The Position:
Summit Search Group has been retained by Ten Ten Sinclair Housing on the recruitment of their next Executive Director. Ten Ten Sinclair Housing Inc. is a long-standing, community-based non-profit organization dedicated to advancing the independent living philosophy for people living with disabilities. For more than 50 years, Ten Ten has provided accessible housing, attendant care, and support services that enable individuals to live with dignity, choice, and autonomy. Through a portfolio of housing sites, including a 75-unit apartment complex and multiple supported housing locations, Ten Ten plays a critical role in Winnipeg’s disability, housing, and community services ecosystem, working closely with government funders, partners, and a diverse membership and Board.
Reporting to the Board of Directors, the Executive Director (ED) provides overall leadership and direction for Ten Ten Sinclair Housing Inc. The ED is responsible for translating the organization’s mission and strategic priorities into effective operations, high-quality services, and sustainable organizational performance. This role balances strategic leadership with hands-on operational oversight, including labour relations, financial management, housing and property oversight, government relations, and stakeholder engagement. The ED leads a large, predominantly unionized workforce and operates in a complex, 24/7 service environment where responsiveness, judgement, and strong people leadership are essential. The role requires a collaborative, values-driven leader who can navigate competing demands while maintaining strong relationships with staff, consumers, funders, and community partners.
Governance, Strategy, & Board Partnership:
- Serve as the Board’s primary operational leader and strategic advisor, ensuring alignment between governance direction and organizational performance
- Implement Board-approved policies, strategic plans, and priorities across all programs, services, and housing operations
- Prepare reports, recommendations, and analysis to support informed Board decision-making
- Foster strong, respectful working relationships with a diverse Board and membership, including individuals with lived disability experience
- Support Board committees and organizational governance processes, including annual meetings and planning activities
People Leadership, Culture & Labour Relations:
- Provide leadership to staff and consumers, promoting a culture grounded in respect, inclusion, safety, and the independent living philosophy
- Oversee human resources practices including recruitment, performance management, succession planning, and policy development
- Lead labour relations strategy, including administration of collective agreements and preparation for collective bargaining
- Ensure appropriate handling of workplace issues such as investigations, workplace safety and health, and employee relations matters
- Act as senior on-call leadership for urgent operational, consumer, or safety issues in a 24/7 service environment
Operational, Financial, & Housing Leadership:
- Oversee day-to-day operations of programs, services, and housing sites, ensuring quality, compliance, and continuous improvement
- Lead financial management including budgeting, financial controls, audit readiness, and reporting to the Board
- Oversee Ten Ten’s role as landlord and housing operator, including leasing, rent administration, and compliance with residential tenancy legislation
- Ensure effective property management, maintenance planning, accessibility standards, and vendor oversight
- Build and maintain strong relationships with government funders, regulators, and community partners while supporting funding sustainability and diversification efforts
Qualifications:
- Senior leadership experience in a non-profit, housing, health, or human services organization, with demonstrated success working with a Board of Directors
- Strong understanding of disability-related services and a clear commitment to the independent living philosophy; lived experience or close community connection is an asset
- Proven experience leading in a unionized environment, including collective agreement administration and labour relations
- Demonstrated financial acumen, including experience with public or government-funded budgets and accountability frameworks
- Excellent leadership, communication, and problem-solving skills with the ability to manage complexity, balance competing priorities, and lead through organizational change
For more information, or to submit your resume, please reach out to Matt Erhard at Summit Search Group, matt.erhard@summitsearchgroup.com
Summit Search Group has a strong commitment to Diversity, Equality and Inclusion. We strive for continuous development, modeling, inclusive behaviors and proactively managing bias throughout our process.
