Strategic Initiatives Program Manager
9 hours ago
Winnipeg, Manitoba, Canada
Manion Wilkins & Associates Ltd.
Full-time
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At GroupHEALTH, we're proud of the work we do, but it's how we do it that truly sets us apart. We're a fast-moving, ever-evolving, stable organization with deep roots and a bold vision: to transform the way Canadians experience benefits. We combine agility with long-term stability to create meaningful impact.
Here, you'll find more than just a job. You'll find a purpose-driven, people-first culture where kindness, collaboration, and curiosity thrive. Whether you've been here fifteen years or fifteen days, you'll notice right away, our people are genuinely invested in one another's success and delivering exceptional experiences to our clients and plan members.
About the Role Do you like turning big ideas into real results, and are you comfortable keeping executives on track? The Strategic Initiatives Program Manager sits in the Transformation Office and works directly with our Executive Leadership Team. You will take initiatives from early idea through intake, prioritization, delivery, and close-out. You will own the plan, the follow-through, and the reporting. At GroupHEALTH, transformation means moving the business forward and everything that goes with it. This role covers a wide range of enterprise work, including M&A activity, product and innovation launches, governance, risk, and privacy initiatives, and a large-scale operational transformation already in progress. You will manage several initiatives at the same time from day one. This role suits a confident, organized operator who can run a room and hold executives accountable to their commitments. Your job is to deliver on strategy, not set it, and to bring the structure and momentum that turn priorities into outcomes. This is a hybrid role based in our Surrey, BC office, with three days per week in the office.
What to Expect in Your First 3 Months First 30 Days:
Complete a full portfolio inventory of all assigned Transformation Office initiatives, including sponsor, scope, status, timeline, key milestones, risks, dependencies, decisions required, and expected business outcomes.
Build effective working relationships with Executive Leadership Team members and initiative sponsors, ensuring expectations, decision points, risks, and required follow-up are clearly understood and actively managed.
First 60 Days:
Implement consistent project governance routines for assigned initiatives, including status updates, RAID tracking, decision logs, action follow-up, and escalation pathways.
Validate priority project plans by confirming near-term milestones, resource needs, dependencies, and key decisions with sponsors and core project teams.
Assess current Transformation Office project practices against the emerging enterprise project management framework and identify areas for alignment, simplification, or flexibility.
First 90 Days:
Produce an initial view of cross-project dependencies, sequencing risks, stakeholder impacts, and potential change saturation across assigned Transformation-led work.
Establish sponsor confidence by demonstrating early value with Executive Leadership Team members, sponsors, and stakeholders through clarity, structure, timely follow-up, and visible momentum.
What You'll Do Transformation Office Project Delivery
Lead assigned Transformation Office initiatives from initiation through close-out, including M&A due diligence coordination, joint venture standups, product and service launches, executive reporting, and other enterprise-sponsored transformation priorities
Translate executive and enterprise priorities into practical project plans, workstreams, timelines, deliverables, and near-term actions
Manage day-to-day project execution, including project plans, status updates, RAID tracking, decision logs, action follow-up, and escalation
Coordinate across business functions, IT, vendors, subject matter experts, and project teams to resolve blockers and maintain delivery momentum
Executive Stakeholder Support and Governance
Work directly alongside Executive Leadership Team members, executive sponsors, and business leaders to clarify priorities, decision points, risks, dependencies, and required follow-up
Prepare concise, decision-oriented project updates, briefing materials, and governance reporting for the Chief Transformation Officer, executive sponsors, steering groups, and applicable governance forums
Facilitate sponsor check-ins, working sessions, project meetings, and decision discussions that are focused, productive, and action-oriented
Influence without direct authority by creating clarity, accountability, timely follow-through, and alignment across executive-sponsored priorities
Business Readiness, Change, and Adoption
Partner with the Change and Communications teams to build business readiness, stakeholder impacts, co
Here, you'll find more than just a job. You'll find a purpose-driven, people-first culture where kindness, collaboration, and curiosity thrive. Whether you've been here fifteen years or fifteen days, you'll notice right away, our people are genuinely invested in one another's success and delivering exceptional experiences to our clients and plan members.
About the Role Do you like turning big ideas into real results, and are you comfortable keeping executives on track? The Strategic Initiatives Program Manager sits in the Transformation Office and works directly with our Executive Leadership Team. You will take initiatives from early idea through intake, prioritization, delivery, and close-out. You will own the plan, the follow-through, and the reporting. At GroupHEALTH, transformation means moving the business forward and everything that goes with it. This role covers a wide range of enterprise work, including M&A activity, product and innovation launches, governance, risk, and privacy initiatives, and a large-scale operational transformation already in progress. You will manage several initiatives at the same time from day one. This role suits a confident, organized operator who can run a room and hold executives accountable to their commitments. Your job is to deliver on strategy, not set it, and to bring the structure and momentum that turn priorities into outcomes. This is a hybrid role based in our Surrey, BC office, with three days per week in the office.
What to Expect in Your First 3 Months First 30 Days:
Complete a full portfolio inventory of all assigned Transformation Office initiatives, including sponsor, scope, status, timeline, key milestones, risks, dependencies, decisions required, and expected business outcomes.
Build effective working relationships with Executive Leadership Team members and initiative sponsors, ensuring expectations, decision points, risks, and required follow-up are clearly understood and actively managed.
First 60 Days:
Implement consistent project governance routines for assigned initiatives, including status updates, RAID tracking, decision logs, action follow-up, and escalation pathways.
Validate priority project plans by confirming near-term milestones, resource needs, dependencies, and key decisions with sponsors and core project teams.
Assess current Transformation Office project practices against the emerging enterprise project management framework and identify areas for alignment, simplification, or flexibility.
First 90 Days:
Produce an initial view of cross-project dependencies, sequencing risks, stakeholder impacts, and potential change saturation across assigned Transformation-led work.
Establish sponsor confidence by demonstrating early value with Executive Leadership Team members, sponsors, and stakeholders through clarity, structure, timely follow-up, and visible momentum.
What You'll Do Transformation Office Project Delivery
Lead assigned Transformation Office initiatives from initiation through close-out, including M&A due diligence coordination, joint venture standups, product and service launches, executive reporting, and other enterprise-sponsored transformation priorities
Translate executive and enterprise priorities into practical project plans, workstreams, timelines, deliverables, and near-term actions
Manage day-to-day project execution, including project plans, status updates, RAID tracking, decision logs, action follow-up, and escalation
Coordinate across business functions, IT, vendors, subject matter experts, and project teams to resolve blockers and maintain delivery momentum
Executive Stakeholder Support and Governance
Work directly alongside Executive Leadership Team members, executive sponsors, and business leaders to clarify priorities, decision points, risks, dependencies, and required follow-up
Prepare concise, decision-oriented project updates, briefing materials, and governance reporting for the Chief Transformation Officer, executive sponsors, steering groups, and applicable governance forums
Facilitate sponsor check-ins, working sessions, project meetings, and decision discussions that are focused, productive, and action-oriented
Influence without direct authority by creating clarity, accountability, timely follow-through, and alignment across executive-sponsored priorities
Business Readiness, Change, and Adoption
Partner with the Change and Communications teams to build business readiness, stakeholder impacts, co