by Terrance Ellis | Nov 25, 2025 | Uncategorized
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…
by Terrance Ellis | Nov 25, 2025 | Uncategorized
Support payroll partners and small business customers in a fully remote role where your customer service skills actually matter. This mid-level position is all about solving real issues in real time so payroll partners can keep their clients covered and compliant without the drama.
About Pie Insurance
Pie Insurance helps small businesses thrive by making workers’ compensation and commercial insurance more affordable and easier to manage. The team blends technology, data, and human support to simplify coverage and billing so owners can focus on running their business. Pie has a values-driven culture and a growing national footprint in the small business insurance space.
Schedule
- Full-time, remote role within the United States (territories excluded)
- Standard weekday business hours with responsiveness to partner requests
- Must be able to respond to payroll partner requests within 24 hours or less
- Requires reliable high speed internet and a consistent, professional home work setup
What You’ll Do
- Handle phone, email, and platform-based communication with payroll partners and internal teams to provide high quality customer service
- Maintain service level agreements set by the Payroll Partner Operations team in a consistent and efficient way
- Process policy issuance, renewals, cancellations, and general questions for payroll partner accounts
- Manage follow up communication and ensure timely responses to partner requests and escalations
- Apply advanced workers’ compensation knowledge to policy, billing, and agency questions
- Build and maintain strong relationships with payroll partners and internal stakeholders
- Identify issues, drive resolution, and anticipate ways to prevent similar problems in the future
- Advocate for payroll partners and insureds by clearly voicing their needs and perspectives
- Support onboarding and training for new hires and teams, including process walkthroughs and feedback
- Help maintain and update SOPs, training materials, and resources for the Payroll Pod
- Assist in testing and training for new processes and systems as they are rolled out
What You Need
- High school diploma or GED required; associate degree, trade or technical certificate, or bachelor’s degree preferred
- At least 1 year experience in a high volume customer contact environment
- At least 1 year insurance customer service, administrative, or sales experience
- Payroll partner customer service experience is preferred
- Strong problem solving skills with the ability to handle simple to moderately complex issues with minimal guidance
- Ability to navigate and solve advanced issues across multiple internal platforms
- Clear, professional verbal and written communication skills, with a focus on relationship building
- Proven ability to work with speed, accuracy, and consistency while reducing unnecessary handoffs
- Developed self-direction and ownership of tasks, deliverables, and timelines
- Comfortable working in a collaborative team environment and considering stakeholder needs
- Experience with G Suite, Salesforce, payment processing systems, and Slack is highly preferred
Benefits
- Base compensation range of 23.50 to 28 dollars per hour, depending on experience and location
- Competitive cash compensation plus equity so you get 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 work from home successfully
If you are ready to grow your insurance career while working remotely and supporting payroll partners who rely on you, this role is worth jumping on.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Nov 25, 2025 | Uncategorized
Support key partners, own complex policy lifecycles, and be the go to problem solver in a fully remote role. If you enjoy deep dive customer service, billing, and audit work in a structured environment, this Partner Specialist position with Pie Insurance is built for you.
About Pie Insurance
Pie Insurance is a technology driven commercial insurance company focused on helping small businesses thrive by making coverage affordable and easy to manage. The team uses data, automation, and a customer first mindset to simplify workers compensation and commercial insurance so owners can focus on running their business instead of fighting paperwork.
Schedule
- Full time, remote role within the United States (territories excluded)
- Standard weekday business hours with regular collaboration across operations, billing, and partner teams
- Requires reliable high speed internet and a professional, distraction free home workspace
What You Will Do
- Serve as a subject matter expert for customer service, billing, and audit processes tied to partner policies
- Manage the full partner policy lifecycle, including policy setup, changes, billing adjustments, audits, and renewals
- Build and maintain strong relationships with assigned partners and internal teams to ensure consistent, clear communication
- Proactively identify, investigate, and resolve issues at any stage of the policy lifecycle and prevent repeat problems where possible
- Deliver high quality support that meets or exceeds established service level agreements and partner expectations
- Own escalations from internal customer service and cross functional teams, including root cause review and resolution updates
- Partner with internal stakeholders to refine workflows and reduce escalations over time
- Support elite partners with a high level of independence, tailoring solutions to their business needs while staying aligned with company policies
- Maintain accurate documentation, notes, and tracking for policy actions, escalations, and outcomes
- Show dependable attendance and punctuality to support team coverage and service commitments
What You Need
- High school diploma or GED required, some college coursework or a bachelor’s degree preferred
- At least 2 years of customer service experience, ideally supporting customers in a structured, metrics driven environment
- At least 1 year of experience providing operational support in a fast paced environment is highly preferred
- Experience with data analysis and a working understanding of workers compensation operational practices required
- Familiarity with insurance products, policy administration, or similar operational roles is a plus
- Comfortable using G Suite tools, Salesforce, collaboration tools such as Slack, and standard office software
- Strong written and verbal communication skills, with the ability to clearly explain issues and close the loop on conversations
- Proven ability to own your workload, manage timelines, and follow through on deliverables without heavy supervision
- Problem solving mindset with the ability to use data, judgment, and creativity to design win win solutions
- Collaborative, team focused approach with the ability to build trust across partners and internal departments
Benefits
- Base pay range of 23.50 to 28 dollars per hour, depending on experience and location
- Competitive cash compensation plus equity, so you truly get a piece of the pie
- Comprehensive health plans
- Generous paid time off
- Future focused 401k match
- Generous parental and caregiver leave
- Mission driven, values based culture where small business customers come first
Roles that combine remote work, subject matter ownership, and direct impact on partner relationships are in demand and move quickly. If you want to grow in insurance operations while staying fully remote, this is a strong option to pursue.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Nov 25, 2025 | Uncategorized
Help small businesses bounce back faster by recovering money on complex workers’ compensation and commercial auto claims. This fully remote subrogation role lets you own a focused caseload, drive recoveries, and directly impact claim cost containment.
About Pie Insurance
Pie Insurance is a tech driven commercial insurance company on a mission to make coverage affordable and as easy as pie for small businesses. They use data, automation, and a customer first mindset to rethink how small businesses buy and experience insurance. As part of the claims team, you’ll help protect those businesses by identifying, pursuing, and securing subrogation recoveries that keep costs under control.
Schedule
- Full time, remote role based anywhere in the United States (territories excluded).
- Standard weekday business hours with collaboration across claims and internal partners.
- Requires reliable, high speed internet and a dedicated, professional home workspace.
What You’ll Do
- Investigate subrogation opportunities by securing new evidence and information across all applicable lines of business.
- Determine potential subrogation recovery amounts and build a clear recovery strategy for each assigned file.
- Evaluate liability and conduct additional investigation as needed to reach optimal settlements.
- Collaborate with front line adjusters to align on case strategy, share new facts, and reassess liability and settlement options.
- Issue subrogation notices in line with state specific regulations and company standards.
- Maintain proactive contact with insureds, claimants, carriers, attorneys, adverse parties, and internal adjusters to move recovery efforts forward.
- Document action plans, investigations, negotiations, and recovery status clearly in claim notes and systems.
- Negotiate workers’ compensation and commercial auto subrogation claims with carriers and other responsible parties, including attorneys and legal reps.
- Assist with the recovery of claim overpayments and negotiate lien/settlement amounts based on case facts.
What You Need
- At least 2 years of experience handling workers’ compensation and/or commercial auto claims subrogation.
- Strong understanding of insurance claim procedures and subrogation workflows.
- Strong written and verbal communication skills with a professional, clear style.
- Confident decision making and critical thinking skills in a fast paced environment.
- Strong negotiation skills with experience settling or resolving disputed liability and damages.
- Ability to learn quickly, take ownership of new responsibilities, and manage a steady caseload.
- Comfort working both independently and as part of a collaborative claims team.
- Experience with G Suite tools, Microsoft Office, and common collaboration platforms.
- High school diploma or GED required; bachelor’s degree preferred.
Benefits
- Base salary range of 70,000 to 90,000 dollars per year, depending on experience and location.
- Competitive cash compensation plus equity so you truly get “a piece of the pie.”
- Comprehensive health plans.
- Generous paid time off.
- Future focused 401k match.
- Generous parental and caregiver leave.
Subrogation roles that blend autonomy, impact on claim outcomes, and fully remote flexibility are not common.
If you’re ready to own your recoveries and help small businesses thrive, this one deserves serious consideration.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Nov 25, 2025 | Uncategorized
Help small business owners stay protected by keeping their commercial insurance billing clean, accurate, and stress free. This mid level remote billing role lets you handle more complex issues while still staying close to customers and agency partners every day.
About Pie Insurance
Pie Insurance is a tech forward commercial insurance company focused on making coverage affordable and as easy as pie for small businesses. They use data and automation to simplify how workers’ comp and other commercial policies are quoted, billed, and serviced. The team is made up of builders and problem solvers who care about doing right by small business owners and each other.
Schedule
- Full time, remote role based anywhere in the United States (territories excluded).
- Standard business hours with some flexibility based on team needs.
- Requires reliable, high speed internet and a quiet, professional home workspace.
What You’ll Do
- Handle Tier II phone, email, and platform based billing communication with customers, agency partners, and internal teams.
- Manage mid level technical billing inquiries, resolving issues accurately and with strong customer service.
- Monitor and maintain service level agreements while staying compliant with federal and state regulations.
- Meet or exceed production goals tied to Billing Tier II work volume and quality.
- Build relationships with agency partners and internal stakeholders to keep communication clear and consistent.
- Research and resolve complex billing issues while looking for ways to prevent similar problems in the future.
- Advocate for the customer’s perspective and help voice customer needs to internal teams.
- Stay current on billing policies, procedures, and system workflows through ongoing training.
- Support onboarding and training of new Tier I billing hires, including shadow sessions and knowledge sharing.
- Complete other billing and operations duties as assigned.
What You Need
- High school diploma or GED required; college coursework or a bachelor’s degree preferred.
- At least 2 years of experience in financial services, collections, or banking.
- At least 1 year of customer service experience in a fast paced, high volume environment.
- Familiarity with Pie’s internal systems and standards is highly preferred (for internal candidates).
- Strong verbal and written communication skills with a professional, customer focused tone.
- Demonstrated problem solving skills and comfort challenging the status quo to improve processes.
- Self directed, proactive, and able to complete work with strong speed, accuracy, and consistency.
- Ability to work well in a team environment and build collaborative relationships across departments.
- Experience with G Suite tools, Salesforce, payment processing systems, and collaboration tools such as Slack.
Benefits
- Base compensation range of 21 to 25 dollars per hour, depending on experience and location.
- Competitive cash compensation plus equity so you truly get a piece of the pie.
- Comprehensive health plans.
- Generous paid time off.
- Future focused 401k match.
- Generous parental and caregiver leave.
Roles where you can grow from Tier II work into deeper ownership while staying fully remote do not sit around long.
If you like solving billing problems, talking to people, and helping small businesses thrive, this one is worth your energy.
Happy Hunting,
~Two Chicks…
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