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, 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.

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