Senior Manager, Strategy and Operations

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 

You will join the central Skip Strategy and Operations team as the dedicated Lead for the Care portfolio, overseeing a mandate split equally between Customer Care (App Users) and Partner Care (Merchants/Restaurants). This role is a first of its kind within the Care portfolio and you will be a key driver in building the functional strategy and operational rigour from the ground up. Acting as the "Chief of Staff" to the Head of Care, you will also dedicate 50% of your time to collaborating with the Partnerships organization. In our matrixed environment, support cannot function in a silo; this role exists to ensure that the operational rigor applied to our Customer and Merchant experiences is tightly coupled with our Commercial strategy. By bridging these worlds, you will serve as the vital link that ensures we don't just win partners, but keep them happy through optimized support and policy

Location: Hybrid- 3 days a week from our Toronto office & 2 days working from home

Reporting to: Director, Strategy & Operations  

These are some of the key components to the position:  

• Architect Operational Strategy: Partner with Care leadership to design the function's operational framework—building resource models, optimizing return on investment, and refining policies that scale our support for millions of customers and merchants

• Identify & Drive Efficiencies: You will actively find opportunities to improve team and process efficiencies and lead efforts to scale standard methodologies across the organization

• Drive Critical Initiatives: Lead high-priority special projects within Care from concept to execution, solving complex operational problems to enable scale (for example: automation roadmaps, service excellence strategy, experimentation)

• Ensure GTM Readiness: Partner with Strategy & Partnerships to translate competitive intel and GTM plans into operational reality, ensuring Care is fully prepped (staffing, policy, training) ahead of every launch

• Bridge Sales & Support: Collaborate with the Partnerships S&O lead to align incentives, ensuring Care insights (churn risks, service friction) are fed directly into commercial planning

• Orchestrate Actionable Intelligence: Define the reporting strategy for key revenue and customer metrics, ensuring analytics teams deliver high-level insights to leadership

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What will you bring to the team? 

• 7-10 Years Experience: Ideally within the customer support ecosystem or operations function

• Strategic Ops Toolkit: You are an analytical thinker who can build your own dashboards. Salesforce experience and SQL proficiency (for querying large datasets) are required

• Matrix Fluency: You have experience working in a shared-resource model. You know how to "own" a portfolio (Care) while being a supportive "partner" to another (Partnerships) without stepping on toes

• Execution Mindset: You are comfortable with ambiguity and fast execution. You can move from high-level strategic planning to deep-dive data analysis in the same day

• Bonus: MBA or MS in a quantitative field

• Bonus: Experience in a three-sided marketplace (Platform, Merchant, Customer)

• Bonus: Experience managing "Care" or "CX" operations (e.g., BPO management, workforce planning)

Why Join Us?

• Senior Exposure: You will work very closely with Senior leaders in the operations, strategic development, partnerships, and customer teams to quickly understand issues and implement solutions

• The Mindset: Our team does not shy away from rolling up our sleeves, slicing and dicing massive sets of information, and building solutions to problems that have not been taken on yet

• Impact: You will have the opportunity to lead high impact projects, directly influencing business critical customer and partner outcome

• Culture: We are a "Top Places to Work" winner. We are proud of our team and the impact we make on the Canadian tech landscape

• Ownership & Autonomy: You will be empowered to own the learning experience and growth you want at Skip, with the guidance and support of the S&O team

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.

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