Field Sales Manager, Small Law

Location: Canada, Toronto, Ontario

The Sales Manager (SM) is responsible for successfully leading a team of Field Sales Executives (FSE's) in the Small Law Firm (SLF) segment in Canada, focused on CoCounsel, Westlaw, Practical Law, Taxnet Pro, and Partner solutions, both driving revenue growth via acquisition of new customers, upselling and retention.

You will be accountable to meet and exceed monthly, quarterly, and yearly sales targets and to increase market share across dynamic, open coverage territories. The Sales Manager ensures that the field sales team is effectively trained, motivated, and coached to pursue high-value opportunities and manage fluid territory assignments as business needs evolve. This is a fully remote position with travel required to support field team members across the region.

Key Responsibilities

• Achieve monthly, quarterly, and annual sales quota across the full product and services portfolio, with FSEs focused on selling the complete range.
• Coach, develop, and lead FSEs and the regional team to meet individual and regional goals.
• Manage open coverage and overlay territories, reallocating based on market opportunity, team capacity, and strategic priorities, while leading the team through shifts and reassignments with minimal disruption to pipeline and customer relationships.
• Recruit and maintain a qualified bench of field sales candidates to shorten time-to-hire and keep high-priority accounts and emerging opportunities covered.
• Deliver accurate, timely sales and account management reports, forecasts, expense reports, and customer evaluation reports, including those requested by channel management.
• Partner with Client Executive teams to ensure the customer experience is without compromise.
• Collaborate with the SDR team, Marketing, and Go-to-Market (GTM) teams on campaigns and regional initiatives.
• Ensure regional compliance with all required reporting and effective use of internal tools, with particular attention to CRM hygiene through territory changes.
• Conduct regular field rides, in-person coaching sessions, and strategic account meetings across the region.
• Lead a team of Retention Specialists responsible for the SLF renewal quota

Required Qualifications

• A Bachelor's degree or equivalent experience
• 5+ years in a successful field sales or account management role
• Experience with successful leadership of field sales teams in B2B marketplace
• Proven ability to lead remote teams and manage performance across dispersed geographies
• Experience managing overlay sales models and/or open territory coverage strategies
• Experience with Coaching Sales Process, product training and professional development in field sales environments
• Adept at forecasting monthly goals and managing territory realignment without sacrificing pipeline accuracy (planning, forecasting and productivity improvement)
• Excellent time management and organizational skills with ability to prioritize across multiple shifting territories
• Strong communication skills: verbal, written and presentation
• Team player, collaborative, with proven ability to build trust and cohesion in remote team settings
• Continuous learner, flexible and open-minded, positive attitude – particularly adaptable to change
• High level of integrity and understanding of sales ethics

Preferred Qualifications

MBA and/or JD a plus

Experience working within the legal industry

Experience selling AI SaaS products is highly desired

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This posting is for proactive recruitment purposes and may be used to fill current openings or future vacancies within our organization.

What’s in it For You?

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Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.

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