Associate Director, Regional Strategy

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.
 

The Associate Director, Regional Strategy will be responsible for defining, testing, and executing SKIPs’ regional growth strategies across Canada. This role will own the development of a localized strategic vision for each market, identifying where and how Skip should grow based on internal data, market dynamics, and competitive pressures.

The successful candidate will leverage deep analytical insights and cross-functional collaboration to determine which cities to prioritize, develop market-specific playbooks for growth, and ensure seamless execution across marketing, partnerships, and operations. This leader will continuously refine SKIP’s approach to local market development through test-and-learn experimentation, ensuring Skip remains the preferred platform for customers, partners, and couriers in every region.

What’s On Your Plate: 

Regional Strategy Development:

• Develop and own the strategic vision for each key region and city, ensuring alignment with Skip’s broader growth and marketplace objectives.
• Identify and prioritize markets for investment and focus based on data-driven analysis of performance, potential, and competitive dynamics.
• Partner with analytics teams to build and maintain market scorecards that guide decision-making on where to play and how to win.

Market Playbook Creation & Execution:

•  Design and implement city-level playbooks outlining strategies for growth, customer acquisition, partner selection, and brand positioning.
• Oversee the execution of these playbooks in collaboration with local and national teams, ensuring consistency and measurable results.
• Continuously refine playbooks based on insights, experiment results, and evolving market conditions.

Cross-Functional Collaboration:

• Partner closely with Marketing, Partnerships, Operations, and Product to ensure strategies are localized and effectively executed.
• Translate national initiatives into regionally relevant programs that resonate with local audiences.
• Act as the key connector between corporate strategy and in-market execution teams.

Experimentation & Learning:

• Design and run test-and-learn pilots in emerging or evolving markets to validate new approaches to growth.
• Analyze results, extract insights, and scale successful tactics across regions.

Foster a culture of experimentation and agility within the regional growth team.

• Bachelor’s degree in Business, Economics, Marketing, or a related field
• 7–10 years of progressive experience in strategy, marketplace operations, or regional business development, ideally within consumer technology, delivery, or retail sectors.
• Strong analytical and strategic thinking skills, with proven success in translating data into actionable business strategy.
• Experience leading cross-functional initiatives in fast-paced, growth-oriented environments.
• Excellent communication and stakeholder management skills; comfortable influencing at all levels.
• Entrepreneurial mindset with a bias for action and comfort with ambiguity.

Core Competencies:

• Strategic & Analytical: Synthesizes market data into clear growth direction.
• Locally Minded: Understands how to tailor strategies to the nuances of each market.
• Collaborative Leader: Aligns cross-functional partners toward shared objectives.
• Innovative & Experimental: Embraces testing, iteration, and learning from failure.
• Execution Focused: Balances big-picture thinking with operational delivery.

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 family 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 with global impact, we’d love to hear from you.

SKIP is proud to be an Equal Opportunity employer. Boxes are for pizza, not people. So however you identify and whoever you love, you are free to be you at Skip. 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.

Are you ready to take your seat? Apply now!
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