Head of Sales – Player-Coach, Fleet Safety Training

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop a nationwide pipeline across both public-sector and commercial accounts

• Identify, qualify, conduct discovery, engage stakeholders, and secure new business

• Promote safety training, compliance, and software-enabled training solutions

• Oversee sales opportunities typically ranging from $5,000 to $20,000, with larger deals approaching approximately $75,000

• Collaborate with senior stakeholders in safety, training, fleet management, finance, and executive roles

• Establish partnerships with insurance, risk, safety, membership, and industry organizations

• Represent the company at trade shows and industry conferences

• Mentor junior Account Executives and Sales Development Representatives through call evaluations, deal strategies, shadowing, and constructive feedback

• Enhance the team's qualification processes, objection management, stakeholder mapping, follow-up techniques, and closing strategies

• Assist in recovery plans for stalled and complex multi-stakeholder deals

• Develop a comprehensive sales playbook, operational cadence, scripts, messaging, and standardized processes

• Maintain accurate and organized HubSpot data for forecasting and team visibility

• Provide updates on pipeline, forecasts, and revenue progress to executive leadership

• Contribute to the hiring and onboarding of future sales professionals

⛳️ Requirements

• A minimum of 5 years in an Account Executive or sales leadership role within public-sector, government-adjacent, commercial SaaS, training, compliance, fleet, transportation, safety, risk, or a similar B2B domain

• Proven experience managing complex, multi-stakeholder sales processes

• Demonstrated ability to generate pipeline, progress deals, and close sales

• Experience in directly managing or significantly coaching BDRs, SDRs, junior AEs, or early-career sales professionals

• Willingness and capability to engage in direct sales while providing coaching to others

• Background in a small-team, resource-aware setting where processes are still being established

• Comfort in selling to practical operators, executive stakeholders, and finance personnel

• Proven ability to work efficiently in a remote environment with strong discipline regarding follow-through, CRM maintenance, and communication

• Bachelor’s degree or equivalent higher education

• Openness to travel as necessary for industry events, trade shows, and important customer meetings

🏝️ Benefits

• Target on-target earnings (OTE) around $220,000

• Stretch earnings potential around $240,000

• Travel opportunities for industry events, trade shows, and significant customer meetings

• Potential for broader sales leadership roles as the team expands