Director of Legal and Compliance

Legal & Regulatory Seattle, Washington Phoenix, Arizona Austin, Texas PORTLAND, Oregon Los Angeles, California Denver, Colorado


Trupanion is a leading provider of medical insurance for cats and dogs in North America. Our mission is to help the pets we all love receive the veterinary care they need. At Trupanion, we offer a collaborative, casual, and pet-friendly environment where everyone is encouraged to be themselves.

Position Summary:

Trupanion is seeking a highly motivated and experienced insurance regulatory specialist to join a fast-paced environment to help grow our Company and the medical insurance for pets category.

In this role, you will be an integral part of the Company’s Regulatory and Compliance Team, and your responsibilities will include managing state regulatory relationships, partnering with our business to develop new products, overseeing governance for our insurance companies, and advising the Company on regulatory issues. Does this sound like you?

Key Responsibilities include:

  • Partnering with U.S. insurance regulators on regulatory matters, including inquiries, market conduct examinations, and financial examinations
  • Further enhancing strong relationships with U.S. regulators
  • Working with our actuarial and finance teams to file new products and file annual financial statements
  • Ensuring compliance with applicable federal and state laws and regulations
  • Licensing individuals and entities
  • Assisting with audits, both internally and of our business partners
  • Partnering with business owners to design and implement initiatives in a fully compliant manner
  • Overseeing governance for U.S.-based insurance companies

What we’re looking for (Please include a cover letter with your application!):

  • Five or more years of regulatory and compliance experience in the insurance industry
  • A law degree and/or an insurance producer’s license, a plus
  • Prior experience engaging with insurance regulators
  • Ability to fit into a fast-paced entrepreneurial environment
  • Ability to demonstrate sound and practical business judgment, sometimes in ambiguous situations
  • Ability to articulate complex insurance regulatory concepts and risk to leaders across the company and our external business partners

You’ll be a good fit if:

  • You're a strategic thinker who can proactively identify, assess, and clearly articulate regulatory risks to assist the business in moving forward thoughtfully and expeditiously
  • You are knowledgeable of and familiar with insurance regulations and privacy laws
  • You have excellent organizational skills and multi-tasking abilities, you consistently follow through and aren't intimidated by short deadlines
  • You have strong written and verbal communication skills
  • You are a standout colleague who can work across the business and with external parties collaboratively and effectively
*Our Corporate HQ is located in Seattle, WA, however, this position is fully remote eligible! 

Benefits and Perks:

  • Bonus opportunities
  • Full medical, dental, and vision benefits at no cost to the employee
  • Four weeks paid time off
  • Five-week sabbatical after five years of employment
  • Restricted Stock Units
  • Open, casual, pet-friendly, and fun office environment
  • Free dog walking services for office pets during business hours
  • Free medical health insurance for your pet (1 dog or cat)
  • Paid time off to volunteer at nonprofit organizations
  • Free on-site gym

About Trupanion:

We’re all about helping pets. We promote a cohesive and nimble team environment, and we hire, develop and promote team members. We trust each other. We are transparent and honest. We care about one another and want to see our team members succeed, personally and professionally. We strive to promote from within and reduce bureaucracy to allow creative thinking. We’re focused on providing continuous training and support to all team members to encourage long-term happiness and success.

Take a look inside our office and see for yourself: 

Trupanion Team DNA:

At Trupanion, we achieve great things together when we are:

  • Caring: We are kind to each other and assume positive intent.
  • Collaborative: We work together to achieve company goals (we not me).
  • Courageous: We are determined, take risks, and make bold moves.
  • Curious: We seek new information to continually better ourselves and our work.
  • Honest: We believe candid communication leads to successful teamwork.
  • Inclusive: We welcome and value all people and perspectives.
  • Nimble: We readily adapt and evolve in pursuit of progress and innovation.

For more information about Trupanion, visit 

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