About The Position

The Underwriter – Sports & Leisure assesses, evaluates, and underwrites specialty insurance risks in the sports, leisure, and entertainment markets. Working with brokers and internal stakeholders, the underwriter balances sound underwriting judgment with responsive service to provide tailored insurance solutions and support profitable portfolio growth. The position is remote and full-time in Canada. The role covers new business submissions, renewals, and endorsements, applying underwriting guidelines, pricing principles, and risk judgment to set appropriate coverage, terms, and conditions. It involves identifying exposures and deciding when further information, risk controls, or referrals are needed; building knowledge of specialty-sector risks and market developments; and proactively managing portfolio performance and renewals. The underwriter builds and maintains broker relationships, responds to inquiries and submissions, and supports new business and portfolio growth. The role also includes maintaining accurate records, complying with internal procedures and applicable regulatory requirements, collaborating on complex underwriting questions, and contributing to improvements in underwriting practices, product knowledge, and processes.

Requirements

  • Minimum 3–5 years of underwriting experience, including direct experience underwriting risks in 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 sector-specific liability exposures, including participant injury, host liquor liability, accident coverage, directors and officers liability, and abuse coverage.
  • 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, including the ability to explain technical insurance concepts clearly and professionally.
  • Strong analytical and critical-thinking skills, sound judgment, and attention to detail.
  • Excellent relationship-building and communication skills, particularly when working with insurance brokers and industry partners.
  • Proactive, solutions-oriented mindset and ability to balance responsive service with disciplined underwriting practices.
  • Strong organizational skills and ability to manage competing priorities in a remote work environment.
  • Collaborative approach, adaptability, and interest in developing expertise in a specialized area of insurance.

Nice To Haves

  • Relevant insurance education or professional designations, such as CIP or FCIP, are considered an asset.
  • Interest in developing specialized knowledge of niche insurance products and emerging risk exposures.

Responsibilities

  • 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 specialty risks.
  • Identify potential exposures, assess risk quality, and determine when additional information, risk controls, or referrals are required.
  • Underwrite risks associated with sports, recreation, leisure activities, and entertainment-related operations, tailoring coverage to individual needs.
  • Stay informed about emerging risks, market developments, and industry trends that may affect underwriting decisions and portfolio performance.
  • Build and maintain productive relationships with insurance brokers and serve as an underwriting resource.
  • Respond to submissions and inquiries in a timely manner, providing guidance on appetite, coverage options, pricing, and underwriting requirements.
  • Identify opportunities to strengthen broker partnerships, generate new business, and grow the specialty portfolio.
  • Monitor portfolio performance and risk quality, and make underwriting decisions that support long-term profitability.
  • Manage renewals proactively, identifying exposure changes and opportunities to improve coverage structures or underwriting outcomes.
  • Maintain accurate underwriting records and documentation, and comply with internal procedures and applicable regulatory requirements.
  • Collaborate with colleagues and stakeholders to resolve complex underwriting questions and deliver effective solutions.
  • Contribute to refining underwriting practices, product knowledge, and processes as the specialty market evolves.
  • Support a customer-focused, solutions-oriented culture that balances broker service with disciplined risk management.
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