Director, Sales Performance & Field Enablement

Job 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. 

The Director of Sales Performance & Field Enablement plays a key role in driving sales, growth capabilities and the partner experience across Trupanion North America. This role leads the sales enablement function, developing and executing learning solutions to equip field teams with the necessary tools, training, and resources to succeed in their roles.  This role serves as a critical link between internal training programs delivered by the L&D team and the day-to-day realities of field sales, partner support, and outbound sales. 

This position is open to candidates in the Seattle area. You will have a hybrid remote/in-office schedule where you will work from our casual, pet-friendly office at least 3 days a week. 

Responsibilities:

• You will work closely with the field leadership team, including Territory Partners, Regional Sales Directors, and the VP of Field Sales, to develop sales strategies and solutions that align with Trupanion’s goals, while identifying knowledge gaps and transforming them into targeted development opportunities. 
• Collaborate with cross-functional teams to develop integrated sales that embed  a mindset that every call, interaction, and partner touchpoint is an opportunity to build trust, engagement, and drive growth. 
• Design and deliver programs and solutions focused on advanced sales, growth, and relationship-building strategies. 
• Create engaging scenario-based learning, role-play exercises, and workshops tailored to partner interactions. 
• Host regular office hours and hot-topic sessions to address emerging challenges from the field and support teams. 
• Collaborate with Partner Support teams (inbound and outbound) to refine skills for converting service calls into relationship- and growth-building conversations. 
• Design and iterate sales enablement solutions based on input and feedback from multiple channels (field, support, operations) to ensure effective programming that is reflective of Trupanion’s goals.  
• Reinforce utilization and adoption of sales support tools like the veterinary portal to better enable sales and partner engagement. 
• Champion a culture of sales and growth by equipping support and field-facing teams to recognize hidden opportunities in everyday partner interactions and convert them into growth outcomes through empathy, relationship-building, and strategic action. 
• Leverage existing KPIs, like same-store sales, veterinary portal usage and define new ones to measure the impact of learning and adoption of growth behaviors. 
• Continuously iterate and evolve programming based on performance data and feedback from field partners and operations.  

Qualifications:

• 10+ years in sales enablement, learning and development, or field coaching/training within healthcare, insurance, animal health, or related industries. 
• Proven ability to translate theory into applied, measurable performance. 
• Expertise in sales coaching, adult learning methodologies, and scenario-based training design. 
• Strong background in relationship-driven sales models, preferably in partner/distributor environments. 
• Exceptional facilitation and coaching skills and comfortable working in role-plays, live workshops, and field settings. 
• Strong analytical mindset, with ability to measure program effectiveness against growth outcomes. 
• Bachelor’s degree required; advanced degree or certifications in coaching/sales enablement preferred. 

Skills:

• Growth Coach: Turns service interactions into growth opportunities by teaching advanced sales concepts. 
• Practical Educator: Bridges the gap between formal training and applied real-world success. 
• Field-Attuned: Grounded in the realities of partner and veterinary practice interactions. 
• Relationship Builder: Models trust-building, active listening, and consultative selling. 
• Continuous Improver: Always looking for ways to sharpen skills, refine strategies, and improve outcomes. 

Compensation:

• The pay range for this position is $120,000 -$150,000, 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's 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.