Strategic Account Executive (AI)

TL;DR

Strategic Account Executive (AI): Leading hirify.global’s largest enterprise opportunities and designing complex, multi-business-unit, multi-geography deals with an accent on executive relationships, deal structure, and AI-native selling. Focus on closing six- and seven-figure contracts, navigating commercial risk, shaping go-to-market strategy, and building trusted partnerships with C-suite stakeholders.

Location: Remote in Canada; Toronto

Salary: CA$375,000–CA$430,000 annually, plus equity and commission.

Company

hirify.global builds an AI platform that helps businesses create better, more human customer experiences.

What you will do

• Lead hirify.global’s largest and most complex enterprise opportunities across multiple business units and geographies.
• Design sophisticated deal structures, manage commercial risk, and negotiate pricing.
• Build trusted relationships with customer C-suite executives and working teams.
• Represent hirify.global alongside its founders in strategic customer engagements.
• Shape account strategy, sales motions, and standards for the broader sales organization.
• Use AI tools for account research, outreach, call summarization, forecasting, and deal execution.

Requirements

• 10–12+ years of enterprise or strategic sales experience managing the largest and most complex accounts.
• Proven success closing multi-million-dollar, multi-stakeholder deals across business units and geographies.
• Experience managing a $1M+ quota and closing complex six- and seven-figure ACV deals.
• Deep C-suite relationships and the credibility to operate as a peer with executive buyers.
• Mastery of deal structuring, risk navigation, pricing, and executive communication.
• Deep familiarity with the AI landscape and experience building go-to-market strategies or sales teams from an early stage.

Culture & Benefits

• Values include trust, customer obsession, craftsmanship, intensity, and family.
• Flexible unlimited paid time off.
• Medical, dental, vision, life insurance, and disability benefits for employees and families.
• Retirement plans, parental leave, and fertility and family-building benefits vary by country.
• Equity eligibility, discretionary benefit stipend, meals, snacks, coffee, and learning opportunities such as free alphorn lessons.