Help small businesses stay protected while you level up your billing and customer service career from home. As a Billing Specialist Tier II with Pie Insurance, you’ll handle more complex billing issues, support agents and partners, and be part of a growing insurtech company that actually feels human.
About Pie Insurance
Pie Insurance makes commercial insurance affordable and simple for small businesses, using technology to streamline how coverage is quoted, billed, and managed. Their mission is to empower small business owners to thrive, not drown in paperwork and confusing policies. As part of the billing team, you’ll be on the front line of that experience.
Schedule
- Full-time, remote role within the United States (territories excluded)
- Standard business hours, with responsiveness to production and SLA goals
- Must have reliable, high-speed internet for remote work
What You’ll Do
- Handle Tier II billing communication via phone, email, and platform-based tools for customers, agency partners, and internal teams
- Monitor service level agreements and ensure billing work remains compliant with federal and state regulations
- Meet and maintain production goals related to Tier II billing work
- Investigate and resolve complex billing issues for small business owners and partners, across all communication channels
- Build strong relationships with agency partners and internal teams to ensure clear, consistent messaging for customers
- Identify root causes of billing problems and suggest ways to prevent future issues
- Advocate for customer needs and voice their perspective in internal conversations
- Maintain up-to-date knowledge of billing policies, procedures, and system standards through ongoing training
- Support onboarding and training of Tier I team members, including shadow sessions and knowledge sharing
- Complete additional duties and projects as assigned
What You Need
- High school diploma or GED required; 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 Pie’s internal systems and processes is highly preferred (or similar billing / insurance systems)
- Strong written and verbal communication skills with a professional, clear tone
- Proven problem-solving skills and the ability to improve workflows and processes
- Self-directed, proactive work style with consistent speed, accuracy, and attention to detail
- Ability to work collaboratively, build strong working relationships, and fully commit to team decisions
- Comfort using G-Suite tools, Salesforce, payment processing systems, and collaboration tools (Slack preferred)
Benefits
- Base pay range: $21–$25 per hour (USD)
- Equity ownership: “a piece of the pie”
- Comprehensive health plans
- Generous PTO
- 401(k) with future-focused company match
- Generous parental and caregiver leave
- Mission-driven, values-based culture focused on making insurance “easy as pie”
If you’re ready to move beyond entry-level billing and handle more complex, meaningful work in a fully remote environment, this is your next step.
Make your move while the role’s still open.
Happy Hunting,
~Two Chicks…