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Broccoli AI is building AI teammates for plumbing, HVAC, electrical, and other trade contractors. The company has grown to $20M+ ARR in under two years and is backed by Khosla Ventures and Y Combinator. Broccoli's AI handles phone answering, appointment booking, customer follow-up, and revenue recovery while integrating with platforms like ServiceTitan.
As Head of Enterprise Sales, you will build and lead the team selling to the largest multi-location operators in home and commercial services. This is a player-coach role where you own the enterprise revenue number, hire and develop Account Executives, and personally close major deals.
Key responsibilities:
- Own enterprise sales targets, build the plan to achieve them, and provide accurate weekly forecasts
- Hire, onboard, and coach a team of enterprise Account Executives
- Refine the sales motion for complex, multi-stakeholder deals across pilot, rollout, and expansion phases
- Lead executive relationships and negotiations, modeling best practices in discovery and deal strategy
- Partner with Customer Success to ensure pilots convert to company-wide rollouts with clear success metrics
- Bring customer insights back to Product and Marketing to build business cases and ROI stories
- Run disciplined operating rhythms with RevOps on pipeline reviews, deal reviews, and forecasting
- Stay connected to the field by visiting customer sites and understanding how large operations function
You are a player-coach who has built and led enterprise sales teams while still enjoying closing deals yourself. You navigate long, complex sales cycles with multiple stakeholders and maintain disciplined forecasting. You sell outcomes rather than features and only close deals you believe will succeed. You use AI tools daily in your work and expect your team to do the same. You take ownership of results and have built enterprise motions from scratch. You're curious about the trades industry and learn quickly.
Qualifications:
- 8+ years of B2B SaaS sales experience with a track record of closing six- and seven-figure enterprise deals
- Experience building, hiring, and leading a team of enterprise or strategic Account Executives
- Proven ability to run complex, multi-stakeholder sales cycles
- Strong forecasting and pipeline discipline with comfort using modern CRM and sales stack tools
- Experience in a high-growth technology company strongly preferred
- Experience selling to multi-location operators, home services, the trades, or vertical SaaS is a plus
