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OCM Strategy Lead

Job in Toronto, Ontario, C6A, Canada
Listing for: Cynet Systems Inc
Full Time position
Listed on 2026-03-10
Job specializations:
  • IT/Tech
    Change Management
  • Management
    Program / Project Manager, Change Management
Salary/Wage Range or Industry Benchmark: 60000 - 80000 CAD Yearly CAD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

Job Description

  • The OCM Strategy Lead will advise executive leadership and senior stakeholders on organizational change management strategies aligned with business objectives across the Insurance Value Chain.
  • The role involves leading transformation initiatives, shaping strategic roadmaps, ensuring stakeholder alignment, and driving measurable business outcomes through structured change management practices.
Responsibilities
  • Advise C-suite and senior stakeholders on OCM strategy aligned with business goals and stakeholder engagement across the Insurance Value Chain.
  • Lead OCM strategy planning activities including stakeholder identification, engagement impact analysis, change readiness assessments, and resistance management.
  • Shape and lead training and communication plans from visioning and roadmap development to execution oversight and value realization.
  • Execute and deliver the OCM roadmap and plan ensuring alignment with strategic objectives while managing risks, dependencies, and stakeholder expectations.
  • Facilitate executive workshops and strategic planning sessions to co-create transformation initiatives.
  • Monitor KPIs and transformation outcomes to ensure measurable business impact and continuous improvement.
Qualifications
  • Master’s degree, MBA, or related advanced degree required.
Experience
  • 10–15 years of experience in Insurance Organization Change Management programs with a mix of advisory and delivery leadership experience.
  • Proven track record of leading strategic engagements and overseeing successful delivery in insurance domains such as underwriting, claims, and policy administration.
  • Strong understanding of OCM activities, insurance operations, regulatory frameworks, and digital transformation trends.
  • Experience working with at least 2–3 leading global insurance carriers.
  • Subject matter expertise in at least 1–2 key insurance domains including policy administration, underwriting, billing, or claims.
  • Experience designing and implementing target operating models, transformation roadmaps, and capability assessments.
  • Demonstrated ability to bridge strategy and execution ensuring transformation initiatives are visionary and actionable.
  • Experience advising on digital transformation including adoption of AI, automation, cloud platforms, and their business impact.
  • Strong stakeholder engagement and governance experience with the ability to influence senior executives and align cross-functional teams.
  • Familiarity with regulatory and compliance considerations in insurance transformation programs.
  • Experience in value tracking and benefits realization ensuring measurable and sustainable outcomes.
  • Exposure to multi-vendor environments and complex delivery ecosystems with the ability to manage dependencies and integration challenges.
Nice to Have
  • Familiarity with insurance platforms such as Guidewire, Duck Creek, or Majesco.
  • Experience with Agile, SAFe, or hybrid delivery models.
  • Strong commercial acumen with the ability to link strategy to execution.
  • Certifications in project or change management such as PMP, Prosci, or SAFe.
  • Excellent communication, facilitation, and leadership skills.
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