Workshop Venture Partners
Founding Head of Engineering, Medley Learning
Workshop Venture Partners, Boston, Massachusetts, us, 02298
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.
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.
We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.
#J-18808-Ljbffr
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.
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.
We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.
#J-18808-Ljbffr