Sr. Technical Project Manager - Agentic AI & ML Platform - Enterprise Delivery

Location: South Brampton: 5 days on-site

Start Date: ASAP

Contract Term: Until end of April 2027. High change of renewal.

Our client, one of Canada's largest retailers, is seeking a Senior Technical Program Manager to support the delivery of enterprise AI, Data, and ML initiatives within their Data & Engineering organization.

This is a highly visible, fast-paced role working closely with senior engineering and data science leadership. The right candidate will be equally comfortable translating complex technical concepts into executive-ready communications and rolling up their sleeves to drive day-to-day delivery across multiple concurrent workstreams.

This is not a traditional PM role. You will be embedded with technical teams working on agentic AI, data platforms, and ML initiatives, and will need the credibility and fluency to operate effectively in that environment.

Responsibilities

Translate complex technical programs and project updates into clear, concise executive presentations and communications for Sr. Directors and above

Drive program delivery across AI, Data, and ML workstreams including timeline management, dependency tracking, and stakeholder coordination

Lead cross-functional coordination across engineering, data science, product, and business teams to keep programs on track

Facilitate technical discussions, capture decisions, and ensure clear accountability and follow-through

Prepare and present program status updates, risks, and recommendations to senior leadership

Identify and proactively manage risks, blockers, and escalations across active workstreams

Support planning and roadmap activities for the Data and ML Engineering portfolio

Must Haves

8-10+ years of experience in Technical Program Management or related roles

Strong technical fluency - ability to understand and communicate AI, data,



and ML concepts credibly with engineering teams and executive stakeholders

Experience supporting AI, GenAI, or ML platform programs

Proven experience preparing and delivering executive-level presentations and communications

Experience managing complex, multi-workstream programs in fast-paced enterprise environments

Solid stakeholder management and cross-functional coordination skills

Excellent written and verbal communication skills

Ability to operate with minimal oversight and drive clarity in ambiguous situations

Nice to Haves

PMP or equivalent certification

Background in retail or large enterprise environments

Experience supporting platform build-out or 0 to 1 initiatives

Familiarity with agile delivery methodologies

Logistics

Location: South Brampton: 5 days on-site

Start Date: ASAP

Contract Term: Until end of April 2027. High change of renewal.

Our client, one of Canada's largest retailers, is seeking a Senior Technical Program Manager to support the delivery of enterprise AI, Data, and ML initiatives within their Data & Engineering organization.

This is a highly visible, fast-paced role working closely with senior engineering and data science leadership. The right candidate will be equally comfortable translating complex technical concepts into executive-ready communications and rolling up their sleeves to drive day-to-day delivery across multiple concurrent workstreams.

This is not a traditional PM role. You will be embedded with technical teams working on agentic AI, data platforms,



and ML initiatives, and will need the credibility and fluency to operate effectively in that environment.

Responsibilities

Translate complex technical programs and project updates into clear, concise executive presentations and communications for Sr. Directors and above

Drive program delivery across AI, Data, and ML workstreams including timeline management, dependency tracking, and stakeholder coordination

Lead cross-functional coordination across engineering, data science, product, and business teams to keep programs on track

Facilitate technical discussions, capture decisions, and ensure clear accountability and follow-through

Prepare and present program status updates, risks, and recommendations to senior leadership

Identify and proactively manage risks, blockers, and escalations across active workstreams

Support planning and roadmap activities for the Data and ML Engineering portfolio

Must Haves

8-10+ years of experience in Technical Program Management or related roles

Strong technical fluency - ability to understand and communicate AI, data, and ML concepts credibly with engineering teams and executive stakeholders

Experience supporting AI, GenAI, or ML platform programs

Proven experience preparing and delivering executive-level presentations and communications

Experience managing complex, multi-workstream programs in fast-paced enterprise environments

Strong stakeholder management and cross-functional coordination skills

Excellent written and verbal communication skills

Ability to operate with minimal oversight and drive clarity in ambiguous situations

Nice to Haves

PMP or equivalent certification

Background in retail or large enterprise environments

Experience supporting platform build-out or 0 to 1 initiatives

Familiarity with agile delivery methodologies

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📌 Sr. Technical Project Manager - Agentic AI & ML Platform - Enterprise Delivery (Toronto)
🏢 S.i. Systems
📍 Toronto