School Success Lead

Workshop Ventures LLC

Job Overview

Location

USA (Remote)

Job Type

Full-time

Full Job Description

📋 Description

• Serve as the first School Success Lead at Medley Learning, building and managing trusted partnerships with K-12 school districts to ensure successful adoption and sustained use of the Medley browser extension.
• Onboard and support educators, multilingual leaders, and administrators through end-to-end implementation, including facilitating training sessions, guiding technical setup, and providing ongoing coaching to ensure seamless integration into daily instruction.
• Manage a growing portfolio of district and school partners, acting as the primary point of contact for implementation, troubleshooting, and strategic guidance tailored to multilingual learner needs.
• Monitor student and teacher engagement metrics, analyze usage patterns, and proactively identify barriers to adoption—then design and deliver targeted interventions to increase meaningful classroom impact.
• Collaborate directly with teachers and school leaders to understand real-time classroom challenges, ensuring Medley’s product development remains grounded in authentic educator experiences and pedagogical needs.
• Design, document, and scale repeatable implementation workflows, onboarding templates, and support systems to enable efficient growth of the School Success function as the customer base expands.
• Translate product usage into measurable educational outcomes by collecting qualitative and quantitative feedback from schools and aligning usage data with instructional goals for multilingual learners.
• Partner closely with Product and Engineering teams to surface customer insights, advocate for educator priorities, and influence product roadmap decisions focused on accessibility, scaffolding, and equity.
• Spend significant time in classrooms and district meetings to observe implementation firsthand, build authentic relationships with educators, and stay connected to evolving K-12 instructional realities.
• Represent Medley at educational conferences, district professional development events, and stakeholder meetings to strengthen brand credibility and expand outreach to new districts serving multilingual populations.
• Maintain detailed records of school interactions, implementation progress, and feedback loops using CRM tools and internal documentation systems to ensure continuity and knowledge sharing as the team grows.
• Act as a mission-driven advocate for equitable access to high-quality instruction, ensuring Medley’s tools serve historically underserved student populations with fidelity and cultural responsiveness.
• Contribute to the early shaping of company culture by helping define success metrics, team norms, and customer-centric practices in a high-growth startup environment.
• Support the expansion of Medley’s reach beyond multilingual learners to include students with disabilities in the coming year, adapting implementation strategies to meet new instructional needs.
• Navigate ambiguity and wear multiple hats in a small team, taking ownership of processes from conception to execution without relying on established frameworks.
• Maintain deep alignment with research-backed pedagogical practices while translating complex instructional strategies into accessible, actionable support for teachers using Medley’s tools.
• Champion inclusion by centering the voices of multilingual learners, their families, and educators in every aspect of the School Success function.

🎯 Requirements

• Deep Multilingual Education Expertise: Meaningful experience supporting multilingual learners in K-12 settings as an ESL Specialist, ELD Specialist, Multilingual Coordinator, Multilingual Director, or similar role; experience with language proficiency assessments strongly preferred.
• School Experience: 5+ years working in K-12 environments as a teacher, instructional leader, administrator, specialist, or similar role with direct familiarity with school operations and educator workflows.
• Facilitation and Relationship Building: Proven ability to build trust with diverse stakeholders and facilitate adult learning sessions, district meetings, and implementation workshops.
• Organization and Systems Thinking: Strong track record of creating structured, scalable processes to manage multiple parallel relationships and implementation timelines.
• Startup Orientation: Comfort with ambiguity, early-stage growth, and wearing multiple hats; ability to thrive in a fast-moving, resource-constrained environment.
• Passion for Educational Equity: Demonstrated commitment to serving underserved student populations, particularly multilingual learners and students with disabilities.

🏖️ Benefits

• Opportunity to join early at a mission-driven company with funding and district momentum, shaping product and culture from the ground up.
• Direct impact on improving access to learning for over 20% of U.S. K-12 students who are multilingual learners or have disabilities.
• Work remotely across the U.S. with flexible hours and autonomy over daily workflow.
• Collaborate with founders and leading education researchers to influence the future of equitable edtech.
• Support for professional growth through exposure to product development, district partnerships, and educational innovation.
• Inclusive work environment that values diverse backgrounds and lived experiences, with special encouragement for multilingual candidates and former multilingual learners.

Skills & Technologies

Senior

Remote

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Workshop Ventures LLC

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About Workshop Ventures LLC

San Francisco-based pre-seed venture capital firm founded in 2021 that invests $125k for 1% equity in early-stage B2B software startups across North America. It runs a rolling 12-week remote accelerator program emphasizing customer development, founder coaching, and fundraising support. The firm targets technical founders solving workflow, data, or infrastructure pain points for mid-market and enterprise customers. Portfolio includes companies like Tactic, Plural, and Fleet. Partners are former operators and repeat founders with exits to Google, Microsoft, and Atlassian.

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