Business Operations & Strategy Lead (Remote, Canada)

Business Operations & Strategy Lead (Individual Contributor) Location: Toronto / Montreal / RemoteCompany: ZestyAI About ZestyAI ZestyAI is transforming how the insurance industry understands and prices risk using advanced AI. We partner with leading insurers to deliver better underwriting, smarter pricing, and improved resilience in the face of climate risk. Role Overview We are looking for a highly versatile Business Operations & Strategy Lead (IC) to help build and scale critical business operations at ZestyAI. This is a unique opportunity for someone who thrives at the intersection of strategy and execution—and wants to move beyond advising into building and operating critical business systems. You will initially focus on improving and scaling how our customers move from pricing through contracting to customer handoff, partnering closely with Sales, Legal, Finance, and Customer Success. Over time, the role is expected to expand into broader operational and strategic initiatives across the company. At the same time, you will design and implement AI-driven systems and workflows that make business operations faster, smarter, and more scalable. This role is especially well-suited for someone who: Enjoys solving ambiguous, cross-functional problems Wants to build and scale processes in a high-growth environment (~$40M–$100M ARR) Is excited to apply AI and automation to real business operations Is motivated by direct ownership of business outcomes What You’ll Do 1) Revenue Execution & Business Operations Serve as the central coordinator for complex enterprise opportunities from pricing through contract execution and customer handoff Partner closely with Sales, Legal, Finance, and Customer Success to improve operational efficiency and execution quality across the customer lifecycle Structure and review commercial terms for pricing integrity, scalability, and operational feasibility Own and evolve key business workflows including approvals, contracting, pricing governance, exception management, and operational readiness Identify bottlenecks, process gaps, and scaling risks across go-to-market operations and drive practical solutions Support operational initiatives tied to customer onboarding, renewals, partner workflows, and cross-functional execution 2) AI-Driven Automation & Process Design Design and implement AI-first workflows and systems that reduce manual effort and compress cycle times Build and deploy agentic solutions (AI agents, copilots, orchestration layers) to support operational decision-making and workflow execution Use AI to augment business processes including pricing analysis, workflow routing, contract generation, knowledge retrieval, and operational monitoring Continuously evolve processes toward adaptive, self-improving systems rather than static workflows Partner cross-functionally to integrate automation into core business operations Act as a force multiplier by increasing organizational leverage without line...