Step into a fully remote underwriting operations role where your accuracy, speed, and problem solving actually move the needle. This position is ideal if you know commercial insurance, thrive in fast-paced back-end work, and want to own the processing side of the workers’ compensation policy lifecycle.
About Pie Insurance
Pie Insurance helps small businesses thrive by making workers’ compensation and commercial insurance more affordable and easier to manage. The team uses data, technology, and a customer-first mindset to simplify quoting, billing, and policy servicing for small business owners. Pie is a fast-growing, values-driven company focused on modernizing how small businesses buy and experience commercial insurance.
Schedule
- Full-time, remote position within the United States (territories excluded)
- Standard weekday business hours, with flexibility based on team needs
- Requires reliable high-speed internet and a quiet, professional home workspace
- Collaboration with product, compliance, underwriting, and operations teams
What You’ll Do
- Process policy servicing tasks for workers’ compensation policies, including policy issuance, endorsements, cancel/rewrites, and other midterm changes
- Handle entity changes and other updates across direct and partner accounts
- Coordinate with renewal teams to flag significant in-term changes and support accurate renewal reviews
- Complete rate verification and functionality testing in various policy rating platforms
- Support batch processing for book rolls and large-volume quoting and submission work
- Work with product and compliance teams to test rating and system functionality, identifying issues and providing feedback
- Process corrective endorsements based on workers’ comp bureau error reports
- Assist Underwriting Assistants and Underwriters with data entry, file prep, and other process-driven tasks as needed
What You Need
- High school diploma or GED required
- At least 3 years of experience in commercial insurance (workers’ compensation strongly preferred)
- Strong problem solving skills with the ability to work through tasks and issues with minimal direction
- Proven self-direction and ownership of workload, deliverables, and deadlines
- Ability to multitask, manage multiple deliverables, and stay organized in a fast-paced environment
- High attention to detail with strong data entry and transcription accuracy
- Developing leadership skills and experience leading work groups or task-based projects is a plus
- Clear written and verbal communication skills, with the ability to adapt messaging to different audiences
- Comfortable with cloud-based systems and tools such as Microsoft Office, Google Workspace, Slack, Salesforce, and Adobe, with the ability to learn new platforms quickly
Benefits
- Base compensation range of 25.25 to 30 dollars per hour, depending on experience and location
- Competitive cash compensation plus equity so you receive a piece of the pie
- Comprehensive health plans
- Generous paid time off
- Future focused 401k match
- Generous parental and caregiver leave
- Remote-first culture with tools and support to help you succeed from home
If you want a remote underwriting operations role where your precision and processing skills directly support small businesses, this is a strong next move.
Ready to level up your insurance career from home? Throw your hat in the ring.
Happy Hunting,
~Two Chicks…