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AI Lead

J&M Group
Toronto, CAN
Full-time
Mid-Senior
Onsite
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Lead Operations, Live Programs | AI-Driven Software Development Lifecycle (AI-DLC)

Reporting to: Delivery & Exec Lead, Live Programs

What is the Opportunity?

Live Programs is the largest and most complex workstream inside AI-Driven Software Development Lifecycle (AI-DLC) program.

As the workstream scales across three cohorts and 66+ nominated programs, it needs a disciplined operations engine to keep governance, reporting, and cross-team coordination running without gaps.

As Lead Operations, you will be that engine.

You will be an embedded, vendor-supplied expert reporting directly to the Director, Live Programs, responsible for the day-to-day operating rhythm of the workstream: PMO governance, RAG and readiness tracking, OC and executive reporting artifacts, and the standup cadence that keeps program pods aligned.

This is not a support role.

You will be trusted to run governance independently, flag risks before they become blockers, and produce reporting that is accurate enough to go in front of senior executives without rework.

You will work closely with AI-DLC Leads across Lines of Business, the Program Manager on the Live Programs pod, and the Program Support Group (PSG), and you should be comfortable operating in a fast-moving, high-visibility environment where the quality of your reporting directly shapes what OC delegates and the Executive Steering Group see.

Governance & Pmo Rigor

Own and maintain the risk, issue, action, and decision logs for the Live Programs workstream, ensuring nothing falls through the cracks across 66+ programs and three cohorts.

Run intake governance support: track program sizing, archetype classification, and cohort sequencing status, keeping the master program tracker current and audit-ready.

Enforce PMO discipline across program pods, including consistent status definitions, RAG criteria, and escalation thresholds.

Reporting & Executive Prep

Produce the weekly RAG and readiness reporting pack, translating raw program status into a clear, executive-ready view for OC and Executive Steering Group sessions.

Prepare OC and ESG briefing materials, including milestone trackers, benefit realization snapshots, and escalation summaries, in the format and cadence the Senior Director requires.

Maintain a single source of truth for program status so that any leader can get an accurate read on the workstream at any time.

Standup & Cross-Pod Coordination

Facilitate the Workstream Team daily standup and cross-pod coordination sessions, tracking dependencies between Live Programs, Platform, Change & Learning, Workforce Evolution, and Operations.

Coordinate meeting cadences, agendas, and follow-up tracking for governance forums tied to the workstream.

Ensure action items from standups and governance sessions are logged, owned, and closed on time.

Risk, Issue & Escalation Management

Identify emerging risks and readiness gaps across programs early, using the readiness scorecard framework (orchestrator embedment, scope definition, team allocation, training, tooling, baseline capture, sponsor engagement) to flag issues before they escalate.

Partner with the Program Manager to triage issues, routing operational blockers for resolution and reserving true escalations for the Senior Director.

Track resolution timelines on open risks and issues, and report on aging items that need executive attention.

Must Have

10 to 15 years of experience in program operations, PMO leadership, or governance roles within large-scale technology transformation or enterprise change programs.

Proven governance and reporting expertise, including experience building and maintaining RAG status reporting, risk and issue logs, and executive-ready status packs.

Strong organizational and process discipline, with the ability to manage a high volume of concurrent programs without losing accuracy or consistency.

Comfort operating independently in a vendor or staff augmentation capacity, able to take direction from an internal leader and deliver reliably with minimal oversight.

Financial services or large regulated enterprise experience, with familiarity operating inside formal governance structures, OC processes, and executive reporting expectations.

Proficiency with standard PMO and reporting tooling such as JIRA, Confluence, PowerPoint, and Excel, and the ability to translate raw data into clean, executive-facing visuals.

Clear, concise written and verbal communication, since your reporting output will be read directly by senior stakeholders.

Nice to Have

Prior experience supporting AI, Agile, or SDLC transformation programs, or familiarity with AI-Native SDLC concepts.

Experience

working inside a vendor delivery model supporting a major financial institution.

Familiarity with benefit measurement frameworks and efficiency baseline methodology.

Why This Role Matters

Live Programs cannot scale from 17 programs in Cohort 1 to 40 or more across Cohorts 2 and 3 without a reliable operations backbone.

The Lead Operations role is what makes the workstream trustworthy at the executive level: accurate reporting, disciplined governance, and a standup cadence that catches problems early.

This role is the difference between a workstream that looks organized on paper and one that actually delivers on its commitments.

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