Regional Delivery Manager

Ready for a challenge?

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.

About This Role

The Regional Delivery Manager is accountable for achieving network KPI & budget targets for the regions they are responsible for. You will be expected to investigate the root cause of issues & trends to identify, and ultimately implement, opportunities for improvement and optimization. You will need to influence stakeholders across the business to achieve your desired outcomes, while functional SMEs will support you with global best practices. In addition to the day‑to‑day operations of the network, you will be asked to propose, analyse and lead experiments to improve outcomes and occasionally support logistics projects.

You are someone who can simultaneously understand a broad set of logistics problems while having the ability to gain deep expertise on a number of technical areas. You are able to use large data sets to draw conclusions, while at the same time have a bias for taking action and making swift decisions. You are passionately committed to excellence, innately curious, deeply analytical, and operate with attention to detail.

Location: Calgary (remote)/Winnipeg (hybrid)/Toronto (hybrid)

Reporting to: Delivery Director

These are some of the key components to the position:

• Full end‑to‑end ownership of Canada‑wide Courier Supply Health to drive performance across key operational metrics, including on‑time delivery, delivery times, undelivered orders, and courier rejections.
• Budget accountability for delivering network costs within or under the regional budget (e.g. cost per order, centralised costs, etc.) for your assigned accountability within Canada. Identify ways to further optimise cost, and calculate cost estimates for changes as required.
• Accountability for operational configurations across pay, incentives, utilisation, assignment logic, cost functions, etc. for your assigned accountability within Canada.
• Implementation and administration of the desired configurations on an on‑going basis (with support from central teams).
• Evaluate potential changes from multiple angles, balancing analytical assessment with a pragmatic point of view. Communicate implications to stakeholders, influencing as needed.
• Leverage analytic tools (statistical, predictive modelling, etc.) to identify segmented, zone‑level network trends and insights on an on‑going basis. Share recommendations & make network decisions based on insights.
• Propose and support network experiments in partnership with tech & data science teams. Assess experiment outcomes and own/approve changes for your assigned regions.
• Use critical‑thinking skills to develop and align regional strategies with corporate & functional priorities. Effectively present ideas to senior management teams.
• Ad hoc project support such as playbook documentation, new zone launches, zone throttling, key cities, zone hour extensions, etc.
• Identify and advocate for continuous improvement opportunities for the network, e.g. via root cause investigations on outliers and escalations.
• Collaborate with global and local stakeholders to align priorities and share best practices.
• Crisis management support as needed to support business continuity.

What will you bring to the team?

• High‑level comfort using data and analysis tools to derive actionable insights.
• Ability to be simultaneously detailed‑oriented while keeping the bigger picture in mind. You can get in the weeds and operate at the lowest level of detail, but can think long‑term.
• Passion for driving positive results with a bias for action.
• Ability to balance informed decision‑making with critical‑thinking with an “owners mindset”.
• Fast‑learner across a breadth of complex, sometimes technical, network tools.
• Passionate about the courier, customer and partner experience.
• Excellent stakeholder management skills – proven ability to drive results in areas that aren't in your immediate responsibility. Ability to manage up and challenge status‑quo.
• Strong communication skills to influence your partners and senior management.
• Willingness to “roll up your sleeves” and work in the details; you thrive in a fast‑paced work environment because rapid change and learning is exciting to you.
• Bachelor's Degree or equivalent work experience in quantitative fields such as Business, Technology, Mathematics, Statistics.

Applicant requirements

• 3+ years experience with data and analysis tools.
• Experience & proven success in a budget‑ownership role (incl. forecasting functions).
• Track record of driving operational targets, ideally in a digital‑first environment.
• Willing to work outside of regular business hours on an exception basis (e.g. during a crisis).

Why work at SKIP?

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.

What We Offer

• Team Vibes: Thrive in a collaborative culture where your ideas matter.
• Tasty Perk: Enjoy a monthly Skip spend allowance—treat yourself!
• More Time Off: Generous PTO with a buy and sell program with up to 5 extra days!
• Family First: Up to 20 weeks top‑up for parental leave.
• Premium Benefits: Flexible medical & dental insurance for you and your family.
• Keep Learning: Access world‑class training resources to power your success.
• Perks Galore: Exclusive offers from Workperks from hundreds of top brands.
• Future Funded: RRSP contributions with diverse investment portfolios.
• We’ve Got You: We’ve got you covered. Access paid sick time to care for yourself or your family when life happens & access to our well‑being support programs.
• Digital Nomads: Family abroad or just want a change of scenery? Enjoy the freedom to work from almost anywhere in the world for 4 weeks a year.
• Career Growth: Fuel your personal and professional evolution through our dedicated mentorship, global mobility pathways, and a wellness‑first culture rooted in true diversity and inclusion.

Compensation range: $93,360.00 — $110,000.00

Final compensation may vary based on skills, experience, and internal equity.

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