Director of Sales Operations and Strategy

Summary

Join Pumpkin, a company committed to providing exceptional care for cats and dogs, as their Director of Sales Operations and Strategy. This fully remote role (with 20% travel) involves designing and optimizing sales processes, leading sales operations and enablement teams, managing strategic projects, and collaborating with cross-functional teams. You will be responsible for performance monitoring, utilizing sales technology, and driving change management initiatives. The ideal candidate possesses 12+ years of experience in sales operations and a proven track record of success in high-growth environments. This is a highly visible role that will significantly impact Pumpkin's revenue growth and customer experience.

Requirements

• 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

Responsibilities

• 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

Preferred Qualifications

• 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

Benefits

• 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