Vice President & General Manager

Checker Flag Leasing

Location: Toronto
Reports to:President
Company: Checker Flag


Checker Flag Leasing is seeking an experienced and results-driven Vice President & General Manager (VP & GM) to lead future business growth and initiatives. Reporting directly to the CEO & President, the successful candidate will manage daily business activities, implement strategic initiatives, and optimize operational efficiency.


  • Revenue Growth: Drive revenue growth across equipment sales, aftermarket parts, repair services, rentals, and leasing.
  • Team Leadership: Lead and mentor a team of 60 employees across 4 locations.
  • Operational Strategy: Develop and implement strategies to enhance service quality, reduce costs, and meet customer expectations.
  • P&L Management: Achieve P&L targets with a focus on gross margin.
  • Workflow Optimization: Streamline workflows to ensure high productivity and first-time accuracy.
  • Collaboration: Work with headquarters on health & safety, AR collections, and IT projects.
  • Performance Monitoring: Monitor KPIs and operational metrics for continuous improvement.
  • Performance Management: Set clear performance expectations and support team development.
  • Organizational Development: Recommend and implement organizational changes to achieve strategic goals. 


  • Education: Bachelor’s degree in Business, Marketing, or a related field.
  • Experience: 10+ years in trailer/heavy-duty truck OEMs and rental/leasing businesses, with proven management and leadership experience.
  • Technical Skills: Knowledge of trade licenses in highway trailers (310J) and trucks (310T). Expertise in process management and lean initiatives.
  • Software: Proficient in Microsoft 365. 

Skills & Competencies:

  • Adaptive to changing environment
  • Strong team leadership and motivational skills.
  • Excellent collaboration and communication abilities.
  • Ability to thrive in a fast-paced, high-volume environment.
  • Superior customer service skills. 
  • Commitment to continuous self-development. 

Please apply here for the opportunity to be a part of our strategic growth journey!

We take pride in knowing that our progress begins with our team members. We provide a supportive working atmosphere with training and career advancement opportunities. We thank all applicants; however, only those selected for an interview will be contacted. Upon request, disability-related accommodations are available for all candidates in the selection process.