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Senior Project Manager

Apply Digital· Project Management
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Hybrid (Toronto, Canada)Full-Time PermanentPosted 2mo ago

About the role

Senior Project Manager at APPLY leading complex digital projects, aligning Agile delivery with an agentic AI-enabled model, and fostering client relationships across digital strategy, products, platforms, and marketing initiatives.

Responsibilities

  • Lead complex digital projects and programs from initiation to completion, managing scope, roadmaps, timelines, resourcing, and budgets across fixed-price and T&M agreements.
  • Translate client business outcomes into actionable project plans, roadmaps, and execution strategies.
  • Own core delivery artifacts end-to-end (SOWs, plans, resource trackers, status reports, risk/issue logs, and closure decks).
  • Identify, manage, and mitigate project risks, issues, dependencies and decisions escalating appropriately to senior stakeholders.
  • Adapt Agile, hybrid-Agile, or waterfall methodologies to match project needs and drive process efficiency.
  • Continuously streamline delivery workflows and status reporting using AI tools and smart automation.
  • Build and share reusable assets—prompts, templates, and best practices—to strengthen the Project Management discipline.
  • Own delivery accountability and guardrails on agentic engagements, ensuring human review and approval for all AI-assisted outputs.
  • Scope and structure work effectively between AI agents and team members, maintaining clear review gates and risk logs.
  • Manage agentic failure modes (hallucinations, model drift, data dependencies, prompt quality) and maintain agent access/permission boundaries.
  • Align client expectations to an agentic operating model, emphasizing outcome-based metrics, transparent AI usage, and fast review cycles.
  • Report on outcome as well as activity — time to value, delivery velocity against a human-only baseline, and measurable value validation — not simply story counts and burn.
  • Serve as the primary point of contact for clients, providing updates on progress, milestones, and scope changes.
  • Facilitate workshops and client meetings with clear agendas and actionable outcomes.
  • Navigate complex stakeholder discussions diplomatically and manage expectations.
  • Identify growth opportunities with Client Services and account leadership.
  • Accurately discern stakeholder requirements and integrate them into planning and execution.
  • Maintain a healthy partnership with Client Services and support account growth activities.
  • Lead cross-functional teams using servant leadership; mentor Project Managers and Coordinators.
  • Resolve team friction with empathy and candor, focusing on solution-oriented outcomes.

Qualifications

  • 8+ years leading end-to-end digital solution delivery in consulting or agency environments for enterprise clients.
  • Proven ability to partner effectively with senior client leadership (Director, VP, C-suite).
  • Expertise in Agile and waterfall delivery frameworks, with flexibility to select the right approach for each engagement.
  • Experience with modern digital ecosystems (Composable/Headless CMS, E-commerce, Loyalty, Personalization, Analytics).
  • Strong proficiency in JIRA, Confluence, Notion, Instagantt, Smartsheet, and Google Suite.
  • Deep knowledge of the full software development lifecycle, CI/CD, and related delivery workflows across product, design, development, and QA.
  • Experience leading headless implementations across platforms (CommerceTools, BigCommerce; Contentful, Contentstack; Talon.one, EagleEye; Stytch, Okta, Auth0; Ninetailed, Segment).
  • Knowledge of AI, machine learning, data analytics, cloud computing, and platform integrations.
  • Demonstrable critical thinking, creative problem-solving, and resilience in a fast-paced environment.

Skills

Required:Project managementAgile / Waterfall methodologiesStakeholder managementAI literacy and agentic delivery

Benefits

  • Agentic Delivery: modern delivery with AI-enabled engagements.
  • An inclusive and safe environment.
  • AI & Strategic Upskilling with training budgets and mentorship.
  • Generous vacation policy with flexible PTO.
  • Customizable extended health and dental plan.
  • Flexible work arrangements (remote/in-office/hybrid).
Last updated Oct 21, 2026. Interested? Apply on the company site.
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