Executive Director

Hesperus Village is seeking a values-driven and community-oriented Executive Director to lead the organization through its next chapter. This is a unique opportunity to steward a vibrant diverse community, foster a culture of participation and belonging, and advance a mission grounded in anthroposophy, relational care, and collaborative governance.The Company
Hesperus Village | Senior Housing Ontario | VaughanHesperus Village is a mission-driven community dedicated to creating a meaningful, inclusive, and supportive environment for older adults. Guided by its Theory of Change, Hesperus Village seeks to strengthen community, belonging, purpose, and supported aging by combining affordable housing, resident-led community life, and collaborative partnerships that promote well-being throughout the aging journey. The community follows the principles of anthroposophy, the organization promotes dignity, purpose, and connection through community living, participatory decision-making, and holistic approaches to aging. Through its commitment to resident well-being, shared leadership, and long-term sustainability, Hesperus Village strives to cultivate a thriving community where individuals can continue to contribute, grow, and live with purpose.The Role
Reporting to the Board of Directors, the Executive Director is responsible for the overall leadership, management, and operation of Hesperus Village. The Executive Director ensures the organization fulfills its mission and strategic objectives while operating in alignment with its values, policies, and governance framework.As the organization's senior leader, the Executive Director provides strategic advice to the Board, oversees financial and operational performance, nurtures a healthy organizational culture, and serves as a key ambassador to residents, families, partners, volunteers, funders, and the broader community.The Executive Director also plays a central role in supporting Hesperus Village's sociocratic governance model, fostering participatory decision-making and collaboration across the organization.Key Areas of Leadership and Oversight
Strategic and Organizational Leadership:
Works closely with the Board of Directors to develop and implement strategic and operational plans, identify emerging opportunities and risks, establish organizational priorities, and ensure alignment with Hesperus Village's mission, vision, values, and long-term sustainability objectives.Governance and Sociocratic Leadership:
Serves as an active participant within the General Circle, supporting effective communication and alignment between governance and operational circles while embedding sociocratic principles, consent-based decision-making, shared accountability, and decentralized leadership throughout the organization.People Leadership and Community Culture:
Recruits, develops, mentors, and supports staff and volunteers while fostering an inclusive, collaborative, and respectful culture grounded in relational care, community engagement, and meaningful participation by residents, families, staff, and volunteers.Financial and Operational Stewardship:
Oversees financial planning, budgeting, revenue generation, facilities management, risk management, compliance, and organizational performance to ensure the long-term health, sustainability, and effectiveness of the organization and its programs.Community and Stakeholder Engagement:
Builds and maintains productive relationships with residents, families, community partners, government stakeholders, donors, and sector representatives while advancing awareness, advocacy, partnership development, and fundraising efforts in support of the organization's mission.The Ideal Candidate
Hesperus Village seeks a thoughtful, collaborative, and purpose-driven leader who brings both strategic capability and a genuine commitment to community-centered work. The successful candidate will be comfortable operating within a participatory governance environment and will appreciate the balance between organizational stewardship, relationship building, and mission advancement.They will possess the ability to navigate complexity with sound judgment, engage diverse stakeholders with authenticity and respect, and lead through influence and collaboration. An appreciation for anthroposophical principles and a commitment to fostering meaningful community participation will be important differentiators.Qualifications and Experience
University degree in business, public administration, social services, nonprofit management, property management, or a related discipline, or an equivalent combination of education and experience.Professional credentials or training in areas such as business administration, housing, property management, nonprofit leadership, governance, fundraising, or community development would be considered an asset.Progressive senior leadership experience, ideally within the nonprofit, housing, seniors' services, healthcare, social services, intentional community, or related sectors.Demonstrated experience working effectively with a Board of Directors and supporting governance processes, preferably within a sociocratic, participatory, or shared-governance framework.Experience overseeing organizational operations including strategic planning, budgeting, risk management, facilities or asset stewardship, program oversight, fundraising, and stakeholder engagement.Knowledge of relevant provincial legislation, regulatory requirements, housing operations, and services impacting seniors and community-based organizations in Ontario.Interest in and appreciation for anthroposophy, community living, and participatory leadership models.Must be eligible to successfully complete a Vulnerable Sector Check.Skills and Attributes
Strategic thinker with the ability to frame complex questions, navigate ambiguity, and guide long-term organizational direction.Collaborative and relationship-focused leader with demonstrated success building partnerships and aligning diverse stakeholders around shared goals.Strong financial and operational acumen, including experience with budgeting, resource planning, performance monitoring, and organizational sustainability.Skilled facilitator who supports participatory leadership, consensus-building, and authentic community engagement.Adaptable and resilient leader who responds effectively to change, uncertainty, and unexpected challenges.Deep appreciation for relational, community-based work and the importance of incorporating diverse voices into decision-making processes.Results-oriented and accountable, with the ability to balance mission, values, operational effectiveness, and long-term impact.Exceptional communication, listening, and interpersonal skills, coupled with a high degree of emotional intelligence and integrity.Hesperus is committed to equity, diversity, and inclusion. We welcome and encourage applications from candidates of all backgrounds and experiences. We will provide support and accommodations to applicants with disabilities, upon request. If you need accommodation in order to participate as a candidate in the recruitment process, please contact View email address on ca.hrm.tc or communicate your needs to the recruitment professional named in the job description.
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