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Business Operations & Strategy Lead

ZestyAI4 days ago
Montreal, QC {{REMOTE}}
Senior Level
Full-Time

Top Benefits

Health, dental, vision plans plus free One Medical membership.
Stock options for all full‑time employees.
401k plan via Mass Mutual partnership.

About the role

  • 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
    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
    1. 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
    1. 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

Benefits

  • Health Coverage - Rich health plans for medical, dental, and vision are complemented by a free One Medical membership
  • Equity - Stock options are granted to all full-time employees. We want you to be and think like an owner!
  • 401k - Save for retirement through our 401k partnership with Mass Mutual
  • FSA & Commuter Benefits - Save with a flexible spending account for medical and dependent needs. Zesty.ai also offers tax-saving commuter benefits
  • Vacation Policy - No time accrual here; take time off as you need. Employees are encouraged to travel and be with their families!
  • Life Insurance - Zesty.ai offers long term disability and life insurance to give you and your family peace of mind
  • Team Outings & Trips - Quarterly team outings and a 3-4 day annual trip is a must for quality team bonding time
  • Workplace Perfection - Find your perfect blend of ergonomics and productivity! Zesty.ai provides a budget to get your home workplace set up for success
  • Monthly Team Lunches - Along with each month’s company-wide meeting comes an opportunity to have your favorite meal delivered right to you
  • Learning & Development - We never stop learning and growing. Feed your mind with a culture that supports and fosters your growth- Is excited to apply AI and automation to real business operations
  • Enjoys solving ambiguous, cross-functional problems
  • Wants to build and scale processes in a high-growth environment (~$25M–$100M ARR)
  • Is motivated by direct ownership of business outcomes
  • Ability to operate effectively in a fast-paced, high-growth environment
  • Details matter - you obsess over finished product
  • Strong problem-solving and structured thinking skills, with the ability to break down complex, ambiguous business problems and drive to practical solutions
  • High ownership mindset—you are comfortable both designing solutions and executing them yourself
  • Strong cross-functional collaboration and stakeholder management skills
  • Zero defect - we all make mistakes, but you find ways to check your work and sense check output
  • Experience driving cross-functional initiatives involving multiple stakeholders and competing priorities
  • 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 building, redesigning, or improving business processes in ambiguous environments, particularly in companies scaling from ~$25M–$100M ARR. Systems integration experience is a plus
  • Understanding of business data structures such as CRM data
  • 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:
  • Exposure to enterprise customer environments, commercial operations, contracting, or complex transaction structures (direct or indirect)
  • Experience working on operational, revenue, pricing, go-to-market, or business process challenges
  • You’ve taken ownership of a messy, cross-functional problem and built a scalable solution—not just recommended one
  • You enjoy working at the intersection of strategy, operations, systems, and execution
  • You are looking to transition from advisory → operator, with direct accountability for outcomes
  • You are excited about AI and agentic workflows and their potential to transform business operations
  • Important (But Learnable on the Job)
  • Familiarity with CRM, CLM, or related systems
  • Industry experience in insurance or enterprise SaaS
  • Deep experience with quote-to-cash workflows or contracting

About ZestyAI

Software Development
51-200

ZestyAI offers insurers and real estate companies access to precise intelligence about every property in North America. The company uses AI, including computer vision, to provide a constantly updated database of 200 billion property insights accounting for every detail that could impact a property’s value and associated risks, including the potential impact of natural disasters. Visit https://zesty.ai for more information.

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