If you’re good at untangling billing problems without making customers feel like a number, this is your lane. You’ll handle Tier II billing requests for small business owners and agency partners, solve the trickier issues, and help prevent repeat problems.
About Pie Insurance
Pie’s mission is to help small businesses thrive by making commercial insurance more affordable and easier to manage. They use technology to simplify how small businesses buy and experience insurance, backed by a team of builders who move fast and care about the customer.
Schedule
Remote (United States only; territories excluded)
Full-time, high-volume support role with SLA and regulatory compliance expectations
Reliable high-speed internet required
What You’ll Do
- Handle Tier II billing support across phone, email, and platform channels for customers and internal partners
- Monitor and maintain service level agreements while staying compliant with federal and state regulations
- Resolve complex billing issues for small business owners and agency partners, with strong documentation and follow-through
- Build relationships with agency partners and internal teams to ensure accurate, consistent communication
- Advocate for the customer, identify root causes, and suggest ways to prevent recurring billing issues
- Participate in ongoing training and support onboarding of new Tier 1 hires (including shadow sessions)
- Complete additional assigned billing and operations tasks as needed
What You Need
- High school diploma or GED (college coursework or bachelor’s preferred)
- 2+ years in financial services, collections, or banking
- 1+ year in customer service in a fast-paced, high-volume environment
- Familiarity with billing policies/processes and strong attention to speed, accuracy, and consistency
- Strong written and verbal communication skills with a customer-first approach
- Proven problem-solving skills and ability to improve workflows and challenge the status quo productively
- Comfortable collaborating across teams and stakeholders
- Tools experience: Google Workspace, Salesforce, payment processing systems, and collaboration tools (Slack preferred)
- 1+ year familiarity with Pie’s internal systems/processes is highly preferred
Benefits
- Base pay: $21–$25/hour (USD)
- Competitive cash compensation plus equity (“a piece of the pie”)
- Comprehensive health plans
- Generous PTO
- Future-focused 401(k) match
- Generous parental and caregiver leave
- Discretionary bonuses may be available based on company performance
If you’re ready to step up from Tier I work and be the person who actually closes the loop on tough billing issues, this is worth moving on now.
Happy Hunting,
~Two Chicks…