Co-Founding Head of Engineering, Medley Learning

Workshop Venture Partners • Boston, MA

3d

About The Position

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 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.
The Opportunity
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.

Requirements

• 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

Nice To Haves

• 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

Responsibilities

• Own the Technical Foundation
• 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
• Build the Engineering Team
• 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

Benefits

• 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.

What This Job Offers

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