RESPONSIBILITIESProgram & Portfolio ManagementLead 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. 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. Coach teams on Waterfall, Kanban, Agile and Agentic delivery methods, selecting the right approach for each engagement and its stage. Agentic & AI-Enabled Delivery LeadershipEstablish 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. Champion reusable and scalable prompts, skills, agents, and automations across the Project Management discipline.

Client & Stakeholder ManagementCultivate 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. Partner with Client Services and account leadership to identify growth opportunities,



bringing commercial awareness to every delivery conversation.

Collaborate with other disciplines to create standardized delivery approaches for common service offerings. REQUIREMENTSProject Management Excellence 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 successfully delivering small-to-medium programs or portfolios (up to $5M annual revenue) from kickoff through closure as a trusted senior delivery partner and partner with Client Services to secure portfolio expansion opportunities.

Ability to demonstrate measurable value and maintain baseline margin targets while proactively mitigating scope, timeline, and commercial risks.

Experience with modern digital ecosystems (Composable/Headless CMS, E-commerce/Commerce, Loyalty, Personalization, Analytics). Strong proficiency in industry-standard project management and collaboration tools including Claude, Gemini, Co-pilot, 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.

Knowledge of technical concepts including AI, machine learning, data analytics, cloud computing, and platform integrations. Demonstrable critical thinking, creative problem-solving, and willingness to take ownership of complex challenges.

Interpersonal Intelligence: High emotional intelligence, navigating conflict with empathy, practicing compassionate candor, and influencing stakeholders without formal authority. Strong accountability for program outcomes, customer‑centric mindset, and adaptability to coach teams in a quick‑changing AI landscape. Experience-based judgment to guide teams, address complex challenges, and serve as a trusted voice in decision‑making.

You will use these tools daily, coach others in them, and comfortably lead discussions around agentic workflows with clients and internal teams. Hands‑on experience using LLMs and AI workflows to accelerate planning, documentation, and reporting, alongside strong critical evaluation skills to refine outputs for quality and set team review standards.

Experience leading program‑level agentic delivery, designing human‑AI workflows, and guiding team change management is a nice to have.

Claude

Code), and MCP connectors is a bonus.

Experience building or sponsoring reusable AI skills, agents, or automations adopted across practice areas is a bonus. GCP Generative AI Leader, Gemini Enterprise, Anthropic Academy) is considered an asset. #

📌 Project Management Lead - Talent Pipeline (Winnipeg)
🏢 Apply Digital
📍 Winnipeg