The Director of AI, Delivery Squad Lead is accountable for the end-to-end execution of AI powered underwriting initiatives (i.e., Life Insurance Underwriting, Automated Underwriting, Underwriting Decision Support, Advisor Underwriting Experience, and Underwriting Transformation). The role translates Solutioning-defined priorities into delivered AI solutions, ensuring execution with speed, quality, and measurable business impact. This role requires a deep understanding of life insurance risk assessment and underwriting decision-making to ensure AI solutions appropriately balance growth, customer experience, risk selection, and operational efficiency.

This role is the single point of accountability for delivery execution, ensuring initiatives are effectively scoped, sequenced, executed, and aligned to timelines, capacity, and governance requirements. The role also provides financial oversight of the delivery portfolio, coordinates dependencies across IT, data, architecture, and business stakeholders, and ensures delivery teams have clear scope, sequencing, and execution expectations. Own the full lifecycle delivery of assigned AI initiatives, from execution planning and backlog readiness through production deployment, adoption, and value realization.

Translate prioritized initiatives into clear work packages, defined scope, team tasks, sequencing, and delivery timelines; Lead the day-to-day execution of data scientists and cross-functional squad members by setting clear accountabilities, monitoring commitments, and maintaining delivery momentum and discipline. Proactively identify risks, remove blockers, and resolve delivery issues to maintain pace and quality. Establish and maintain the squad’s delivery operating rhythm, including sprint planning, backlog management, quality controls, and performance reviews.

Apply deep domain expertise in life insurance risk assessment, underwriting philosophy, and risk selection to guide solution design, prioritize opportunities, and ensure AI capabilities address meaningful underwriting challenges. Leverage deep domain expertise to tailor execution plans to operational, regulatory, and market context, driving measurable business impact Actively bridge business strategy and technical delivery by contextualizing priorities with industry trends, stakeholder needs, and organizational objectives to ensure alignment and value realization. Align delivery to business strategy and defined scope provide delivery feasibility, capacity, dependency, and sequencing input without owning intake or portfolio prioritization decisions.

Underwriting AI Delivery Leadership Lead execution of the underwriting AI portfolio, ensuring each approved initiative progresses through planning, build, validation, production deployment, adoption, and outcome measurement. Translate underwriting priorities into executable roadmaps and delivery plans. Partner with underwriting leaders to modernize underwriting operations through AI.

Partner with underwriting leaders to plan and execute change, training, communications, and operating-process updates required for adoption of AI-enabled underwriting capabilities. Lead the translation of complex underwriting challenges into data-driven and AI-enabled solutions through close collaboration with data scientists, engineers, and business stakeholders. Identify opportunities to standardize and reuse underwriting data, models, components, controls, and delivery patterns across products and business units, and coordinate their implementation with platform owners.

Balance growth, risk, operational efficiency, and customer experience objectives.



Cross-Functional Delivery Orchestration Lead cross-functional delivery across data science, engineering, product, business teams, and shared services. Orchestrate delivery across underwriting, actuarial, product, distribution, data science, engineering, risk, compliance, technology, architecture, and other shared-service partners.

Maintain an integrated dependency plan across systems, data, architecture, controls, operating processes, and delivery partners; Confirm stakeholder decisions, control requirements, operating readiness, and handoffs at each stage of the delivery lifecycle.

Portfolio

Management & Delivery Orchestration Maintain the integrated delivery portfolio view for approved underwriting AI initiatives, showing alignment to segment priorities, OKRs, AI strategy, dependencies, milestones, capacity, risks, and expected outcomes. The portfolio may include automated underwriting platforms, underwriting requirement optimization, advisor-facing underwriting assistants, underwriting knowledge and decision-support capabilities, fraud detection, and future-state underwriting transformation initiatives. Coordinate delivery across initiatives by identifying cross-portfolio dependencies, assessing execution trade-offs, and escalating decisions that require Product, Solutioning, or stakeholder prioritization.

Maintain disciplined execution through project controls, risk management, performance reporting, and transparent escalation; Resource & Budget Management Own resource and financial planning for the approved delivery portfolio, aligning squad capacity, external spend, and funding requirements to committed outcomes and delivery milestones. Provide leadership with decision-ready budget updates, including actuals, forecasts, variance drivers, funding risks, and cost estimates for approved or emerging opportunities.

Delivery

Governance & Reporting Operate within established intake, delivery governance, risk, compliance, architecture, and responsible AI frameworks, ensuring required approvals and evidence are completed before key delivery gates. Contribute delivery estimates, dependency assessments, resource requirements, acceptance criteria, and technical feasibility input so approved initiatives are ready for squad execution. Provide timely, decision-oriented reporting on progress, milestones, capacity, financial performance, risks, dependencies, outcomes, and required leadership actions.

Ensure each initiative has approved KPIs, baseline measures, target outcomes, accountable business owners, and an agreed measurement approach before delivery begins. Track delivery, adoption, operational, customer, risk, and financial measures through implementation and value realization. Build squad delivery capability by coaching cross-functional teams, strengthening delivery practices, and reinforcing predictable, high-quality execution.

Life insurance underwriting, risk assessment, and risk selection principles, including understanding mortality and morbidity drivers, underwriting decision frameworks and AI-enabled decision support.

Experience with insurance product manufacturing and distribution, including advisor and customer experience. Enterprise AI product and solution delivery experience,



including cross-functional execution from planning through production deployment and value realization. Understanding of agentic AI patterns and safeguards, including orchestration, planning, memory, tool use, permissions, auditability, failure handling, and human escalation.

Experience with grounding, retrieval-augmented generation, prompt design, evaluation, observability, and responsible AI controls for accurate, reliable, and compliant GenAI solutions.

Experience delivering enterprise GenAI solutions, with knowledge of foundation models, orchestration, APIs, vector retrieval, data integration, deployment, adoption, and value realization.

Experience applying advance analytics, machine learning, AI, or decision science to solve complex underwriting, risk management, or insurance business challenges. Demonstrated ability to manage delivery risks, dependencies, resources, budgets, governance, and executive-level portfolio reporting. Strong stakeholder leadership and ability to bridge underwriting business priorities with technical delivery.

We’ll recognize and support you in a flexible environment where well-being and inclusion are more than just words.

Manulife Financial

Corporation is a leading international financial services provider, helping people make their decisions easier and lives better. At Manulife/John Hancock, we embrace our diversity. We strive to attract, develop and retain a workforce that is as diverse as the customers we serve and to foster an inclusive work environment that embraces the strength of cultures and individuals.

We are committed to fair recruitment, retention, advancement and compensation, and we administer all of our practices and programs without discrimination on the basis of race, ancestry, place of origin, colour, ethnic origin, citizenship, religion or religious beliefs, creed, sex (including pregnancy and pregnancy-related conditions), sexual orientation, genetic characteristics, veteran status, gender identity, gender expression, age, marital status, family status, disability, or any other ground protected by applicable law. All information shared during the accommodation request process will be stored and used in a manner that is consistent with applicable laws and Manulife/John Hancock policies. 113,260.00 CAD - $210,340.00 CAD Employees also have the opportunity to participate in incentive programs and earn incentive compensation tied to business and individual performance. The actual salary will vary depending on local market conditions, geography and relevant job-related factors such as knowledge, skills, qualifications, experience, and education/training. com for the salary range for your location.

Manulife offers eligible employees a wide array of customizable advantages, including health, dental, mental health, vision, short- and long-term disability, life and AD&D; insurance coverage, adoption/surrogacy and wellness benefits, and employee/family assistance plans. We also offer eligible employees various retirement savings plans (including pension and a global share ownership plan with employer matching contributions) and financial education and counseling resources. Our generous paid time off program in Canada includes holidays, vacation, personal, and sick days, and we offer the full range of statutory leaves of absence.

We use data and analytics technologies, such as artificial intelligence (AI), and automated processing tools, to analyze and process the information you provide to us or third parties in the application process. For more information, please refer to our personal information collection statement. #

📌 Director, AI Delivery Squad Lead, Underwriting (Toronto)
🏢 Manulife
📍 Toronto