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About the Role

As a Senior Project Manager at APPLY, you'll play a critical role in delivering exceptional digital solutions and fostering strong client relationships. You will lead complex projects spanning digital strategy, products, platforms, and marketing initiatives, driving excellence in project delivery while championing Agile methodologies and ensuring client satisfaction through effective communication and strategic problem-solving. You are an AI-forward delivery leader accountable for making APPLY's agentic model work by setting guardrails, owning review gates, and keeping human judgment at the center of all outputs.

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 clear, concise, and proactive updates on progress, milestones, and scope changes.
• Facilitate key workshops and client meetings (strategy sessions, UX reviews, demos) with clear agendas and actionable outcomes.
• Navigate complex stakeholder discussions diplomatically, managing expectations and delivering difficult news early and constructively.
• Partner with Client Services and account leadership to identify growth opportunities and ensure business value alignment.
• Accurately discern stakeholder requirements and integrate them into planning and execution; actively manage client expectations, and delegate where appropriate rather than becoming a single point of dependency.
• Maintain a healthy partnership with Client Services and support account growth activities, bringing commercial awareness to delivery conversations.
• Lead cross-functional teams (Strategy, Design, Engineering, QA, Data) using servant leadership to foster collaboration and high performance.
• Guide, mentor, and coach Project Managers and Coordinators, proactively supporting their professional development.
• Resolve team friction with empathy and candor, diffusing tension and focusing on solution-oriented outcomes.
• Exemplify project management at APPLY, earning trust from both the project team and the leadership team.

Requirements

• 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 the 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 industry-standard project management and collaboration tools including 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 such as e-commerce (CommerceTools, BigCommerce), CMS (Contentful, Contentstack), Loyalty (Talon.one, EagleEye), Identity (Stytch, Okta, Auth0), and Personalization (Ninetailed, Segment).
• Knowledge of technical concepts including AI, machine learning, data analytics, cloud computing, and platform integrations.
• Demonstrable critical thinking, creative problem-solving, and willingness to tackle complex challenges.
• A can-do attitude, passion for digital products, and resilience to work in a flexible, fast-paced environment.
• Impeccable written and verbal communication skills; ability to effectively bridge the gap between executive summaries and technical detail, provide proactive updates, and communicate complex or difficult news with transparency and clarity.
• High emotional intelligence, reading rooms effectively and navigating conflict with empathy; practice compassionate candor, resolving tensions by focusing on solutions, and can influence stakeholders without formal authority.
• Customer-centric leadership, taking full accountability for project outcomes rather than just tasks; lead with a coaching instinct, fostering growth in those around you, and maintain the resilience and adaptability required to thrive in a fast-changing, AI-driven environment.
• Hands-on experience using LLMs (e.g., Claude, Gemini) and AI workflows to accelerate planning, documentation, and reporting, with a drive to continuously adapt as tools evolve.
• Proven critical evaluation skills to review and refine AI outputs for accuracy, quality, and strategic alignment before client delivery.
• A genuine hunger for all things AI and a commitment to keep growing with a field that changes month to month.
• Direct experience leading agentic delivery—structuring ceremonies where AI drafts and humans decide, introducing AI workflows to clients, and managing the associated change.
• Familiarity with BMAD methodology, Markdown, CLI-based AI tools (e.g., Claude Code), and MCP connectors.
• Track record of building reusable AI skills, agents, or automations adopted by other team members.
• Relevant AI certifications (e.g., Google Cloud Generative AI Leader, Gemini Enterprise Certified Partner Specialist, Anthropic Academy).
• Experience working in Commerce and/or Loyalty programs.
• Technical background in Computer Science.
• PMP, Agile, or Scrum Master certification.
• Experience delivering AI or agentic products for clients, not only using AI to deliver traditional products.

Skills

• AI
• Machine Learning
• Data Analytics
• Cloud Computing
• Platform Integrations
• Agile
• Waterfall
• Digital Strategy
• Digital Products
• Digital Platforms
• Marketing Initiatives
• Project Management
• Client Relationship Management
• Communication
• Problem-Solving
• Agentic Delivery
• LLMs (Claude, Gemini)
• AI Workflows
• Critical Evaluation
• BMAD methodology
• Markdown
• CLI-based AI tools
• MCP connectors
• Commerce
• Loyalty Programs
• Computer Science
• PMP
• Scrum Master

Location

• Canada
• ET (Eastern Timezone)

Work Type

• Hybrid
• Remote

Experience Level

• Senior
• 8+ years

Education Level

• PMP, Agile, or Scrum Master certification
• Relevant AI certifications (e.g., Google Cloud Generative AI Leader, Gemini Enterprise Certified Partner Specialist, Anthropic Academy)

Benefits

• Modern tools, systems and approaches
• Value your time, safety, and health
• Work community where you can thrive and grow
• Agentic Delivery: Broaden your skills on a range of engagements with international brands that have a global impact.
• An inclusive and safe environment
• AI & Strategic Upskilling: Accelerate your professional growth with generous training budgets and mentorship, with a specific focus on Agentic AI expertise and the critical human skills required for the future of work.
• Generous vacation policy: Flexible personal time off (PTO); allowing ample time away from work to promote overall well-being.
• Customizable benefits: Tailor your extended health and dental plan to your needs, priorities, and preferences.
• Flexible work arrangements

About the Company

• APPLY is the Agentic Customer Experience (ACx) partner for the world's most ambitious consumer and entertainment brands.
• We bring together deep domain expertise across Retail, CPG, Sports, and Media with AI-native delivery capability, designing and delivering agentic solutions that turn CX vision into commercial reality.
• We are the partner of choice for brands like Arc'teryx, NFL, Lululemon, and Kraft Heinz.

Equal Opportunity

• APPLY is a safe, respectful, and inclusive community where differences are celebrated.
• We are committed to equal opportunity and fostering a workplace where everyone belongs.
• For recruitment accommodations, please email careers@applydigital.com.