Two Chicks With A Side Hustle

If you’re good at untangling money questions without losing your cool, this is a solid mid-level billing seat. You’ll handle more complex customer and partner billing issues (Tier II), protect SLAs and compliance, and keep things moving without a bunch of handoffs.

About Pie Insurance
Pie’s mission is to make commercial insurance affordable and simple for small businesses, using tech to modernize the insurance experience.

Schedule

  • Remote (U.S. only, territories excluded)
  • Full-time
  • Base pay range: $21–$25/hr

What You’ll Do

  • Handle Tier II billing support via phone, email, and platform tools
  • Resolve more complex billing inquiries for small business customers and agency partners
  • Monitor and maintain SLAs while staying compliant with state and federal regs
  • Meet production goals for Tier II billing work
  • Build relationships with agency partners and internal teams to keep communication consistent
  • Investigate root causes, fix billing issues, and help prevent repeat problems
  • Advocate for the customer’s perspective internally
  • Stay current on billing policies through ongoing training
  • Support onboarding/training of Tier 1 hires (shadow sessions, guidance)
  • Other duties as assigned

What You Need

  • High school diploma/GED (college coursework preferred)
  • 2+ years in financial services, collections, or banking
  • 1+ year customer service in a fast-paced, high-volume environment
  • Strong written and verbal communication (clear, professional, steady under pressure)
  • Strong problem-solving and process mindset (improve workflows, not just close tickets)
  • Self-directed, proactive, consistent accuracy and speed
  • Comfortable collaborating cross-functionally
  • Tools: G-Suite, Salesforce, payment processing systems, collaboration tools (Slack preferred)
  • Note: they say familiarity with Pie’s internal systems is “highly preferred” (that’s usually internal-candidate-friendly, but not always)

Benefits

  • Competitive compensation + equity (“a piece of the pie”)
  • Comprehensive health plans
  • Generous PTO
  • 401(k) match
  • Parental and caregiver leave
  • Potential discretionary bonuses (based on company performance)

Happy Hunting,
~Two Chicks…

APPLY HERE.