Founding Head of Engineering, 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 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 as Founding Head of Engineering, joining a company with a working product in multiple districts, strong demand, and backing from Workshop Ventures.

You'll be hands-on from the start. You’ll take over a team of 3 engineers, then own the technical architecture, improve reliability and cost efficiency, and scale the team to 15-20 people as Medley grows. You'll partner with the CEO and Head of Product (once hired) on roadmap priorities, but your focus is building the engineering organization and shipping excellent software.

• Architect and evolve the browser extension, AI systems, and teacher/admin portal

• Make infrastructure and system design decisions

• Drive LLM cost optimization while maintaining quality

• Build observability to understand usage and maintain reliability at scale

• Hire, mentor, and retain excellent engineers

• Establish processes: code review, testing, deployment, and incident response

• Create a culture of ownership and shipping frequently and reliably

• Technical excellence: 6+ years building software, with proven ability to architect scalable systems and ship production-grade code

• AI/LLM expertise: Hands-on experience building LLM-integrated products, including cost optimization

• Modern stack proficiency: Strong TypeScript, React, Node.js, and cloud infrastructure (AWS preferred)

• Engineering leadership: Experience managing engineers, running sprints, and building team processes

• Startup orientation: Thrives in early-stage environments where you're hands-on coding while making strategic decisions

• Engineering leaders who've scaled teams through significant growth

• Technical leads at startups who've owned architecture end-to-end

• Experience with browser extensions or education technology

• Background optimizing LLM costs and latency at scale

• Full Stack TypeScript: WXT browser extension, React frontend, Node.js backend

• Data: MongoDB Atlas

• Infrastructure: AWS (Docker/ECS, S3), Terraform

• AI: Anthropic, OpenAI, Gemini, ElevenLabs

Founding equity: Significant stake reflecting your role building the company from the ground up.

Hard problems: Build AI systems at the intersection of LLM optimization, pedagogy, and scale.

Direct impact: Your work helps millions of students access grade-level content.

Strong backing: Workshop Ventures provides funding, operational support, and access to proven entrepreneurs.

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