For More Info click on this link:

https://prospercanada.org/en/about-us/careers 

JOB POSTING

DIRECTOR, OPERATIONS

(Organization-wide capacity planning, project management, and operational effectiveness)

 

WHO WE ARE:

visit our website https://prospercanada.org/en/about-us 

 

 

THE OPPORTUNITY

 

Reporting to and working closely with the Vice President, Impact and Operations, the Director, Operations will lead the establishment of Prosper Canada’s project management function, strengthening how the organization plans, monitors, and manages complex cross-team initiatives. They will also implement organizational capacity planning and management and, over time, lead other priority operational effectiveness initiatives.

 

This role operates at an enterprise level, influencing strategic decision-making, resource allocation, and organizational priorities, and contributing to the evolution of organizational strategy through operational insights and systems thinking.

 

Our context

 

Prosper Canada is a highly collaborative, project-based organization operating in a matrixed environment. As our projects have grown in number, scale, and complexity, we have identified the need to establish robust project management processes and practices across the organization, starting with a small number of large high-priority projects involving many teams, accompanied by strengthened organizational capacity planning and management.

 

Near-term focus for this role  

 

Our immediate goal is to improve project planning, monitoring, and management by establishing a central project management function that can directly support high priority projects, while also building internal project management processes, tools and skills to enable teams to clearly delineate project objectives, activities, dependencies, timelines, and deliverables; actively monitor progress; and effectively address risks, delays and capacity and resource challenges.

 

For high-priority projects, participating teams will retain responsibility for delivering project outputs and outcomes but will be supported by the Director, Operations to translate strategy into clear plans; strengthen their work planning, monitoring, and coordination; and to identify and effectively manage project dependencies, risks, and capacity/resource constraints in a more timely way.

 

In tandem, the Director, Operations will be responsible for establishing broader organizational capacity planning and management processes to help us better align our capacity with our priorities and identify and address capacity shortfalls. This will include helping leadership to understand how work is distributed across teams and where constraints exist, and to assess the delivery implications of new funding opportunities and strategic shifts and how new initiatives can be realistically absorbed.

 

This is a senior leadership role for a builder who thrives on complexity and is motivated by the opportunity to help Prosper Canada more effectively align its strategy, capacity and actions to deliver greater impact.

 

How the role will evolve

 

Over time, the scope of the central project management function will expand to support a broader portfolio of initiatives.  Clear criteria will guide which projects are supported directly by the function and which remain managed by teams while adhering to shared project management standards and processes. 

 

As this function matures, additional internal capacity may be added, including dedicated project management roles. Once capacity planning and project management are more mature organizational functions, the scope of this function will also evolve to include new operational effectiveness priorities and initiatives.

 

The Director’s responsibilities will evolve accordingly, shifting from direct project management leadership toward broader oversight, prioritization, and leadership of Prosper Canada’s capacity planning, project management, and operational effectiveness portfolio.

 

Reports to: Vice President, Impact and Operations

Direct reports: None (at this stage)

Location: Toronto (hybrid)

 

SUMMARY OF RESPONSIBILITIES 

 

Note: The weighting of responsibilities reflects Year 1 expectations but will evolve and shift over time as the project management and capacity planning functions become more established, internal capability grows, and new operational effectiveness priorities emerge.

1.      Establishing and leading Prosper Canada’s central project management function (35%)

 

Design, launch and lead a practical, fit-for-purpose central project management function that strengthens Prosper Canada’s ability to coordinate complex projects and initiatives and anticipate risks, dependencies, and competing priorities across the organization. This includes.

Building the project management function

•       Clarifying and strengthening shared understanding of project management roles, decision-making, and accountability across teams.

•       Developing and supporting adoption of shared project management tools, templates, standards, and processes through live project work.

•       Defining criteria for how projects are prioritized and supported, including which initiatives are directly led by the PM function versus managed within teams using shared standards.

•       Establishing expectations for how funder, reporting obligations, and accountability milestones are tracked and supported across projects

 

Improving visibility and governance of projects

•        Developing project roadmap and governance reporting that provides leadership with a clear view of priority initiatives, risks, interdependencies, sequencing issues, and emerging pressure points.

•       Strengthening organization-wide visibility into priorities, cross-team interdependencies, and project delivery risks, through data-driven insights and analysis

 

Enabling prioritization and planning decisions

•       Supporting leadership in making informed prioritization and sequencing decisions by surfacing risks, trade-offs, and capacity pressures visible earlier

•       Providing forward-looking analysis to support decisions on intake of new initiatives, funding opportunities, or strategic shifts

•       Partnering with Business Development and senior leaders to assess how new initiatives can be successfully absorbed into the existing portfolio, including identifying resource gaps, sequencing implications and potential trade-offs

 

2.      Lead project management for select high-priority, multi-team projects (20%)

 

Directly support project planning, coordination, and monitoring for a limited number of complex, high-priority projects where alignment, coordination, and delivery discipline are critical to success. This includes:

 

•       Working with relevant team leads to plan, coordinate, and monitor multi-team initiatives from initiation to completion and facilitate solutions as needed to keep projects on time and on budget.

•       Translating strategic priorities into clear project objectives, timelines, milestones, and  deliverables, in partnership with team and subject-matter leads.

•       Facilitating development of shared project plans, regular reporting and check-in rhythms, and coordinating mechanisms that improve cross-team collaboration.

•       Supporting alignment on priorities, trade-offs, and next steps to enable effective decision-making and execution.

•       Identifying issues early and enabling timely course correction as scope, priorities, or capacity change.

•       Building trust-based relationships and fostering shared ownership for project outcomes across participating teams, senior leadership, and external partners.

 

3.      Build organization-wide project management capability (20%)

 

Because the Director, Operations directly manage only a limited number of complex high priority projects in the near term, a core part of the role is strengthening project management capability across the organization so that teams can effectively plan and project manage their own work and coordinate effectively with other teams using shared project management practices and tools. This includes:

 

•       Building project management capability and confidence across teams through training, facilitation, coaching, and learning-by-doing.

•       Supporting adoption of shared project management practices, processes, and tools.

•       Reinforcing clear expectations for how projects are managed across the organization, regardless of where project management responsibility sits

•       Using effective change management approaches to support teams in transitioning towards more consistent and transparent project planning and coordination practices

•       Contributing to a culture of collaboration, accountability, and continuous improvement by establishing clear frameworks and performance expectations for project delivery across teams.

 

4.      Build organizational capacity planning and management processes (15%)

 

Lead the development and implementation of organizational processes, practices, and tools that improve visibility into and management of staff capacity across programs and internal functions. This includes:

 

•       Designing and implementing practical approaches to capacity planning and monitoring that provide greater visibility into how staff time and effort are allocated across initiatives

•       Establishing simple, sustainable processes for ongoing capacity tracking and review to support planning, prioritization, and workload management within and across teams.

•       Inform organizational budgeting and workforce planning decisions through capacity and resource insights

•       Identify and escalate financial and operational risks related to spend, capacity constraints and delivery feasibility

 

5.      Foster operational alignment and coordination (10%)

 

As the Chair of Prosper Canada’s new Senior Operational Leadership Table (SOLT), the Director will work with other Directors, and HR and Finance Managers, to strengthen operational coordination, collaboration, and effectiveness across the organization. This includes working with SOLT members to:  

• Coordinate development of SOLT meeting agendas, chair meetings, and ensure clear follow-up on decisions and action items across SOLT members.
• Improve alignment on priorities and sequencing of activities.
• Identify and effectively address major project delivery risks.
• Bring project management insights into cross-team planning and operational decision-making.
• Identify recurring delivery challenges and facilitate practical improvements to organizational processes and ways of working.
• Model an integrated and realistic approach to planning across teams and initiatives.
• Recommend improvements to organization policy or operations to the Executive Team where necessary.
• Escalate issues that cannot be resolved by SOLT to the Executive Team, with clear costed recommendations.

 

 

WHAT SUCCESS IN THIS ROLE LOOKS LIKE OVER THE NEXT 2 YEARS

 

A practical and trusted central project management function is established. Prosper Canada has a clear fit-for-purpose function that strengthens project planning, management, coordination, and delivery discipline across teams.

 

Priority multi-team projects are effectively managed and coordinated to achieve deliverables on time and on budget. Robust project planning and management of the organization’s most complex initiatives ensures optimal coordination, collaboration, and accountability;  timely and effective management of risks and dependencies; and agile adaptation when circumstances require.

 

Shared project management processes, practices and tools are in place and actively used by all teams. Organizational project management expectations and processes are clearly communicated and understood by all teams, and staff have the training, tools, and support they need to effectively plan and manage their projects and be accountable for their successful execution.  As a result, teams are working in coordinated and sustainable ways, are more accountable, and are less reliant on informal workarounds.

 

A clear and scalable approach to project management support is in place. The organization has a robust project  management function in place, with clearly defined roles and consistently applied criteria for which initiatives receive direct project management support, and the capacity and structure to expand support over time.

 

The function is seen as a trusted enabler of alignment and coordinated execution. The Director, Operations and their function are viewed as practical, collaborative, and value-adding, strengthening delivery without creating unnecessary bureaucracy.

 

Organizational capacity is visible and actively managed.  Team and project leads have a clear understanding of how work is distributed across teams, where capacity constraints exist, and how to make realistic decisions about priorities and new commitments.

 

Leaders have the information and insights they need to make effective decisions. Senior leaders have timely reliable insights into project progress, risks, dependencies, and capacity pressures that enable them to manage emerging issues, adjust priorities, and allocate capacity and resources.

 

New initiatives are integrated into the portfolio with greater clarity and discipline. Funding opportunities and strategic shifts are assessed with a clear understanding of delivery implications, including capacity, sequencing, and resource requirements.

 

 

 

EXPERIENCE AND COMPETENCIES 

Candidates must clearly demonstrate how they meet the essential criteria set out in the table below to be considered for an interview.  Candidates should highlight desirable criteria they possess to gain a competitive edge over other candidates at shortlisting or interview stage.

 

ESSENTIAL CRITERIA

DESIRABLE CRITERIA

Minimum (non-negotiable) qualifications, skills, experience, and/or knowledge needed to perform the job effectively.

Preferred nice-to-have attributes, like additional certifications or advanced skills, that give a candidate a competitive edge but are not critical to performing core job duties.

Experience

•       8+ years of progressive experience leading complex projects and/or operations, contributing to strategic planning and organization / enterprise-level decision-making

•       5+ years of experience driving improvement in project management and/or broader operational effectiveness and managing related organizational change and adoption

•       Experience helping to establish a project delivery, PMO, or operational effectiveness function and strengthening project management practices in environments without established PM maturity, particularly where subject-matter experts retain responsibility for project delivery

•       Experience with portfolio-level planning, prioritization, and capacity management

•       Demonstrated experience leading complex, cross-functional initiatives involving multiple stakeholders, dependencies, and competing priorities

•       Experience influencing senior leaders and working across teams to improve coordination, execution, and decision-making, driving change without formal authority

•       Experience working in a nonprofit, public sector, or mission-driven organization.

•       Experience supporting initiatives with funder, reporting, compliance, and/or accountability requirements.

•       Experience working across sectors (e.g., community, business, government, funders).

•       Experience enabling effective collaboration and accountability in matrixed environments.

•       Experience using project management tools – e.g., ClickUp, Monday.com, Asana, Smartsheet

 

Skills and knowledge

•       Strong strategic and system thinking

•       Ability to translate organizational priorities into practical delivery approaches

•       High emotional intelligence and relationship-building skills

•       Excellent communication, facilitation, and coaching skills

•       Ability to bring clarity and momentum to complex evolving work

•       Ability and confidence to make sound judgments in complex and emergent contexts where there can be high uncertainty

•       Ability to lead peers through example and influence rather than direct authority

•       Ability to surface risks, trade-offs, and capacity pressures in ways that support action and decision-making

 

•       Knowledge of multiple project management methodologies (waterfall, agile, hybrid).

•       Knowledge of the Canadian financial empowerment, poverty reduction, and/or economic inclusion landscape.

Qualifications

•       Post-secondary education in a relevant field (e.g., Public Administration, Business Administration/Management, Nonprofit Management), or equivalent practical experience.

•       Project management certification

•       Change management and/or other related certification

•       Bilingualism (French/English)

 

WHAT WE OFFER

 

Prosper Canada offers the opportunity to work in a mission-driven, values-based environment where you can help to drive large-scale social impact.

 

Our staff enjoy:

 

•         Supportive work policies in a hybrid office environment

•        A collaborative work environment with a strong culture of learning and innovation

•        Opportunities for learning and professional development and to participate in cross-team working groups and projects.

 

Compensation package: The salary range for this position is $107,500 to $120,000.  Upon successful completion of a 3-month probation period, the successful candidate will also participate in a full suite of employee benefits including:

 

•       Group medical and dental benefitsEX

•       Employee Assistance Program

•       Employer RRSP contribution

•       Membership in the Common Good retirement savings plan

•       20 paid vacation days

•       3 paid personal days and 15 paid sick days

•       Paid time off when we close the office from Christmas Eve through New Year’s Day. 

 

PLICATION DETAILS / HOW TO APPLY

 

Employment Type:                    Full-time permanent 

Vacancy status:                           New role   

Job location:                                Suite 700, 60 St. Clair Avenue E., Toronto ON M4T 1N5 

Travel:                                          5% per year 

Application deadline:               May 3, 2026  

Start date:                                     June 2026 

How to apply:                           Please email a cover letter and resume to 

 with subject line: “Application for Director, Operations”

 

Prosper Canada values and welcomes:

 

•       Applicants from racialized groups, including, black, Indigenous, and people of colour.

•       Applicants of all gender expressions and sexual orientations, including queer, trans, and two-spirit people.

•       Your personal experience of living on a low income, being a newcomer, or living with a disability, and the insights and perspectives this would bring to your work.

•       Your understanding of the concepts of institutional and structural racism and bias and their impact on underserved and under-represented communities.

•       Your ability to build empathetic relationships with a broad range of people, including people from diverse communities living on low incomes.

 

If you do not meet all our requirements, but believe your skill set and experience are applicable or transferable, we would still love to hear from you.

 

We encourage candidates from equity-seeking groups to self-identify in your cover letter and to highlight how your lived experience helps you understand the needs and challenges of equity-seeking groups. We are committed to making accommodation for all candidates and staff with temporary or permanent disabilities. Applicants who may require an accessible format of this job description or accommodation to have a successful interview are encouraged to contact us.

 

Interviews with candidates may be conducted virtually or in person for candidates in the Greater Toronto Area. We thank all applicants for their interest, however, only those selected for an interview will be contacted.

 

The interview process would include HR Phone screening, Interview, Professional reference checks and Offer to the final selected candidate.

Note: Artificial intelligence (AI) is not used to screen, assess, or select applicants for this role.

Thank you for your interest in working at Prosper Canada.

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