Head of Enterprise Sales

About Broccoli 🥦 At Broccoli, we're building AI teammates for the people who build and maintain our world. We partner with plumbing, HVAC, and electrical contractors, the hardworking businesses that keep homes and communities running, and replace fragmented software and repetitive manual work with AI that actually gets the job done. Our AI teammates answer phones, book appointments, follow up with customers, recover missed revenue, and help contractors deliver exceptional customer experiences, all while integrating seamlessly with platforms like ServiceTitan. Before we wrote a single line of code, we visited more than 140 contractors to understand how these businesses truly operate. That firsthand experience shaped everything we've built. Today:

• Hundreds of contractors rely on Broccoli every day.

• We've grown to $20M+ ARR in under two years.

• We're trusted by everyone from independent contractors to some of the largest private equity backed operators in the home services industry.

• We're backed by Khosla Ventures and Y Combinator.

We're still just getting started.

About this role We're looking for a Head of Enterprise Sales to build and lead the team that brings Broccoli to the largest operators in home and commercial services: multi-location trades brands operating across Plumbing, HVAC, Electrical, Pest Control, and more. You'll own the enterprise number, hire and coach a team of Account Executives, and help design the motion for long, multi-stakeholder deals where cross-functional teams all need to say yes. This is a player-coach role: you'll set the strategy, and you'll also be in the room closing our most important deals.

What you'll do

• Own the enterprise number. Set targets with leadership, build the plan to hit them, and forecast accurately every week.

• Hire, onboard and coach a team of enterprise AEs.

• Continuously refine how we find, qualify, pilot and close multi-location, complex operators, from first meeting through security review, pilot, rollout and expansion.

• Lead executive relationships and complex negotiations, and model what great discovery and deal strategy look like.

• Partner with Customer Success so that a first set of locations turns into a company-wide rollout, with clear success criteria defined up front.

• Bring what you hear from enterprise buyers back to Product and Marketing, and help build the business case, ROI story and references that large operators need.

• Run a tight operating rhythm by partnering with RevOps on pipeline reviews, deal reviews, forecasting and the tooling that keeps the team focused on selling.

• Stay close to the field. Ride along, visit call centers and dispatch floors, and learn how these large operations actually run.

Who you are

• A player-coach. You've built and led an enterprise sales team, and you still love running a deal yourself.

• A disciplined closer. You know how to navigate long cycles with many stakeholders, and your forecasts hold up.

• Customers first. You sell outcomes, not features, and you only close deals you believe will succeed.

• AI-native in how you work. You use AI tools daily to prep, research and follow up, and you expect your team to do the same.

• An owner. You take responsibility for the team, and you’ve built an enterprise motion from zero before.

• Curious about the trades. You want to understand how our customers make money, and you pick things up fast.

Qualifications

• 8+ years of B2B SaaS sales experience, including a track record of closing six- and seven-figure enterprise deals.

• Experience building, hiring and leading a team of enterprise or strategic AEs.

• Proven ability to run complex, multi-stakeholder sales cycles.

• Strong forecasting and pipeline discipline, and comfort with a modern CRM and sales stack.

• 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.