Remote Business Operations & Strategy Lead (Remote, Canada)

Business Operations & Strategy Lead (Individual Contributor)

Location: Toronto / Montreal / Remote
Company: 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 linear process overhead

3) Strategic Initiatives & Operational Scale

• Support high-impact operational and strategic initiatives across the business as company needs evolve


• Help drive cross-functional initiatives related to:




• Pricing and monetization strategy


• Customer contracting and commercial operations


• Operational readiness for new products or workflows


• Partner and vendor operational processes


• Customer onboarding and lifecycle optimization


• Internal knowledge management and workflow standardization


• KPI definition and operational reporting


• AI enablement across business functions


• Help leadership identify opportunities to simplify operations, improve scalability, and increase organizational effectiveness


• Contribute to special projects that sit at the intersection of strategy, operations, and execution

What We’re Looking For

Core Capabilities (Must-Have)

• Strong problem-solving and structured thinking skills, with the ability to break down complex, ambiguous business problems and drive to practical solutions


• Details matter - you obsess over finished product


• Zero defect - we all make mistakes, but you find ways to check your work and sense check output


• Ability to operate effectively in a fast-paced, high-growth environment


• Strong cross-functional collaboration and stakeholder management skills


• High ownership mindset—you are comfortable both designing solutions and executing them yourself

Relevant Experience (Flexible Pathways)

We are open to candidates from multiple backgrounds, including strategy consulting, business operations, RevOps, finance, or similar roles. You should bring some combination of the following:

• Experience working on operational, revenue, pricing, go-to-market, or business process challenges


• Exposure to enterprise customer environments, commercial operations, contracting, or complex transaction structures (direct or indirect)


• Understanding of business data structures such as CRM data


• Experience building, redesigning, or improving business processes in ambiguous environments, particularly in companies scaling from ~$40M–$100M ARR. Systems integration experience is a plus.


• Familiarity with AI tools, automation, or system design thinking (hands-on experience and/or python familiarity is a plus; strong learning mindset is essential)


• Experience driving cross-functional initiatives involving multiple stakeholders and competing priorities

What Will Set You Apart

• You’ve taken ownership of a messy, cross-functional problem and built a scalable solution—not just recommended one


• You are excited about AI and agentic workflows and their potential to transform business operations


• You are looking to transition from advisory → operator, with direct accountability for outcomes


• You enjoy working at the intersection of strategy, operations, systems, and execution

Important (But Learnable on the Job)

• Deep experience with quote-to-cash workflows or contracting


• Familiarity with CRM, CLM, or related systems


• Industry experience in insurance or enterprise SaaS

What matters most is your ability to learn quickly, build systems, and drive outcomes.