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Broccoli AI is building AI teammates for contractors in plumbing, HVAC, and electrical services. The company has grown to $20M+ ARR in under two years and is backed by Khosla Ventures and Y Combinator. They partner with hundreds of contractors to replace fragmented software and manual work with AI that handles phone answering, appointment booking, customer follow-up, and revenue recovery while integrating with platforms like ServiceTitan.
As Head of Revenue Operations, you will build and lead a team across GTM Engineering, Program Management, Enablement, and Analytics. You'll report directly to the CRO and own the systems, tooling, processes, training, and operating rhythms of the revenue organization. A core part of this role is owning the AI roadmap for revenue—identifying where AI can eliminate busywork and sharpen decisions across the customer lifecycle, from prospecting and call prep through deal review, onboarding, renewals, and expansion.
Key responsibilities include:
- Developing and executing the AI roadmap for revenue operations, getting hands-on with tools to remove administrative burden from reps and CSMs
- Building, hiring, and coaching a multi-disciplinary team spanning GTM Engineering, Program Management, Enablement, and Analytics
- Partnering with Sales and Customer Success leadership on targets, territory design, capacity planning, quota setting, forecasting, and pipeline management
- Owning the CRM and GTM stack, data model, and integrations to ensure reps have accurate information and leadership has a single trusted view
- Designing onboarding, training, and certification programs to accelerate rep productivity
- Establishing operating cadences that keep the team aligned without excessive meetings
- Leading analytics and reporting on funnel health, conversion, retention, expansion, and rep productivity
- Staying close to the field by riding along on discovery calls, attending onboarding sessions, and spending time with customers' operations teams
You are a builder-leader who has scaled a revenue operations function and still enjoys hands-on work with workflows, automations, and dashboards. You are AI-native in your approach, using AI tools daily and having shipped AI-driven workflows that changed how teams operate. You are customer-first in your decision-making, prefer shipping working v1s quickly over perfecting plans, and take ownership of outcomes. You are rigorous and analytical, able to explain complex forecasts in plain language, and hold high quality standards. You are curious about the trades and home service businesses, and you learn quickly.
Qualifications:
- 10+ years of experience in Revenue Operations, Sales Operations, GTM Strategy, or a related field, with meaningful time in a leadership role
- Track record of leading and growing multi-disciplinary teams across GTM Engineering, Program Management, Enablement, and Analytics
- Hands-on experience applying AI tools and automation to sales and customer success workflows, with demonstrated impact
- Deep experience with GTM planning including targets, territories, capacity, forecasting, and pipeline management
- Strong command of CRM and GTM systems (Salesforce, HubSpot, or similar) and the data behind them
- Exceptional analytical skills and comfort working directly with data (SQL or similar a plus)
- Experience in a high-growth technology company strongly preferred; experience selling to SMBs, the trades, or home services is a plus
