Manager, Digital Strategy & Transformation

Recrute Action•Toronto, ON

3d•Hybrid

About The Position

Dynamic contract opportunity in the insurance industry focused on digital strategy, transformation, and executive-level communications. This hybrid Toronto-based role supports enterprise initiatives, combining strategic analysis, stakeholder coordination, and operational execution within a fast-paced digital environment.

Requirements

Bachelor’s degree required in a relevant field.
5+ years of experience in strategy, transformation, management consulting, chief of staff, product operations, or digital program roles.
Strong problem-solving ability with experience structuring ambiguity into actionable plans.
Proven ability to create executive-ready materials with advanced PowerPoint skills.
Demonstrated ability to collaborate and influence across functions and seniority levels.
High attention to detail with strong coordination, prioritization, and follow-through skills.
Experience supporting digital strategy or digital transformation initiatives.
Background in a product-led or agile environment.
Familiarity with agile tools and ways of working such as Jira, Rally, or Confluence.
Experience contributing to digital product work across discovery to delivery.
Experience in financial services or other regulated environments.
Change management or operating model design experience.

Responsibilities

Support digital strategy development, refreshes, and prioritization.
Structure ambiguous problems and synthesize insights into clear options and recommendations.
Develop and refine executive-level presentations, briefing materials, and one-pagers.
Ensure clear narratives, decision points, and concise messaging for leadership audiences.
Prepare agendas, pre-reads, meeting decks, and logistics.
Capture decisions, track action items, and escalate risks or issues as needed.
Support operating model evolution, governance discussions, and ways of working improvements.
Document processes, frameworks, and operating principles.
Consolidate status updates, metrics, and reporting across workstreams.
Assist with budget tracking, forecasting inputs, and leadership reporting.
Maintain core team assets including org charts, onboarding materials, and team sites.
Support onboarding, access setup, and tool coordination.
Enable consistent use of templates, tracking, and operating cadence.
Support communications and adoption activities for organizational or process changes.
Provide hands-on support for product-related work such as research synthesis, roadmap inputs, prioritization, or data analysis.