impact for millions of students. We're hiring a Head of School Success to own the entire customer journey from onboarding through renewal and expansion, while also building the operational backbone that enables Medley to scale. You'll be the bridge between our school partners and our product team, driving engagement, usage, and product love.

Requirements

• Customer Success Foundation : Proven ability to drive engagement, adoption, and retention. You build systems, track metrics, and deliver results.
• School Experience : 5+ years working inside K-12 schools. You understand district operations, culture, and politics.
• Education Domain Expertise : Deep knowledge of instructional implementation for multilingual learners and/or students with disabilities. You speak credibly with ELL Directors, Special Education leaders, and Chief Academic Officers.
• Systems Builder : You create processes, documentation, and scalable operations from the ground up.
• Player-Coach Mentality : Comfortable being hands-on now while building toward team leadership. You do the work and design the systems.
• Product Mindset : You think like a product owner, translating customer needs into actionable insights and envisioning new service offerings.

Nice To Haves

• Former educators who transitioned into consulting, operations, or customer success
• Customer Success leaders from EdTech companies with experience implementing instructional tools and scaling teams from early traction to significant adoption
• Professionals with experience working with district leaders on instructional strategy and change management

Responsibilities

• Act as the bridge between customers and product
• Build implementation and success systems from scratch
• Drive usage, engagement, and measurable student impact
• Lay the groundwork for a future team in Customer Success, Implementation, and Service Delivery
• Own the Customer Journey
• Own and manage a portfolio of district and school partners through the entire customer journey from handoff to renewal
• Lead end-to-end implementation: rostering/data import, setup, training, troubleshooting
• Drive usage through proactive account maintenance and customer health monitoring
• Identify and execute expansion opportunities within existing partners
• Build Medley’s Success & Operations Infrastructure
• Design and implement scalable processes for onboarding, usage monitoring, support workflows, and documentation
• Build customer success systems and processes in HubSpot to track metrics, manage workflows, scale and automate key operations
• Develop customer communications: newsletters, user resources, community content, and self‑serve materials
• Create internal playbooks, data dashboards, and health scoring models that guide future hires and team growth
• Cross Functional Leadership
• Partner with Sales on demos, renewals, and expansion conversations
• Triage customer feedback to Product and Engineering teams
• Support cross-functional operations wherever needed as part of a scrappy, fast-moving early-stage team

Benefits

• Direct impact at scale : Your work will help millions of multilingual learners and students with disabilities access the same grade-level content as their peers.
• Build from the ground up : Shape the customer success function at a company with strong early traction and proven product-market fit. As Medley scales, there is significant potential to grow.
• Mission-driven team : Work alongside founders and teammates who are deeply committed to educational equity and improving outcomes for underserved students.
• Meaningful problems : Bridge the gap between cutting-edge AI technology and real classroom impact, translating pedagogical needs into product insights.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1-10 employees