Technology Manager - Courier

Software Engineering - Winnipeg Winnipeg, MB


We’re revolutionizing the way humanity eats, and there’s a lot of room for optimization and growth. That’s where you come in. Your ingenuity will help us continue to drive innovation, making an impact on the reliability, performance, and scalability of Skip’s industry-leading technology.

What’s On Your Plate:

  • Delivering defined business goals.
  • Fostering a strong team.
  • Professional development of team members.
  • Contributing and adhering to patterns and processes.
  • Managing stakeholder expectations.
  • Measuring success.
  • Using best practices to improve products/ services or processes
  • Responsible for the performance and results of a team within own discipline or function. 
  • Defining the team’s operating standards and practices.
  • Day-to-day supervision of the team.

Recipe for Success:


  • Understands working with and developing a team of Engineers, Product Managers, UX Designers, and Support Technicians.
  • Understands SKIP—both in terms of the team’s objectives and those of the company as a whole.
  • Manages the software development process from idea to release.
  • Manages technical projects and deployments.
  • Works independently and solves complex problems.
  • Uses best practices to improve products, services, and processes.
  • Manages shifting priorities; is flexible and proactive in a sometimes unpredictable environment.
  • Communicates effectively in person and in writing.


  • In-depth understanding of a specific discipline within Technology (ex: Product management or software engineering or design or end-user computing). Has subject matter expertise and experience.
  • In-depth understanding of a specific product area or technology (ex: Search iOS or networking).
  • Good understanding of how to drive a high-performance culture within their team.
  • Broad understanding of Skip's day-to-day business, strategies, and priorities across the company as a whole.
  • Basic understanding of all disciplines within their team (EX: software engineering, product management, design, research). 


  • Commercial experience, some of which has been working at a Senior to Principal level.
  • Proven track record of delivering high-quality work and driving best practices across teams and departments.
  • Experience of looking broadly across the discipline of software development, both within SKIP and the wider marketplace.
  • Successful stakeholder management experience.
  • Business or accounting experience is useful.
  • Proven leadership skills in coaching, mentoring, performance management, and related fields.  

Why work at Skip? 

Picture this: you, dressed in your fave casual attire, amongst a team of friendly and passionate colleagues. You feel pride knowing your input and uniqueness are not only embraced but make an impact on a major Canadian company and its satisfied customers. As the company grows, so do you — you meet and surpass new challenges every day.

That’s just a small taste of what it’s like to work at one of Canada’s leading tech companies. If you’re hungry for opportunity, growth, and something meaningful in a dynamic, yet casual environment, we’d love to hear from you.

Note: All employees will be asked to sign a Consent for Disclosure of Personal Information in order to complete a background check. Job offers will be conditional upon results that the Company determines to be satisfactory.