Medley Learning is hiring a Chief Technology Officer for WorkHero, an AI-powered back office platform for skilled trades. As a hands-on CTO, you will set the technical vision, design scalable systems, and build the engineering team from the ground up. You will work directly with the founders on high-impact product and architectural decisions.
What You'll Do
- Set the technical vision and architectural blueprint for the platform and workflow engine.
- Design scalable, event-driven, AI-enabled systems that support rapid growth and complex workflows.
- Partner closely with Product and Operations to prioritize high-leverage features and define the technical roadmap.
- Make high-impact architecture and build vs. buy decisions that set the company up for the long term.
- Establish engineering best practices, code quality standards, and technical processes that enable speed with stability.
- Recruit, mentor, and grow a high-performing engineering team and future technical leaders.
- Ensure engineering efforts align with company goals, performance metrics, and operational realities.
What We're Looking For
- 10+ years of software development experience with deep architectural or systems design leadership.
- Experience owning technical direction or platform strategy at a startup or high-growth company.
- Proven ability to build and lead high-performing engineering teams.
- Experience making high-leverage technical decisions (architecture, infrastructure, build vs buy, scalability, data, AI integration).
- Ability to create process, clarity, and structure without slowing down innovation.
- Excellent communication and collaboration skills across technical and non-technical teams.
- Comfortable making decisions in ambiguous, fast-moving environments.
- Passion for solving real-world problems and building systems that unlock human potential.
Nice to Have
- Located in greater Boston area or willing to relocate.
- Experience scaling engineering orgs (from early stage to multiple teams or layers of leadership).
- Experience with event-driven or workflow-based systems.
- Experience blending human + AI collaboration in products or operations.
- Knowledge of the skilled trades, HVAC, or similar service industries.
Technical Stack
- Typescript Frontend & Backend with React & Koa in NodeJS
- NX Monorepo with shared typing & libraries
- MongoDB Atlas
- AWS - Docker in ECS, S3, Hosted RabbitMQ
- IAC Managed in Terraform
- Firebase Auth & GCP services
- AI Tools: Anthropic, OpenAI, Gemini, Deepgram
Team & Environment
You will be a core member of the leadership team and report directly to the founders.
Benefits & Compensation
- Competitive salary
- Meaningful equity
- Full benefits
- Flexible, hybrid work environment
Work Mode
This is a hybrid position based in the Greater Boston area.
We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.
