Head of Sales

Probook•New York, NY

2d•Onsite

About The Position

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.

Requirements

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

Responsibilities

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