Founding Head of Engineering

Medley Learning; United States; On-site; USD 180,000 - 260,000; Full time

Benefits offered by this job

Founding equity

Impactful work in education

Strong backing from Workshop Ventures

Job summary

An innovative education technology company in the United States is seeking a Founding Head of Engineering to join their team. The role involves owning the technical foundation, architecting and evolving products, and building a top-tier engineering team. Ideal candidates will have 6+ years of experience, strong proficiency in TypeScript, React, and Node.js, as well as AI/LLM expertise. This is a unique opportunity to make a direct impact on millions of students' access to grade-level content while also holding founding equity in a growing company.

Qualifications

• 6+ years building software, architecting scalable systems, and shipping production-grade code.
• Hands-on experience building LLM-integrated products, including cost optimization.
• Experience managing engineers and building team processes.

Responsibilities

• Own the technical foundation and architect the product.
• Hire, mentor, and retain excellent engineers.
• Establish processes for code review, testing, and deployment.
• Build observability and scalable reliability across systems.
• Hire, mentor, and retain engineers; establish coding reviews, testing, deployment, and incident response processes.

Skills

Technical excellence

AI/LLM expertise

Strong TypeScript

React

Node.js

Cloud infrastructure

Tools

AWS

MongoDB Atlas

Docker

Terraform

Job description

About Medley Learning

Medley is a software solution that fosters inclusive, rigorous classrooms. Medley allows a classroom of diverse learners to 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 three 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.

What You’ll Do

• 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

Required Qualifications

• 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

Preferred Backgrounds

• 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

Our Tech Stack

• 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

Why Join Medley

• 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.