Head of Sales – Player-Coach, Fleet Safety Training
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Job Description
Head of Sales selling fleet safety training and software to public-sector and commercial customers nationwide. Coaching sellers while building repeatable sales processes and recurring revenue growth.
Responsibilities:
- Build a nationwide pipeline across public-sector and commercial accounts
- Prospect, qualify, run discovery, navigate stakeholders, and close new business
- Sell safety training, compliance, and software-enabled training solutions
- Manage sales opportunities commonly ranging from $5,000–$20,000, with larger opportunities reaching roughly $75,000
- Engage safety, training, fleet, executive, finance, and other senior stakeholders
- Develop partnerships with insurance, risk, safety, membership, and industry organizations
- Represent the company at trade shows and industry events
- Coach junior AEs and SDR-level talent through call reviews, deal strategy, shadowing, and feedback
- Improve team qualification, objection handling, stakeholder mapping, follow-up, and close strategy
- Support recovery plans for stalled and complex multi-stakeholder deals
- Create a sales playbook, operating cadence, scripts, messaging, and repeatable processes
- Maintain clean and accurate HubSpot data for forecasting and team visibility
- Report pipeline, forecast, and revenue progress to executive leadership
- Help hire and onboard future sellers
Requirements:
- 5+ years of Account Executive or sales leadership experience in public-sector, government-adjacent, commercial SaaS, training, compliance, fleet, transportation, safety, risk, or another transferable B2B environment
- Experience owning complex, multi-stakeholder sales cycles
- Evidence of creating pipeline, advancing deals, and closing business
- Experience directly managing or meaningfully coaching BDRs, SDRs, junior AEs, or early-career sales talent
- Ability and willingness to sell directly while coaching others
- Experience operating in a small-team, resource-conscious environment where the playbook is still being built
- Comfort selling to practical operators, executive stakeholders, and finance stakeholders
- Ability to work effectively in a remote environment with strong discipline around follow-through, CRM hygiene, and communication
- Bachelor’s degree or equivalent college education
- Willingness to travel as needed for industry events, trade shows, and key customer meetings
Benefits:
- Target OTE around $220,000
- Stretch potential around $240,000
- Travel for industry events, trade shows, and key customer meetings
- Opportunity for broader sales leadership as the team scales
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