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. About the Role 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, RevOps, 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. What You Bring Experience 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 Skills 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 outcomesPlayer-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 Nice to Have Experience at SMB SaaS companies (HR tech, payroll, scheduling, POS, and similar) A track record of working cross-functionally to drive GTM success Why Candidates Love This Opportunity 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 #J-18808-Ljbffr