Help small businesses stay protected by keeping billing accurate, clear, and stress-free. In this mid-level role, you’ll solve complex billing issues, support agency partners, and deliver a customer experience that feels easy and human.
About Pie Insurance
Pie Insurance empowers small businesses by making commercial insurance more affordable and simpler to access. The company uses technology to modernize how coverage is purchased and experienced, with a mission-driven team focused on helping customers thrive.
Schedule
- Remote role (U.S. only; territories excluded)
- Must have reliable, high-speed internet
- Work involves Tier II phone, email, and platform-based support in a fast-paced, high-volume environment
What You’ll Do
- Handle Tier II billing inquiries via phone, email, and platform-based communication for customers and cross-functional partners
- Monitor and maintain service level agreements while staying compliant with federal and state regulations
- Consistently meet production goals related to Tier II billing work
- Resolve complex billing issues for small business owners and partners across all channels
- Build strong relationships with agency partners and internal teams to ensure accurate, consistent customer communication
- Identify root causes, drive resolutions, and anticipate ways to prevent repeat billing issues
- Advocate for the customer by voicing needs and perspective internally
- Maintain knowledge of billing policies and procedures through ongoing training
- Support onboarding and training for new Tier I hires, including shadow sessions
- Complete other duties as assigned
What You Need
- High School Diploma or GED (Bachelor’s degree or college coursework preferred)
- 2+ years of experience in financial services, collections, or banking
- 1+ year of customer service experience in a fast-paced, high-volume environment
- Familiarity with billing workflows, problem-solving, and process improvement
- Strong verbal and written communication skills with a professional, customer-first approach
- Ability to work independently, take initiative, and deliver accurate work with speed and consistency
- Collaborative mindset with experience working across teams and stakeholders
- Experience with tools such as Google Workspace, Salesforce, payment processing systems, and collaboration tools (Slack preferred)
- Familiarity with Pie’s internal systems and processes (highly preferred)
Benefits
- Competitive cash compensation ($21–$25 USD base range)
- Equity (“a piece of the pie”)
- Comprehensive health plans
- Generous PTO
- 401(k) match
- Generous parental and caregiver leave
- Eligible team members may receive discretionary bonuses based on company performance
Hiring is moving, so if this fits, don’t overthink it.
Bring your billing skills somewhere that actually respects the customer experience and the details.
Happy Hunting,
~Two Chicks…