Director Insurance - Digital Strategy & Delivery

BMO•Toronto, ON

4d•CA$94,600 - CA$176,000•Onsite

About The Position

The Director Insurance - Digital Strategy & Delivery is a senior insurance transformation leader accountable for enterprise insurance strategy execution, fiscal planning, and modernization investment outcomes across BMO Insurance. This role translates insurance business strategy and capital allocation decisions into delivered results through disciplined portfolio management, investment prioritization, modernization delivery, and business line architecture alignment. The Director leads complex, multi-year strategies spanning core insurance platforms, data and AI, distribution, and operating model modernization. The role ensures investments are strategically aligned, financially sound, architecturally coherent, and operationally sustainable, delivering measurable value across Retail, Advisory, and Institutional insurance businesses.

Requirements

8+ years in insurance strategy, transformation, consulting, or enterprise delivery roles.
Demonstrated ability to drive execution through a combination of internal teams, PMO and project management functions, and external partners to de-risk complex enterprise initiatives and ensure sustained progress.
Strong strategy development and executive presentation skills, with a proven ability to align and influence senior stakeholders and partners through clear narratives and effective delivery.
Proven experience leading large-scale insurance modernization programs with measurable business outcomes.
Strong financial and investment acumen, including business cases, capital planning, portfolio governance, and benefits realization.
Solid understanding of insurance operating models, platforms, and regulatory environments.
Working knowledge of AI technologies, Insure AI applications, and Agentic AI concepts.
Demonstrated expertise in enterprise governance, vendor management, and executive engagement.
Demonstrated ability to work effectively across Technology, AI, Data, Procurement, Risk, Finance, and Strategy partners to align objectives and execute complex, enterprise-scale initiatives.

Nice To Haves

Former consultant with insurance strategy and modernization experience.
Direct exposure to insurance fiscal planning, investment governance, or enterprise portfolio management.
Experience with Canadian life insurance and wealth management ecosystems.
Insurtech, AI innovation, or digital product strategy experience.
Familiarity with enterprise architecture, platform modernization, and data/AI operating models.

Responsibilities

Operationalize insurance strategy through clearly sequenced modernization roadmaps aligned to growth, efficiency, and risk priorities.
Own funding investment planning, capital allocation, re-forecasting, and performance tracking across the insurance portfolio.
Shape and communicate clear, compelling strategies through high-quality executive narratives and presentations that align stakeholders, partners, and delivery teams around a shared modernization journey.
Define, govern, and prioritize initiatives through rigorous business cases, stage gates, and outcome-based funding decisions.
Ensure initiatives align to target business architecture, technology standards, and long-term sustainability.
Structure and manage strategic vendor partnerships to deliver predictable outcomes and value realization.
Lead technology and AI change while safeguarding core insurance operations and regulatory commitments.
Work closely with Technology, AI, Procurement, Risk, Finance, Data, and Strategy partners acss the enterprise to align priorities, mobilize resources, and execute initiatives forward at pace.
Act as a strategic execution partner to Insurance leadership, translating enterprise and line-of-business strategies into funded, sequenced modernization initiatives.
Own the insurance modernization investment portfolio, including capital planning, multi-year forecasting, re-prioritization, and benefits realization tracking.
Lead annual and in-flight fiscal planning for modernization initiatives (CapEx/OpEx), ensuring financial discipline, transparency, and value-for-money decisions.
Balance growth, efficiency, regulatory, and resiliency investments, making trade-offs explicit and evidence-based.
Develop clear, decision-ready strategy materials, roadmaps, and business cases that frame trade-offs, sequencing, and outcomes for executive and enterprise audiences.
Build and maintain an enterprise-aligned insurance modernization roadmap integrating product, distribution, platform, data, and AI capabilities.
Identify high-impact insurance opportunities and develop robust business cases (ROI, NPV, TCO, CSM impact, risk, and feasibility).
Conduct insurance-specific financial modeling to support prioritization, funding approvals, and stage-gate decisions.
Ensure initiatives are architected end-to-end for long-term business sustainability and operational scalability.
Partner with Architecture, Technology, and Business leaders to ensure initiatives align to target insurance business architecture, operating models, and platform strategy.
Drive coherence across process, data, technology, and organizational design, reducing fragmentation and technical or operational debt.
Ensure modernization decisions consider enterprise reuse, interoperability, and future-state scalability across Retail, Advisory, and Institutional businesses.
Establish and run portfolio, operating, and steering governance cadences with clear decision rights and escalation paths.
Drive cross-functional execution with disciplined scope, milestone, dependency, and risk management.
Drive execution end-to-end through a mix of internal teams, project managers, PMO functions, and external delivery partners.
Establish clear accountability, delivery cadence, and escalation paths to de-risk execution and ensure forward progression.
Actively intervene to resolve delivery friction, resourcing constraints, or dependency issues that impede momentum.
Maintain executive-ready dashboards covering financials, delivery performance, value realization, and risk posture.
Serve as a Strategic Program Leader within the Transformation Office, integrating insights across workstreams.
Lead identification and scaling of Insure AI and Agentic AI use cases (e.g., autonomous workflows, underwriting support, advisor enablement).
Translate emerging technologies into practical insurance modernization strategies that improve productivity and retire legacy constraints.
Partner with internal teams, innovation hubs, and Insurtechs to pilot, industrialize, and operationalize solutions.
Leverage external delivery partners, system integrators, and advisory firms selectively to accelerate execution, mitigate delivery risk, and supplement internal capacity and capability.
Lead procurement and contracting, establishing outcome-based SLAs, KPIs, and commercial models.
Manage partner performance to ensure delivery predictability, financial control, and regulatory compliance.
Coordinate closely with Legal, Risk, Compliance, and Procurement on third-party risk and governance.
Lead Insurance business line Business Continuity Planning, Disaster Recovery and operational resilience requirements.
Lead operational technology change management, communications, training, and adoption efforts across insurance lines.
Proactively resolve process, policy, and capability blockers to embed new ways of working.
Partner across Technology, AI, Data, Procurement, Risk, Finance, and Strategy functions to align modernization initiatives to enterprise standards, funding guardrails, and risk requirements.
Coordinate execution across business teams, PMO, and partner delivery resources to ensure initiatives move from strategy to implementation without stall or dilution of outcomes.
Mobilize cross-functional teams to move initiatives from strategy through delivery, ensuring clear ownership, sequencing, and decision-making.
Resolve cross-enterprise dependencies and constraints (architecture, data, funding, risk, sourcing) to maintain delivery momentum.
Act as the connective tissue between business strategy, enabling functions, and delivery teams to ensure initiatives progress predictably.
Build and deliver high-impact presentations, briefs, and storytelling artifacts that translate complex strategies, financials, and delivery plans into clear, actionable narratives.
Bring executives, business leaders, and partners along the transformation journey by aligning perspectives, managing expectations, and securing sustained sponsorship.
Tailor messaging for different stakeholder groups (executives, delivery teams, partners) to ensure clarity, confidence, and momentum.
Develop clear, decision-oriented materials for executives, SteerCo, and enterprise forums.
Provide a strong insurance business voice, clarifying scope, trade-offs, outcomes, and value realization.
Align cross-functional teams around strategic objectives, fiscal guardrails, and roadmap milestones.