Head Of Sales (AI)

TL;DR

Head of Sales (AI): Leading the sales organization to build scalable SMB-to-Enterprise motions for an AI-native accounting platform with an accent on RevOps architecture and high-velocity sales playbooks. Focus on driving enterprise deals, coaching a growing team of Account Executives, and integrating agentic AI capabilities into the sales workflow.

Location: Must be based in Toronto, Canada (In-person, 5 days per week)

Company

hirify.global is an AI-native accounting platform backed by OpenAI, General Catalyst, and Google Ventures, dedicated to automating back-office tasks for business owners and accounting firms.

What you will do

• Build and refine the repeatable SMB accountant sales motion, including discovery, qualification, and forecasting.
• Coach Account Executives through live call participation and deal strategy.
• Establish and own RevOps fundamentals, including pipeline architecture and reporting.
• Personally drive initial enterprise deals with top-tier accounting firms.
• Partner with the Head of Customer to align sales strategy with activation feedback.
• Implement AI-native sales workflows to optimize rep efficiency and headcount scaling.

Requirements

• 7+ years in B2B sales or entrepreneurship, with at least 3+ years in a sales leadership role.
• Proven experience scaling a high-velocity sales motion from scratch.
• Strong RevOps instincts with experience designing pipeline stages and conversion metrics.
• Hands-on player-coach mentality with a track record of closing deals.
• Active user of AI tools in professional workflows with a clear vision for agentic sales.
• Must be able to work in-person in Toronto, 5 days per week.

Nice to have

• Experience selling into accounting firms or financial services (e.g., Xero, Gusto, Ramp).
• Experience scaling a sales team from 2-3 to 15+ reps.
• Background in building or shipping agentic AI sales capabilities.
• Experience blending consulting or strategy with frontline sales roles.

Culture & Benefits

• Top-of-market OTE with meaningful equity participation.
• Comprehensive medical, dental, and vision benefits for employees and dependents.
• Health and commuter stipends.
• Regular team meet-ups in Palo Alto.
• High-growth, early-stage environment with a focus on diverse, creative talent.