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LEAP Legal Software US

Regional Sales Manager - Eastern Canada

Sorry, this job was removed at 04:13 p.m. (EST) on Monday, Nov 24, 2025
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In-Office
Toronto, ON, CAN
In-Office
Toronto, ON, CAN

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We are seeking an ambitious, talented, and driven Regional Sales Manager to join our Toronto team as our sales team is growing and scaling. This role works closely with the VP of Sales to develop new strategies to increase productivity within our New Business Sales team in Eastern Canada. Experience in people management is essential, as the role has overall responsibility for the team of sales professionals and is ultimately accountable for training, mentoring, and guiding a high-velocity team of 4 to 8 sales Business Development Professionals overseeing geographically assigned territories. The main focus of this position is to drive profitable sales of the full range of LEAP software and service offerings in a designated region through a targeted, industry vertical-based selling approach. It also involves effectively leading the Sales Team in their efforts to achieve successful sales engagements and maintain excellent Client relationship management.

About LEAP
LEAP is the leading provider of Legal Practice Productivity Solutions in the world and is part of ATI – one of the largest international LegalTech companies. For more than 30 years, our curiosity and commitment to continual improvement have kept us reimagining productivity tools for lawyers and their staff to support our guiding purpose, which is to ‘Help lawyers who help people.’ The market-leading software we develop, and support is used by more than 100,000 lawyers and their staff in small and medium-sized law firms.

Working alongside our international team of passionate high achievers, you’ll join a fast-growing technology business where things seldom stay the same for long. With more than 1000 smart, caring and ambitious ‘LEAPsters’ working together across Australia, Canada, the United States, the United Kingdom, the Republic of Ireland, Poland and New Zealand, you’ll be in good company here.

KEY RESPONSIBILITIES AND ACCOUNTABILITIES

  • Develop a deep understanding of the legal tech market and how our innovative software disrupts it
  • Ensure proper policies and processes are followed within the team
  • Devise effective territory and marketing strategies, and collaborate with leadership as needed
  • Maintain proper and accurate forecasting
  • Develop a deep understanding of your pipeline, and assist/coach on individual opportunities to ensure maximum success and closing rates
  • Assist in sales calls and onsite visits as needed
  • Recruiting and leading Business Development Professionals to achieve sales goals
  • Coach, lead, and develop the team to ensure everyone meets their full potential
  • Ensure and keep a strong employee morale on your team, and maintain strong teamwork within the sales organization
  • Participate in industry or promotional events (e.g. trade shows) as needed

REQUIRED QUALIFICATIONS

  • Demonstrated success in consultative SaaS sales
  • Proven experience as a Territory Sales Manager (minimum 3 years; references strongly preferred)
  • Consistent record of meeting or exceeding targets
  • Strong negotiation and consultative sales skills
  • Proficient in MS Office and familiarity with Salesforce is an asset
  • Strong organizational and leadership abilities
  • Customer-focused mindset and a practical, common-sense approach to business
  • Ability to thrive in a fast-paced environment
  • Excellent communication skills

BENEFITS

What you'll get

Why work at LEAP?

There are endless opportunities within our business to progress and grow your career and full training is provided so an aptitude and hunger to learn is essential. We offer:

  • Competitive compensation with uncapped commission structure
  • Excellent group insurance benefits
  • RRSP with employer matching
  • Generous Paid Time Off (PTO), including starting at 4 weeks’ vacation, sick days, floater/personal days and volunteer days
  • Hybrid working model at our beautiful and modern downtown Toronto office as well as work from home days
  • Collaborative and inclusive work environment filled with learning and support

At LEAP,

We care about what we do and the people we work with

We continually improve to be the best

We NEVER EVER GIVE UP!

At LEAP we are committed to fostering an inclusive and accessible environment. We are dedicated to building a workforce that reflects the diversity of the community in which we live, including those with disabilities. LEAP is committed to providing accommodations in all parts of the hiring process. If you require accommodation, we will work with you to meet your needs

What you need to know about the Toronto Tech Scene

Although home to some of the biggest names in tech, including Google, Microsoft and Amazon, Toronto has established itself as one of the largest startup ecosystems in the world. And with over 2,000 startups — more than 30 percent of the country's total startups — Toronto continues to attract new businesses. Be it helping entrepreneurs manage their finances, simplifying business operations by automating payroll or assisting pharmaceutical companies in launching new drugs, the city's tech scene is just getting started.

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