Head of School Success

Head of School Success at Workshop Venture Partners

We are looking to recruit a Head of School Success to lead the newly established School Success function at Medley Learning
, an AI‑driven educational technology platform from Workshop Venture Partners.

Compensation range: $100,000–130,000 per year, based on skills and experience.

Location: Cambridge, MA

Medley is a software solution that supports relational, rigorous classrooms for diverse learners. It delivers scaffolds for multilingual learners and students with disabilities while teachers control the supports. Medley’s AI adds rather than replaces content, and after a successful pilot it has been deployed by dozens of districts and is now expanding to support over 20% of U.S. K‑12 students.

Our work is guided by advisors including Eleanor Laurans, Dr. Margo Gottlieb, and Dr. Timothy Boals. The company is backed by Workshop Ventures, a venture studio committed to climate and education innovations.

You will be a founding team member, building the School Success function and culture from scratch, and shape the direction of a high‑growth company.

• Own the customer journey from onboarding to renewal and expansion.
• Build the operational backbone that enables Medley to scale.
• Bridge between our school partners and product teams, driving engagement, usage, and product love.

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

• Proven ability to drive engagement, adoption, and retention; build systems, track metrics, and deliver results.
• 5+ years working inside K‑12 schools; deep understanding of district operations, culture, and politics.
• Expertise in instructional implementation for multilingual learners and/or students with disabilities.
• Strong ability to build processes, documentation, and scalable operations.
• Player‑coach mentality: hands‑on execution while building toward team leadership.
• Product mindset: translate customer needs into actionable insights and envision new service offerings.

• Former educators who transitioned to consulting, operations, or customer success.
• Customer success leaders from EdTech companies with experience implementing instructional tools and scaling teams.
• Professionals who have worked with district leaders on instructional strategy and change management.

• A school insider: lived and breathed K‑12 education; knows how decisions are made and navigates bureaucracy.
• Detail‑oriented and strategic: tracks usage data & health metrics, cuts through noise to find what matters.
• Relationship builder: builds trust quickly with diverse stakeholders from teachers to district C‑suite.
• Efficient and scrappy: thrives in lean, fast‑moving environments, manages multiple priorities.
• Passionate about equity: committed to Medley’s mission to help underserved learners achieve grade‑level access.
• Collaborative: works seamlessly across Sales, Product, and Engineering.

• Direct impact at scale: help millions of students access high‑quality content.
• Build from the ground up: lead a growing customer success function in early growth stage.
• Mission‑driven team: work with founders & teammates committed to educational equity.
• Meaningful problems: bridge AI technology with classroom impact, turning pedagogical needs into product insights.

We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.

How to Apply
:
Submit application through Workshop Venture Partners portal. The position remains open until filled.