Director – North American Sales Performance and Field Enablement

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 and Field Enablement is responsible for transforming how our teams sell, grow, and engage with partners across the North American Markets. This role bridges the gap between formal training and applied field execution, ensuring that field sales and outbound engagement teams are equipped to have the knowledge, skills, tools, and support needed to perform effectively and deliver measurable results. 

This position translates learning into sales performance, field empowerment, and measurable growth. The Director serves as a strategic partner, facilitator, and performance consultant who identifies opportunities, prioritizes initiatives, and drives solutions from concept through delivery and evaluation. This role is responsible for assessing field needs, designing and developing learning experiences and enablement resources, delivering programs, and measuring impact to ensure meaningful behavior change and business results. 

This role reports to the Senior Director, North American Partner Continuing Education Programs to ensure ongoing alignment between overarching curriculum design, field enablement, and sales performance initiatives and opportunities. 

This is a remote position open to candidates across the United States or Canada. If you're based in the Greater Seattle Area, you will have a hybrid remote/in-office schedule that requires you to work from our casual, pet-friendly office 3 days a week. 

Key Responsibilities 

Field Sales Enablement & Coaching 

• Design, develop, and deliver applied learning experiences — including scenario-based workshops, live coaching, role-plays, and reinforcement strategies — focused on real partner interactions. 
• Host office hours, peer forums, and skill-building sessions addressing current challenges in veterinary, breeder, and shelter engagement. 
• Partner with  North American sales leaders, including Regional Sales Directors, as well as Territory Partners to identify needs, prioritize development opportunities and strengthen same-store and new-store growth.  
• Proactively recognize trends, skill gaps, and emerging opportunities through field observation, stakeholder feedback, and performance data, translating those insights into targeted learning and enablement solutions.  

Partnership with Continuing Education Programs 

• Collaborate with the Senior Director, North American Partner Continuing Education Programs to identify learning priorities and align development initiatives with organizational goals. 
• Lead the design, development, implementation, and continuous improvement of field development programs including monthly webinars, regional training experiences, sales enablement resources, sales effectiveness programs, and onboarding. 
• Translate business needs and educational objectives into practical tools, experiences, and resources that drive measurable field performance improvements. 

Sales & Growth Optimization 

• Instill a Sales, Sales, Sales / Grow, Grow, Grow culture across all sales and partner-facing functions. 
• Reinforce the strategic use of tools like the veterinary portal, practice value model, and print resources to enhance partner engagement and experience. 
• Develop learning and enablement strategies that support organizational priorities, product launches, hospital-facing initiatives, incentive programs, and growth-focused field behaviors. 
• Equip teams to leverage consultative selling, effective discovery, objection handling, and relationship-building techniques that drive partner engagement, conversion, and growth. 

Measurement & Continuous Improvement 

• Track key metrics tied to performance lift — lead growth, footprint growth, resource adoption, conversion rates, engagement levels, and partner adoption. 
• Identify emerging opportunities, performance risks, capability gaps, and trends,  proactively recommending and implementing enablement strategies and solutions that improve business outcomes. 
• Evaluate performance trends, competing business needs, and organizational priorities to recommend and prioritize development initiatives with the greatest potential impact. 
• Partner with Market and Outbound Engagement leadership to measure program impact, evaluation, ROI, and continuously improve enablement efforts. 

Qualifications 

• 10+ years in sales enablement, partner growth, or performance coaching, ideally within animal health, pet insurance, or related industries. 
• Strong record of identifying business needs and turning training, coaching, and enablement solutions into measurable sales results. 
• Proven ability to collaborate across departments and levels of leadership. 
• Strong facilitator, coach, and communicator who thrives in dynamic, partner-driven environments. 
• Demonstrated experience in instructional design and adult learning, with the ability to independently assess needs and create effective instructor-led, virtual, blended, and on-demand learning solutions. 
• Data-driven and adept at assessing performance metrics, identifying opportunities, influencing decisions, measuring impact, and informing strategy. 
• Strong prioritization skills, with the ability to balance multiple initiatives and drive work from concept through execution.  

Leadership Competencies 

• Field-Centric Mindset: Keeps the needs of field sales and partner teams at the center of every initiative. 
• Sales Growth Orientation: Translates learning into real-world revenue and engagement gains. 
• Collaborative Leader: Works cross-functionally with continuing education, operations, and sales teams to ensure consistency and impact. 
• Coach at Heart: Focused on people, growth, and performance through mentorship and applied skill-building. 
• Innovator: Always seeking new ways to engage, enable, and elevate. 
• Performance Catalyst: Recognizes opportunities, turns ideas into practical solutions, and maintains momentum from concept through delivery to achieve meaningful results. 

Compensation:

• The pay range for this position is $130,000 - $145,000 USD 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.

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.