Managing Director, Commercial Sales

Element Fleet Management; Canada; Hybrid; CAD 233,000 - 275,000; Full time

Job summary

A leading fleet management company is seeking a seasoned sales leader to develop and implement a national go-to-market strategy for B2B clients across Canada. The ideal candidate will have over 10 years of experience in sales and commercial leadership, with a strong ability to engage C-suite executives and guide the full sales process. This position offers a competitive salary up to $275,000 annually and remote work flexibility.

Benefits

Comprehensive health and welfare benefits

Paid time-off programs including vacation, sick leave, and holidays

Opportunity for career advancement

Culture of innovation and empowerment

Qualifications

• 10+ years of progressive B2B sales and commercial leadership experience.
• Demonstrated success leading enterprise-level sales teams.
• Proven ability to engage and influence C-suite executives.

Responsibilities

• Lead the national go-to-market strategy for new B2B clients.
• Cultivate and maintain strong relationships with senior executives.
• Guide the full sales process from lead generation to contract implementation.

Skills

B2B sales experience

Financial acumen

Consultative selling

Exceptional communication

Influencing C-suite executives

Education

Bachelor’s degree in Business, Finance, or a related field

MBA preferred

Job description

Overview

Employer Industry: Fleet Management

What to Consider

• Salary up to $275,000 annually
• Opportunity for career advancement and growth within the organization
• Remote work flexibility, with a preference for candidates in Toronto
• Comprehensive health and welfare benefits for qualified roles
• Culture of innovation, empowerment, decision-making, and accountability
• Paid time-off programs including vacation, sick leave, and holidays for qualified roles

What to Expect (Job Responsibilities)

• Lead the national go-to-market strategy to win new B2B clients and expand the client base across Canada
• Cultivate and maintain strong relationships with senior executives and decision-makers at client organizations
• Leverage sales analytics, CRM data, and market intelligence to identify growth opportunities and optimize the sales funnel
• Guide the full sales process from lead generation to contract negotiation and implementation
• Collaborate with cross-functional teams to ensure cohesive, customer-centric execution

What is Required (Qualifications)

• 10+ years of progressive B2B sales and commercial leadership experience in financial services, fleet management, or a related industry
• Demonstrated success leading enterprise-level sales teams and closing high-value, consultative deals
• Proven ability to engage and influence C-suite executives through strategic insight and credibility
• Strong command of financial acumen, relevant market insights, and solution-based selling
• Exceptional communication, executive presence, and ability to inspire at all levels

How to Stand Out (Preferred Qualifications)

• Bachelor’s degree in Business, Finance, or a related field; MBA preferred
• Experience leading digital and AI-focused sales organizations
• Track record of scaling revenue through data-driven, customer-centric strategies