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Insurance Leadership Jobs in Ontario (NOW HIRING)

Anna Raeli Insurance Agency

Insurance Agent

King City, ON · On-site

CA$45K - CA$70K/yr

I have been a Desjardins insurance agent since 1998. I previously worked for two agents prior to ... Responsibilities Develop leads, schedule appointments, identify customer needs, and market ...

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Insurance Leadership information

What is insurance leadership?

Insurance leadership refers to the roles and responsibilities of individuals who guide and manage insurance organizations or teams. Leaders in this field set strategic direction, oversee operations, ensure compliance with regulations, and drive growth and innovation within the company. They often focus on developing talent, improving customer experience, and adapting to industry changes such as new technologies and evolving risk landscapes. Effective insurance leaders require strong communication, analytical, and decision-making skills to succeed in a dynamic and highly regulated industry.

What are the key skills and qualifications needed to thrive in insurance leadership?

To thrive in Insurance Leadership, you need deep knowledge of insurance products, market trends, and regulatory requirements, typically supported by a degree in business, finance, or a related field and significant industry experience. Familiarity with insurance management platforms, data analytics tools, and relevant certifications such as CPCU or CLU is often expected. Strong strategic thinking, communication, and team management skills distinguish top performers in this role. These capabilities are essential for driving organizational growth, ensuring compliance, and effectively leading teams in a competitive and regulated industry.

What are some common challenges faced by professionals in insurance leadership roles, and how can they be addressed?

Insurance leaders often encounter challenges such as adapting to evolving regulations, managing a diverse workforce, and driving digital transformation within their organizations. Successfully addressing these challenges requires strong change management skills, continuous professional development, and fostering open communication across teams. Leaders who prioritize innovation, invest in staff training, and maintain a customer-centric approach are better equipped to navigate industry shifts and guide their organizations toward sustained growth.

What is the difference between Insurance Leadership vs Insurance Underwriter?

AspectInsurance LeadershipInsurance Underwriter
Required CredentialsTypically requires leadership experience, industry certifications, and sometimes advanced degreesRequires industry certifications like CPCU or AIC, and a relevant bachelor’s degree
Work EnvironmentStrategic, managerial, and cross-departmental focus in corporate settingsAnalytical, detail-oriented work primarily in underwriting departments
Employer & Industry UsageUsed in insurance companies, agencies, and brokerages for leadership rolesCommonly employed in insurance companies, focusing on risk assessment and policy pricing

Insurance Leadership roles focus on strategic decision-making, team management, and overall company direction, often requiring extensive industry experience. Insurance Underwriters concentrate on evaluating risks, setting premiums, and approving policies, with a strong emphasis on analytical skills. While both roles are vital in the insurance industry, they serve different functions and require distinct skill sets.

What are popular job titles related to Insurance Leadership jobs in Ontario?

For Insurance Leadership jobs in Ontario, the most frequently searched job titles are:

What job categories do people searching Insurance Leadership jobs in Ontario look for?

The top searched job categories for Insurance Leadership jobs in Ontario are:

What cities in Ontario are hiring for Insurance Leadership jobs?

Cities in Ontario with the most Insurance Leadership job openings:

Insurance Leadership jobs near you
Infographic showing various Insurance Leadership job openings in Ontario as of August 2026, with employment types broken down into 84% Full Time, 13% Part Time, and 3% Contract. Highlights an 90% In-person, 7% Hybrid, and 3% Remote job distribution.

Senior Director - Insurance Advisory

Insurance Talent Group

Toronto, ON • Hybrid

$145K - $148K/yr

Full-time

Retirement

Posted 4 days ago

Job description

Senior Director, Advisory Services
Hybrid | Toronto, ON
Overview
We are working with one of Canada's most established and respected member-based organizations — a true leader of leaders within the non-profit and professional association space.
This organization operates at the intersection of advocacy, member services, insurance, financial planning, and strategic leadership, supporting a highly sophisticated professional membership base with complex financial and insurance needs.
This is not a traditional corporate insurance leadership role. Success here requires someone who understands how to operate within a board-led, member-driven organization, where leadership means balancing commercial growth, stakeholder management, governance, and member trust.
The ideal candidate will bring a strong blend of private sector performance and public/non-profit leadership experience, with the ability to navigate both strategic growth and organizational complexity.
The Role
The Senior Director, Advisory Services will lead the strategy, growth, and operational execution of the advisory and insurance services division across Ontario and Atlantic Canada.
This role is responsible for driving sales performance, business development, member engagement, advisor leadership, and strategic partnerships while ensuring strong governance, compliance, and a differentiated member experience.
The focus is on building scalable growth while maintaining the credibility and trust expected within a professional association environment.
Key Responsibilities Sales Strategy & Business Development
  • Develop and execute annual sales strategies, business plans, and revenue targets across advisory services
  • Analyze sales performance, premium trends, revenue growth, and advisor productivity using data and reporting insights
  • Lead business development initiatives across insurance, retirement, investment, and pension solutions
  • Drive member engagement strategies to improve product penetration and long-term retention
  • Identify and build new internal and external partnerships that support strategic growth

Leadership & Advisory Oversight
  • Lead, coach, and develop advisory leadership teams and advisors across multiple product lines
  • Provide in-field sales support, mentorship, and strategic guidance
  • Oversee hiring, performance management, coaching, and advisor development
  • Build training frameworks around advanced insurance planning, retirement strategies, and financial advisory best practices
  • Support advisor contracting, licensing, compliance, and continuing education requirements
Operations, Governance & Compliance
  • Oversee advisory operations, compliance standards, reporting accuracy, and process consistency
  • Manage KPIs, advisor NPS, and operational efficiency improvements
  • Ensure adherence to regulatory requirements, licensing obligations, and internal governance expectations
  • Work closely with senior leadership, internal stakeholders, and board-facing teams to support strategic decision-making
  • Manage escalations, member concerns, and opportunities for service improvement

What We're Looking For
  • University degree in Business, Commerce, Marketing, or related field
  • Strong executive-level experience in:
    • Insurance
    • Investments
    • Retirement Planning
    • Pension Strategy
    • Financial Planning
    • Estate and Insurance Planning
  • Deep understanding of advisory sales, insurance operations, and member/client strategy
  • Experience leading within a board-run, governance-heavy organization
  • Strong people leadership and executive communication skills
  • Ability to operate effectively across both strategic planning and day-to-day operational leadership

Licensing & Designations
  • Active LLQP required
  • CFP and/or CLU strongly preferred
  • Strong understanding of incorporated professionals and advanced planning strategies is highly valued

Ideal Background
This role is particularly well suited for someone with a blend of:
  • Private sector insurance / financial leadership
  • Public sector or non-profit executive experience
  • Professional association leadership
  • Board-facing stakeholder management experience
Someone who understands both commercial accountability and governance-driven leadership will be strongest here.
Compensation & Structure
  • Salary range: $145000 - $148,000+
  • Bonus program
  • Pension plan
  • Comprehensive benefits package
  • Hybrid work environment (Toronto office presence required)
  • Strong executive visibility and long-term leadership opportunity

Fit
This role is ideal for someone who wants to lead inside an organization where trust, governance, and strategic influence matter as much as revenue growth.
This is a high-visibility leadership role for someone who understands how to drive results inside a sophisticated, board-led environment.