Corporate Counsel - Canada

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Toronto, ON, CAN
In-Office
Healthtech • Insurance • Pet
Trupanion provides medical insurance for cats and dogs across North America and has helped innovate their industry.
The Role
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 are seeking a talented Canadian lawyer with an interest in advancing their career in the financial services industry, or who already has a strong foundation in corporate and commercial law, as well as insurance regulatory law. Reporting to our Associate General Counsel, you will be responsible for legal and regulatory compliance initiatives, corporate governance, and ad-hoc projects related to the company’s insurance operations. You have a knack for providing insightful, thorough, focused, and risk-based legal guidance. Your stakeholders rely on you as a trusted advisor to provide timely, pragmatic, business-oriented solutions while effectively managing legal and regulatory risk. With a focus on delivering exceptional results, your strong relationship-building skills, articulate communication, and solid business acumen will support and complement 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 proposing and implementing 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 to the in the areas of sales, complaint handling, and licensing  
  • Additional projects and duties as assigned 

Qualifications: 

  • 3 - 6 years of post-call legal experience, ideally with 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 license 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.  

Additional Information

Benefits and Perks:

  • Employer-paid extended health coverage for you and your family
  • Trupanion will partner with Wealthsimple to register your RRSP, pension, etc.
  • Four weeks of paid time off 
  • Five weeks, paid, sabbatical after five years of employment
  • Employer-paid medical insurance for one pet (cat or dog)
  • Paid time off to volunteer at nonprofit organizations
  • Open, casual, pet-friendly, and fun work environment

For more information about Trupanion, visit https://trupanion.com/about

Learn more about how Trupanion has revolutionized our industry and the reimbursement model: https://www.youtube.com/watch?v=vdWZ4KHiPTQ

Trupanion is an equal opportunity employer and embraces diversity. We are committed to building a team that represents a variety of backgrounds, abilities, perspectives, and skills.

We will ensure that individuals are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodation.

Trupanion Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Trupanion and has not been reviewed or approved by Trupanion.

  • Leave & Time Off Breadth Time off is seen as generous, with PTO, sabbatical opportunities, flexible time for sick/safe/wellness needs, and paid volunteer days highlighted. These elements support recovery time and work–life balance.
  • Healthcare Strength Health coverage breadth is emphasized, including medical, dental, vision, mental health, transgender healthcare, life insurance, and disability support. Employer-paid employee premiums on core medical plans further strengthen perceived coverage value.
  • Wellbeing & Lifestyle Benefits Pet-related and lifestyle perks stand out, including company-paid insurance for one pet and a pet‑friendly workplace, alongside a lifestyle spending account. Commuter support, snacks, and home‑office stipends further round out everyday benefits.

Trupanion Insights

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The Company
HQ: Seattle, WA
1,053 Employees
Year Founded: 1999

What We Do

Trupanion is a rapidly growing player in the pet medical insurance space. We are known for superior coverage and top-notch customer service. We pride ourselves on swift claims resolutions and providing the best medical insurance care available.

Why Work With Us

We are all driven by the mission to help pets receive the best medical care. We are always learning and trying new things as a company and it is a great place to build your career.

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