Project Manager - Enterprise Workforce Management

About Us

MakeShift is a leading provider of employee scheduling and time & attendance software, helping organisations, especially in complex, 24/7 environments, create smarter, more humane schedules. Our platform is built around a simple idea: when frontline teams feel supported and respected, everything works better.

We’re a remote-first team rooted in Calgary’s tech community, working with customers across healthcare, retail and other industries to improve how work fits into people’s lives.

About the Role

We’re looking for an experienced senior Project Manager to lead mission-critical implementation and delivery projects for large enterprise clients, with a strong focus on healthcare and other highly regulated, multi-stakeholder environments. In this role, you will:

• Own the project from contract signature through go-live.

• Be the primary operational bridge between MakeShift and the client, working closely with executives, clinical/operational leaders, and IT.

Key Responsibilities

Lead Enterprise Implementations

• Take end-to-end responsibility for complex WFM implementation projects, from mobilization through hypercare and handoff.

• Build realistic, transparent project plans that balance scope, risk, and the day-to-day realities of frontline operations.

Coordinate the Right Experts

• Work closely with functional & technical consultants, integration developers, and client SMEs who own detailed configuration, union rules, and rotation design.

• Ensure their work is sequenced, resourced, and tracked properly within the broader plan.

Navigate Complex, Unionized Environments

• Manage projects involving unionized, 24/7 staffing models, multiple stakeholder groups, and regulatory/clinical constraints.

• Facilitate workshops and decision-making sessions where HR, unions, clinical leaders, IT, and finance all have a stake.

Steer Integrations & Technical Delivery

• Coordinate technical workstreams.

• Ensure technical decisions and timelines are clearly understood by business stakeholders, and vice versa.

Own Governance, Risk & Communication

• Set up and run governance structures: steering committees, working groups, and regular status forums.

• Maintain clear project documentation (charters, RAID logs, decision logs, cutover plans).

• Surface risks early with proposed options, not just problems.

Bridge Waterfall & Agile Ways of Working

• Use structured, PMP-style planning for client milestones and external dependencies.

• Collaborate with internal Product and Engineering teams who operate in Agile, aligning sprints and releases to client commitments.

Drive a People-First Delivery Experience

• Partner with Customer Success and client change/communications teams to support training, adoption, and a smooth transition to the new way of working.

What We’re Looking For

Experience & Background

• 7+ years of Project Management experience, ideally in SaaS implementation.

• Proven track record leading large, complex enterprise implementations with a preference for delivering Workforce Management (WFM) or scheduling/time solutions.

• Experience working in or with regulated and/or unionized environments (healthcare, public sector, large enterprises, etc.).

• Active PMP certification is required.

Skills & Attributes

• Comfortable with project and work management tools (e.g., MS Project, Smartsheet, Asana) and collaboration tools (e.g., Jira, Confluence, Miro, Teams/Zoom).

• Comfortable facilitating meetings with executives, clinicians, HR/Payroll, IT, and unions.

• You can reset a plan, re-negotiate scope, and keep people aligned when things change.

• You don’t wait to be told; you anticipate issues, propose options, and follow through.

Tools

• Comfortable with project and work management tools (e.g., MS Project, Smartsheet, Asana) and collaboration tools (e.g., Jira, Confluence, Miro, Teams/Zoom).

Nice-to-Haves

• Experience with healthcare systems such as Epic, Meditech, and Cerner.

• Change Management experience or certification (e.g., Prosci/ADKAR).

• Previous experience reporting directly to C-level leadership or presenting in executive steering committees.

Why This Role at MakeShift

• Impact that matters: Your work directly affects how organizations staff and support real people, every day.

• Big seat at a small table: You work on our highest-profile customers, with a strong voice in how we deliver.

• Fully Remote Environment: We are a remote-first company that values autonomy and results.
  

Please submit your resume and a brief cover letter highlighting a specific complex enterprise WFM project you delivered to careers@makeshift.ca.