Trupanion is a leading provider of medical insurance for cats and dogs in North America. Our mission is to help loving, responsible pet owners budget and care for their pets. At Trupanion, we offer a collaborative, casual, and pet-friendly environment where everyone is encouraged to be themselves. 

We’re looking for a Canadian lawyer with direct, hands-on experience in the insurance industry.

You’ll bring strong expertise in insurance regulatory law and a solid foundation in corporate and commercial law obtained in a top tier Canadian Law firm. Reporting to our Associate General Counsel, you’ll lead key legal and regulatory compliance initiatives, support corporate governance, and take on a variety of projects tied to our insurance operations. You’re known for delivering thoughtful, risk‑based legal advice that’s both practical and business-friendly. Stakeholders see you as a trusted partner who provides timely, clear guidance and helps the company navigate legal and regulatory complexities. With strong communication skills, sound judgment, and the ability to build strong working relationships, you’ll play a vital role in supporting our Legal & Compliance team.

At Trupanion, we believe in a flexible workplace! We know that talented pet-loving professionals are everywhere. This is a remote position open to candidates anywhere in Canada.

Responsibilities:

• Provide ongoing legal and regulatory analysis and advice as it pertains to the property and casualty insurance operations in Canada
• Ensure compliance with applicable provincial, territorial, and federal insurance laws and regulations, and ensure compliance programs are current and commensurate with the scope and scale of the Canadian operations
• Advise on legal and regulatory risks and potential impacts of business decisions, providing mitigation strategies and appropriate escalation
• Research and draft memoranda on relevant insurance, legal, and regulatory issues
• Provide legal guidance as it pertains to product development, enhancement, and distribution
• Manage subsidiary corporate governance and compliance filings for our Canadian operations across all Canadian provinces (including Quebec)
• Draft and review contracts relating to the insurance-specific operations of the subsidiaries, and review vendor contracts to ensure legal and regulatory risks are mitigated
• Develop legal and compliance training, as needed 
• Help maintain and develop policies, standards, and checklists 
• Review insurance-related marketing, disclosures, and incentives
• Monitor, identify, and interpret new legislation and proactively propose and implement solutions 
• Participate in cross-functional compliance projects
• Provide legal support in the areas of sales, complaint handling, regulatory audits, and licensing 
• Additional projects and duties as assigned

Qualifications:

• This position requires previous experience in the insurance industry
• 4 - 7 years of post-call legal experience, ideally with a background in corporate/commercial, and regulatory compliance for property & casualty insurance
• LLB or JD from an accredited university in Canada and call to the Bar in a Canadian province or territory
• Experience gained at a top-tier law firm 

Skills: 

• Excellent communication and cross-functional collaboration skills
• Ability to exercise sound judgment with a track record of delivering results and pragmatic, risk-based legal advice 
• Leads with integrity and positive intent, actively includes and values diverse perspectives, and collaborates in a way that reflects our Team DNA and supports shared success
• Superb accuracy and attention to detail 
• Exceptional time management and organization skills, with the ability to meet deadlines and manage competing priorities in a fast-paced environment 
• Ability to impact and influence both internal and external stakeholders and provide exceptional customer service 
• Certification in data privacy and/or experience in Canadian privacy law (preferred) 
• Expertise in marketing and advertising laws (preferred) 
• Experience working with commercial, technology, and AI contracts in regulated industries is an asset   
• French Language bilingualism or working language proficiency is an asset