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.

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. Partner with Marketing, Growth, and Legal Operations to optimize lead quality, minimize time-to-contact, and streamline handoffs. 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. ~ Hands-on experience building and owning team forecasts from scratch. ~ Scrappy / Agile Environment: Prior experience in small, rapid-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. #

📌 Director, Sales Retail & E-Commerce (Toronto)
🏢 Success Matcher Recruitment
📍 Toronto