Company Description

Trupanion is a leader in medical insurance for cats and dogs, on a mission to help loving, responsible pet owners’ budget and care for their pets. We’re transforming the pet healthcare experience by working closely with veterinary practices to deliver value, transparency, and peace of mind.

At Trupanion, we’re more than insurance—we’re a mission-driven tech company focused on helping pets live longer, healthier lives. We foster a collaborative, inclusive, and nimble environment where team members are empowered to think creatively, grow professionally, and make an impact.

Learn more about how Trupanion pays veterinarians directly here: Watch on YouTube

Job Description

We’re seeking a strategic and results-driven sales leader to join us as Regional Sales Director – Vet Channel (Great Lakes Region). In this key role, you’ll lead the performance and growth of business-to-business partnerships across a multi-territory region, with a focus on increasing veterinary hospital engagement, same-store sales, and high-quality lead generation.

Reporting to the VP of Veterinary Growth, you’ll collaborate closely with our Territory Partners (independent business consultants) and cross-functional teams to exceed ambitious growth targets in a rapidly scaling and ever-evolving market.

This is a high-impact role ideal for a leader who thrives in a fast-paced, field-based role and is energized by coaching, influencing without authority, and building lasting business relationships.

Location: Great Lakes Region near major airport (eg. ORD, MDW, IND, DTW, MSP)

Travel Requirement: 70% (approx. 15 days/month)

What You’ll Do:

• Lead the execution of field strategy to drive revenue and partnership expansion within the assigned region.
• Partner with Territory Partners to coach, support, and influence hospital staff and leadership to drive enrollment performance.
• Build and maintain strong relationships across veterinary hospitals and internal teams.
• Conduct frequent in-field visits (60–70% travel) to develop, coach, and evaluate regional opportunities.
• Monitor performance data to identify trends, adjust strategies, and optimize sales effectiveness.
• Lead strategic planning for territory goals and partnerships to maximize regional performance.
• Track success through key metrics including hospital engagement, same-store sales, partner experience, and claims efficiency.
• Collaborate with marketing, operations, and training teams to launch effective campaigns and tools.
• Serve as the primary point of contact for Territory Partners, ensuring clear communication, timely information sharing, and actionable feedback.

Who You Are:

• Strategic Leader: You set goals, manage performance, and inspire others to achieve results.
• Data-Driven: Comfortable interpreting dashboards to identify trends and shape sales strategies.
• Influential Coach: Adept at mentoring others without direct authority and driven by shared success.
• Relationship-Oriented: Builds trust quickly and sustains long-term, value-based partnerships.
• High-Energy Executor: Thrives in a fast-moving, field-based role with regular travel and autonomy.

What You Bring:

• 5+ years in sales leadership, managing distributed teams or multi-region operations.
• 5+ years of experience building B2B partnerships (veterinary industry preferred).
• Proven track record of achieving or exceeding territory sales goals.
• Familiarity with CRM systems (e.g., Dynamics), route planning tools (e.g., Portatour), and analytics platforms (e.g., Tableau).
• Strong coaching and performance management experience.
• Able to travel 70% across your assigned region.

Preferred Qualifications:

• Experience working with — or operating as, a small business owner or veterinary industry partner.
• Familiarity with pet insurance or the veterinary ecosystem.
• Passion for pets and alignment with Trupanion’s vision, mission and values.

Compensation:

The pay range for this position is $105,000 - $135,000, 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:

• Full medical, dental, and vision benefits at no cost to the employee
• Four weeks of paid time off and 9 paid float holidays (you can decide which days are most important to you!)
• Five-week sabbatical after five years of employment
• Open, casual, pet-friendly, and fun office environment
• Free medical health insurance for your pet (1 dog or cat)
• Paid time off to volunteer at nonprofit organizations
• Seattle Office Amenities: Free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards.

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 accommodations. Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.