Director, Frontline Programs (Full-time)

Director, Frontline Programs (Full-time)

Who We Are

Prosper Canada is a national charity driving bold change that enables more people to prosper.

Working with government, business and community partners across Canada, we are expanding life-changing financial empowerment services, innovating for greater inclusion and impact, and pursuing systemic change to remove barriers to financial well-being for people with low and modest incomes.

Diversity is at the core of what we do and who we support to build financial health. Our financial empowerment efforts focus on equity-seeking groups, including people with low incomes, Indigenous Peoples, members of racialized communities, and people living with disabilities. In our work, we seek diverse perspectives that represent the lived experience, needs and challenges of the people we serve. Our goal is a Canada where everyone has the opportunity and support they need to achieve financial well-being and live with dignity, stability, and possibility.

In our organization, we value being collaborative, human-centred, and forward-thinking and strive to create a culture where all feel valued, respected, and a true sense of belonging. We see power in diversity, equity, and inclusion; recognize, accept, and celebrate our differences; and believe we can help everyone thrive by being our boldest true selves.

Join us in supporting and empowering everyone in Canada to prosper.

The Opportunity

The Director, Frontline Programs provides strategic leadership and oversight of Prosper Canada’s Frontline Programs. This role requires a mission-driven, strategic, entrepreneurial and values-based leader who can engage, align and mobilize diverse teams, partners and stakeholders to advance a bold national vision for scaling high-impact and inclusive community financial empowerment services in Canada.

Working closely with senior Prosper Canada leaders and external community, government, philanthropic, and financial sector partners and stakeholders, the Director is responsible for leading the growth and development of Canada’s community financial empowerment field and helping to ensure that everyone in Canada has access to the financial help they need to achieve financial wellbeing – no matter who they are, where they live, or their starting point.

They are accountable for overseeing and developing our national system of free, high-quality, community-delivered, financial help services, funded through our Resilient Futures program, and achieving our 4-year goal of helping 1 million people with low and moderate incomes to build their financial wellbeing and access $2 billion in additional income.

In parallel, they are responsible for driving innovation to grow our frontline impact and broaden the inclusion and reach of financial empowerment supports across Canada. This includes adapting service models, tools and resources to better serve diverse communities.

The Director, Frontline Programs provides strategic leadership and oversight of Prosper Canada’s Frontline Programs Department which is accountable for advancing efforts to enhance and sustainably scale access quality and inclusive community delivered financial help services for people with low and moderate incomes across Canada.

Reporting to the VP, Impact and Operations, the Director oversees a multi-disciplinary Department with three core functions:

• Our Community Services & Impact Group (CSI) is responsible for ensuring the delivery of comparable, inclusive, high-quality financial empowerment services across Canada. Working with our national network of community service partners, they manage these relationships, monitor program delivery, build capacity through learning and training opportunities and resources, and foster peer engagement and learning through our national online community of practice.
• Our Service Innovation & Inclusion Group (SI&I) is responsible for the design, development, testing, and scale-readiness of high-quality, inclusive, financial empowerment service models and tools, and applying human-centred design throughout the innovation cycle to ensure impact, equity and accessibility.
• Our Grant Administration Team (GA) is responsible for administering our Resilient Futures grant fund and other project grants. This includes designing and administering calls for proposals, grant allocation, fund disbursements, compliance monitoring, and reporting.

The Director is accountable for the leadership and performance of all three functions, ensuring plans, priorities and target outcomes align with and advance with Prosper Canada’s strategic priorities, that roles and responsibilities are clearly defined, and there is strong cross-team coordination. In addition, the Director is expected to optimize the use of systems, people, and resources across these functions to strengthen community partner experience, ensure accountability for and achievement of funded outcomes, manage risk, and translate learning into continuous service and system improvement.

Reports to: Vice President, Impact and Operations

Direct reports:

• Senior Manager, Service Innovation & Inclusion (SI&I)
• Senior Manager, Community Services & Impact (CSI)
• Manager, Grant Administration (GA)

Indirect reports: 9+ roles across GA, CSI and SI&I

Summary of key Responsibilities

Sets direction and aligns Frontline Program functions (20%)

Sets clear strategic direction for Frontline Programs and ensures alignment across service innovation and inclusion, partner engagement, and grant administration to advance a cohesive approach to partner granting, management, and support delivery.

• Sets and advances a clear vision for Frontline Programs aligned with Prosper Canada’s organizational priorities.
• Translates multi-year organizational priorities into executable Frontline Program plans with clear outcomes, milestones, success measures, and accountabilities across teams.
• Advances the implementation of Frontline Program multi-year plans by driving annual operational planning, ensuring coherence and alignment across across Frontline functions and other Prosper Canada teams
• Ensures Frontline Program plans are adaptable and responsive to emerging risks, opportunities, capacity and resource constraints, and system-level changes, adjusting plans as needed.

Ensures strong performance, accountability, and results (20%)

Accountable for the overall performance of the Frontline Program Department, ensuring funded initiatives deliver intended outcomes with consistency, quality, and effective risk management:

• Ensures frontline initiatives are delivered on time, on budget, and to agreed quality standards, supported by consistent expectations, detailed work plans, and performance oversight.
• Ensures Frontline Program team frameworks, methodologies, systems, and standards are in place to enable reliable, high-quality, partner-facing work across teams.
• Holds Frontline Program senior leaders accountable for ensuring the adoption, consistent implementation, and continuous monitoring and improvement of core operating systems and tools within their teams.
• Strengthens consistency and quality across partner-facing work through shared partner management and support frameworks, systems, and expectations.
• Leverages data, evaluation, and partner insights to routinely inform decisions and drive continuous improvement across the Frontline Program project portfolio and functions.
• Proactively works with Frontline Program managers and senior managers to identify and manage delivery, financial, capacity, relationship, and compliance risks.

Strengthens partner experience and external relationships (15%)

Ensures community partners experience coordinated, high-quality support, learning, and engagement and provides senior external leadership:

• Ensures frontline community partners experience a coordinated, transparent, and supportive journey across the full granting and project delivery lifecycle.
• Ensures partner engagement practices balance both foster accountability and support partners where needed to overcome challenges and be successful.
• Maintains senior-level relationships with key external partners, funders, policymakers, and other relevant eco-system stakeholders.
• Represents Prosper Canada’s frontline work in national conversations related to financial empowerment service delivery, innovation, and inclusion.

Builds, develops and supports high-performing and inclusive teams (20%)

Builds leadership capacity across Frontline Programs and fosters inclusive, high-performing teams grounded in clarity, collaboration, and staff development and wellbeing:

• Leads, coaches and supports development of 3 direct reports from the CSI, SI&I and GA teams, helping them to strengthen team performance and be effective in their leadership roles.
• Ensures Frontline Program staff capacity, workload and wellbeing are actively managed by CSI, SI&I and GA leaders, particularly during periods of growth, peak activity, and/or change.
• Fosters a culture of clarity, collaboration, learning, and continuous improvement across the Frontline Programs Department.
• Ensures consistent application of organizational performance management and development policies and processes for all CSI, SI&I and GA staff and the provision of team and individual learning and training opportunities as needed.
• Champions accountability, equity, and inclusion across Frontline Program Department leadership, in staff management and program delivery.

Contributes to organizational strategy, advocacy, and sustainability (10%)

Contributes to Prosper Canada’s long-term sustainability by helping to shape our organizational strategy, strengthening alignment between frontline delivery and funding priorities, and ensuring frontline insights inform broader decision making:

• Contributes to organizational strategy development, planning, and decision-making.
• Supports funding strategy and sustainability by collaborating with Business Development and other internal teams to mobilize resources and build/manage funder relationships.
• Facilitates collection and use of frontline insights to inform and strengthen our system change engagement and advocacy efforts, in partnership with the Systems Change Program team.

Drives organizational alignment, operational effectiveness, and sustainability (15%)

As a member of Prosper Canada’s new Senior Operational Leadership Table (SOLT), the Director helps to drive operational alignment and improvement across teams to support effective delivery of organizational strategies and associated operating plans:

• Actively collaborates with other Directors to align on and advance operational priorities, manage cross-team interdependencies, and address operational risks.
• Helps to strengthen organizational processes, policies, and practices to improve operational role clarity, efficiency, and cross-team accountability.
• Brings Frontline Program staff and partner insights to SOLT discussions to inform development and implementation of operating plans and related problem solving and decision-making.
• Supports alignment of Frontline Program operations with available funding, organizational capacity and capability considerations, and emerging risk and opportunities.
• Works collaboratively with other Directors and HR and Finance managers to ensure operational plans are integrated, realistic, and achievable.
• Helps ensure consistent and effective people management practices across teams, supporting leadership capability and staff wellbeing in a matrixed environment.

WHAT SUCCESS IN THIS ROLE LOOKS LIKE OVER the next 2-3 years

• Clear and scalable operating processes and infrastructure
  All Frontline Programs teams (SI&I, CSI, and GA) operate with well-defined, fit-for-purpose systems, processes, and tools that support consistent high-quality performance, enable staff effectiveness, and scale reliably as programs and partnerships grow.
• Integrated Frontline Program portfolio direction
  Frontline Programs operate under a clear, integrated, multi-year plan that aligns Service Innovation & Inclusion, Community Services & Impact, and Grant Administration with Prosper Canada’s strategic priorities, clear capacity decision-making guardrails, and performance expectations.
• Innovation that translates into scale and impact
  Service Innovation & Inclusion initiatives consistently generate high-quality, inclusive service models, tools, and insights that are ready for adoption or scaling, and are effectively integrated into partner delivery, funding strategies, and organizational decision-making.
• Consistent, high-quality partner experience across the project lifecycle
  Community partners experience coordinated, reliable, and high-quality engagement across innovation, learning, funding, and compliance functions, with clear accountability and support throughout the full grant and service lifecycle.
• Strong grant stewardship and funder confidence
  Grant Administration operates with strong governance, compliance, and financial stewardship, resulting in timely reporting, effective risk management, and high levels of confidence among funders and internal leaders.
• Effective matrixed program delivery
  Senior Frontline Program leaders and their teams work effectively within a matrixed environment, collaborating seamlessly with other internal teams to deliver complex projects and initiatives with clarity of roles, shared accountability, and minimal friction.
• High-performing, supported leadership and teams
  Senior Frontline Program leaders are well-supported, clear in their roles, and accountable for outcomes, with teams that are engaged, resilient, and able to sustain performance during periods of growth, complexity, and change.
• Frontline learning shapes organizational strategy and influence
  Insights from frontline delivery, innovation, and partner engagement are systematically surfaced and used to inform organizational strategy, funding priorities, policy engagement, and national leadership in financial empowerment.

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

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

Desirable criteria

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

• Senior leadership experience: 10+ years in non-profit, public, or social impact environments with accountability for complex programs or portfolios.
• Portfolio leadership: experience leading multi-year, multi-team, multi-stakeholder initiatives with responsibility for outcomes, budgets, and risk.
• People leadership: demonstrated success leading and developing senior managers and high-performing, inclusive teams.
• Partner and funder engagement: experience working with community-based organizations, funders, and/or government partners.
• Strategic integration: proven ability to align strategy, operations, systems, and resources across multiple functions.
• Change leadership: experience leading teams through significant organizational growth and transformation, maintaining performance, and staff wellbeing.
• Financial empowerment or related service delivery: experience delivering or overseeing financial empowerment, social services, or adjacent fields.
• Cross-sector influence: experience working across community, government, financial sector, or philanthropic environments.
• Funding and sustainability: experience supporting funding strategies, proposal development, or funder relationships.
• National or multi-region scope: experience working across multiple regions or within national organizations.

Skills and knowledge

• Strategic leadership: setting direction, establishing priorities, and translating strategy into clear plans and accountabilities.
• Performance oversight: monitoring outcomes, managing risk, and using data and learning to inform decisions.
• People leadership: coaching senior leaders, and supporting staff development and wellbeing
• Relationship leadership: building trust and influence with senior internal staff and external partners.
• Complexity management: navigating ambiguity and competing priorities while maintaining clarity and momentum.
• Communication: synthesizing complex issues and communicating clearly to diverse audiences.
• Equity and inclusion: strong understanding of equity-seeking communities and systemic barriers faced by people living on low incomes.
• Systems-building: experience building, strengthening or implementing new operational systems, processes, and tools across teams or portfolios.
• Matrixed delivery: experience enabling effective collaboration and accountability in matrixed or cross-functional environments.
• Sector context: knowledge of the Canadian financial empowerment, poverty reduction, or economic inclusion landscape.
• Trauma-informed practice: understanding of trauma-informed approaches in leadership and service delivery.
• Language skills: bilingual in English and French, with the ability to communicate effectively in both languages.

Qualifications

• Education: Post-secondary education in a relevant field (e.g., public policy, community development, social innovation, business administration, or equivalent experience).
• Additional credentials: project management, change management, or leadership certifications.

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 probation period, the successful candidate will also participate in a full suite of employee benefits including:

• 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
• Group medical and dental benefits
• Employee Assistance Program
• Employer RRSP contribution and membership in the Common Good retirement savings plan

EMPLOYMENT DETAILS and HOW TO APPLY

Employment Type: Full-time

Posting type: Existing vacancy

Job location: 60 St. Clair Avenue E., Toronto, ON

Travel: 5% per year

How to apply: Please email a cover letter and resume to hr@prospercanada.org

with subject line: “Application for Director, Frontline Programs”

Application deadline: March 31, 2026

Start date: April/May 2026

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 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 their cover letters and to highlight how their lived experiences help them 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 on hr@prospercanada.org.

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.

Follow us on LinkedIn to be notified when career opportunities are available.