Underwriter - Sports & Leisure (Remote Canada)

Insurance Underwriter – Sports & Leisure

Type: Remote | Full-Time

About Our Client

Our client is a well-established Canadian specialty insurance organization with a strong reputation for delivering tailored insurance solutions for unique and complex risks. With deep expertise in specialty underwriting and a commitment to serving niche markets, the organization partners with insurance brokers to provide flexible, practical coverage for businesses and organizations that require more than traditional insurance solutions.

Operating in a dynamic and evolving segment of the insurance industry, the company is known for its specialized knowledge, relationship-driven approach, and dedication to finding solutions for hard-to-place risks. Its focus on niche industries allows its team to develop meaningful expertise, build lasting broker partnerships, and make a tangible impact on the success of its clients.

This is an exciting opportunity for an insurance professional to join a specialized underwriting team focused on the sports, leisure, and entertainment sector. You'll have the opportunity to work with a diverse range of risks, apply your technical expertise, strengthen broker relationships, and contribute to a growing specialty portfolio — all within a remote work environment that offers the opportunity to build your career in a distinctive area of the insurance market.

Key Responsibilities

As the Underwriter – Sports & Leisure , you will be responsible for assessing, evaluating, and underwriting specialty insurance risks within the sports, leisure, and entertainment markets. Working closely with brokers and internal stakeholders, you will balance sound underwriting judgment with responsive service to deliver tailored insurance solutions while supporting profitable portfolio growth.

Your responsibilities will include:

• Risk Assessment & Underwriting:

  • Review, analyze, and evaluate new business submissions, renewals, and endorsements to determine risk acceptability, coverage requirements, and appropriate terms and conditions.

  • Apply underwriting guidelines, pricing principles, and sound judgment to develop competitive, sustainable insurance solutions for a variety of specialty risks.

  • Identify potential exposures, assess risk quality, and determine when additional information, risk controls, or referrals are required.

• Sports & Leisure Specialty Expertise:

  • Underwrite a diverse range of risks associated with sports, recreation, leisure activities, and entertainment-related operations.

  • Develop a strong understanding of the unique exposures associated with specialty businesses and organizations, tailoring coverage solutions to their individual needs.

  • Stay informed about emerging risks, market developments, and industry trends that may influence underwriting decisions and portfolio performance.

• Broker Relationships & Business Development:

  • Build and maintain productive relationships with insurance brokers, serving as a knowledgeable and approachable underwriting resource.

  • Respond to submissions and inquiries in a timely manner, providing clear guidance on appetite, coverage options, pricing, and underwriting requirements.

  • Identify opportunities to strengthen existing broker partnerships, generate new business, and support the continued growth of the specialty portfolio.

• Portfolio Management & Profitability:

  • Monitor portfolio performance, evaluate risk quality, and make informed underwriting decisions that support long-term profitability.

  • Manage renewals proactively, identifying changes in exposure and opportunities to improve coverage structures or underwriting outcomes.

  • Maintain accurate underwriting records and documentation, ensuring compliance with internal procedures and applicable regulatory requirements.

• Collaboration & Continuous Improvement:

  • Work collaboratively with colleagues and other stakeholders to resolve complex underwriting questions and deliver effective solutions.

  • Contribute to the refinement of underwriting practices, product knowledge, and processes as the specialty market evolves.

  • Support a customer-focused, solutions-oriented culture that balances strong broker service with disciplined risk management.

Qualifications

To succeed in this role, candidates should demonstrate the following:

• Education & Experience:

  • Minimum 3-5 years of experience in underwriting, with direct experience underwriting risks within the Sports, Leisure & Entertainment sector.

  • Demonstrated experience assessing specialty risks and developing appropriate coverage terms, conditions, and pricing for sports, recreation, leisure, or entertainment-related businesses and organizations.

  • Strong understanding of the unique liability exposures associated with this sector, including participant injury, host liquor liability, accident coverage, directors and officers liability, and abuse coverage.

  • Relevant insurance education or professional designations, such as CIP or FCIP, are considered an asset.

• Technical Skills:

  • Ability to analyze insurance submissions, assess exposures, interpret policy wording, and make sound risk-based decisions.

  • Familiarity with underwriting guidelines, rating methodologies, and insurance policy administration systems.

  • Strong written communication and documentation skills, with the ability to explain technical insurance concepts clearly and professionally.

  • An interest in developing specialized knowledge of niche insurance products and emerging risk exposures.

• Key Competencies:

  • Strong analytical and critical-thinking skills, with sound judgment and attention to detail.

  • Excellent relationship-building and communication skills, particularly when working with insurance brokers and other industry partners.

  • A proactive, solutions-oriented mindset and the ability to balance responsive service with disciplined underwriting practices.

  • Strong organizational skills and the ability to manage competing priorities in a remote work environment.

  • A collaborative approach, adaptability, and a genuine interest in building expertise within a specialized area of insurance.

About Us

Executrade is one of Western Canada’s most comprehensive full-service recruitment firms, with over 50 years of expertise in connecting talented professionals with leading organizations.

We are proud to apply principles of diversity, equity, and inclusion in all our recruitment practices, ensuring equal opportunities for all candidates. Our commitment to these values enables us to match organizations with a diverse range of top talent, fostering workplace cultures that thrive on innovation, collaboration, and respect.

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