Senior Project Manager at applydigital – Toronto | Jobyssey

ABOUT APPLY

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. For more information, visit .

LOCATION: APPLY is hybrid/remote friendly. The preferred candidate should be based in Canada, working in hours that align to ET (Eastern Timezone).

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. Reporting into the Project Management team, 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 bring a background from the digital agency or consultancy side, with proven experience delivering integrated digital experiences alongside a collaborative, team-oriented mindset. As a champion of project management best practices, you'll bring fluency in Agile while adapting, growing, and optimizing teams to apply the best methodologies for the right problems — driving flawless execution and delivery for your clients. You have your pulse on the day-to-day details but care about the big picture, and can move effortlessly between the two to drive transformation for your clients' businesses.

You are also, unapologetically, an AI-forward delivery leader. APPLY delivers through an agentic model in which human practitioners work alongside AI agents across the project lifecycle, and the Senior Project Manager is accountable for making that model work: setting the guardrails, owning the review gates, and keeping human judgment at the centre of everything that leaves our door. You are hungry for all things AI, you enjoy pulling apart your own processes to make them better, and you are energised rather than unsettled by how quickly this landscape moves.

RESPONSIBILITIES

Project & Program Management

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.

Agentic & AI-Enabled Delivery

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.

Client & Stakeholder Management

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.

Team Leadership

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

Project Management Excellence

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.

Communication & Soft Skills

Communication Excellence: You possess impeccable written and verbal communication skills. You can effectively bridge the gap between executive summaries and technical detail, provide proactive updates, and communicate complex or difficult news with transparency and clarity.
Interpersonal Intelligence: You demonstrate high emotional intelligence, reading rooms effectively and navigating conflict with empathy. You practice compassionate candor, resolving tensions by focusing on solutions, and can influence stakeholders without formal authority.
Leadership & Mindset: You are customer-centric, taking full accountability for project outcomes rather than just tasks. You 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.

AI & Agentic Delivery

As APPLY operates on an agentic model, hands-on AI fluency is essential. You will use these tools daily and comfortably engage in technical discussions around agentic workflows.

Required:

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. You experiment, you share what you learn, and you expect the way you work in twelve months to look different from today.

Strong bonus

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).

Nice to Have

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.

WHAT SUCCESS LOOKS LIKE

You have delivered at least two medium-to-large projects of each engagement type — Upstream, Midstream, and Downstream — from kickoff through closure.
Your clients would describe the experience as transparent, well-run, and better than what they have had elsewhere.
Your engagements demonstrate measurable value against an agreed baseline, not just completed activity.
Something you built, improved, or documented is being used by PjMs beyond your own project.

LIFE AT APPLY

People are at the core of everything we do at APPLY. We provide you with modern tools, systems and approaches, value your time, safety, and health, and strive to build a work community where you can thrive and grow. Here are a few benefits we offer to support you:

Agentic Delivery: Our people work in a modern way to deliver client outcomes. Broaden your skills on a range of engagements with international brands that have a global impact.

An inclusive and safe environment: We’re truly committed to building a culture where you are celebrated and everyone feels welcome and safe.

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: Work-life balance is key to our team’s success, so we offer 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: We work in a variety of ways, from remote, to in-office, to a blend of both.

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. Learn more in our Diversity, Equity, and Inclusion (DEI) section. For recruitment accommodations, please email [email protected].

Senior Project Manager

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