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.