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GreenShield

Director - Strategy & Operations Enablement - Hybrid

GreenShield
Posted 3 days ago
Toronto, CA (Hybrid)

Key Details

Top Skills Required

Business Case DevelopmentChange ManagementValue Tracking +17 more

Description

Reporting to the SVP, Product, Experience and Health Outcomes, this role will play a critical role in shaping portfolio strategy, connecting priorities across teams, and translating strategic direction into disciplined execution and measurable business impact. The Director, Strategy & Operations Enablement will build and run the operating mechanisms that align Product, Customer Experience, Health Outcomes and cross-functional partners around a shared agenda. 
The role is accountable for strengthening the strategy-to-execution system: annual and quarterly planning, portfolio governance, prioritization, executive reporting, performance management, competitive landscape monitoring, and operational enablement. It will ensure the team is focused on the right work, has the right forums and decision mechanisms, and can demonstrate progress against outcomes that matter to the clients and the business. 
This is a high-impact, enterprise-facing role for a strategic operator who can bring structure to ambiguity, connect insight to action, and help the organization move from intent to execution with pace, transparency, and discipline. 

Responsibilities:

  • Work directly with the SVP and leadership team to help formulate strategy, frame strategic choices, connect insights across teams, and translate direction into annual and quarterly priorities, integrated plans, measurable outcomes, and clear accountabilities. 
  • Act as an integrator across Product, Experience, Health Outcomes and enterprise partners: surfacing patterns, identifying interdependencies, and helping leadership see the bigger picture behind decisions and trade-offs. 
  • Partner closely with Corporate Strategy to ensure Product, Experience, and Health Outcomes priorities are aligned with enterprise strategy, informed by competitive and market insights, and reflected in executive planning and decision-making forums. 
  • Own the strategy-to-execution cadence, including planning cycles, leadership forums, decision governance, executive updates, performance reviews, and follow-through on key actions. 
  • Build and maintain an integrated view of portfolio priorities, milestones, risks, dependencies, investment trade-offs, and performance against committed outcomes. 
  • Lead competitive landscape and market intelligence efforts across health benefits, digital health, product experience, personalization, member engagement, and adjacent sectors; convert insights into implications for strategy, roadmap choices, and differentiation. 
  • Establish operating mechanisms that improve decision quality, prioritization discipline, cross-functional alignment, and visibility into execution progress. 
  • Partner with Finance and business leaders on budget planning, forecasting, resource allocation, business cases, and value tracking to ensure investments are tied to strategic priorities and measurable impact. 
  • Support the definition and evolution of the operating model, including governance, roles, processes, decision rights, ways of working, and management routines across Product, Experience, and Health Outcomes. 
  • Drive preparation of executive-ready materials, including strategy narratives, decision papers, board and EC updates, planning documents, performance dashboards, and cross-functional communications. 
  • Identify opportunities to simplify, standardize, and improve core planning and operating processes, enabling teams to execute with greater speed, consistency, and accountability. 
  • Lead or incubate high-priority strategic initiatives that require focused orchestration, problem solving, change management, or cross-functional mobilization. 

Job Details

Job Type
full time

Required Skills

Business Case DevelopmentChange ManagementValue TrackingForecastingLeadershipResource AllocationPerformance ManagementProblem-solvingExecutive ReportingAdaptabilityCompetitive IntelligenceCommunicationStrategic ThinkingStrategic PlanningPrioritizationOperating Model DesignPortfolio GovernanceMarket IntelligenceBudget PlanningPortfolio Strategy