Two sentences that grab attention and tell remote job seekers why this role matters.
This role is all about keeping Workers’ Comp policies accurate from day one through renewal, so small businesses stay protected and compliant. If you’re the person who catches what others miss and can process cleanly at speed, you’ll be a backbone of the underwriting lifecycle.
About Pie Insurance
Pie Insurance helps small businesses thrive by making commercial insurance more affordable and easier to buy and manage. They use technology to modernize the commercial insurance experience, with a mission-driven, values-led team.
Schedule
- Full-time
- Remote (U.S. only; territories excluded)
- Reliable high-speed internet required
What You’ll Do
- Process Workers’ Comp policies across the lifecycle (issuance, endorsements, policy changes, renewal prep)
- Complete midterm change endorsements and entity changes
- Handle cancel/rewrites and other policy updates as needed
- Coordinate with renewal teams on significant in-term changes to support year-over-year review accuracy
- Support rate verification/testing and batch processing work across rating platforms
- Assist with corrective endorsements tied to Workers’ Comp bureau error reports
- Partner with Product, Compliance, Engineering to test rates and system functionality and provide feedback
- Support underwriting assistant and underwriting teams with data entry and file prep when needed
What You Need
- High school diploma or GED
- 3+ years of commercial insurance experience
- Strong problem-solving with minimal direction
- Proven self-management of deliverables, timelines, and follow-through
- Ability to multitask and hit deadlines in a fast-paced environment
- High attention to detail and accurate transcription between sources
- Strong written and verbal communication, with the ability to adjust to different audiences
- Comfort with cloud-based tools (Microsoft Office, Google Workspace, Slack, Salesforce, Adobe) and learning new systems quickly
- Some experience leading small workgroups or task forces on specific projects (developing leadership)
Benefits
- Competitive cash compensation
- Equity (a “piece of the pie”)
- Comprehensive health plans
- Generous PTO
- 401(k) match
- Parental and caregiver leave
- Potential discretionary bonus eligibility (based on company performance and role eligibility)
Roles like this move fast. If your strength is clean processing, policy accuracy, and owning the details without being babysat, this one’s a solid fit.
Happy Hunting,
~Two Chicks…