Head of Sales

Success Matcher Recruitment; Toronto; Hybrid; CAD 150,000 - 210,000; Full time

Benefits offered by this job

Hybrid work model

Job summary

Success Matcher Recruitment is seeking a strategic, hands-on Head of Sales to unify our sales lawyer teams under one leader and drive predictable revenue growth. With inbound leads and multiple practice areas, you will own revenue targets and build a scalable sales organization.

You will lead coaching cadences, set quotas, and recruit top talent while partnering with Marketing, Growth, and Legal Operations to optimize lead quality and handoffs.

Qualifications

• 5+ years of total sales experience.
• 1-2+ years in direct sales management.
• Experience with high-velocity, short-cycle sales.
• Authorized to work in Canada without sponsorship; willing to commute to Toronto.

Responsibilities

• Lead and scale a team of 8-9 sales lawyers across multiple practice areas.
• Own revenue forecasting end-to-end with pipeline reviews.
• Coach and develop reps via call reviews and role plays.
• Recruit top sales lawyers and set quotas and ramp schedules.
• Collaborate with Marketing, Growth, and Legal Operations to optimize leads and handoffs.

Skills

Leadership

Pipeline forecasting

Coaching

Talent management

Cross-functional collaboration

Direct sales management

Strategic thinking

Education

Juris Doctor (JD)

Job description

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.