Head of Sales (AI SaaS)

Location: Downtown Toronto, Canada; in person, 5 days per week

Company

hirify.global is building an AI-native accounting platform that automates back-office work for business owners and accounting firms.

What you will do

• Lead and coach a growing team of Account Executives in a player-coach capacity.
• Build repeatable, scalable SMB-to-enterprise sales motions and design the sales methodology, stages, and playbook.
• Establish and own GTM recruiting, RevOps, sales enablement, pipeline stages, forecasting, and conversion metrics.
• Personally drive complex, multi-threaded enterprise deals with major accounting firms.
• Partner with Customer leadership to use activation feedback to improve qualification and deal selection.
• Introduce agentic AI capabilities into sales workflows to improve scalability.

Requirements

• 7+ years of B2B sales or entrepreneurship experience selling SaaS or services.
• 3+ years of experience leading a sales team.
• Experience scaling a high-velocity sales motion from scratch rather than inheriting an existing playbook.
• Player-coach approach with the ability to participate in live deals and coach representatives.
• Strong RevOps experience, including designing pipeline stages, forecasting processes, and conversion metrics.
• Experience using post-sales or activation data to change ICP or qualification criteria, plus a current point of view on applying AI in sales.

Nice to have

• Experience selling to accountants, bookkeepers, or accounting firms.
• Experience scaling a sales team from 2–3 representatives to 15+.
• Experience building or shipping agentic or AI-native sales capabilities.
• Consulting, banking, or strategy experience combined with frontline Account Executive experience.

Culture & Benefits

• Top-of-market OTE and meaningful equity at an early-stage company.
• Variable compensation tied to new-logo accountant deals and activated ARR.
• Employee-friendly equity structure with QSBS eligibility, early exercise, and an extended exercise window.
• Medical, dental, and vision benefits for employees and dependents.
• Apple laptop and headset, health and commuter stipends, regular team meet-ups in Palo Alto, and a dedicated Toronto office.