Head of Sales

Kick • Toronto, ON

1d • Onsite

About The Position

As Founding VP of Sales, you'll lead a team of 4 Account Executives and growing. You will build the repeatable, scalable SMB - Enterprise motions that scale us to $100M+ and beyond, taking a chunk of Quickbook’s $13 Billion business. To start, this is a true player-coach role: you'll be in deals, building the playbook, and scaling the team, while standing up RevOps from scratch, with a clear path to SVP of Revenue owning pre- and post-sales as the business grows.

Requirements

• 7+ years in B2B sales or entrepreneurship as a business owner selling SaaS or services with at least 3+ years of leading a sales team
• Has scaled a high-velocity sales motion from scratch, not inherited an existing playbook
• A player-coach by default: comfortable jumping on a live call to save a deal, then debriefing with the rep
• Strong RevOps instincts; has personally designed pipeline stages, forecast process, and conversion metrics
• Has explicitly changed ICP or qualification criteria based on post-sales / activation data
• Personally uses AI in their workflow today (Granola, Clay, Gong-style agents, etc.) and has a point of view on what to make agentic versus what should stay human

Nice To Haves

• Sold into accountants, bookkeepers, or accounting firms (e.g., Xero, Gusto, Pilot, Float, Bill, Ramp, Brex)
• Scaled a sales team from 2-3 reps to 15+
• Built or shipped agentic / AI-native sales capabilities, not just used vendor tools
• A background blending consulting, banking, or strategy with a frontline AE chapter

Responsibilities

• Build the repeatable SMB accountant sales motion: discovery, qualification, stage definitions, conversion metrics, weekly forecast cadence
• Coach AEs live on calls, ride along on real deals, and carry your own bag where it accelerates the team
• Stand up and own RevOps fundamentals: pipeline architecture, attribution, leadership and investor reporting.
• Personally drive our first 1-3 enterprise deals with Top 50 accounting firms (multi-threaded, multiple stakeholders)
• Partner closely with our Head of Customer on activation feedback, selling the right deals rather than just the most deals
• Drive AI-native sales by bringing agentic capabilities into the workflow to compress rep headcount needs as we scale

Benefits

• Top-of-market OTE, plus meaningful equity at a high growth, early stage company
• Variable comp tied to new-logo accountant deals and activated ARR
• Employee-friendly equity: QSBS eligible, early exercise, extended exercise window
• Medical, dental, and vision benefits (employee + dependents)
• Apple laptop/headset, health and commuter stipends
• Regular team meet-ups in Palo Alto, plus a dedicated Toronto office

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed