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 exact 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.

📌 Head of Sales (Greater Toronto Area)
🏢 Success Matcher Recruitment
📍 Greater Toronto Area