One of Canada's most recognized and trusted immigration brands is seeking a strategic, hands-on Head of Sales to unify their sales lawyer teams under a single leader and drive predictable revenue growth. With over 3 million monthly visitors across their digital media properties generating 100% inbound leads, this role will own the revenue target, alongside four rapidly expanding legal practice areas.
Key Responsibilities Leadership & Team Growth: Direct and scale a high-performing team of 8-9 sales lawyers across Citizenship by Descent and four emerging practice areas (Express Entry, Work Permits, Family Sponsorship, and Criminal Inadmissibility).
Pipeline & Forecasting Ownership: Own revenue forecasting end-to-end. Translate top-line targets into precise capacity and hiring plans, running weekly pipeline reviews to ensure consistent execution.
Coaching & Performance: Establish a rigorous coaching cadence- including call reviews, role plays, and 1-on-1s, optimized for a high-velocity motion where deals close in 1-2 calls.
Talent Management: Recruit top sales lawyers, set quotas and ramp schedules,



and proactively address underperformance.
Cross-Functional Collaboration: Partner with Marketing, Growth, and Legal Operations to optimize lead quality, minimize time-to-contact, and streamline handoffs.
Key Qualifications 5+ years of total sales experience , including at least 1-2+ years in direct sales management.
High-Velocity Track Record: Proven success managing high-volume, short-cycle sales motions in B2C, SMB, or high-velocity SaaS.
Direct Forecasting Ownership: Hands-on experience building and owning team forecasts from scratch.
Scrappy / Agile Environment: Prior experience in small, fast-paced, or growth-stage companies.
Location & Work Authorization: Must be currently authorized to work full time in Canada without sponsorship and based in (or willing to commute to) Toronto for a hybrid office schedule.
Bonus: A Juris Doctor (JD), legal background, or LegalTech experience is a significant plus, but not required.

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📌 Head of Sales (Ontario)
🏢 Success Matcher Recruitment
📍 Ontario