Insurance Leadership Jobs in Ontario (NOW HIRING)

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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.

Mandate

• Insurance strategy and enterprise alignment: Operationalize insurance strategy through clearly sequenced modernization roadmaps aligned to growth, efficiency, and risk priorities.
• Fiscal planning and investment portfolio management: Own funding investment planning, capital allocation, re-forecasting, and performance tracking across the insurance portfolio.
• Strategy articulation and stakeholder alignment: 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.
• Business casing and funding governance: Define, govern, and prioritize initiatives through rigorous business cases, stage gates, and outcome-based funding decisions.
• Business architecture and delivery governance: Ensure initiatives align to target business architecture, technology standards, and long-term sustainability.
• Vendor and ecosystem leadership: Structure and manage strategic vendor partnerships to deliver predictable outcomes and value realization.
• Change, continuity and adoption: Lead technology and AI change while safeguarding core insurance operations and regulatory commitments.
• Enterprise partnership and mobilization: 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.

KEY RESPONSIBILITIES:

Insurance Strategy, Investment Planning and Portfolio Management

• 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.

Strategy, Roadmap and Business Case Development

• 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.

Business Architecture and Enterprise Alignment

• 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.

Initiative Governance and Delivery

• 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.

AI and Technology Modernization Leadership

• 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.

Vendor Management, Contracting and Partner Ecosystem

• 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.

Business Continuity and Change Management

• 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.

Enterprise Partnership and Cross-Functional Execution

• 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.

Executive Engagement and Communications

• 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.

QUALIFICATIONS:

• 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.

Preferred Background:

• 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.

Core Competencies:

• Insurance strategy execution and portfolio leadership.
• Fiscal discipline and investment governance.
• Enterprise business architecture thinking.
• Executive communication and presence.
• Analytical rigor and decision quality.
• Change leadership and adoption enablement.
• Vendor negotiation and value realization.
• Risk management and operational resilience.

Success Metrics (KPIs / OKRs):

• Portfolio initiatives delivering realized ROI versus approved business cases.
• Accuracy and discipline of capital planning, forecasts, and re-prioritization.
• Cycle time from idea to business case to funding to delivery.
• Value delivered, including efficiency, cost avoidance, revenue enablement, and risk reduction.
• Adoption and satisfaction across insurance business stakeholders.
• Delivery predictability including scope, schedule, and budget adherence.
• Operational resilience and BCP readiness.
• Partner performance and time-to-value.

The above represents BMO Financial Group's pay range and type.

Salaries will vary based on factors such as location, skills, experience, education, and qualifications for the role, and may include a commission structure. Salaries for part-time roles will be pro-rated based on number of hours regularly worked. For commission roles, the salary listed above represents BMO Financial Group's expected target for the first year in this position.

BMO Financial Group's total compensation package will vary based on the pay type of the position and may include performance-based incentives, discretionary bonuses, as well as other perks and rewards. BMO also offers health insurance, tuition reimbursement, accident and life insurance, and retirement savings plans. To view more details of our benefits, please visit:https://jobs.bmo.com/global/en/Total-Rewards

About Us

At BMO we are driven by a shared Purpose: Boldly Grow the Good in business and life. It calls on us to create lasting, positive change for our customers, our communities and our people. By working together, innovating and pushing boundaries, we transform lives and businesses, and power economic growth around the world.

As a member of the BMO team you are valued, respected and heard, and you have more ways to grow and make an impact. We strive to help you make an impact from day one - for yourself and our customers. We'll support you with the tools and resources you need to reach new milestones, as you help our customers reach theirs. From in-depth training and coaching, to manager support and network-building opportunities, we'll help you gain valuable experience, and broaden your skillset.

To find out more visit us at https://jobs.bmo.com/ca/en.

BMO is committed to an inclusive, equitable and accessible workplace. By learning from each other's differences, we gain strength through our people and our perspectives. Accommodations are available on request for candidates taking part in all aspects of the selection process. To request accommodation, please contact your recruiter.

Note to Recruiters: BMO does not accept unsolicited resumes from any source other than directly from a candidate. Any unsolicited resumes sent to BMO, directly or indirectly, will be considered BMO property. BMO will not pay a fee for any placement resulting from the receipt of an unsolicited resume. A recruiting agency must first have a valid, writt...