Head of Sales (Player–Coach) – Enterprise Software

UrrlyWashington, DC
75d$175,000 - $200,000Remote

About The Position

Our client builds training and performance support systems for mission-critical, highly regulated industries in the energy sector—primarily nuclear and utilities. Their software ensures operators maintain compliance, competency, and safety in environments where human error has real-world consequences. Backed by one of the most reputable private equity firms in the Northeast, the company is entering a scale phase with aggressive growth plans, including international expansion. This is not an HR LMS sale. The solutions serve operations, safety, and compliance teams with qualification and certification workflows aligned directly to regulatory frameworks. Our client is hiring a Head of Sales as a player–coach (roughly 70% coach / 30% sell). This leader will manage and grow a small AE team, establish a top-of-funnel engine, and drive new-logo acquisition while building on strong renewal momentum. You’ll work directly with the interim CRO and CEO while owning the path to CRO yourself.

Requirements

  • 6–10+ years in enterprise B2B sales with regulated/mission-critical buyers (energy, industrial, defense, aviation, EHS, pharma, etc.)
  • Proven player–coach: managed AEs while personally closing six-figure+ multi-stakeholder deals
  • Outbound and pipeline builder from low brand awareness; CRM/process discipline
  • Strong forecasting rigor (MEDDICC or equivalent) in HubSpot (preferred) or Salesforce
  • Executive presence with Ops/Safety/Compliance/IT buyers; consultative and credible
  • High EQ/IQ, grit, and a genuine passion for sales—able to run through walls and bring the team with you

Nice To Haves

  • Sold compliance, training, or workforce-qualification solutions
  • Exposure to nuclear, utilities, or other regulated verticals
  • International market entry experience
  • Early-stage playbook creation; PE-backed scale-up experience

Responsibilities

  • Lead a 3-AE pod (+ RevOps resource) focused on new-logo growth
  • Act as a player–coach: close deals personally while hiring, coaching, enabling AEs
  • Build a repeatable pipeline engine: outbound (HubSpot/Apollo), webinars, conferences, partners
  • Drive demo productivity to ~8 new demos/AE/month (or 6 if AM duties apply)
  • Establish forecast discipline: stage definitions, dashboards, hygiene, cadences in HubSpot
  • Partner with marketing on monthly webinars and an 8–10 conference annual strategy
  • Close complex enterprise deals (nuclear ACVs $100–200K+; utilities $20K SW + $200K services)
  • Lead international nuclear expansion: account plans, associations, lighthouse wins
  • Strengthen RevOps reporting while maintaining speed to revenue
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