Chapter Director Jobs in Saskatchewan (NOW HIRING)

About the Organization

Summit Search Group has been retained by the Canadian Lawyers Insurance Association (CLIA) on the recruitment of a Chief Executive Officer. Founded in 1988 as a direct response to an unstable professional liability insurance market, CLIA is a not-for-profit reciprocal insurance exchange established by and for Canada’s provincial and territorial law societies. As a reciprocal exchange, CLIA operates on a fundamentally different model than a traditional insurer: surplus revenue generated beyond claims and operating costs accumulates in individual subscriber equity accounts rather than flowing to shareholders. An annual operating budget is created and approved by the Board of Directors for administrative expenses, new program development and loss prevention initiatives. This is the “reciprocal advantage,” and it is central to CLIA’s value proposition.

CLIA’s subscribers are the law societies of nine provinces and territories across Canada, with the lawyers regulated by those societies representing the actual insured individuals. CLIA issues a master policy to each member society, sets standard limits and policy terms, and administers claims exceeding individual society deductibles. The product suite includes a core mandatory professional liability program, a voluntary excess program offering coverage up to $35M above the mandatory limit, a cyber insurance program, and a compensation fund. CLIA also provides claims management services to subscribers and maintains a dedicated loss prevention function.

Headquartered in Regina, Saskatchewan, CLIA operates with a small, highly capable team and an annual operating budget of approximately $3 million.

The Opportunity

Due to retirement CLIA is seeking a Chief Executive Officer to lead the organization through its next chapter of strategic growth. This is a rare appointment: a chance to become only the second CEO in CLIA’s modern history, stepping into an organization that is well-capitalized, well-governed, and well-staffed, with a clear strategic plan in place and ready to execute. Reporting to the Board of Directors, the CEO will serve as the primary relationship holder with CLIA’s subscriber law societies, the face of the organization in reinsurance markets, and the operational steward of a mandate that spans claims oversight, financial management, and loss prevention strategy. The role demands a leader who is comfortable navigating a regulated and governance-driven environment, skilled at building trust with sophisticated stakeholders, and ready to drive an ambitious and well-defined strategic agenda.

In practice, this means overseeing a small, high-performing team while carrying personal accountability for the relationships and decisions that matter most. The CEO will work with CLIA’s broker to negotiate reinsurance renewals directly, including engagement with international markets, and will serve as the primary point of contact for the provincial and territorial law societies whose members CLIA exists to protect.

On the operational side, the CEO will lead priorities that include strengthening claims management capabilities, building financial surplus within a growing cyber insurance program, and expanding voluntary excess participation. Loss prevention is a particular focus, and the evolving implications of AI adoption and cybersecurity across the legal profession add both urgency and depth to that work. Strategically, the CEO will work to grow the subscriber base, deepen existing relationships, and position CLIA for continued relevance in a profession that is changing quickly. This is a role with real external visibility, meaningful internal leadership responsibility, and a strategic agenda that rewards both operational discipline and forward thinking.

Key Responsibilities

• Lead all aspects of CLIA’s operations, including claims management, loss prevention, financial stewardship, and insurance program administration, ensuring a high standard of performance across a lean, high-trust team.
• Build and maintain trusted, long-term relationships with subscriber law societies and their leadership, serving as CLIA’s primary point of contact and a credible voice for the organization’s mandate and value.
• Negotiate reinsurance renewals and support new program development in partnership with reinsurers and brokers, including participation in international market negotiations.
• Report to and work closely with the Board of Directors, providing transparent reporting, strategic recommendations, and operational updates that support sound governance and well-informed decision-making.
• Drive execution of the 2026–2028 strategic plan across all pillars, including financial performance, subscriber growth, voluntary excess expansion, claims system implementation, and loss prevention innovation.
• Lead, develop, and retain a small, cohesive team, carrying forward the high-trust culture of the organization while establishing a confident and independent leadership identity.

Qualifications

• A background in insurance, , law, or financial services, or a demonstrated ability to quickly build credibility and fluency within a specialized, regulated industry context; the board is open to multiple professional pathways.
• Proven relationship-building skills, with a track record of earning trust with sophisticated, governance-minded stakeholders such as boards, regulatory bodies, member organizations, or professional associations.
• Leadership experience at or near the executive level, with the ability to lead and retain a small, high-performing team in a culture-sensitive environment; strong candidates ready to step up from a senior leadership role will be considered.
• Demonstrated comfort operating in a board-governed, accountability-driven environment, including experience reporting to or collaborating with a board of directors.
• Experience in association management, reciprocal insurance, or regulated professional body environments is considered a strong asset, as is familiarity with reinsurance markets, claims oversight, or the legal services sector.

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.