Job Description

About Medley Learning

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 timeconsuming work of scaffolding to match each student's needs.

This is AI done right: not creating lots of new lowquality content, but instead adding justright supports to existing gradelevel content. After a successful spring pilot, Medley is expanding to paid district partnerships this fall. We initially built it for 5 million multilingual learners, and are adding support for students with disabilitiesultimately helping 20%+ of K-12 students. Learn more at medleylearning.com.

About Workshop Ventures

Workshop is a venture studio building and investing in startups in climate and education. Our team of entrepreneurs and operators leverages deep industry insights to identify urgent unsolved problems and supports founders to develop breakthrough innovations. We are led by Eleanor & Chad Laurans, cofounders of SimpliSafe, which they built and scaled into one of the largest home security companies in the country. Eleanor also brings deep education experience, having worked in and around districts for 20+ years, most recently as the CFO of Boston Public Schools.

The Opportunity

• Up to $3M in committed funding from Workshop
• Working early product actively used in multiple districts
• Paying customers and a strong pipeline of interested schools
• Deep partnerships with multilingual education thought leaders
• Handson support from Workshop's team of engineers, product leaders and business partners

You'll own significant equity and work alongside the founding CEO to build the technical foundation that becomes Medley's competitive advantage.

The Role

We're hiring a CTO to build the technical foundation for an AIfirst education platform. You'll work directly with the CEO to turn pedagogical practices into scalable systemsbuilding tools that transform how millions of students access gradelevel content.

You will:

• Architect the browser extension and AI systems that deliver realtime scaffolds to students, as well as the teacher and adminfacing management portal.
• Own technical strategy and make key architecture decisions.
• Reduce LLM costs significantly while maintaining product quality.
• Partner with the CEO on product roadmap and priorities. Build observability in the product to understand usage and increase impact at scale.
• Build and lead a highperforming engineering team.
• Stay current with AI developments and integrate them when they add real value.

Required Qualifications

• Technical excellence: 10+ years of software development experience with proven ability to architect scalable systems and ship productiongrade code
• AI & ML expertise: Deep understanding of LLM implementation, optimization, and cost management
• Startup experience: Demonstrated experience at a startup or as a founder. Thrives in earlystage, ambiguous environments
• Leadership: Can attract, mentor, and retain great engineers
• Mission alignment: Passion for education equity and improving outcomes for underserved students

Preferred Backgrounds

• Technical cofounders or founding CTOs at education or missiondriven startups
• Engineering leaders who've scaled products from early traction to significant adoption
• AI/ML engineers who've optimized LLM costs and performance at scale
• Chrome extension or browserbased application development experience
• Fullstack proficiency with deep expertise in at least one area
• Product development, management, and/or design experience a plus
• Experience delivering studentfacing or consumerfacing products at scale

Our Tech Stack:

Heres a glimpse of our current technology stack and what you can expect to work with at the start:

• Full Stack TypeScript
  • WXT + TypeScript Browser Extension
  • React Frontend
  • Node.js Backend
• MongoDB Atlas
• AWS - Docker in ECS, S3
• IAC Managed in Terraform
• Firebase & GCP services
• AI Tools: Anthropic, OpenAI, Gemini, ElevenLabs

Why Join Medley

• Meaningful cofounder equity: You'll own a significant stake in the business that reflects your role as a true cofounder building the company from the ground up.
• Solve hard technical problems: Build AI systems at the intersection of LLM optimization, pedagogy, and scale in one of the fastestmoving areas of technology.
• Direct impact at scale: Your work will help millions of students who currently lack adequate support to access the same gradelevel content as their peers.
• Exceptional backing and support: Workshop provides operational support, gotomarket expertise, and access to education leaders and investors. Workshop's founders are proven entrepreneurs who know how to scale startups successfully.

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

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