[Hiring] Head of Sales @Urrly

Role Description

If you are a hands-on sales builder who still wants to carry a number, coach rising sellers, and shape the go-to-market engine—not just inherit someone else's playbook—this is a high-visibility opportunity to lead growth for a long-established, PE-backed safety training and software company. You'll sell directly into public-sector and commercial fleet environments while building the process, cadence, and team capability needed to scale recurring revenue nationwide.

What You Will Own

• Carry and Close Your Own Book
  • 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 into EMS, fire, fleet, logistics, warehouse, transportation, and related environments.
  • Manage deal sizes that commonly range from $5,000–$20,000, with larger opportunities reaching roughly $75,000 and some government deals requiring longer procurement cycles.
  • Engage buyers ranging from day-to-day safety and training operators to fleet executives, finance leaders, and other senior stakeholders.
  • Develop partnerships with insurance, risk, safety, membership, and industry organizations.
  • Represent the company at trade shows and industry events.
• Coach and Build the Sales Team
  • Coach junior AEs and SDR-level talent through call reviews, deal strategy, shadowing, and timely feedback.
  • Help sellers improve qualification, objection handling, stakeholder mapping, follow-up, and close strategy.
  • Support recovery plans for stalled deals and complex multi-stakeholder opportunities.
  • Create a practical sales playbook, operating cadence, scripts, messaging, and repeatable process.
  • Keep HubSpot clean, accurate, and useful for forecasting and team visibility.
  • Report pipeline, forecast, and revenue progress to executive leadership.
  • Help hire and onboard future sellers as the function grows.

Qualifications

• You have 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.
• You have owned complex, multi-stakeholder sales cycles and can show evidence of creating pipeline, advancing deals, and closing business.
• You have directly managed or meaningfully coached BDRs, SDRs, junior AEs, or early-career sales talent.
• You are still energized by selling yourself—not just inspecting someone else's forecast.
• You know how to operate in a small-team, resource-conscious environment where the playbook is still being built.
• You are comfortable selling to practical operators as well as executive and finance stakeholders.
• You can work effectively in a remote environment with strong discipline around follow-through, CRM hygiene, and communication.
• You have a bachelor's degree or equivalent college education.

Backgrounds That May Transfer Well

• Public sector, local government, or government-adjacent sales
• Fleet, transportation, logistics, delivery, warehouse, or vehicle-intensive operations
• EMS, fire, emergency services, or public safety markets
• Safety, compliance, workforce training, or certification-based solutions
• Vertical SaaS or recurring-revenue products sold into operational teams
• Insurance, risk management, brokers, associations, or member organizations

Compensation

• The base salary range is $110,000–$120,000 annually, with a 50/50 base-variable structure and target OTE around $220,000.

Why This Role Is Different

This is not a large-company sales management role where every process, enablement asset, and resource already exists. It is a builder role for someone who wants ownership. You will have the chance to influence the sales motion at a company with an established customer base, a real market need, upgraded technology, and executive attention on growth. For the right person, this can be a step toward broader sales leadership as the team scales.