🧾 About the Role
Pie Insurance is on a mission to empower small businesses by making commercial insurance affordable and as easy as pie. As the Customer Service Manager, Vendor and Operations, you’ll lead the performance of Pie’s internal and outsourced support teams, driving innovation, process optimization, and scalable service delivery across multiple insurance lines. This role is perfect for a strategic operator who thrives on uncovering the “why,” crafting data-backed business cases, and building high-performing teams in a fast-evolving environment.
✅ Position Highlights
• $85,000–$110,000 per year
• Full-Time
• 100% Remote (U.S.-based only)
• Competitive cash + equity (“a piece of the pie”)
• Comprehensive health, dental, and vision coverage
• Future-focused 401(k) match
• Generous PTO + caregiver leave
📋 What You’ll Own
• Lead the daily and strategic operations of customer service teams across live support, new product lines, and back-office functions
• Develop and operationalize a segmented support model to meet customer experience goals while managing cost
• Set clear performance expectations with team scorecards, aligning with Pie’s broader objectives
• Own governance over workforce management, quality, and training initiatives
• Present operational improvement business cases to drive cross-team impact
• Analyze performance trends and identify workflow inefficiencies using data and stakeholder input
• Lead, coach, and develop direct reports and support talent development within the team
• Collaborate with executives, internal stakeholders, and outsourced vendors to drive results
• Travel up to 20% as needed for team coordination and strategy
🎯 Must-Have Traits
• Bachelor’s degree required
• 5+ years in customer service, with 2+ years in a leadership role managing internal and outsourced teams
• Experience collaborating with WFM, training, and QA teams
• Strong data analysis skills; spreadsheet fluency and basic modeling preferred
• Insurance industry knowledge strongly preferred, especially multi-line support and policy lifecycle understanding
• Proven ability to develop talent, optimize operations, and present strategic recommendations
• Thrives in ambiguity with a solutions-first mindset
• Communicates with clarity, empathy, and candor
💻 Remote Requirements
• Must live and work in the U.S. (territories excluded)
• Reliable high-speed internet
• Home office setup suitable for confidential communication
💡 Why It’s a Win for Remote Job Seekers
• Make a real impact at one of America’s Best Startup Employers (2025)
• Collaborate with a mission-driven, values-aligned team
• Influence Pie’s operational future while supporting the success of small businesses
• Enjoy transparent leadership, equitable pay, and a flexible, supportive culture
✍️ Call to Action
If you’re a builder, a coach, and a strategist who sees operations as a vehicle for world-class customer service, this is your seat at the table. Apply now and help Pie serve up simplicity in a complex industry.