RTOERO: CEO
POSITION:
CEO (Chief Executive Officer)
LOCATION:
Toronto, Ontario
POSITION DETAILS:
Full Time, Permanent, Hybrid
REPORTS TO:
Board of Directors
DIRECT REPORTS:
Chief Financial Officer, Chief Administrative Officer, Director of Benefits, Director of Marketing, Communications & Member Services, Director of Information Technology, Director of People, Culture & Volunteer Engagement
WEBSITE:
THE ORGANIZATION
RTOERO is a bilingual, trusted advocate for healthy, active aging, rooted in Canada’s education sector. With over 87,000 members in 51 districts, RTOERO manages a non-profit group insurance program that covers more than 100,000 people nationwide. Membership is open to anyone working in or retired from any role in education in Canada, along with their immediate family members. In January 2026, RTOERO will become Entente Education Canada.
Guided by a belief in building a better future together, the organization harnesses the power of community to support individual well-being and advance societal progress.
We provide essential health, wellness and travel benefits so our members can explore their journeys with confidence. We connect our members to each other as volunteers, as leaders and in support of individuals in need. We support research and drive advocacy to advance the interests of seniors and increase their contribution to society at every age.
We believe in the power of our community to secure a better future.
In addition to the organization’s programs and services, the RTOERO Foundation was created in 2011 to help realize the ideals of a society in which seniors get the care and support they need and play an active role in the things that matter to them.
This charitable arm of RTOERO focuses its efforts exclusively on the health and wellbeing of older adults by supporting innovative research and programs, improving health care and promoting social engagement.
THE POSITION
This isn’t just another executive position – it’s a chance to lead a national organization that directly improves the lives of those who work in and retire from the education community. Candidates with a passion for making a real impact will find meaning and fulfillment.
With demographic shifts and rising retiree health needs, this sector is evolving rapidly. A visionary leader will be excited by the chance to innovate in benefit design and member advocacy – creating real change at scale.
You are a vigorous, inspirational, and forward-thinking Chief Executive Officer (CEO). The role will actively work with the Board to set and implement the strategic vision of the organization for the present and the long-term.
As the CEO, you are the strategic and operational leader of RTOERO. Reporting to the Board, you are responsible for driving the mission, vision, and values of the organization while ensuring high-quality delivery of services to members. You demonstrate exceptional skills and strengths in key areas including government relations and advocacy; building and maintaining relationships; organizational governance; and public policy. The CEO must manage, mentor, and motivate staff to accomplish RTOERO’s objectives while servicing member needs and maintaining fiscal responsibility.
RESPONSIBILITIES
Strategic Leadership
Oversee and implement the strategic plan aligned with the mission and values.
Lead organizational growth and innovation in product offerings, partnerships, and member engagement.
Explore opportunities to broaden the RTOERO membership.
Represent RTOERO to key stakeholders, including government agencies, insurance partners, member associations, and the public.
Stay current on and assess the impact of social, political and economic issues and conditions on retirees and older adults.
Carry out the policy directives of the Board of Directors with the assistance of the Senior Management Team and staff.
Attend relevant meetings and conferences at the local, provincial and national level where the interests of RTOERO members and older adults in general are addressed.
Develop briefs, presentations and position papers for submission to Canadian governments and other agencies and organizations.
In conjunction with the Chair, liaise with the Ontario Teachers’ Federation (OTF) and its affiliates as well as other organizations such as OTPP, OMERS, CAAT, provincial governments, and other retiree and older adult organizations on matters of mutual interest and the interests of retirees in general.
Oversee the operation, renovation and management of the RTOERO building at 18 Spadina Road in Toronto and its tenancies. Attend the Condominium Corporation AGM as a voting member in March every year.
Financial Stewardship
Develop and manage annual budgets in alignment with strategic priorities, for approval by the Board of Directors.
Ensure sound financial controls and reporting practices.
Optimize organizational resources to maintain sustainability and value for members.
Monitor the finances of RTOERO and 1316342 Ontario Inc., with the assistance of professional investment, accounting and auditing staff and services.
Oversee the investment of RTOERO's various investment reserve funds, in accordance with the current Investment Policy of the Board.
Operational Management
Oversee daily operations, including benefit program delivery, administration, customer service, and communications.
Ensure the delivery of high-quality, member-focused services.
Monitor industry trends and ensure RTOERO remains competitive and relevant.
Ensure the effective administration and operation of the RTOERO Office, by hiring and providing professional growth and on-going performance assessment of staff.
Connect regularly with the Executive Director of the RTOERO Foundation to support achieving its strategic goals, in alignment with RTOERO’s vision and mission.
Board Relations
Collaborate with the Board of Directors to develop governance policies, strategic direction, and performance metrics.
Report regularly on progress toward the strategic plan, financial performance, and emerging risk or opportunities.
Work closely with the Board Liaisons to assist districts in interpreting and implementing the By-law and Policies of RTOERO.
Participate (non-voting) at Board, Standing and Advisory Committee meetings.
Serve as voting member of the RTOERO Foundation Board.
Monitor the activities of the various Committees and Work Groups to ensure the directives of the Board of Directors are being addressed.
Keep the Board Chair apprised of any issues related to changes in health insurance.
In conjunction with the Chair, represent RTOERO with outside organizations/agencies and governments across Canada.
Stakeholder Engagement
Foster relationships with insurance carriers, wellness providers, and travel benefit partners.
Advocate on behalf of members with government and regulatory bodies.
Cultivate partnerships within the education and retirement sectors.
CANDIDATE QUALIFICATIONS
Minimum 15 years of progressive senior leadership experience, preferably in the educational, not-for-profit, or public sectors.
Proven track record of strategic planning, financial management, and stakeholder engagement.
Demonstrated ability to represent and advocate on behalf of RTOERO to all three levels of government across Canada.
An understanding of the challenges and opportunities facing older adults and retirees.
Experience working with or in service of retirees, the education sector, or member-based organizations is an asset.
A fearless networker with the ability to develop strong relationships both internally and externally.
Skillful in managing and developing relationships with a Board, staff, and members of an organization.
Strong management skills with experience in human resources development.
Demonstrated success in working effectively with a Board of Directors.
Excellent written and oral communication skills.
RTOERO is a bilingual, national organization; fluency in French is an asset.
University degree. Certification in a relevant field would be an asset.
CANDIDATE ATTRIBUTES
An enterprise-level strategic thinker with an entrepreneurial mindset.
A born networker who constantly expands from within and outside the organization, opening up possibilities, expanding RTOERO’s reach, and presenting opportunities for strategic partners and alliances.
Curious and observant. Listens to internal and external stakeholders and looks for opportunities.
Strives for excellence. Tests, evaluates, and course corrects. Fosters an environment of learning and constant improvement.
Embodies an innovative mindset, nurturing the following traits in themselves and others: risk tolerance, openness to ideas, action-oriented, and emotional stability.
Identifies and resolves issues quickly, problem-solves and generates solutions.
Delights in the delivery of a job well done with a roll-up-the-sleeves work ethic and a pragmatic, results-oriented approach.
Builds and leverages an inclusive culture which values diversity of experience and opinion, recognizing that this is foundational to creativity, innovation, and the future success of RTOERO.
Ability to communicate with credibility and respect to Board, staff, and external stakeholders.
Unquestionable integrity and character. Demonstrably high standards of moral, ethical, and professional behaviour.
Possesses high emotional intelligence and the ability to apply it appropriately.
Ensures high standards across all accountabilities. Goes above and beyond to ensure accuracy in all that they do.
COMPENSATION
A competitive compensation package including a base salary (range between $300,000 to $320,000 for the first year), matching contribution to a defined pension plan, comprehensive health & dental benefits, and generous vacation time will be provided.
Work will be performed at 18 Spadina Road, RTOERO's Head Office, with occasional travel. Some work may be in hybrid format and conducted occasionally from home.
HOW TO APPLY
We invite candidates to apply by email with your cover letter and résumé no later than Sunday, September 21, 2025. Send to Searchlight Partners: RTOERO@searchlightpartnersgroup.com
RTOERO is an equal-opportunity employer and committed to fair and accessible employment practices. We strongly support and value diversity in the workplace. Applications from all qualified candidates are welcome, and individuals from equity-seeking groups are encouraged to apply.
We thank applicants for their interest, however; only those advancing in the process will be contacted.