Two Chicks With A Side Hustle

(Remote – U.S.)

🧾 About the Role
Pie Insurance is seeking a Billing & Collections Specialist (Tier III) to lead the charge on complex billing inquiries, audit refunds, and high-level escalations. In this senior-level role, you’ll deliver white-glove service to small business customers and agency partners, ensuring accurate resolution and proactive problem-solving. You’ll be a key voice in challenging conversations and a core contributor to process improvement and training efforts.


Position Highlights
Title: Billing & Collections Specialist Tier III
Location: Fully Remote – U.S.
Compensation: $22.50 – $27/hour
Benefits: Competitive equity, healthcare, PTO, 401k match, caregiver/parental leave
Reports to: Billing & Collections Team Lead
Team Culture: Collaborative, mission-driven, tech-savvy


📋 What You’ll Own
• Handle Tier III customer inquiries via phone, email, and platform-based communication
• Process billing tasks: audit refunds, rescissions, collections, daily error report resolution
• Engage in high-stakes agency/customer billing escalations and resolutions
• Meet internal SLAs while ensuring compliance with federal and state regulations
• Partner cross-functionally with internal stakeholders to resolve complex issues
• Assist in onboarding and mentoring peers; contribute to resource documentation
• Act as a key player in Billing UAT and system testing


🎯 Must-Have Traits
• Strong communicator: empathetic, clear, and solution-focused
• Calm under pressure, especially during complex or escalated calls
• Able to work independently while contributing to team goals
• Self-directed with strong attention to detail and task ownership
• Curious, adaptive, and eager to improve processes


🛠️ Qualifications
• High school diploma or GED required (college coursework preferred)
• 2+ years of financial services, collections, or banking experience
• 2+ years of customer service in high-volume environments
• Prior experience with internal Pie systems preferred
• Proficiency in G-Suite, Salesforce, payment processing platforms
• Familiarity with Slack or other team collaboration tools


💻 Remote Requirements
• Reliable internet and quiet work environment
• Ability to manage high-volume communication with accuracy
• Flexibility and adaptability in a fully distributed team


💡 Why It’s a Win for Billing Pros
• Help America’s small businesses stay covered and thrive
• Join a tech-forward company on a mission to make insurance accessible
• Enjoy a generous compensation package, equity, and supportive benefits
• Collaborate with passionate peers who care deeply about the work


✍️ Call to Action
If you’re ready to bring tenacity, professionalism, and a sharp billing mind to a company empowering entrepreneurs—apply now. Let’s make insurance easy as Pie.