Head of Sales
On-siteToronto, Ontario, Canada
Job Summary
Build the repeatable SMB accountant sales motion by defining discovery, qualification, and conversion metrics while personally driving the first 1-3 enterprise deals with Top 50 accounting firms. Coach Account Executives live on calls, ride along on real deals, and stand up RevOps fundamentals including pipeline architecture and investor reporting. Execute a player-coach approach by jumping on live calls to save deals and debriefing with reps, leveraging AI-native capabilities to compress headcount needs. This Founding VP of Sales role leads a team of four Account Executives to scale the business to $100M+, partnering with the Head of Customer on activation feedback. Based in Downtown Toronto, the position requires 7+ years in B2B sales or entrepreneurship with a track record of scaling sales teams from scratch.
Required Qualifications
- 7+ years in B2B sales or entrepreneurship as a business owner selling SaaS or services
- at least 3+ years of leading a sales team
- Has scaled a high-velocity sales motion from scratch
- 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
- has a point of view on what to make agentic versus what should stay human
- Location: Downtown Toronto, in person, 5 days per week
Desired Qualifications
- 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
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