Head of Engineering - WorkHero

Workshop Venture Partners • Boston, MA

2d • Hybrid

About The Position

WorkHero is building the AI-powered back office for the skilled trades, starting with the $50B+ HVAC industry. We have exciting traction and just closed a $5M seed round to expand our engineering and product organization, as well as add additional services. We’re looking for the technical leader who can help drive our next chapter of growth. About WorkHero Tens of thousands of small HVAC contractors—who keep our homes comfortable and enable the climate transition—are drowning in administrative work. Legacy software is clunky, full-time admins are costly, and owners spend over 20 hours a week on paperwork. WorkHero is changing that. Our platform combines agentic AI with human-in-the-loop operations to autonomously handle the back-office workflows that crush small business owners — from invoicing, permits, and rebates to pricebooks and warranty registration. Instead of forcing contractors to learn new tools, our AI agents do the work — executing complex administrative tasks end-to-end while human account managers provide oversight and operational coaching. The result: real work gets done, autonomously — helping small contractors grow profitable, resilient businesses and accelerating heat pump adoption nationwide. We’re proud to have the support of Navitas Capital, Workshop Ventures, York IE, and strategic angels including a former ServiceTitan executive. Our advisors include Chad Laurans (Founder of SimpliSafe) and Gerald Chertavian (Founder of Year Up). The Role We’re hiring a Head of Engineering to lead the development of our agentic back office 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 architectural expertise, product intuition, and the drive to build an enduring company and high performing team. What You'll Do In your first 6–12 months, you’ll set the technical direction of the platform, design core systems, and work closely with the founders on product and architectural decisions. You’ll still dive into code when necessary, but your highest leverage will come from designing scalable systems, aligning teams, and building the foundation for long-term growth. As we scale, your role will evolve to focus on technical strategy, organizational design, and developing high-performing engineering leaders.

Requirements

• 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 Haves

• Preference for those 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

Responsibilities

• Set the technical vision and architectural blueprint for our 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 us 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

Benefits

• 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, hybrid work environment
• A mission-driven team that values impact and integrity
• We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 1-10 employees