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Interim Manager, Delivery Management Office

- - - Doing business to business, person to person. Payworks is a leading workforce management solutions provider and multi-year winner of the Canada’s Best Managed Companies program. We are proudly Canadian and committed to developing world-class products and providing a progressive workplace culture where Doing Right by People is our purpose.

With clients of all sizes and nearly 700 employees, we currently have an exciting opportunity on our Operations team for the right candidate. Because when it comes to great people, there’s always room for one more.

DOING RIGHT BY PEOPLE – IT’S WHAT WE DOReporting to the VP of Operations, the Interim Manager, Delivery Management Office (DMO) leads the department for the duration of a 15-month term. This role runs the DMO day-to-day, including the project management team of employees and contractors, portfolio operations, evolving DMO practices, tooling and templates, delivery execution across strategic initiatives, and vendor and contract governance for the DMO. You will partner with the VP, Operations on portfolio prioritization and portfolio-level KPI tracking, and own delivery excellence within the DMO.

Success requires strong operational and people leadership, a track record of building and running high-performing project teams, comfort leading a blended team of employees and contractors, and the ability to influence effectively at working and senior levels across functions.

WHY YOU SHOULD CHOOSE PAYWORKS+ Comprehensive employer paid benefits, including a Health Spending Account, for you and your family and excellent pension plan with employer contributions.+ Plenty of professional development opportunities.+ Community-minded culture – Receive two paid days per year to volunteer and lots of opportunity to “Pay it Forward”.+ Time and flexibility to meet your needs – Hybrid work model with flexible work options, plus 3 weeks vacation to start, flex time and parental leave perks.+ Cool perks – Annual Lifestyle Spending Account, fun office environment and events, and more!

BUILD. LEAD. DELIVER. – IT’S WHAT YOU’LL DO+ DMO Leadership & Delivery Execution — Lead the DMO day-to-day, ensuring consistent,



high-quality delivery of strategic projects across the portfolio. Lead and develop a team of 5–10 project managers, both employees and contractors, fostering a culture of accountability, collaboration, and delivery excellence. Maintain and evolve DMO practices, tooling, and templates to support consistent execution and PM effectiveness.

Oversee portfolio operations, including resource allocation, workload balancing, and delivery cadence across projects, and surface risks, dependencies, and blockers early, escalating to the VP, Operations and functional stakeholders as needed.+ Portfolio Reporting & Governance — Provide portfolio-level project health reporting, including status, milestones, risks, and delivery KPIs across DMO projects. Support the VP, Operations on portfolio reporting to leadership. Partner with Finance on contractor budget tracking, invoice accuracy, and vendor management for DMO resources, and maintain PM governance standards including SOW lifecycle, vendor contracts, and procurement processes for DMO engagements.+ Project-Embedded Change Management — Ensure every project in the DMO portfolio has embedded change management planning and execution, applying the enterprise methodology in partnership with the People team.

Monitor post-initiative feedback to assess adoption and business impact, feeding learnings back into DMO practice.+ Cross-Functional Partnership — Act as the connective tissue across functions at the working level, translating project objectives into actionable plans and coordinating cross-functional delivery. Partner with client-facing, technical, and support functions to ensure DMO activities consider internal and external customer impact. Represent the DMO in cross-functional committees, standing meetings, and delivery forums.

WHAT YOU’LL NEED TO SUCCEED+ 6+ years of experience in project management, portfolio delivery, or delivery operations leadership,



with a track record of running high-performing project teams.+ Experience leading project managers, including a mix of employees and contractors, in a matrixed or cross-functional environment.+ Strong operational leadership and stakeholder management skills, with the ability to influence at working and senior levels across the business.+ Practical knowledge of change management principles as applied within project delivery.+ Experience managing SOW lifecycles, vendor contracts, and delivery-related budget tracking.+ Comfort with a fixed-term interim engagement and the ability to establish credibility quickly.

BONUS SKILL SET+ Background in payroll, HR, SaaS, or similarly regulated, customer-facing environments is an asset.+ Comfort and experience with AI tools and reporting (Claude, Power BI, etc.) is an asset.+ Project Management Professional (PMP) designation or similar is an asset.

We are proud to support a Flexible Work Plan that recognizes the diverse needs and lifestyles of our people. The Interim Manager, Delivery Management Office, has the option to work fully from the Payworks Winnipeg office or on a hybrid work model, working in the office at least three (3) days a week. This is a fixed-term interim engagement of 15 months.

Payworks is committed to providing an inclusive, accessible environment, and collaborating with employees, clients and guests to identify and effectively remove barriers, in a manner that respects the principles of independence, dignity, integration, reasonable accommodation and equal opportunity. Payworks welcomes and encourages applications from all persons. Individuals applying for employment with Payworks may request accommodations at all stages of recruitment and employment from Human Resources.

Employees at Payworks come from different backgrounds, and we celebrate those differences. We are looking for the best candidate for this opportunity, but do not expect applicants to meet every qualification in order to be considered.

We may use AI-assisted tools for organization, sorting, and workflow management — however, we pride ourselves on a high-touch, human-centered process.

This posting is for an existing vacancy within our team.

Please visit our careers page to see more job opportunities.

📌 Interim Manager, Delivery Management Office (Winnipeg)
🏢 Payworks
📍 Winnipeg