Company Description 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.

Job Description We’re looking for a Canadian lawyer with direct, hands-on experience in the insurance industry. You’ll bring a solid foundation in corporate and commercial law, along with strong expertise in insurance regulation. 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 multinational 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 authoritative and comprehensive legal services meeting the commercial and strategic needs of the business
• Advise on legal and regulatory risks and mitigation strategies, and supporting good governance through appropriate discussion and escalation of issues
• Manage the subsidiary corporate governance and compliance for our Canadian operations across all Canadian provinces (including Quebec)
• Draft and review contracts relating to the insurance-specific operations of the subsidiaries
• Assist with evolving regulatory compliance matters in the Canadian legal environment; conduct research across the subsidiary operating jurisdictions
• Develop legal and compliance training, as needed
• Help maintain and develop policies, standards, and checklists
• Identify and analyze new legislation and proactively propose and implement solutions
• Ensure compliance with applicable provincial, territorial, and federal insurance laws and regulations
• Support internal stakeholders with clear, practical legal advice tailored to business needs
• Participate in vendor management, including reviewing terms and ensuring legal and regulatory risks are mitigated
• Participate in cross-functional compliance projects
• Provide regulatory and compliance support and advisement in the areas of sales, complaint handling, and licensing
• Additional projects and duties as assigned

Qualifications

• This position requires previous experience in the insurance industry
• 3 - 6 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

Skills

• Excellent leadership, communication, and cross-functional collaboration skills
• An LLB or JD from an accredited university and licensed to practice in your governing jurisdiction
• Experience gained at a top-tier law firm
• Track record of delivering results and pragmatic, risk-based legal advice
• 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 (preferred)
• Experience working with commercial and technology contracts; U.S. contracts or ability to flex into cross-border work is a plus (preferred)
• Expertise in marketing and advertising laws (preferred)
• French Language bilingualism or working language proficiency an asset

Compensation

• Competitive salary, commensurate with experience, on a full-time schedule.
• Along with base salary, Trupanion employees may be eligible for monthly bonuses.
• We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years.