Director of Sales Operations and Strategy

Pumpkin promises uncompromising care to the cats & dogs we love unconditionally. By helping prevent future health risks and ensuring access to gold-standard veterinary medicine and individualized support when it matters most–we aim to enable $1/2B in life-extending and life-saving treatment over the next five years.

How we’re making this happen:

Premium Insurance: Best-in-class coverage to enable the best, most advanced treatments and therapies when it matters most – without compromise

Innovative Wellness Plans: Personalized preventive care products designed with vets to prevent, reduce, and detect health risks earlier to extend quality of life

5-Star Experience: Concierge service & experience powered by pet experts and industry-leading technology to make decisions and providing care stress-free & frictionless

Mission-Driven Culture: We put pets' best interests at the center of everything we do. We dream big and solve big problems. We embrace speed, agility, and fearlessness to jump the highest fences, dig new and bigger holes, and fight for the toys we believe in.

We’re seeking a strategic and results-driven Director of Sales Operations and Strategy to lead the evolution of our sales operations in the veterinary channel. This highly visible role will design and implement scalable sales processes that improve sales effectiveness, accelerate revenue growth, manage strategic sales projects, and enhance the overall clinic and customer experience. You’ll work cross-functionally with sales leadership, marketing, operations, finance, and product to ensure our go-to-market engine is operating at peak performance.

This will be a fully remote position. Some travel will be required (20%)

• Sales Process Design & Optimization: Design and optimize end-to-end sales processes—from lead intake through close—to improve conversion rates, cycle time, and sales team productivity.
• People Leadership: Oversee the Sales Operations and Sales Enablement teams, with opportunities to build and grow the department as the organization scales.
• Strategic Project Management: This role will manage rollout  of strategic, often cross functional, projects.  This includes field and cross-functional workstream rollout coordination, project tracking and reporting, and stakeholder and executive management. .  This may include rollout of new products, features, or major account relationships. 
• Performance Monitoring & Insights: Partner with the Data team to define and track key performance indicators (KPIs) to assess sales effectiveness. Analyze pipeline data to surface trends, identify gaps, and recommend improvements.
• Sales Technology & Tools: Own the evaluation, implementation, and ongoing optimization of sales technology tools—including CRM and sales engagement platforms. Ensure systems are configured to support workflows, reporting, and rep effectiveness.
• Cross-Functional Collaboration: Align sales processes with broader business functions by collaborating closely with marketing, product, finance, and operations teams.
• Sales Enablement Partnership: Champion enablement efforts in partnership with the Sales Enablement team—ensuring reps are effectively trained on tools, cadences, and processes. Develop clear documentation, guidance, and resources that empower the team to execute with consistency and confidence.
• Change Management & Communication: Lead change initiatives related to process improvements. Communicate clearly and manage adoption across the sales org with minimal disruption.
• Documentation & Governance: Maintain accurate and up-to-date documentation of all sales processes and SOPs. Ensure a consistent, repeatable approach to how we sell.

• 12+ years of progressive experience in sales operations, process optimization, and go-to-market strategy—preferably in a multi-channel, high-growth sales environment
• Excellent project management skills with ability to drive complex, high-impact initiatives from concept to completion while managing multiple priorities
• People management experience with a track record of developing high-performing teams
• Deep expertise in CRM platforms (e.g., Salesforce, Dynamics 365), sales enablement tools, and workflow automation.
• Strategic mindset with ability to connect day-to-day operations to broader business objectives and lead effective change management initiatives
• Outstanding communication and stakeholder management skills—comfortable engaging with senior leaders, collaborating across departments, and partnering with frontline sales leadership 
• Strong analytical skills with experience defining KPIs and extracting actionable insights from sales pipeline data
• Experience with process mapping and documentation tools (e.g., Lucidchart, Miro, Confluence)
• Bachelor’s degree in Business, Marketing, or a related field; advanced degree is a plus.

• Proven success in complex channel sales environments is highly desired.
• Experience with B2B/B2B2C sales processes, including strategic partnerships, influencer/advocacy models, and multi-stakeholder selling environments
• Experience in, or familiarity with animal health, insurance B2B sales or pet insurance

The compensation for this position ranges from $130,900 - $187,000 (annually). Compensation may vary outside the listed range, based on a number of factors including but not limited to location, qualifications, performance, skills and experience. The compensation range listed is just one component of Pumpkin’s total compensation package for employees. Total compensation packages, depending on the position, may also include incentive compensation, discretionary bonuses, and other short or long-term incentives. If hired, employees will be in an ‘at-will position’ and Pumpkin reserves the right to modify compensation (as well as any other discretionary payment or benefit program) at any time, including for reasons related to individual performance, company or individual department/team performance, and market factors.

Benefits and Perks:

Comprehensive contributions to medical, dental and vision for colleagues and dependents.

Generous PTO and Paid Holidays

401k with company match.

The opportunity to join a team where every team member has the autonomy and support they need to boss their role and make empowered decisions.

Pet Friendly Offices, Stocked Kitchens, Team Workouts, Team Outings and much more!

Pumpkin's Core Values:

Pets Come First: Put what’s best for pets at the center of everything we do

Trust the Pack: Help families make empowered pet care decisions

Jump Fences: If there’s a will, there’s always a way over them

Share Toys: Be generous with our gifts and amazing things will happen

Dig New Holes: Challenge conventions to create the future of pet health care

Pumpkin is proud to be an affirmative action and equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, protected veteran status, or any other characteristic protected by federal, state or local laws.