AI-Driven Delivery Lead for Digital Programs

APPLY; Canada; Hybrid; CAD 110,000 - 160,000; Full time

Job summary

APPLY is seeking a Project Management Lead based in Canada to oversee multi-track digital initiatives in a hybrid/remote-friendly setup. You will manage programs up to $5M annually, coordinate delivery across disciplines, and steer AI-enabled, agentic workflows with a focus on outcomes and client satisfaction.

You will balance high-level strategy with hands-on delivery, coaching teams in Agile, Waterfall, and agentic approaches, while aligning stakeholders to measurable results and value

Qualifications

• 8–15 years leading end-to-end digital solution delivery in consulting or agency environments for enterprise clients, including multi-track programs.
• Proven ability to build trusted relationships with senior client leadership (Director, VP, C-suite).
• Expertise in Agile, Kanban, waterfall and agentic delivery frameworks, with the judgment to select and coach the right approach for each engagement.
• Strong commercial acumen across program budgets, forecasting, fixed-price and T&M agreements, and proposal estimates.
• Previous experience delivering small-to-medium programs or portfolios (up to $5M annual revenue) from kickoff through closure as a trusted senior delivery partner.

Responsibilities

• Lead small-to-medium programs and portfolios (up to $5M annual revenue) with multiple tracks of work, providing day-to-day delivery direction to the Project Managers aligned to your program and running individual tracks yourself where needed.
• Develop, maintain, and execute program delivery plans, including milestones, deliverables, dependencies, and resource allocation across all tracks.
• Proactively manage risks, issues, dependencies, assumptions, and decisions across programs and projects to resolution.
• Enforce project management best practices and refine or establish processes to address gaps.
• Oversee team capacity planning in collaboration with discipline leads, and act as backfill for your Project Managers when needed.
• Keep the program knowledge base organized, current, and usable by the whole team.
• Coach teams on Waterfall, Kanban, Agile and Agentic delivery methods, selecting the right approach for each engagement and its stage.
• Establish delivery guardrails for agentic engagements, ensuring human review and approval for all AI‑assisted outputs across workstreams.
• Structure work between AI agents and team members with clear review gates, risk logs, and permission boundaries.
• Align senior client stakeholders to an agentic operating model, emphasizing outcome‑based metrics, transparent AI usage, and fast review cycles.
• Report on outcome as well as activity at program level — time to value, delivery velocity against a human‑only baseline, and measurable value validation.
• Champion reusable and scalable prompts, skills, agents, and automations across the Project Management discipline.
• Cultivate and manage direct client relationships at middle-management and executive levels, acting as the senior delivery voice on your programs.
• Communicate program status, risks, and trade‑offs clearly to internal teams and external stakeholders, delivering difficult news early and constructively.
• Provide guidance on complex and challenging client situations, diffusing tension and choosing a path to resolution.
• Partner with Client Services and account leadership to identify growth opportunities, bringing commercial awareness to every delivery conversation.
• Contribute to RFPs, pitches, and proposals for new and existing clients.
• Develop and present program delivery approaches to prospective clients, including timelines, ways of working (including agentic delivery models), resourcing plans, and budget estimates.
• Collaborate with other disciplines to create standardized delivery approaches for common service offerings.
• Experience contributing to pitches, RFPs, or delivery approaches for new business.

Skills

Project management

Agile

Waterfall

Kanban

Client relations

Budgeting

AI delivery

Leadership

Tools

JIRA

Confluence

Notion

Smartsheet

Google Workspace

Job description

APPLY is seeking a Project Management Lead based in Canada to oversee multi-track digital initiatives in a hybrid/remote-friendly setup. You will manage programs up to $5M annually, coordinate delivery across disciplines, and steer AI-enabled, agentic workflows with a focus on outcomes and client satisfaction.

You will balance high-level strategy with hands-on delivery, coaching teams in Agile, Waterfall, and agentic approaches, while aligning stakeholders to measurable results and value