Director, Head of Sales Operations (AI)

Location: Remote in Canada or the U.S., with required EST or CST working hours; occasional travel is required for client meetings, industry events, conferences, and team collaboration.

Salary: $240,000–260,000 USD or $200,000–230,000 CAD, depending on experience; amounts include base salary and variable incentive.

Company

hirify.global provides a healthcare SaaS platform that digitizes appointment check-in, engages patients, improves operational efficiency, optimizes staffing, and supports clinical care.

What you will do

• Lead annual and quarterly sales planning across territories, capacity, quotas, compensation, account segmentation, and go-to-market coverage.
• Own forecasting cadence, pipeline hygiene, stage definitions, forecast reviews, and bookings-to-revenue reconciliation.
• Build commercial reporting for pipeline, win/loss performance, retention, renewals, upsell, productivity, and account performance.
• Own the Salesforce-centered sales technology stack, including administration, integrations, roadmap, vendor management, and data governance.
• Define and deploy AI agents, predictive analytics, and workflow automation to improve forecast accuracy, identify deal risk, and reduce non-selling work.
• Lead deal desk operations, quote-to-cash improvements, sales best practices, and the development of the Sales Operations team.

Requirements

• Bachelor’s degree.
• 10+ years of experience in sales operations, revenue operations, or commercial strategy, including 3+ years leading the function or a significant portion of it.
• Prior people management experience.
• Hands-on Salesforce expertise covering administration, reporting, and process design; experience with broader revenue technology stacks is valuable.
• Experience with forecasting, territory and quota planning, sales compensation, and commercial analytics in a quota-carrying sales organization.
• Strong analytical and communication skills, with proficiency in Excel or Google Sheets and experience translating complex data into executive-level insights.

Nice to have

• Experience in media, advertising, point-of-care marketing, life sciences, or healthcare technology.
• Experience with Salesforce Einstein or Agentforce, generative AI assistants, SQL, Power BI, or similar tools.
• Experience scaling commercial functions through AI and automation.

Culture & Benefits

• 100% remote work with home office expense reimbursement.
• Flexible PTO and 8 company holidays.
• Monthly reimbursement for cell phone, internet, and wellness expenses.
• Paid parental leave and insurance coverage for employees and pets.
• Continuing education and professional certification reimbursement.
• Inclusive environment with employee resource groups and professional growth opportunities.