Chief Technology Officer

Company: Workshop Venture Partners
Location: Boston
Posted on: May 17, 2025

Job Description:

WorkHero is building the AI-powered back office for the skilled trades.Tens of thousands of small HVAC businesses across the U.S. are overwhelmed by administrative work. WorkHero pairs experienced office managers with custom-built AI tools to reduce administrative burden and help owners grow thriving businesses.Why it matters:

• We are helping local HVAC owners stay independent-growing their businesses and building meaningful wealth for themselves and their families.
• We are accelerating climate goals by expanding the capacity of small HVAC companies who are responsible for installing the millions of heat pumps our planet needs.
• We are proving that you can blend human expertise and AI to create exciting roles for our employees and exceptional results for customers.WorkHero is an early-stage company with exciting traction and strong support from angel investors and . Our advisors include Chad Laurans (founder of SimpliSafe, the $1B+ home security company) and Gerald Chertavian (founder of Year Up, a $200M per year non-profit).The Role:We're hiring a hands-on CTO to lead the development of our AI-first platform. You'll work directly with the founders to turn service insights into scalable systems-building tools that supercharge human workflows and transform small business operations. This role blends product intuition, deep engineering skill, and the drive to build an enduring company and high performing team.What You'll Do:In your first 6-12 months, you'll be deep in the code-building core systems, shipping features, and shaping the product alongside the founders. As we grow, your role will evolve into technical leadership, strategy, and team development. You'll also play a key role in the product development cycle, partnering closely with the Product team on day-to-day decisions and roadmap planning.You will:
  • Build AI-powered workflows using the latest in LLMs to amplify our office management team
    • Architect scalable, event-driven systems to support rapid growth
    • Pair with Product and Service teams to turn user feedback into actionable, tactical product improvements
    • Contribute to roadmap planning and help prioritize features that deliver real impact
    • Own the technical strategy and make high-leverage architecture decisions
    • Recruit, mentor, and lead a high-performing engineering team
    • Stay current with AI advancements and integrate them when they drive real-world valueWhat We're Looking For:We're looking for a rare hybrid: someone who can ship code today, lead a team tomorrow, and shape the AI-driven tools of the future.You have:
      • At least 10 years of software development experience
      • Experience managing and hiring for high performing teams
      • Experience with AI/ML, particularly in applying AI & ML to product development
      • Experience building products at a startup or as a founder
      • Full-stack proficiency, with deep expertise in at least one area
      • Strong communication and collaboration skills
      • Comfortable making decisions in uncertain environments
      • Passion for solving real-world problems for small businessesNice-to-haves:
        • Experience managing offshore or distributed teams
        • Experience with Event Driven Systems
        • Experience blending human and AI workflows
        • Knowledge of the HVAC industry or similar tradesOur Tech Stack:Here's a glimpse of our current technology stack and what you can expect to work with on day one.
          • Full Stack TypeScript
            • React Frontends
            • KoaJS Backend
            • CRXJS + TypeScript Browser Extension
            • React Native Mobile App
            • NX Monorepo with shared typing & libraries
            • MongoDB Atlas
            • AWS - Docker in ECS, S3, Hosted RabbitMQ
            • IAC Managed in Terraform
            • Firebase & GCP services
            • AI Tools: Anthropic, OpenAI, Gemini, DeepgramWhy Join Us:
              • Shape the future of a high-growth, venture-backed company as a core member of the leadership team
              • Be at the forefront of Human-AI systems, building transformative tech that scales small business support in ways previously unattainable
              • Build tech that makes life easier for thousands of small business owners
              • Competitive salary, meaningful equity, and full benefits
              • Flexible, remote-first work environment with autonomy to build your team
              • A mission-driven team that values impact and integrityWe are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.
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Keywords: Workshop Venture Partners, Medford , Chief Technology Officer, IT / Software / Systems , Boston, Massachusetts