Head of Sales

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?

• The Tailwinds: $700B industry with clear tailwinds: AI adoption, labor shortages, and generational transitions creating demand for operational modernization. We are defining the category, not fighting for share.

• The Traction: $XXM ARR in 18 months. Product-market fit proven; now we're scaling.

• The Team: <60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).

• The Greenfield Ownership: You own the outcomes, not just the relationships. And we have a lot of strategic accounts that need owning.

Compensation & Benefits

• Equity: Meaningful early-stage equity

• Health: Comprehensive medical, dental, and vision

• Perks: $500 monthly Ramp card for commuting, meals, gym, etc. (plus $25 in nightly meal delivery credit) and really good office snacks

• Access: Direct access to world-class investors and advisors