Insight Global is looking for a Senior Product Manager (Strategy & Execution) to join a large retail enterprise client on a contract basis (this role is expected to move to full-time directly with the client after 6 months). This role will support a highly strategic product portfolio focused on complex B2B solutions, driving both long-term product vision and near-term execution. The successful candidate will operate across 2–3 concurrent initiatives, balancing strategic planning with hands‑on oversight of delivery. This role will play a critical part in shaping the future state of the product landscape (including 2027 planning), aligning business and engineering stakeholders, and ensuring priorities are clearly defined, sequenced, and executed effectively.

Required Skills and Experience

8+ years of experience in Product Management with ownership across product strategy, roadmap, and execution in complex enterprise environments

Proven ability to define and articulate product vision and strategy, incorporating competitive landscape, business priorities, and market opportunities

Strong experience managing product intake, prioritization, and roadmap sequencing with explicit supporting rationale

Demonstrated ability to translate complex problems into structured deliverables (product briefs, business cases, buy versus build analysis, success metrics, and risk mitigation plans)





Experience building and presenting business cases to senior leadership and CXO-level stakeholders

Strong stakeholder management skills with the ability to align business, engineering, and cross‑functional teams on product strategy and execution

Proven ability to oversee multiple concurrent initiatives (2–3+) while ensuring timely and cost‑effective delivery

Experience identifying and removing delivery blockers, managing risks, and driving successful product outcomes

Strong analytical and strategic thinking capabilities, including evaluating what is working versus not working and defining forward‑looking solutions

Excellent communication skills with the ability to simplify complex concepts for both technical and non‑technical audiences

Experience mentoring or supporting junior Product Managers and contributing to team delivery excellence

Nice to Have Skills and Experience

Experience working with enterprise B2B or platform‑based products

Familiarity with strategic frameworks such as competitive analysis, buy versus build, and product discovery methodologies

Experience supporting long‑term strategic planning and future‑state product roadmaps (e.g., 1–3 year horizons)

Previous experience presenting roadmap updates and strategic initiatives to senior leadership

Experience working in highly matrixed, cross‑functional environments with multiple stakeholder groups

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📌 Senior Product Manager (Markham)
🏢 Insight Global
📍 Markham