Regional Sales Director - Vet Channel (Great Lakes)

TrupanionChicago, IL
$105,000 - $135,000Remote

About The Position

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.

Requirements

  • 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.
  • 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.

Nice To Haves

  • 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.

Responsibilities

  • 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.

Benefits

  • Full medical, dental, and vision benefits at no cost to the employee
  • Four weeks of paid time off and 9 paid float holidays
  • Five-week sabbatical after five years of employment
  • Free medical health insurance for your pet (1 dog or cat)
  • Paid time off to volunteer at nonprofit organizations
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