Chief Operating Officer

Lead Operations and IT to effectively and efficiently support Sustainable Growth.

Are you a dynamic, visionary leader ready to play a pivotal role in shaping the future of a growing organization? We are seeking an accomplished and strategic Chief Operating Officer to join our executive leadership team. In this role, you will be integral in driving operational excellence, profitability, and organizational effectiveness across all departments.

About the Role

As the COO you will oversee and direct Information Technology, Risk Management, Real Estate and Facilities Management, HR Policies for the Group of Companies, and the overall operational effectiveness of our organization. You will work closely with the CEO, the Board and subsidiary company Presidents to set strategic direction, optimize business processes, and implement best-in-class practices to ensure we exceed our performance goals.

Key Responsibilities

Strategic Leadership

• Partner with the CEO and executive team to define short- and long-term goals for the organization.
• Support strategic initiatives, mergers & acquisitions, and market expansion as required.
• Serve as a trusted advisor to the Board, providing financial, operational, and risk insights to inform decision-making.

Operational Oversight

• Drive overall operational effectiveness by designing, implementing, and refining business processes to support growth and efficiency.
• Monitor and report on key performance indicators (KPIs) to ensure alignment with strategic objectives.
• Collaborate across departments to facilitate smooth operations, resolve bottlenecks, and enhance cross-functional communication.
• Responsible for real‑estate, lease agreements and facilities management

Information Technology (IT)

• Oversee the IT department, ensuring that technology initiatives align with organizational goals and support business operations.
• Oversee information security through appropriate policies and procedures, including appropriate access controls and monitoring where appropriate.
• Lead digital transformation and innovation projects, including deployment of AI.
• Ensure cybersecurity best practices and compliance with data privacy regulations.

Risk Management

• Identify, assess, and mitigate key organizational risks, including operational, financial, technological, and regulatory risks.
• Create and maintain a robust risk management framework and disaster recovery plans.
• Ensure compliance with all applicable laws and regulations, and other statutory requirements relevant to our industry.
• Manage the Property & Casualty Insurance Program for the Group of Companies

Human Resources (HR) Policies

• Lead the development, implementation, and continuous improvement of HR policies and practices aligned with our strategic priorities.
• Work closely with the HR team on talent planning, recruitment, retention, compensation, and performance management initiatives.
• Foster a culture of engagement, inclusion, and high performance.
• Oversee the Group Benefit Plan design and procurement for the Group of Companies.

Qualifications and Experience

• Bachelor’s degree in Finance, Business Administration, or related field is required.
• Previous experience in insurance is preferred
• Minimum 15 years of progressive leadership experience in senior financial and operational roles, with prior experience at the executive level.
• Proven experience managing cross-functional teams, including finance, IT, HR (regarding strategy and policies), and operations.
• Demonstrated experience with digital transformation, ERP systems, and leveraging technology for business improvement.
• Exceptional problem-solving, analytical, and strategic thinking abilities.
• Excellent communication, negotiation, and interpersonal skills.
• Adept at change management and driving organizational improvements in fast‑paced environments.
• Demonstrated ability to develop and maintain relationships with key stakeholders, including the Board, regulators, auditors, and external partners.

Key Competencies

• Values Alignment: Aligned with the Cowan Values of Integrity, Collaboration, Accountability, Respect and Client‑Focus.
• Leadership: Visionary, collaborative, and able to inspire and align diverse teams toward common goals. Development of leaders.
• Integrity: Unwavering commitment to ethical standards, transparency, and fiduciary responsibility.
• Results Orientation: High level of initiative and drive to achieve or exceed goals.
• Change Management: Skilled in leading organizations through transformation and continuous improvement.
• Communication: Articulate, persuasive, and comfortable presenting to boards, investors, and large groups.
• Analytical Acumen: Strong ability to analyze complex data, uncover insights, and make informed decisions quickly.

Who we are

Proudly independent and Canadian‑owned, Cowan Insurance Group has been a true market leader in the insurance industry since 1927. With an extensive range of product offerings and integrated commercial and personal insurance, group benefits, and wealth management solutions, we provide our clients with outstanding customized, comprehensive insurance and risk management professional advice and placement.

Recognized as one of Canada's Most Admired Cultures and a Canada’s Best Managed Companies Platinum Club Member, Cowan Insurance Group’s award‑winning client‑centric approach emphasizes innovation, excellence, and collaboration. Join our team as we prepare for our centennial celebration in 2027!

What sets us apart?

Be in good company

Integrity matters. It drives our award‑winning workplace culture and fuels our collective desire to help our clients, employees, and communities thrive.

Challenge your thinking

You are valued for your passion, drive and creativity. The pace is fast but the work is meaningful, interesting, and complex, just the way you like it.

Grow together

We believe in your potential. If you’re looking to develop your expertise with learning opportunities and mentoring, we’ll make that happen.

Benefits and perks

• Competitive salary
• Participate in our comprehensive benefits plan on day one — no waiting period
• Company‑matched Retirement Savings Plan
• Company‑paid training and development courses
• Community involvement

Are you interested?

Please Apply!

This is a new position.

This position is subject to appropriate background checks that may include credential, employment, credit, criminal and reference checks.

Artificial Intelligence (AI)

Cowan Insurance Group does not use AI directly; however, platforms we partner with may use AI, including screening for keywords and minimum qualifications. Our human recruiters review candidate’s qualifications prior to decisions being made.

While we appreciate the interest of all applicants, we will contact only those selected for interviews. If you are an applicant with disabilities and require accommodations, please let us know at the time of our contact so that we may arrange for their provision.

We are an Equal Opportunity Employer. Candidates will be selected strictly on the basis of an individual’s technical qualifications, knowledge and experience, as they relate to the requirements of a particular position. Selections will be made without regard to: age, ancestry, colour, race, citizenship, ethnic origin, place of origin, creed, disability, family status, marital status, gender identity, gender expression, record of offences, sex, or sexual orientation.

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