Outside Sales Supervisor

Outside Sales Supervisor generating revenue and supervising B2B sales teams at WM. Leading coaching initiatives and optimizing sales processes while working remotely in Canada.

Posted 4/25/2026full-timeVancouver • 🇨🇦 CanadaMid-LevelSenior💰 CA$87,340 - CA$105,270 per yearWebsite

About the role

Key responsibilities & impact

Generates and retains profitable revenue by supervising a team of salespeople including outside sales representatives, territory managers and account managers.
Supervises other types of salespeople as directed by senior sales management.
Supervises and supports the Account Executive (AE) channel by establishing clear operating rhythms, processes, and performance standards that enable consistent execution across a remotely distributed team.
Partners closely with Outside Sales Managers (OSMs) to drive shared revenue accountability by providing pipeline visibility, coaching insights, and process discipline across the AE channel.
Leads adoption, consistent use, and optimization of the sales technology stack including Salesforce, Conquer, Ambition, and Microsoft Copilot, ensuring tools are leveraged to increase selling time, improve pipeline health, and create data-driven coaching opportunities.
Utilizes CRM and performance data to manage pipeline hygiene, funnel alignment, and forecast accuracy for the AE channel, identifying risks and trends early and collaborating with MSMs on corrective actions.
Identifies patterns and performance trends across calls, activity, and pipeline data to create observable behaviors and structured coaching moments that improve effectiveness, skill development, and results.
Maintains an ongoing training, coaching, and development program focused on process execution, sales effectiveness, and continuous improvement.
Leads change management and continuous improvement initiatives.
Supports programs and initiatives that drive team performance toward departmental and organizational goals while ensuring compliance with company policies, operating standards, and sales processes.
Collaborates cross-functionally with Operations, Dispatch, Pricing, Safety, Sales Enablement, Billing, and corporate partners to resolve issues, improve customer experience, and ensure strong handoffs throughout the sales and service lifecycle.
Oversees personnel needs including onboarding support, coaching, skill development, and performance feedback.

Requirements

What you’ll need

Bachelor's degree (accredited) or in lieu of degree, High School Diploma or GED (accredited) and four (4) years of relevant B2B sales experience.
Five years of direct business to business sales and account management experience, including cold calling and phone-based prospecting.

Benefits

Comp & perks

Medical
Dental
Vision
Life Insurance
Short-Term Disability
Stock Purchase Plan
Company match on RRSP
Paid Vacation
Holidays
Personal Days

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

B2B salesaccount managementcold callingphone-based prospectingpipeline managementforecast accuracycoachingtrainingchange managementprocess execution

Soft Skills

leadershipteam supervisioncollaborationcommunicationcoaching insightsperformance feedbackskill developmentproblem-solvingorganizational skillscontinuous improvement

Certifications

Bachelor's degreeHigh School DiplomaGED