Manager, Stop Loss – Remote

Lead a specialized stop loss team from your home office while owning high impact claims operations. This role is built for a seasoned stop loss leader who can balance strategy, audit oversight, and day-to-day coaching without losing the details.

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 health plans. The company focuses on flexible, cost-effective benefit solutions backed by strong operational performance and responsive client service. Allied’s remote-friendly culture lets experienced leaders drive results from anywhere while still feeling connected and supported.

Schedule
Full-time, fully remote position based out of Chicago, Illinois.
Standard weekday business hours in a computer-based environment.
Requires reliable high-speed internet via cable or fiber (at least 100 Mbps download / 25 Mbps upload) to support collaboration, reporting, and system access.

What You’ll Do

  • Manage the day-to-day operations of the Stop Loss department, including workflow, staffing, systems, and reporting.
  • Work closely with the Director of Stop Loss to set expectations, meet business goals, and drive innovation.
  • Oversee all stop loss filings (specific and aggregate), reimbursements, and advance funding claims to ensure timely, accurate handling.
  • Perform and oversee weekly audits of specific claims to confirm filings and reimbursements are correct.
  • Maintain and improve tracking tools and logs for members over specific deductibles and stop loss activity.
  • Coordinate reprocessing of claims based on carrier negotiations and contract details.
  • Lead the filing of aggregate claims and secure corresponding reimbursements.
  • Manage the cash flow impact of advance funding by selecting appropriate claims and monitoring paybacks.
  • Request and review reporting for mid-year takeover stop loss policies.
  • Assess existing processes and design/implement policies and procedures that improve efficiency and align with corporate strategy.
  • Troubleshoot issues across teams and remove obstacles to keep operations running smoothly.
  • Directly manage team members, including assignments, performance goals, one-on-ones, coaching, and performance reviews.
  • Set clear expectations, provide training, and ensure quality standards and audit metrics are met.
  • Attract, develop, and retain talent while fostering a culture of urgency, accountability, and collaboration.
  • Take on special projects and additional duties as needed.

What You Need

  • Bachelor’s degree or equivalent relevant work experience.
  • At least 5 years of stop loss experience at a TPA or stop loss carrier.
  • At least 3 years in a supervisory or management role with proven leadership results.
  • Intermediate proficiency with Microsoft Word, Excel, and PowerPoint.
  • Strong knowledge of group health insurance/benefits (preferred).
  • Excellent written and verbal communication skills.
  • Proven ability to manage operations, drive process improvements, and meet deadlines.
  • Strong decision-making, problem-solving, and relationship-building skills.
  • Comfortable leading in a fully remote environment with clear expectations and accountability.

Benefits

  • Salary range of $70,000 to $75,000 per year, based 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.

If you’re already the “go-to” stop loss expert and ready to step into (or level up in) leadership with full remote flexibility, this is one to take seriously.

Step into a role where your decisions shape operations, protect clients, and develop a high-performing team.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Appeals Specialist – Remote

Use your medical claims experience to solve real problems instead of watching claims bounce back and forth. This fully remote Appeals Specialist role lets you own the appeals process from start to finish, making sure members and clients get clear, accurate outcomes.

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 health plans. They focus on flexible, cost-effective benefits backed by strong operational support, clinical programs, and client service. Allied runs a remote-friendly culture where detail-oriented, accountable people can thrive from anywhere.

Schedule
Full-time, fully remote position based out of Chicago, Illinois.
Standard weekday business hours in a computer-based/home office environment.
Requires reliable high-speed internet via cable or fiber (at least 100 Mbps download / 25 Mbps upload) for systems access and virtual collaboration.

What You’ll Do

  • Log and track all appeals received under the Allied Advocate program.
  • Review appeals and supporting documentation to assess completeness and appropriateness.
  • Review Summary Plan Documents (SPDs) to determine the validity of appeals.
  • Document claim specifics and appeal details in internal systems (including Qiclink and databases).
  • Route appeal documentation to internal business partners for review and resolution.
  • Coordinate and follow up with business partners on aging appeals to keep cases moving.
  • Compose appeal responses when necessary and communicate outcomes clearly.
  • Communicate with other departments and clients as needed to clarify information and support resolution.
  • Prioritize incoming referrals to complete all tasks within required timelines.
  • Perform other appeals-related duties as assigned.

What You Need

  • Bachelor’s degree or equivalent work experience.
  • At least 2 years of comprehensive experience handling medical claims appeals.
  • Proficiency with Microsoft Office Suite or similar software.
  • Ability to analyze claim situations and take appropriate, informed actions.
  • Strong verbal and written communication skills.
  • Solid analytical and problem-solving skills.
  • Excellent organizational skills, attention to detail, and time management.
  • Ability to learn new systems and adapt to process changes.
  • Comfort sitting for long periods and communicating by phone in a remote environment.

Benefits

  • Hourly pay in the range of $20.00–$21.00, based on experience and qualifications.
  • Fully remote work with a supportive, remote-friendly 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.

Appeals roles that let you specialize in medical claims, stay fully remote, and build a real career path don’t stay open forever.

If you’re confident with claims, love digging into details, and want to be the person who gets appeals over the finish line, this is your move.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Stop Loss Data Specialist – Remote

Work from home in a numbers-driven role that actually matters to the bottom line. As a Stop Loss Data Specialist, you’ll be the person making sure big dollar claims are filed, tracked, and reimbursed correctly so plans stay protected and claims stay on track.

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 health plans. The company focuses on flexible, cost-effective benefit solutions backed by smart operations, data, and strong client service. Allied runs a remote-friendly culture where organized, detail-oriented people can thrive from anywhere.

Schedule
Full-time, fully remote role based out of Chicago, Illinois.
Standard weekday business hours in a computer-based/home office environment.
Requires reliable high-speed internet via cable or fiber (minimum 100 Mbps download / 25 Mbps upload) to support file work and system access.

What You’ll Do

  • Perform monthly audits to confirm all stop loss claims have been filed and all reimbursements have been received.
  • Update and manage stop loss tracking tools and specific logs to monitor members over the specific deductible.
  • Review, record, and reconcile stop loss reimbursements with accuracy and clarity.
  • Gather and prepare data required to file Rx stop loss claims.
  • Request and track Actively at Work forms from clients.
  • Manage the cash advance process, including identifying claims for cash advance and mailing cash advance checks once reimbursements are received.
  • Work closely with Stop Loss Claim Specialists on administrative, organizational, and auditing tasks.
  • Handle assorted operational duties as assigned to keep the stop loss department running efficiently.

What You Need

  • High school diploma or equivalent (some college or equivalent work experience preferred).
  • 1–2 years of experience in an office environment.
  • Strong organizational skills and meticulous attention to detail.
  • Solid analytical and problem-solving skills.
  • Clear verbal and written communication skills.
  • Proficiency with Microsoft Office Suite or similar software.
  • Strong time management skills and a proven ability to meet deadlines.
  • Ability to function well in a fast-paced, sometimes high-pressure environment.
  • Preferred: Medical claims experience, accounting or finance background, and/or experience with a TPA or other insurance company.

Benefits

  • Hourly pay in the range of $23.00–$24.00, depending on experience and qualifications.
  • Fully remote work with a supportive, remote-friendly 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.

If you’re detail-obsessed, steady under deadlines, and ready to own a high-impact operational role from home, this deserves a spot at the top of your list.

Lock in a remote position where your accuracy and follow-through directly protect clients and their plans.

Happy Hunting,
~Two Chicks…

APPLY HERE.

EDI Coordinator – Remote

Work from home in a role that actually keeps the whole operation moving. As an EDI Coordinator, you’ll be the person making sure critical data files get where they need to go, on time, clean, and ready for payment and processing.

About Allied Benefit Systems
Allied Benefit Systems is a Chicago based benefits administrator that partners with employers nationwide to deliver flexible, self-funded health plan solutions. The company focuses on efficient operations, client service, and smart use of data to manage costs and improve the member experience. Allied embraces a remote friendly culture where strong communicators and detail driven problem solvers can thrive from anywhere.

Schedule
Full-time, fully remote role based out of Chicago, Illinois.
Standard weekday office hours with extended computer work in a home office environment.
Requires reliable high speed internet via cable or fiber (minimum 100 Mbps download / 25 Mbps upload) to support file transfers and system access.

What You’ll Do

  • Receive and submit daily files to and from various vendors.
  • Process 837 files and convert them into .txt files for use in internal systems.
  • Prepare files to be loaded into internal processing systems for claims, eligibility, and payment workflows.
  • Conduct eligibility checks by matching enrollee and member demographics to the internal master database.
  • Accurately route completed claims to the correct internal mailboxes and departments.
  • Perform data entry and monitor EDI databases for any issues or anomalies.
  • Document processing workflows and support internal staff and external trading partners with EDI related questions.
  • Upload outbound files and download inbound files each day, recording file counts and batch audits.
  • Identify and resolve failed transactions, including missing acknowledgements.
  • Perform other related duties as assigned.

What You Need

  • High school diploma or GED.
  • Data entry experience; ability to type at least 6,000 keystrokes per hour with accuracy.
  • Basic knowledge of Word, Excel, and Access; prior experience with Access and Excel is a plus.
  • Strong attention to detail and accuracy in all data handling.
  • Ability to handle multiple tasks at once and stay organized.
  • Good problem solving skills and a self motivated mindset.
  • Ability to work both independently and as part of a team in a remote environment.
  • Clear, professional communication skills.

Benefits

  • Hourly pay in the range of 20 to 21 dollars per hour, depending on experience.
  • Fully remote role with a remote friendly culture and support to set you up for success.
  • Medical, Dental, Vision, Life, and Disability insurance.
  • Generous Paid Time Off.
  • Tuition Reimbursement and Employee Assistance Program (EAP).
  • Technology stipend to help cover remote work needs.

If you’re detail obsessed, comfortable living in spreadsheets and systems, and want a stable remote role in the benefits world, this is a strong option.

Lock in a work from home job where accuracy, consistency, and quiet focus really matter.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Case Manager I – Remote

Use your health insurance and case management experience to actually change member outcomes, not just push paperwork. This fully remote Case Manager I role lets you weave together vendors, clinicians, and members to build care plans that improve health and control costs.

About Allied Benefit Systems
Allied Benefit Systems is a Chicago based benefits administrator that partners with employers nationwide to design and manage self funded group health plans. They specialize in flexible, cost effective benefit solutions backed by strong client service and clinical programs like Enhanced Case Management. Allied’s remote friendly culture is built on accountability, communication, and helping members navigate complex healthcare with confidence.

Schedule
Full time, fully remote position based out of Chicago, Illinois.
Standard weekday business hours with occasional flexibility needed to meet deadlines and member or client needs.
Home office setup with reliable high speed internet (minimum 100 Mbps download / 25 Mbps upload) required for systems access and virtual collaboration.

What You’ll Do

  • Review clinical notes, claims data, and baseline case information for members across multiple health scenarios, including behavioral health, wellness, specialty prescriptions, and maternity.
  • Develop strategic care plans that connect members to specialized vendor partners and Allied Care Clinicians who can best support their needs.
  • Implement care plans by coordinating with members, clients, internal Allied teams, and vendor partners to keep services aligned and moving.
  • Work closely with the Clinical Case Management team and other Case Managers to obtain clinical information, present cases, and collaboratively troubleshoot escalated issues.
  • Communicate with the Centers for Medicare & Medicaid Services (CMS) and other carriers to obtain essential member information.
  • Facilitate and maintain prescription drug vendor relationships, including member setup, ongoing support, and pricing negotiations when needed.
  • Document the impact of casework to highlight both cost savings and improved member health outcomes tied to the care plan.
  • Complete weekly and monthly administrative tasks to keep reporting, documentation, and workflow current.
  • Serve as a liaison between clients, brokers, members, Allied executives, and internal departments to keep everyone aligned on case status and strategy.
  • Identify opportunities to improve internal processes within Enhanced Case Management and across Allied departments, and collaborate on solutions.

What You Need

  • Bachelor’s degree or equivalent work experience.
  • At least 2 years of experience with group health insurance and self funded health plans.
  • Excellent verbal and written communication skills with strong customer service instincts.
  • Strong organizational skills, attention to detail, and the ability to manage multiple cases and deadlines at once.
  • Demonstrated ability to review information, assess problems, and propose realistic, effective solutions.
  • Solid analytical and problem solving skills.
  • Proficiency with Microsoft Office Suite or similar software.
  • Preferred: Experience with Medicare, Medicaid, case management, and prescription drug benefits.
  • Preferred: Background in a clinical role, social work, or hospital system environment.
  • Preferred: Life and Health Insurance Producer License (not required).

Benefits

  • Salary range of $48,000 to $55,000 per year, based on experience and qualifications.
  • Remote first culture with support to set you up for success at home.
  • Medical, Dental, and Vision insurance.
  • Life and Disability insurance.
  • Generous Paid Time Off.
  • Tuition Reimbursement.
  • Employee Assistance Program (EAP).
  • Technology stipend to support your remote work setup.

If you know your way around self funded health plans and want a remote role where case management actually drives outcomes, this is worth a serious look.

Put your experience to work for members who truly need an advocate on their side.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Medical Billing Specialist I – Remote

Work from home while keeping the numbers clean and the cash flow steady. This remote Medical Billing Specialist role is built for someone who loves invoices, accuracy, and getting accounts right the first time.

About Allied Benefit Systems
Allied Benefit Systems is a Chicago based benefits administrator that partners with employers to deliver flexible, cost effective health benefit solutions. The company supports clients across the country with customized plan designs, strong service, and a focus on efficient administration. Allied values accountability, customer focus, and technical excellence in a fully remote friendly culture.

Schedule
Full time, fully remote role based out of Chicago, Illinois.
Standard office hours with extended computer work in a home office environment.
Requires reliable high speed internet (minimum 100 Mbps download and 25 Mbps upload via cable or fiber) to stay connected and productive.

What You Will Do

  • Process and submit accurate and timely invoices to clients.
  • Follow up on outstanding payments and resolve billing discrepancies.
  • Communicate with clients about billing questions, payment status, and account updates.
  • Maintain detailed, accurate records of all billing and collection activity.
  • Assist with month end closing and reporting tasks.
  • Collaborate with internal departments to ensure accurate and timely billing.
  • Set up new client accounts for the new book of business and update existing accounts as needed.
  • Audit accounts to confirm that setups and changes were allocated correctly.
  • Create and maintain Excel spreadsheets and Access databases to track services and activity for multiple clients.
  • Assist with file imports using multiple systems, state reporting calculations and filings, and client invoicing and audits.
  • Perform other related duties as assigned.

What You Need

  • High school diploma or equivalent.
  • At least 2 years of experience in billing and collections.
  • Strong communication and problem solving skills.
  • Proficiency with Microsoft Office and familiarity with accounting or billing software.
  • Strong attention to detail and accuracy in all work.
  • Ability to work independently and as part of a team.
  • Comfort working in a computer based role with extended periods of sitting.

Benefits

  • Hourly pay of 20 dollars per hour.
  • Remote first work environment and culture.
  • Medical, Dental, and Vision insurance.
  • Life and Disability insurance.
  • Generous Paid Time Off.
  • Tuition Reimbursement.
  • Employee Assistance Program.
  • Technology stipend to support remote work.

Remote billing roles with stable pay and real benefits are not on the market forever.

If you are organized, numbers focused, and ready to work from home for a growing benefits company, this is your sign to move.

Happy Hunting,
~Two Chicks…

APPLY HERE.