Senior Sales Manager

Full-Time | In-Office 4 Days/Week | Competitive Base + Variable + Equity

Are you a builder at heart who thrives in high-velocity, outbound-first sales environments? We’re working with a fast-moving tech company that makes critical tools for small business teams and is now scaling a new AI-powered product. They’re looking for a Senior Sales Manager to join their growing Toronto team as a founding sales leader.

This is a foundational sales leadership role where you’ll:

• Hire, onboard, and coach a high-energy team of 5–8 outbound sales reps
• Define, implement, and iterate on playbooks for selling AI solutions to small and local business owners
• Turn early traction into a repeatable, scalable revenue engine
• Serve as a player-coach — joining calls, shaping strategy, and teaching by doing
• Collaborate closely with Product, Marketing, Rev Ops, and People teams to align GTM execution

This role is hybrid in Toronto (4 days in-office) and requires someone who enjoys rolling up their sleeves, building from scratch, and driving measurable results.

• 5–8+ years in high-velocity B2B SMB sales with a heavy outbound focus
• 3+ years of people leadership experience managing and scaling sales teams
• A history of growing a product from early ARR (~$1M) to meaningful revenue

• Demonstrated ability to build and document sales processes from scratch
• Strong understanding of the SMB buyer and ability to sell to non-technical, time-pressed owners
• Comfortable explaining and selling AI-enabled products in clear, practical terms
• A metrics-driven mindset with experience coaching to performance outcomes
  
  Player-coach mentality — you lead by example
• Detail-oriented, process-minded, and comfortable in scrappy environments
• Curious about using AI tools to enhance sales execution and productivity
• Excited by building teams and motions, not just maintaining them

• Experience at SMB SaaS companies (HR tech, payroll, scheduling, POS, and similar)
• A track record of working cross-functionally to drive GTM success

• Be a founding sales leader shaping the future of how AI is adopted by small business customers
• Competitive compensation with base + variable + equity
• Work with a bold, collaborative team that values curiosity and urgency
• Help accelerate growth for a product used by thousands of businesses nationwide