Jobs in Vaughan

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Within 25 km of Vaughan

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Success Matcher Recruitment

Head of Sales

Toronto, ON, Canada

$150,000 to $180,000 CAD / year · Full-time

Within 25 km of Vaughan · About 22.9 km from the city centre

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Job details

Pay: $150,000 to $180,000 CAD / year
Job type: Full-time
Experience: 5+ years of total sales experience, including at least 1–2+ years in direct sales management.
Posted: Oct 9, 2026

Original 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.

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More about this job

Responsibilities

Lead and scale a team of sales lawyers across established and emerging legal practice areas, owning revenue targets, forecasting, pipeline reviews, and capacity and hiring plans. Coach and recruit team members, manage performance, and collaborate with Marketing, Growth, and Legal Operations to improve lead quality, response times, and handoffs.

Requirements

Requires at least five years of sales experience, including one to two or more years in direct sales management, with a record of success in high-volume, short-cycle sales and hands-on ownership of team forecasting. Candidates should have experience in a small, fast-paced or growth-stage company and be authorized to work full-time in Canada without sponsorship; a JD, legal background, or LegalTech experience is a plus.

Skills

Sales Leadership
Team Management
Revenue Forecasting
Pipeline Management
Sales Coaching
Recruiting
Quota Setting
Performance Management
Capacity Planning
Hiring Planning
B2C Sales
SMB Sales
High-Velocity Sales
Cross-Functional Collaboration
Lead Management

Visa sponsorship

Not detected in the job text

Keywords

Sales Leadership
Revenue Growth
Revenue Forecasting
Pipeline Reviews
Capacity Planning
Hiring Plans
Sales Coaching
Call Reviews
Role Plays
One-On-One Meetings
Recruiting
Quotas
Ramp Schedules
Performance Management
B2C Sales
SMB Sales
High-Velocity Sales
Inbound Leads
Lead Quality
Time-To-Contact
Legal Services
Immigration
Citizenship By Descent
Express Entry
Work Permits
Family Sponsorship
Criminal Inadmissibility
LegalTech
Toronto
Hybrid Work

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