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Supervisor, Flagging Operations


  • Req ID: 100609
  • Department: Engineering
  • Job Type: Full-Time
  • Position Type: Non-Union
  • Location: Toronto, Ontario
  • Country: Canada
  • % of Travel: 10-20%
  • Job Grade: 5


Canadian Pacific is a transcontinental railway in Canada and the United States with direct links to major ports on the west and east coasts, providing North American customers a competitive rail service with access to key markets in every corner of the globe. CP is growing with its customers, offering a suite of freight transportation services, logistics solutions and supply chain expertise. Visit to see the rail advantages of CP.



The Supervisor Flagging Operations will be responsible for directing and validating rules compliant flagging work as assigned by the Senior Project Manager Public Works in Southern Ontario and Quebec to ensure adherence to applicable Federal regulations and standards, including Transport Canada, CSA & AREMA, along with CP specifications and Geotechnical compliance in order to protect train operations and track safety.



  • Schedule the flagging workload as set up by the Senior Project Manager Public Works to set up flagging with Road Masters and/or RTW employees for utility and 3rd party entry permit related work.
  • Conducts efficiency testing and site inspections to validate compliance with applicable rules and flagging agreements.
  • Reviews construction reports to validate required flagging support requirements.
  • Ensures terms and conditions of all Utility Agreements are adhered too.  
  • Maintain files and works with SAP billing module to obtain reports and review of billing information for utility crossings, ensuring information and invoicing is current and accurate for record keeping purposes.
  • Interfaces with CP Public Works and Real Estate for Right of Way perpendicular crossings for leasing and property sales.
  • Works in conjunction with the Fiber & Tower site group for interconnection utility underground crossings.



  • A post-secondary diploma in Engineering, Business  Management, or other related disciplines would be an asset:
  • Previous experience within the railroad industry, transportation, Right of Way field, and or project management; Knowledge and or familiarity with Engineering practices & standards:
  • Ability to make decisions using independent judgement in a fast paced environment; Excellent planning, organizational and negotiating skills; Able to prioritize work.
  • Effective, written and oral communication skills; Capable of working collaboratively with diverse organizational groups under limited supervision; Able to handle multiple inquiries simultaneously.
  • Proficiency or ability to learn SAP, MS Excel, general use of AutoCAD and other relevant computer applications.
  • Positive and enthusiastic work ethic and attitude.
  • At times able to interface and conference in Senior Leaders.



  • Flexible and competitive benefits package
  • Competitive company pension plan
  • Employee Share Purchase Plan
  • Performance Incentive Program 
  • Annual Fitness Subsidy



As an employer with national presence, the possibility does exist that the location of your position may be changed based on organizational requirements.


Background Investigation:

The successful candidate will need to successfully complete the following clearances:    

  • Criminal history check
  • Reference check


Management Conductor Program:

Becoming a qualified conductor or locomotive engineer is the single best way for a management employee to learn the business at CP. You may be required to obtain a certification or to maintain your current certification/qualification as a conductor or locomotive engineer.


CP is an equal opportunity employer committed to the principles of employment equity and inclusion. We welcome applications from all qualified individuals. All applicant information will be managed in accordance with the federal Personal Information Protection and Electronic Documents Act ("PIPEDA"). 

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