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…
by Terrance Ellis | Nov 25, 2025 | Uncategorized
Work from home as the go-to treasury expert who keeps client money clean, reconciled, and moving. This role is ideal if you like structure, numbers, and building better processes instead of just following them.
About Allied Benefit Systems
Allied Benefit Systems is a Chicago based benefits administrator that partners with employers nationwide to design and manage self funded health plans. The Treasury Services team supports that mission by making sure client accounts are set up correctly, reconciled on time, and handled with tight financial controls. Allied offers a remote friendly culture where detail focused finance pros can grow.
Schedule
Full time, fully remote role based out of Chicago, Illinois.
Standard weekday business hours in a computer based environment.
Requires a dedicated home workspace and reliable high speed internet via cable or fiber (at least 100 Mbps download and 25 Mbps upload).
What You’ll Do
- Complete monthly reconciliations of client accounts in Great Plains.
- Process new business banking setups (BPO and ASO) and make banking changes for existing business.
- Maintain vendor records for print fulfillment and support VCC/EFT implementation.
- Complete check tracer processes and submit Positive Pay files to help prevent fraud.
- Upload, track, and troubleshoot treasury related transactions and file movements.
- Create, document, and improve Treasury Services processes as operational needs evolve.
- Provide day to day support to the Treasury Services team on issues, questions, and process gaps.
- Lead training for new hires and existing team members as needed.
- Handle other treasury and operations duties as assigned.
What You Need
- Bachelor’s degree in accounting or equivalent work experience.
- At least 2 years of experience as a Treasury Analyst.
- Strong attention to detail, accuracy, and follow through.
- Excellent written and verbal communication skills.
- Strong organizational and time management skills with a track record of meeting deadlines.
- Proficiency with Microsoft Office Suite, especially Excel and Word.
- Experience with financial management systems such as Great Plains or similar.
- Solid computer skills with tools like Excel, Access, and Power BI.
- Strong analytical and problem solving skills with solid financial and math abilities.
- Ability to work independently in a remote environment and collaborate with a broader team.
Benefits
- Hourly pay in the range of 23 to 24 dollars per hour, depending on experience and qualifications.
- Fully remote role with a supportive, remote friendly culture.
- Medical, Dental, and Vision insurance.
- Life and Disability insurance.
- Generous Paid Time Off.
- Tuition Reimbursement and Employee Assistance Program (EAP).
- Technology stipend to support your home office setup.
Remote treasury roles that blend hands on reconciliations, process ownership, and team support do not sit open forever.
If you are ready to be the subject matter expert the team relies on, this is your next move.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Nov 25, 2025 | Uncategorized
Use your benefits knowledge and bilingual skills to own a book of business from home. This fully remote Account Manager role lets you be the go-to partner for employers and brokers while serving clients in both English and Spanish.
About Allied Benefit Systems
Allied Benefit Systems is a Chicago-based third-party administrator that partners with employers nationwide to design and manage self-funded group health plans. They’re known for flexible, cost-effective benefit solutions, strong client relationships, and a remote-friendly culture where people who communicate well and take ownership can thrive.
Schedule
Full-time, fully remote position (Chicago, IL home base).
Standard weekday business hours, with occasional flexibility for client or broker meetings and virtual presentations.
Requires a dedicated home workspace and reliable high-speed internet (cable or fiber, at least 100 Mbps download / 25 Mbps upload).
What You’ll Do
- Serve as the primary day-to-day contact for an assigned book of Allied clients and their brokers, in both English and Spanish.
- Act as the liaison between clients/brokers and Allied executives and internal departments involved in administering self-funded health plans.
- Provide ACA compliance updates, resolve claim issues, and share industry and legislative information in clear, client-friendly language.
- Conduct quarterly performance meetings to review reporting, strengthen relationships, and ensure overall client satisfaction and retention.
- Lead new client implementations, including internal implementation meetings, tracking open items, and driving installation to completion.
- Communicate plan design changes, contract details, accounting/billing updates, and vendor partner changes to internal teams.
- Prepare and deliver employee presentations, administrative procedures training, website training, and reporting reviews in English and Spanish.
- Produce and analyze ad hoc reports for clients, brokers, and Account Executives as requested.
- Support renewals by managing claim reviews, coordinating stop-loss marketing, and aligning on service expectations.
- Identify opportunities to cross-sell additional Allied services to existing clients.
What You Need
- Bachelor’s degree or equivalent work experience.
- 2–4 years of experience in an Account Manager role.
- Ability to read, write, comprehend, and present confidently in both English and Spanish.
- Working knowledge of employee medical benefit plans; experience with group health and self-funded plans preferred.
- Excellent verbal and written communication skills and strong customer service instincts.
- Comfortable with public speaking and presenting benefits and compliance information in both languages.
- Proficiency with Microsoft Office Suite (Word, Excel, PowerPoint; Access a plus).
- Strong organizational skills, attention to detail, and time management with a track record of meeting deadlines.
- Ability to prioritize tasks, delegate when appropriate, and function well in a fast-paced environment.
- Life and Health Insurance Producer license preferred (or willingness to pursue).
Benefits
- Salary range of $70,000–$75,000 per year, depending on experience and qualifications.
- Fully remote role within a supportive, remote-first culture.
- Medical, Dental, Vision, Life, and Disability insurance.
- Generous Paid Time Off.
- Tuition Reimbursement and Employee Assistance Program (EAP).
- Technology stipend to support your home office setup.
Bilingual account management roles that are fully remote, client-facing, and benefits-focused don’t stay open long.
If you’re ready to be the trusted voice for your clients in both English and Spanish, this is your move.
Happy Hunting,
~Two Chicks…
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