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Head of Sales
Job
Probook
New York, NY (In Person)
Full-Time
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81
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Job Description
Who We Are Probook is the AI dispatcher for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate. Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 band-aid fix and a $20,000 system replacement. By automating previously high-touch workflows around the clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation. The Role This is not a sit-back leadership role. The Head of Sales will be in the trenches, leading from the front, jumping into deals, and helping shape the playbook as Probook AI scales. You will oversee a team of Account Executives across mid-market and enterprise accounts while building the structure, rigor, and momentum needed to accelerate growth. The ideal candidate is a true player-coach: someone who thrives in fast-paced environments, loves winning deals, and knows how to turn a strong team into a high-performing, scalable sales organization. What you will do Own and drive revenue performance across Commercial and Enterprise segments Lead, coach, and scale a team of Account Executives Support and close complex, high-value deals directly Lead deal strategy, multi-threading, negotiation, and execution Run disciplined deal reviews, pipeline inspections, and forecasting cadences Elevate team performance through hands-on coaching and accountability Improve outbound motion and pipeline generation in a scaling environment Build and refine repeatable sales processes while maintaining speed and agility Partner closely with Marketing, Product, and Customer Success to align go-to-market efforts Hire, onboard, and develop top-performing sales talent Qualifications Experience leading B2B SaaS sales teams in high-growth environments across mid-market and enterprise segments Proven track record of driving revenue growth and scaling teams Strong experience managing complex, multi-threaded sales cycles Player-coach mindset with a hands-on, execution-oriented approach Operational rigor in forecasting, pipeline management, and sales process development Ability to balance speed and structure in a scaling organization Strong coaching instincts and a passion for developing talent Why Join Probook?