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Chief Operating Officer

Chief Operating Officer

Pathways Executive Search
locationToronto ON Canada
remoteOnsite
PublishedPublished: 2026-02-23
ExpiresExpires: 2026-04-24
Full Time
5 - 10 years of experience
$110,000 - $130,000 per year

Chief Operating Officer

The Organization

Founded in 1972, Wigwamen Incorporated (Wigwamen), a non-profit and charitable organization, is Ontario’s oldest and largest urban Indigenous housing provider. Highly regarded within the non-profit housing sector and winner of the Ontario Non-Profit Housing Association’s “Award for Excellence” in 2016, Wigwamen has a long-serving and skilled team that fosters a collaborative working environment across all levels.

Wigwamen is committed to providing decent, safe and affordable housing to thousands of Indigenous and non-Indigenous families, singles and seniors. Owning and operating more than 865 units in Toronto and Ottawa, the Wigwamen portfolio includes a mix of units--single and semi-detached homes, duplexes, triplexes and others—that are well-maintained and provide a safe home for tenants.

Wigwamen is currently expanding developments in both Toronto and Ottawa to meet the demand for more affordable housing units. It provides a variety of positive and creative supports for its tenants through relevant social programming and student scholarships.

Vision

Wigwamen aspires to:

Steadily expand its portfolio of affordable housing in a fiscally responsible manner;

Provide programming in support of the community; and

Increase public awareness of affordable housing and its positive impact on the community.

Mission

To provide safe, reliable and affordable housing primarily to the Indigenous Community.

Values

To act with integrity and respect to ensure everyone, including tenants, government partners, and donors are able to trust the words and actions of Wigwamen.

To operate as more than just a business by showing compassion to tenants, the general public and our employees.

To demonstrate professionalism throughout all levels of the organization.

To enhance and maintain the quality of our housing portfolio on a consistent basis. To embrace an entrepreneurial spirit to utilize our capabilities and expand our business opportunities.

To learn more about Wigwamen, please visit: https://www.wigwamen.com/

The Opportunity

Wigwamen has a strong track record of growth and a secure housing stock. The Chief Operating Officer (COO) of Wigwamen will play a pivotal role in driving operational excellence forward and ensuring the efficient execution of strategic long-term activities. The COO will have an opportunity to co-lead the planning and execution of Wigwamen’s future housing expansions, as well as its unique approach to services and supports offered across its social initiatives.

Reporting to the Chief Executive Officer and working with managers and staff throughout the organization, the COO will plan, direct, coordinate and oversee all aspects of day-to-day operations. They will bring a strong track record of leadership within the non-profit housing sector along with an understanding of the needs of the urban Indigenous community. They will be responsible for providing operational updates to the Board of Directors.

Key Responsibilities

1.Define and develop corporate strategies, policies, procedures, and programs. Convert organizational strategies and policies into specific objectives for subordinate areas of responsibility and monitor the accomplishment of such objectives.

2.Optimize operational efficiency and effectiveness in alignment with Indigenous values.

3.Enhance human resources management, including policy development and implementation, hiring and supervision of program and other staff.

4.Foster positive and productive government, community, and tenant relations.

5.Guided by the Board and co-led by the CEO take the lead in the planning and development of a new strategic plan.

6.Assist the CEO and CFO with financial planning and reviews, and oversight of the financial management of the corporation.

7.Prepare funding proposals and oversee funding agreements and budgets.

8.Take a lead role with new housing developments and other projects.

9.Report to the CEO on all matters that relate to the activities of the corporation and be responsible for ensuring that the company fulfils its contractual and legal obligations.

10.Prepare written reports for the CEO, the Board of Directors, and/or funders, as required.

11.Act on behalf of the CEO in their absence.

The Candidate

Qualified candidates will have proven experience working within the complexities and tempo of urban not-for-profit housing organizations and developers. They will be responsible for the day-to-day operations of the organization, always keeping tenants' needs in mind. They must be highly motivated, responsive and adaptive to Wigwamen’s dynamic work environment.

Overseeing Wigwamen’s expansive housing portfolio requires a strong leader who can make quick, sound and informed decisions. They must be proactive, collaborative and supportive of Wigwamen’s staff throughout the cycles if capital planning, development, financing and operations.

Qualified Indigenous applicants will be prioritized through the selection process.

Qualifications, Skills, and Abilities

Excellent interpersonal, verbal communication, report writing and facilitation skills.

An understanding of the importance of respecting client confidentiality.

A record of sound executive judgement and decision-making.

Computer competency, including Word, Excel, e-mail, and other applications.

Experience in project development.

Financial analysis and budget management.

Demonstrated ability to engage effectively with urban Indigenous communities. Strong advocacy skills to represent Indigenous communities within broader organizational or project contexts.

Experience in facilitating strategic, financial and operational planning

Experience working with and reporting to a board

Education

A post-secondary degree in a related or complementary field such as Business, Planning, Architecture, or equivalent combination of education and experience; a combination of education and lived experience will be taken into consideration.

The Candidate continued

Experience

Proven track record of success in a senior leadership role in the non-profit housing or related sectors, with a minimum of 5 years of experience in operations management and leadership.

A comprehensive understanding of the non-profit housing sector, housing issues and related legislation. Experience in related reporting, measurement, and evaluation.

Experience in the planning and development of new affordable housing projects. Experience working with various levels of government, including Indigenous, municipal, provincial and federal.

Demonstrated financial management and personnel administration abilities. A record of building and maintaining relationships with community partners and funders.

A demonstrated record of providing leadership and motivating others, organizing work schedules, providing effective staff supervision, and developing policies and procedures.

Strong, positive relationships with Indigenous communities, particularly the Urban Indigenous population.

The City: Toronto

The name Toronto is derived from the Mohawk word “tkaronto,” which means “where there are trees standing in the water.” It is the traditional territory of many nations, including the Mississaugas of the Credit, the Anishnabeg, the Chippewa, the Haudenosaunee, and the Wendat peoples. It is now home to many diverse First Nations, Inuit and Métis peoples, along with other Indigenous groups that represent this valued community.

Toronto has a population of 2.8 million people, making it the largest city in Canada, the fourth-largest city in North America, one of the top 25 cities globally for its quality of living, and the best place to live in Canada, according to MoneySense. Toronto welcomes 40 million tourists a year. It supports a lively art and culture scene that includes museums, galleries, performing art organizations, and many festivals (including the Indigenous Art Festival). Toronto is recognized as one of the most diverse and multicultural cities in the world.

Toronto is the home to Ontario’s Parliament Buildings as well as multiple postsecondary institutions – Humber College, George Brown College, the University of Toronto (the largest university in Canada), Toronto Metropolitan University, York University and OCAD University. Toronto schools reflect the diversity of the population. The four school boards – English public, French public, English Roman Catholic and French Roman Catholic – provide many options, including French immersion programs. There are also several private, secular and religious schools and boarding schools.

The Royal Ontario Museum is an iconic building boasting the Michael Lee-Chin Crystal inspired by the ROM’s extensive gem and mineral collection; the design was quickly dubbed the ‘crystal’ because of its crystalline shape. The Royal Ontario Museum has a unique 100-year history of conducting groundbreaking research in all areas of art, culture, and nature.

Just offshore from the city centre are the Toronto Islands known as ‘Menecing,’ meaning “On the Island” in the Ojibwa language. The islands are home to parklands and the Billy Bishop Toronto City Airport. The island community is considered the largest urban car-free community in North America.

To Apply

To apply, please submit a cover letter and resume in PDF format to Pathways Executive Search outlining your interest, qualifications, and experience.

Email: Applications@PathwaysExecutiveSearch.com, please include Wigwamen in the subject line.

For more details or to further explore this important leadership opportunity, please contact:

Laurie Sterritt • Managing Partner

Pathways Executive Search

Telephone: (778) 838-4569

LaurieS@PathwaysExecutiveSearch.com

Amelia Williams • Senior Consultant

Pathways Executive Search

Telephone: (905) 995-3148

AmeliaW@PathwaysExecutiveSearch.com

Pathways Executive Search is an international executive recruitment firm, known for its ability to attract and recruit talent in culturally grounded ways. Guided by Indigenous values and principles of Indigenous inclusion, Pathways walks with those looking to broaden candidate pools, find qualified and experienced candidates, and live out their values and commitment to creating workplace cultures where people can thrive.

Required degree level

  • Executive/Leadership

Years of experience (Optional)

  • 5 - 10 years of experience

Salary range

  • $110,000 - $130,000 per year