Help small business owners and agency partners untangle more complex billing issues with speed, accuracy, and calm customer service. If you’ve done high-volume billing, collections, banking, or financial services work and you’re comfortable resolving escalated questions across phone, email, and platforms, this is a solid mid-level move.
About Pie Insurance
Pie’s mission is to make commercial insurance affordable and easy for small businesses by using technology to modernize how insurance is bought and managed. They support small business customers with a remote-first team and a strong benefits package.
Schedule
- Remote (US only, territories excluded)
- Full-time
- High-speed internet required
- Not eligible for visa sponsorship (must be authorized to work in the US)
What You’ll Do
- Handle Tier II billing support through phone, email, and platform-based communication
- Monitor and maintain service level agreements while staying compliant with state and federal regulations
- Consistently meet production goals tied to Billing Tier II work
- Resolve complex billing issues for small business customers and partners across channels
- Build relationships with agency partners and internal teams to deliver consistent, accurate communication
- Identify root causes of billing issues and recommend ways to prevent repeat problems
- Advocate for the customer perspective and voice customer needs internally
- Stay current on billing policies and procedures through ongoing training
- Support onboarding of new Tier I hires, including shadow sessions
- Complete other duties as assigned
What You Need
- High school diploma or GED (college coursework or bachelor’s preferred)
- 2 years of experience in financial services, collections, or banking
- 1+ year of customer service experience in a fast-paced, high-volume environment
- Strong written and verbal communication skills with professional customer-facing tone
- Demonstrated problem-solving skills and ability to improve workflows and processes
- Self-directed, proactive, and able to complete work with speed and accuracy
- Team-oriented mindset with strong collaboration skills
- Experience with G-Suite tools, Salesforce, payment processing systems, and collaboration tools (Slack preferred)
- Preferred: familiarity with Pie’s internal systems and processes
Benefits
- Base pay range: $21–$25/hour
- Competitive cash compensation
- Equity (“a piece of the pie”)
- Comprehensive health plans
- Generous PTO
- 401(k) with company match
- Parental and caregiver leave
- Potential discretionary bonuses based on company performance
This is a legit “Tier II” role, meaning you’ll get the tougher tickets and the expectations that come with it. If you like solving problems instead of just forwarding them, you’ll fit.
Happy Hunting,
~Two Chicks…