Head of Engineering

About Broccoli Broccoli is building the AI operating system for home service businesses. We work with plumbing, HVAC, and electrical contractors — the people who keep homes running — and we replace fragmented tools and manual workflows with AI agents that actually do the work. Our AI assistants answer phones, book jobs, follow up with customers, and drive revenue — fully integrated into systems like ServiceTitan. We started by going door-to-door, meeting 100+ contractors, and understanding how these businesses actually run. That shaped everything we’ve built. Today: Hundreds of contractors use Broccoli to run their front office We’ve grown from $0 → millions in ARR in under a year We’re trusted by both single-location operators and the largest PE-backed roll-ups Raised $25M+ from Khosla Ventures and YC Head of Engineering @ Broccoli We’re looking for a Head of Engineering to build and lead a high-performing engineering org that can ship ambitious product outcomes with speed, quality, and accountability as we scale. You’ll own the health, output, and growth of the engineering team — making sure the right people are in the right roles, the management layer is strong, and recruiting, culture, and execution all reinforce each other. This is not a “headcount first” role: you should be obsessed with motivating and getting maximum leverage out of the current team and be willing to make hard calls when needed. You will also set the pace by example — willing to dive into the work, do what it takes during critical moments, and hold the bar high for yourself and the team. What You’ll Do Build and lead a high-performing engineering organization that can ship ambitious product and infra work with speed, quality, and accountability Partner closely with the CTO on technical strategy, architecture, and roadmap prioritization Partner closely with the CEO & CTO to communicate company vision and strategy Own engineering execution and deadlines Build a culture where high performers are energized — people feel real ownership, are recognized and rewarded for impact, and are motivated to do the best work of their careers here AI-first: You’re bullish on AI and always looking for ways to push velocity through AI-assisted workflows Own engineering recruiting end-to-end with the CTO and People team Work "in the trenches" with the team: we're in the office 5 days a week What You’ll Bring 8+ years of engineering experience 3+ years of leadership experience with 15-40 member engineering teams Experience building and scaling an engineering org Strong people leadership skills: you’ve hired, leveled, developed, and retained high-performing engineers and managers Clear and concise communication; you create alignment, set context, motivate teams, and make decisions in the face of ambiguity Bonus: Head of engineering experience at Series A - Series C startup Broccoli is an equal-opportunity employer and complies with all applicable federal, state, and local fair employment practice laws.