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Direct Recruiters Inc.
Head of SalesDirect Recruiters Inc. • Toronto, ON, Canada
Head of Sales

Head of Sales

Direct Recruiters Inc. • Toronto, ON, Canada
30+ days ago
Job type
  • Full-time
Job description

Overview

  • Healthcare technology company helping large provider organizations manage and scale their technology investments responsibly
  • Provides a platform supporting governance, monitoring, and performance tracking across complex operational environments
  • Enables healthcare organizations to measure and demonstrate measurable value from technology initiatives
  • Combines industry expertise with purpose-built tooling to help organizations adopt innovation without introducing unnecessary risk
  • Early-stage company positioned in the rapidly growing healthcare AI infrastructure and oversight market

Position Responsibilities

  • Own the full commercial motion end-to-end including pipeline advancement, closing, contracting, and market intelligence feedback
  • Co-sell alongside founders for first 60 days, then lead independently
  • Break into new accounts from cold with no SDR support
  • Manage 9 to 12 month enterprise sales cycles with multi-stakeholder buying committees
  • Target of 6 closed enterprise partnerships in year one, $3M quota, $500K+ ARR per deal
  • Buyers include CIO, CMIO, Chief AI Officer, and operational leadership at large US health systems

Experience & Skills

Required Experience and Qualifications

  • 5+ years of enterprise health system sales experience at the C-suite level
  • 3+ years of new logo, cold-outbound closing track record
  • 3+ years of early-stage or category-creation experience
  • Demonstrated ability to master technical domains without being a technical expert
  • Proven track record closing enterprise deals into large US health systems at the C-suite level
  • History of closing new logos from cold, not just account expansion
  • 2+ years selling non-budgeted or emerging category solutions and creating demand where none exists
  • Ability to translate value across stakeholder levels from end user through CFO
  • Owns meeting prep, follow-up, contracts, and deal diagnosis with minimal direction
  • Actively uses AI as a core part of their workflow
  • Builds genuine relationships internally and externally

Preferred Experience and Qualifications

  • 2+ years of experience selling AI, governance, or emerging technology solutions into healthcare
  • Comfort operating without a finished playbook or defined team structure
  • Experience owning the full commercial motion long-term as a solo contributor

Compensation $300k-$350k, Health Insurance, Paid Vacation

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Head of Sales • Toronto, ON, Canada

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