Medley Learning · 1 week ago
Founding Head of Engineering
United States
Full-time
Remote
Director/Executive
6+ years expMedley Learning is a software solution that fosters inclusive classrooms, designed to support diverse learners. As the Founding Head of Engineering, you will lead a team in architecting and evolving the technical foundation while scaling the engineering organization to meet growing demands.
Higher Education
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
Qualification
Required
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
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
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.
Company
Medley Learning
Medley does what you would do if you had unlimited time to support multilingual learners – automatically adding research-backed, customized scaffolds to your existing grade-level content.
2-10 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase