Senior Strategy & Operations Manager (Toronto) Full Time NEW

About Starling

Starling operates the delivery network behind local food distribution. We partner with food makers, retailers, and enterprise clients to coordinate fast, reliable last-mile deliveries — and we’re scaling into new markets.

The business is growing in complexity faster than it’s growing in headcount. This role exists because we need someone who can see the whole system clearly enough to know where it’s breaking — and be comfortable enough in the details to actually fix it.

The Role

We’re looking for a highly analytical, execution-focused Senior Strategy & Operations Manager to own delivery operations while helping us scale into new markets.

This is a wide-scope role for someone who creates clarity rather than waiting for it. You’ll work directly with the founder and cross-functionally with dispatch, client teams, and drivers to identify problems, build the analytical case for solutions, and then actually implement them.

What You’ll Do

Operations Strategy & Execution

• Design and implement delivery routes across active markets based on changing demand
• Optimizing route fulfillment and analyze driver utilisation, cost structure and network reliability
• Own live operations during high-volume delivery periods: real-time decision-making and escalation resolution
• Identify and lead high-impact projects focused on scaling Starling across all markets

Analytics & Planning

• Build and maintain models, dashboards, and business cases that drive operational decision-making
• Own planning cycles (weekly, quarterly) including forecasting, capacity planning, and performance tracking against targets
• Use data to surface patterns before they become incidents — and build the processes that prevent recurrence

Cross-Functional Ownership

• Work across dispatch, client success, and leadership to develop, pilot, and build out new operational initiatives
• Bring clarity to complex problems for the people who need to act on them — whether that’s the founder, a client, or a driver
• Use AI tools, including Claude, as a force multiplier: analysis, SOPs, synthesis, scenario planning

Driver & Network Operations

• Own driver coverage, performance, and retention across active markets
• Build the accountability systems and feedback loops that make quality consistent at scale
• Lead onboarding and training processes as the driver network grows

What We’re Looking For

• 5+ years of experience in a strategy, operations, or analytical role — consulting, finance, or a high-growth company where the work was genuinely complex
• Strong analytical instincts — comfortable turning route data, incident logs, or financial models into a clear story and a clear decision
• Proficiency in Excel and comfortable building business cases from scratch
• Able to operate without guardrails: you define your own priorities and hold yourself accountable to them
• Clear, direct communicator who can tailor the message for stakeholders at any level
• Genuinely AI-native — you already use tools like Claude to move faster and think better, not as a novelty

Preferred

• Experience in marketplace, logistics, or last-mile operations
• Experience at a startup or in high-growth environments where the playbook didn’t exist yet
• Comfort with routing or dispatch systems (OnFleet or similar)