Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Head of Sales

Success Matcher Recruitment

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.
#J-18808-Ljbffr
Vacancy posted 3 days ago
Similar jobs that could be interesting for youBased on the Head of Sales in Toronto, ON vacancy
  •  ...Head of Sales | Toronto Monex is a leading global financial solutions provider, offering a complete set of tools to support business growth and strategic financial operations. We specialize in FX risk management and international payments, helping corporate and institutional... 
    Suggested
    Local area
    Worldwide
    Relocation

    Monex Global

    Toronto, ON
    1 day ago
  •  ...media, SEO, creative, programmatic, and marketing automation - and we're now investing in the growth of our sales organization. The Opportunity We're hiring a Head of Sales - a role built to design and lead our commercial engine, not just execute against one. This hire... 
    Suggested
    Long term contract
    Immediate start

    One Core Media

    Toronto, ON
    1 day ago
  • $178.2k - $236k per year

     ...The role / impact As Head of Sales, Canada, you will drive the overall performance and success of Xero across the region, with a primary focus on our accounting and bookkeeping partner channel. Reporting to the Country Manager, you will hold end-to-end accountability for... 
    Suggested
    Permanent employment
    Full time
    Work at office
    Local area
    Work from home
    Flexible hours

    xero

    Toronto, ON
    1 day ago
  • $159.3k - $199.2k per year

     ...About the Team The Canada Ads Sales Team is responsible for the marketing vision, development, and growth of our advertising partnerships across CPG, New Verticals, and Restaurants. This team is rapidly growing, and is seeking additional team members to build an industry... 
    Suggested
    Long term contract
    Full time
    Temporary work
    Local area

    Doordash

    Toronto, ON
    19 days ago
  •  ...Head of National Accounts & Institutional Sales Vanguard, a global leader in investment management, is seeking an accomplished and transformative Head of National Accounts & Institutional Sales for Vanguard Canada to develop and lead all B2B distribution strategies and... 
    Suggested
    Long term contract

    Vanguard Canada

    Toronto, ON
    1 day ago
  •  ...Monex Canada is seeking a Head of Sales to lead and expand its commercial FX and payments sales function nationwide from Toronto. This player-coach role will build and manage a high-performing team, own revenue delivery, and engage directly with strategic client relationships... 

    Monex group

    Toronto, ON
    1 day ago
  • A leading wealth management platform is seeking a Head of Sales to drive pipeline growth and convert leads into agreements. This executive role requires 5+ years of sales experience in fintech or wealth management, with a proven track record in closing significant deals. Candidates... 

    Super Advisor

    Toronto, ON
    14 hours ago
  •  ...Head of Sales (Wealth Platforms – Canada & U.S.) We’re looking for a Head of Sales who knows how to close. Someone who’s built and run a real pipeline — fast-moving, high-volume, and full of serious prospects — and can turn qualified leads into signed, multi-advisor deals... 
    Full time

    Super Advisor

    Toronto, ON
    14 hours ago
  • $200k - $300k per year

     ...authentic selves, you can do your best work and inspire others to do the same. About the role: We’re looking for a Founding Head of Enterprise Sales to own sales execution across strategic accounts, with a particular focus on Fortune 1000 brands, large enterprise design... 
    Long term contract
    Full time
    Contract work
    For contractors
    Internship
    Immediate start
    Remote work
    Home office

    Creative Market

    Toronto, ON
    more than 2 months ago
  • $165k - $206k per year

     ...career opportunities across engineering, manufacturing, research, sales, and technology. As a foundation-owned company, ZEISS is committed...  ...cinema lenses, and precision optical systems. What’s the role? The Head of Sales ZEISS Medical Technology Microsurgery is responsible for... 
    Long term contract
    Remplacement
    Contract work
    Remote work
    Monday to friday
    Flexible hours

    Carl Zeiss Canada Ltd.

    Toronto, ON
    4 days ago
  •  ...covering the most popular Linux distributions, end-of-life systems, programming languages, and much more. We’re looking for a Head of Direct Sales to lead TuxCare’s direct sales organization across North America and EMEA. Reporting to the Chief Revenue Officer, you will... 
    Full time
    Remote work
    Worldwide
    Flexible hours

    TuxCare

    Toronto, ON
    8 days ago
  •  ...One Core Media, a Toronto-based digital marketing agency, is hiring a Head of Sales to design and lead our commercial engine. This player-coach role requires proven agency-side sales leadership and direct people management experience. You will build scalable processes,... 

    One Core Media

    Toronto, ON
    1 day ago
  •  ...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... 

    Success Matcher Recruitment

    Toronto, ON
    3 days ago
  • $200k per year

     ...Position: Head of Go-To-Market Salary: $200,000 base salary to $400,000 on-target earnings (OTE) Location: This role is Toronto-based...  ...our revenue engine. Reporting directly to the CEO, you will own sales, marketing, customer success, account management, and partnerships... 
    Work at office

    Fiscal.ai

    Toronto, ON
    15 days ago
  •  ...revenue per visitor. Catch conversion drops the same day and bring the cause and the fix. Manage our CRO agency and decide with the Head of Growth when work moves in-house. Report CRO KPIs weekly and run the weekly CRO & Funnels meeting. Requirements Fully... 
    Full time
    Remote work
    Weekend work

    KittySpout

    Toronto, ON
    1 day ago
  •  ...go-to-market strategy in North American sports and culture market (Canada, US). Build and lead a high-performing commercial team (sales, business development, marketing). Drive revenue growth by identifying, targeting, and closing opportunities with sports clubs, entertainment... 
    Long term contract
    Local area

    Arenametrix

    Toronto, ON
    4 days ago
  •  ...insights, and stay ahead of the curve in a rapidly evolving world. Head of Platforms, Americas Your Mission As Head of Platforms for...  ...: Drive the full lifecycle of cutting-edge platforms - from pre-sales and strategy to active deployment in production. Engineering-... 
    Work at office
    Remote work
    Home office

    Datatonic

    Toronto, ON
    3 days ago
  •  ...Join to apply for the Head of Customer Success role at Kinsta® Kinsta is one of the top‑managed WordPress hosting companies, with a...  ...such as upsells and renewals. The Account Management team within our Sales department is responsible for these efforts and is one of the... 
    Remote work
    Flexible hours

    Kinsta®

    Toronto, ON
    4 days ago
  • This role is open to Canada based candidates Only About Search Atlas Search Atlas is an agentic marketing platform. We combine SEO, content, site management and AI automation into one system. ~$30M+ ARR, 215 employees, thousands of active customers ~ Category creators...
    Hourly pay
    Remote work

    Search Atlas

    Toronto, ON
    4 days ago
  • $160k - $180k per year

     ...and we are looking for ambitious people to join our mission. About The Role Hi, I’m Sarah, Chief of Staff at Loop. I'm hiring a Head of Risk to take ownership of the day-to-day risk function at Loop, owning everything from KYC/B and AML to credit risk, collections, and... 
    Internship
    Live In
    Work at office
    Immediate start
    Trial period

    Loop-Financial

    Toronto, ON
    4 days ago
  •  ...Overview Head of Technology role at Kainos. Join to apply for the Head of Technology role at Kainos . At Kainos, we’re problem solvers, innovators, and collaborators, driven by a shared mission to create real impact. We are a people-first culture where ideas are... 
    Long term contract
    Full time
    Live In
    Shift work

    Kainos

    Toronto, ON
    4 days ago
  •  ...We're looking for an exceptional Head of Growth to own paid customer acquisition across our portfolio of youth and adult sports brands, including soccer, basketball, and volleyball, operating throughout the Greater Toronto Area and South Florida. You'll take full ownership... 
    Local area

    AGS Youth Soccer Club

    Toronto, ON
    3 days ago
  •  ...Reports to: CEO Location: Toronto (Hybrid) Compensation: 180k + performance bonus We’re looking for a Head of Partnerships to help lead CanadaVisa’s next stage of growth. You’ll build on our audience, established relationships and technology to grow our partnerships... 
    Internship

    CanadaVisa

    Toronto, ON
    14 hours ago
  •  ...Head of Risk, Payments Location: Toronto Department: Product and Engineering Reports to: SVP of Product and Engineering Build trust into the future of global payments Veem helps businesses move money across borders with greater speed, visibility, and control... 
    Long term contract

    Veem Inc.

    Toronto, ON
    4 days ago
  • $170k - $220k per year

     ...across several leaders and, often, the CEO. We're hiring a full-time Head of Operations to become the operational backbone of the company:...  ...full-time operational anchor alongside a fractional CFO and VP of Sales , and a true partner to the CEO through a pivotal growth chapter.... 
    Full time
    Internship
    Remote work
    Flexible hours
    Shift work
    Weekend work

    Tali Ai

    Toronto, ON
    more than 2 months ago
  •  ...we partner with Aeroplan and other leading Canadian financial and telecom brands. About the role Chexy is hiring its first CMO / Head of Marketing to own how Canadians come to know, try and stick with Chexy. You report to the CEO, sit on the leadership team, and own... 
    For contractors
    Work at office

    Chexy Inc.

    Toronto, ON
    3 days ago
  •  ...driven environment, we want to hear from you!**The Opportunity**The Head of Portfolio & Brand Strategy is responsible for defining and...  ...Manager while partnering closely with the Head of Innovation, VP Sales, and Director of Trade Marketing to develop integrated commercial... 
    Long term contract
    Full time
    Internship
    Remote work
    Shift work

    MTL Cannabis Corp

    Toronto, ON
    4 days ago
  •  ...an individual You are passionate about technology, innovation, and investment RECRUITMENT PROCESS: ~ Introductory call with our Head of HR ~ Pre-case with our COO & MD ~1 Case Study with our VP ~ Final on-site interview with Managing Director, CEO, and coffee... 
    Full time
    Work at office
    Local area
    Worldwide

    Praxy

    Toronto, ON
    2 days ago
  • $210k - $298.5k per year

     ...everyone everywhere! Download Mistplay on the Google Play Store here and follow us on Instagram, Twitter and Facebook. The Global Head of User Acquisition (Director, UA) is a crucial leadership role sitting at the center of our growth engine. The User Acquisition Director... 
    Remote work
    Night shift
    Afternoon shift

    Mistplay

    Toronto, ON
    3 days ago
  •  ...companies lose revenue. We fix that. Now we’re installing a Head of GTM to turn founder-driven strategy into repeatable enterprise...  ...Publishing ICP Turn positioning into enterprise-grade messaging Arm Sales with narrative that wins Build case studies that actually... 
    Internship
    Work at office
    Remote work
    Home office
    Flexible hours

    Cache Ventures

    Toronto, ON
    more than 2 months ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Head of Sales. Be the first to apply!