Skills

Leadership Sales Coaching Marketing

Job Specifications

Sr. Sales Manager — Hybrid (Toronto, ON)

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 outcomes

Traits

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

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

About the Company

Capital and code don’t build companies, people do. Helping AI-centric, VC/PE-backed organizations solve high-value problems by recruiting elite teams. Executive Search & Contingent Staffing Core Functions: Executive, Sales, Marketing, Customer Success, Product, and Operations Industry Specialization: AI/ML, SaaS, MarTech, AdTech, FinTech, HealthTech, Cybersecurity, CDP Know more