Take on the toughest workers’ comp files from the comfort of home. This Complex Claims Adjuster role lets you own catastrophic and large loss claims end-to-end while directly impacting outcomes for small businesses across the country.
About Pie Insurance
Pie Insurance makes commercial coverage affordable and as “easy as pie” for small businesses. They use technology to simplify how policies are quoted, billed, and serviced so owners can focus on running their business. As part of the claims team, you’ll sit at the center of that mission, balancing empathy for injured workers with smart cost containment for employers.
Schedule
- Full-time, remote role within the United States (territories excluded)
- Standard business hours with flexibility based on claim and mediation schedules
- Must have reliable, high-speed internet suitable for remote work
- Occasional virtual and in-person mediations, conferences, or trials as needed
What You’ll Do
- Independently manage catastrophic and large loss workers’ compensation claims from initial setup through closure
- Conduct timely three-point contact and ongoing investigation as new facts emerge
- Make compensability decisions within statutory timelines and jurisdictional requirements
- Set, review, and adjust reserves within authority, aligned with case facts and company best practices
- Administer statutory medical and indemnity benefits accurately and on time
- Direct and control litigation strategy with defense counsel while managing legal fees and costs
- Identify early resolution opportunities, evaluate exposure, and negotiate settlements (including structured settlements and Medicare Set-Asides)
- Attend mediations, settlement conferences, and trials (virtual and in person) to represent Pie’s interests
- Prepare and present large loss updates and claim summaries to internal and external stakeholders
- Collaborate with Complex Claims Practices and Claims Leadership to refine SOPs, processes, and claim protocols
- Participate in roundtables, build action plans, and mentor junior adjusters on complex claim handling
What You Need
- High school diploma or equivalent required; bachelor’s degree or college coursework preferred
- Minimum 7 years of workers’ compensation claim adjusting experience (carrier experience preferred)
- At least 2 years handling catastrophic / high-exposure workers’ compensation claims
- Experience handling multiple jurisdictions in the Eastern Region
- Active workers’ compensation licenses/certifications in applicable states
- Advanced knowledge of jurisdictional rules, regulatory requirements, CMS/MSA requirements, and complex claim adjudication
- Strong litigation management experience, including strategy, negotiation, and settlement valuation
- Proven ability to evaluate high-dollar, high-exposure files and make sound, timely decisions
- Advanced written and verbal communication skills, including presenting complex information to senior leadership
- Comfortable using G-Suite and collaboration tools (Slack preferred)
- Ability to work independently, manage a heavy caseload, and see issues through with minimal direction
- Track record of mentoring or supporting less experienced adjusters
Benefits
- Base salary range: $95,000–$120,000 USD
- Competitive cash compensation plus equity (“a piece of the pie”)
- Comprehensive health plans
- Generous paid time off
- Future-focused 401(k) match
- Generous parental and caregiver leave
- Inclusive, values-driven culture with a clear mission to help small businesses thrive
Bring your complex claims expertise to a team that actually values it—roles at this level and salary band don’t stay open long.
If you’re ready to own the tough files, shape outcomes, and level up your career in a fully remote role, this one is worth throwing your hat in the ring.
Happy Hunting,
~Two Chicks…