Sr. Agile Program Manager to support GenAI transformation initiatives for a large insurance

Sr. Program Manager, GenAI

Duration: Until December 31,

Location: Toronto or Waterloo (Hybrid; primarily virtual with monthly onsite. Fully remote considered for exceptional candidates)

Project: AI Centre of Excellence (AI COE)

Job Description:

We are seeking an experienced Agile Program Manager to support GenAI transformation initiatives across a large, matrixed organization. This contractor role focuses on program management, agile ceremonies, governance, and execution support for GenAI related‑ capabilities and initiatives across multiple GenAI initiatives, workstreams, and stakeholder groups.

The Agile Program Manager will work closely with technology, platform, innovation, and governance partners to ensure GenAI initiatives, such as shared capabilities, onboarding and adoption efforts, and cross-team coordination, are well-planned, transparent, and outcome-focused. This role operates in a high ambiguity, fast‑ e‑volving environment and requires strong program management discipline paired with comfort navigating emerging technology domains.

Key Responsibilities

GenAI Program Execution

• Manage GenAI initiatives by leading agile ceremonies, executive reporting and coach on agile ways of working.
• Coordinate day‑to‑day execution across workstreams, aligned to enterprise priorities.
• Track scope, milestones, risks, dependencies, and delivery progress across initiatives.
• Support the integration and mobilization of teams into active workstreams and evolve the program toward a scalable, repeatable enablement model.

Agile Delivery & Reporting

· Apply Agile and SAFe program‑level practices to manage flow, sequencing, and delivery across multiple initiatives.

· Help teams navigate cross‑team dependencies and delivery constraints inherent in enterprise GenAI enablement.

· Support reporting through JIRA and Planview Portfolio, including AgilePlace.

· Support program‑level metrics, dashboards, and executive updates focused on cycle time, throughput, adoption progress, and value realization, enabling informed leadership decision‑making.

Enterprise & Executive Stakeholder Coordination

· Support program management activities related to shared GenAI platforms, services, and tooling that enable teams to build or adopt GenAI solutions.

· Track onboarding, enablement, and adoption activities across teams leveraging GenAI capabilities.

· Track and support the rollout of reusable GenAI capabilities, patterns, and enablement assets that can be leveraged across multiple teams to accelerate delivery and reduce duplication.

· Act as an execution connector across GenAI platform teams, innovation, data, security, architecture, and business stakeholders.

· Support the operating cadence of GenAI working groups, enablement forums, and cross‑functional sessions.

Continuous Improvement & Risk Management

• Identify delivery risks, capacity constraints, and process gaps impacting GenAI initiatives.
• Support continuous improvement by capturing learnings and recommending execution or governance refinements.

· Contribute to the evolution of Sun Life’s GenAI program execution model as maturity increases.

Required Qualifications & Experience

• 8-12+ years proven experience managing complex, cross-functional programs in Agile, SAFe, or hybrid delivery environments.
• Demonstrated experience supporting technology enablement, platform, or innovation programs (GenAI, AI, data, cloud, or emerging technology preferred).
• Strong understanding of Agile principles and program-level‑ coordination.
• Experience operating in central orchestration models supporting enterprise programs
• Experience operating in large, matrixed enterprises with senior stakeholders.
• Excellent stakeholder management, communication, and execution skills.
• Proficiency in agile program management tools (JIRA, Planview)

Preferred Qualifications

• Direct experience supporting GenAI, AI, data, or advanced analytics programs.
• Experience working with enterprise GenAI platforms or enablement ecosystems.
• Familiarity with risk, security, and governance considerations in GenAI adoption.
• Agile or program management certifications (Disciplined Agile, SAFe, Scrum, PMI)
• Experience standing up new programs, operating models, or ways of working in ambiguous or emerging domains.
• Bachelor's degree in related field.

Interview Process

• Mode: Virtual
• Rounds: 2
• Panel: Hiring Manager + 1–2 GenAI/platform stakeholders