Born in the Prairies, now part of a worldwide network, Skip is a tech company with an entrepreneurial spirit and the drive to be the best. We're a people-first, collaborative company with a fun, dynamic and innovative environment. Our vision is to empower everyday convenience. Whether it’s a Friday-night feast, a post-gym poke bowl, grabbing some groceries or sunscreen, our tech platform connects tens of millions of customers with hundreds of thousands of restaurant, grocery and convenience partners across the globe.
This is a brilliant opportunity to help build and deliver a new, world-class Customer Services (CS) operation focused on our home-market outsourced contact centers.
As the Program Manager for the Canadian Market CS Portfolio, you will drive the delivery calendar, roadmaps, and supporting PMO governance. You will act as a critical bridge—partnering closely with Product, Tech, Data, WFM, Finance, and Operations to optimize internal delivery and enable effective, data-driven decision-making. Working alongside the Head of Experience, you will also play a key role in shaping strategic planning, business cases, and future team organization.
This portfolio is large, varied, and fast-paced. We are looking for a proactive self-starter who can seamlessly connect the dots and see the bigger picture, while still enjoying getting stuck into the operational details. If you want a rewarding role where you can truly influence our strategic direction and be at the heart of building a world-class CS proposition, this is it.
Location: Hybrid- 3 days a week from our Winnipeg office & 2 days working from home
Reporting to: Head of Experience
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Own Large-Scale Delivery: Lead the end-to-end execution of strategic, high-impact Customer Service initiatives, ensuring they launch on time, on budget, and drive measurable results.
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Master the Critical Path: Proactively manage cross-portfolio dependencies, mitigate risks, and clear blockers to keep our fast-moving Customer Service strategy on track.
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Drive Cross-Functional Alignment: Partner with Product, Tech, Data, Operations, and Commercial teams to scope, sequence, and resource projects for maximum value.
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Champion Agile Governance: Shape program cadence, planning cycles (annual/quarterly), and KPI tracking to provide senior stakeholders with clear visibility and data-driven insights.
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Navigate Competing Priorities: Partner across teams to transparently prioritize deliverables and manage resource needs, ensuring we maximize value in a dynamic environment.
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Influence & Collaborate: Build trusted relationships across peer groups and senior leadership to align goals, manage change, and champion the Customer Service vision.
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Elevate Delivery Excellence: Implement best-practice tools and lead continuous improvement efforts—like retrospectives and post-mortems—to optimize how we deliver.
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Extensive experience leading large-scale, cross-functional programs within a fast-paced operational, digital, eCommerce, or tech environment.
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Deep expertise in various program management methodologies (Agile, Waterfall, Hybrid) with a proven track record of partnering closely with Product and Tech teams to deliver complex changes.
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Exceptional stakeholder management and communication skills, with a demonstrated ability to influence across peer groups and confidently present up to executive and board levels.
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An outcome-driven mindset with strong commercial acumen, experience managing large-scale budgets, and a history of shaping programs to maximize business value.
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A proactive, strategic approach to problem-solving—someone who sees the big picture, anticipates risks "one step ahead," and thrives when navigating ambiguity and shifting priorities.
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A positive, collaborative attitude with a willingness to roll up your sleeves to get things done, taking immense pride in delivery excellence.
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Familiarity with collaboration tools like Jira, Asana, SmartSheets, Trello and Slack, with a strong preference for experience in a contact center environment.
SKIP is the kind of workplace that garnered a “Top Places to Work in Manitoba” and it was no small coincidence. We set out to make this a place our employees are proud to tell their Mothers, Fathers, friends and anyone who will listen that they work here. SKIP team members feel pride knowing their 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, fun and challenging environment, we’d love to hear from you.
SKIP is proud to be an Equal Opportunity employer. We are committed to fostering a diverse and inclusive environment where all employees feel they truly belong and where everyone is included, seen, heard and respected.
In keeping with our values, all applicants will receive consideration for employment regardless of gender identity or expression, sexual orientation, race, ancestry, national origin, religion, age, marital/domestic partner status, (dis)ability, neurodivergence, or any other characteristic protected by law. Should you require any accommodations throughout the hiring process, we encourage you to reach out to your talent acquisition specialist.
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.
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