Head of Enterprise Sales

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.