Head of Sales (Ontario)

Head of Sales (Ontario)

18 Aug
|
Direct Recruiters
|
Ontario

18 Aug

Direct Recruiters

Ontario

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 current 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 (Ontario)
🏢 Direct Recruiters
📍 Ontario

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