Insurance Ceo Jobs in Ontario (NOW HIRING)

About the Company
Our client is a large nonprofit organization. They are looking for a Chief Operating Officer (COO) to join their team! Why Work Here

• Lead operations for a mission-driven organization making a meaningful community impact
• Opportunity to shape strategy and scale programs
• Collaborative leadership environment
• Hybrid work environment

About the Opportunity
1. Organizational Leadership & Strategy

• • Partner with the CEO to develop and implement organizational strategy and annual operating plans
  • Provide leadership across departments to ensure alignment with mission, goals, and impact objectives
  • Lead cross-functional collaboration and continuous improvement initiatives
  • Act as a strategic advisor to the CEO and Board on operational and financial matters
  • Support governance through reporting, policy development, and risk oversight

2. Finance & Administration

• • Responsible for an organization budget of $12 million
  • Oversees all financial operations, including budgeting, forecasting, reporting, and audits
  • Ensure strong internal controls, compliance with CRA and Ontario nonprofit regulations, and stewardship of funds
  • Monitor organizational financial health and provide insights for decision-making
  • Lead financial planning for seasonal workforce scaling and program expansion
  • Supervise finance staff or external partners (e.g., auditors, accountants)

3. Operations & Facilities

• • Lead day-to-day operations to ensure efficiency, safety, and quality across all sites
  • Oversee facilities management, including maintenance, capital planning, and regulatory compliance
  • Support operational readiness for seasonal ramp-up (staffing, logistics, infrastructure)
  • Implement systems and processes that improve productivity and service delivery
  • Manage vendor relationships and contracts

4. Information Technology & Systems

• • Oversee IT infrastructure, data systems, and cybersecurity practices
  • Ensure technology supports organizational needs, including program delivery and reporting
  • Lead digital transformation initiatives where appropriate
  • Ensure data integrity, privacy compliance, and effective reporting systems

5. Programs & Client Services

• • Provide executive oversight to program and client service delivery teams
  • Ensure programs are effective, equitable, and aligned with mission impact goals
  • Monitor program outcomes, KPIs, and continuous improvement efforts
  • Support development of new programs or expansion opportunities
  • Promote a client-centered, inclusive service culture

6. Risk Management, Compliance & Organizational Resilience

• • Lead the development, implementation, and continuous improvement of the organization’s enterprise risk management framework
  • Identify, assess, and mitigate operational, financial, strategic, reputational, and safety risks across all functions
  • Ensure compliance with applicable federal, provincial, and municipal regulations, as well as funder requirements and accreditation standard
  • Develop and maintain business continuity and emergency response plans, with particular attention to seasonal scaling of operations
  • Partner with program leaders to ensure appropriate risk controls are embedded in client services and program delivery
  • Monitor risk indicators and provide regular reporting to the CEO and Board
  • Foster a culture of risk awareness, accountability, and proactive issue identification across the organization
  • Manage insurance coverage and claims processes in coordination with external advisors

7. People Leadership & Culture

• • In collaboration with the Chief People Officer, lead, mentor, and develop a diverse team of
  • leaders and staff while supporting Human Resources initiatives related to workforce planning, including seasonal staffing requirements.
  • Foster a collaborative, mission-driven organizational culture
  • Promote staff engagement, accountability, and performance excellence

About You

• Bachelor’s degree in business administration, nonprofit management, or related field (Master’s preferred)
• Experience in a charitable organization reliant on fund development and working
• 8–12+ years of senior leadership experience, preferably in the nonprofit or public sector
• Demonstrated experience overseeing finance, information technology, operations, risk management, and program delivery functions.
• Experience in organizations with seasonal workforce scaling or multi-site operations is an asset
• Experience supporting Board and Committee governance processes, including presentations, reporting, and executive-level stakeholder engagement.
• Experience overseeing large-scale seasonal operations, workforce mobilization, or high volume service delivery environments is strongly preferred.
• Strong financial acumen and operational management expertise
• Demonstrated experience in enterprise risk management and compliance
• Strategic thinker with the ability to translate vision into actionable plans
• Excellent leadership, coaching, and team development skills
• Strong understanding of nonprofit governance and the regulatory environment in Ontario
• Effective communicator with strong stakeholder management skills
• Problem-solving and decision-making under complexity and growth conditions
• Demonstrated ability to lead within and complex and evolving environment, balancing strategic priorities and operational demands

Salary Range
$160 ,000 - $180,000 / year How to Apply
Click the “Apply Now” button and follow the instructions to submit your resume. Please know that we only accept documents in MS Word or Rich Text formats.
When referencing this job, quote #482768 This position for employment is for a current vacancy with Vaco/Highspring’s client. You must currently reside within the Greater Toronto Area and be permitted to work in Canada to be considered for this opportunity. A recruiter will be in touch with you if your profile meets our client’s requirements for this role. Determining compensation for this role (and others) at Vaco/Highspring depends upon a wide array of factors including but not limited to the individual’s skill sets, experience and training, licensure and certifications, office location and other geographic considerations, as well as other business and organizational needs. With that said, as required by local law in geographies that require salary range disclosure, Vaco/Highspring notes the salary range for the role is noted in this job posting. The individual may also be eligible for discretionary bonuses, and can participate in medical, dental, and vision benefits as well as the company’s 401(k) retirement plan. Additional disclaimer: Unless otherwise noted in the job description, the position Vaco/Highspring is filing for is occupied. Please note, however, that Vaco/Highspring is regularly asked to provide talent to other organizations. By submitting to this position, you are agreeing to be included in our talent pool for future hiring for similarly qualified positions. Submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. Further assessment of candidates beyond this initial phase within Vaco/Highspring will be otherwise assessed by recruiters and hiring managers. Vaco/Highspring does not have knowledge of the tools used by its clients in making final hiring decisions and cannot opine on their use of AI products.
EEO Notice

Vaco by Highspring is an Equal Opportunity Employer and does not discriminate against any employee or applicant for employment because of race (including but not limited to traits historically associated with race such as hair texture and hair style), color, sex (includes pregnancy or related conditions), religion or creed, national origin, citizenship, age, disability, status as a veteran, union membership, ethnicity, gender, gender identity, gender expression, sexual orientation, marital status, political affiliation, or any other protected characteristics as required by federal, state or local law.

Vaco by Highspring and its parents, affiliates, and subsidiaries are committed to the full inclusion of all qualified individuals. As part of this commitment, Vaco by Highspring and its parents, affiliates, and subsidiaries will ensure that persons with disabilities are provided reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact HR@vaco.com .

Vaco by Highspring also wants all applicants to know their rights that workplace discrimination is illegal .

Representation Notice

By submitting to this position, you agree that you will be giving Vaco by Highspring the exclusive right to present your as a candidate for the foregoing employment opportunity. You further agree that you have represented information about yourself accurately and have not affirmatively misrepresented your qualifications. You also agree to maintain as confidential, to the fullest extent permitted by law, any information you learn from Vaco by Highspring about the position and you will limit disclosure of information about the position only to the extent necessary to perform any obligations in furtherance of your application. In exchange, Vaco by Highspring agrees to exercise reasonable efforts to represent you through all solicitation, job screening and resume dispersal.

For residents of Ontario, Canada: Based on Highspring’s discussions with its Client, Highspring’s understanding is that this position for employment is a current vacancy (either through Highspring as a contractor or with the client directly).

Privacy Notice

Vaco by Highspring and its parents, affiliates, and subsidiaries (“we,” “our,” or “Vaco by Highspring”) respects your privacy and are committed to providing transparent notice of our policies.

• California residents may access Vaco by Highspring HR Notice at Collection for California Applicants and Employees here .
• Virginia residents may access our state specific policies here .
• Residents of all other states may access our policies here .
• Canadian residents may access our policies in English here and in French here .
• Residents of countries governed by GDPR may access our policies here .

Additionally, submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. More details about Vaco by Highspring’s use of AI can be found here (). Further assessment of candidates beyond this initial phase will be conducted by recruiters and hiring managers. Vaco by Highspring does not know and cannot opine on if its client’s use of AI products in hiring.

Pay Transparency Notice

Determining compensation for this role (and others) at Vaco by Highspring depends upon a wide array of factors including but not limited to:

• the individual’s skill sets, experience and training;
• licensure and certification requirements;
• office location and other geographic considerations;
• other business and organizational needs.

With that said, as required by local law, Vaco by Highspring believes that the following salary range referenced above reasonably estimates the base compensation for an individual hired into this position in geographies that require salary range disclosure. The individual may also be eligible for discretionary bonuses.