Head of Sales - Training Software

We are seeking a talented seller to help build our growing sales organization. We sell driver / operator training and software focused on specific markets. Our company has been in operation since the 1980s, and has over 3,000 active customers.
This is a remote position and candidates can reside in any major US city.
This role splits focus between carrying a quota (40%)—targeting recurring revenue from commercial and government fleets—and coaching/managing a small team (60%). The team will handle higher-volume, lower-ticket sales prospects.
The ideal candidate is entrepreneurial, ready to build a sales playbook and lead by example. This is a first-line manager/sales position for a successful B2B sales rep with up to 12 years experience and some management experience. This position can advance to a VP role within the company.
Company Overview
Our markets span commercial fleets, state and local government and other organizations that have vehicles (ex: logistics & warehouses). We are best established with Private and Public Ambulance Fleets, Fire Departments, and Local Governments. We also have products focused on Forklifts and other specialty vehicles (school bus, straight truck, etc).
Key Responsibilities
"Player" Responsibilities (Individual Contributor)
Managing an individual book of business across government and commercial sectors: Prospecting, qualifying, and closing deals independently.
Developing partnerships with insurance carriers, risk management firms, safety networks, and membership organizations
On-the-job mentoring: Conducting live call reviews, shadowing AE meetings, and providing immediate feedback.
Required Qualifications
5 - 12 years of experience as an Account Executive or Sales Representative selling into public-sector, government-adjacent, or SaaS commercial organizations
Proven track record managing complex, multi-stakeholder deals
Experience with ambiguity and working in an entrepreneurial environment
Ability to coach and mentor junior sales talent, and grow into a more established leadership role over time
Bachelor’s degree required
Preferred / Nice-to-Have Qualifications
Background or direct experience in:
EMS or Emergency services (public or private)
Fleet safety or driver training
Compensation
Base salary $130K, total comp at plan $240K plus full benefits and car allowance.

Work arrangement
No