Underwriting Service Specialist II – Remote

Two sentences that grab attention and tell remote job seekers why this role matters.
This role is all about keeping Workers’ Comp policies accurate from day one through renewal, so small businesses stay protected and compliant. If you’re the person who catches what others miss and can process cleanly at speed, you’ll be a backbone of the underwriting lifecycle.

About Pie Insurance
Pie Insurance helps small businesses thrive by making commercial insurance more affordable and easier to buy and manage. They use technology to modernize the commercial insurance experience, with a mission-driven, values-led team.

Schedule

  • Full-time
  • Remote (U.S. only; territories excluded)
  • Reliable high-speed internet required

What You’ll Do

  • Process Workers’ Comp policies across the lifecycle (issuance, endorsements, policy changes, renewal prep)
  • Complete midterm change endorsements and entity changes
  • Handle cancel/rewrites and other policy updates as needed
  • Coordinate with renewal teams on significant in-term changes to support year-over-year review accuracy
  • Support rate verification/testing and batch processing work across rating platforms
  • Assist with corrective endorsements tied to Workers’ Comp bureau error reports
  • Partner with Product, Compliance, Engineering to test rates and system functionality and provide feedback
  • Support underwriting assistant and underwriting teams with data entry and file prep when needed

What You Need

  • High school diploma or GED
  • 3+ years of commercial insurance experience
  • Strong problem-solving with minimal direction
  • Proven self-management of deliverables, timelines, and follow-through
  • Ability to multitask and hit deadlines in a fast-paced environment
  • High attention to detail and accurate transcription between sources
  • Strong written and verbal communication, with the ability to adjust to different audiences
  • Comfort with cloud-based tools (Microsoft Office, Google Workspace, Slack, Salesforce, Adobe) and learning new systems quickly
  • Some experience leading small workgroups or task forces on specific projects (developing leadership)

Benefits

  • Competitive cash compensation
  • Equity (a “piece of the pie”)
  • Comprehensive health plans
  • Generous PTO
  • 401(k) match
  • Parental and caregiver leave
  • Potential discretionary bonus eligibility (based on company performance and role eligibility)

Roles like this move fast. If your strength is clean processing, policy accuracy, and owning the details without being babysat, this one’s a solid fit.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Entry Data Specialist – Remote

Two sentences that grab attention and tell remote job seekers why this role matters.
This role is all about making internal automation and AI workflow pilots actually work in the real world. You’ll test prototypes, track adoption, and document what’s changing so the business can scale improvements without chaos.

About Keller Executive Search
Keller Executive Search is a global executive search firm that recruits senior leaders for prominent brands and organizations. This role sits within Keller’s internal team, supporting productivity and process improvements in a fast-paced professional services environment.

Schedule

  • Full-time
  • Remote (listed in Chicago, IL)

What You’ll Do

  • Assist with testing prototypes, collecting feedback, and iterating improvements
  • Maintain lightweight dashboards to track adoption and performance
  • Support internal pilots focused on automation and AI-enabled workflows
  • Document use cases, success criteria, and change impacts for stakeholders
  • Partner with IT and operations to ensure solutions are secure and scalable
  • Use tools like Power Automate to track work, report progress, and maintain documentation

What You Need

  • Hands-on interest in automation, analytics, or AI-enabled productivity tools
  • Comfort learning new tools quickly and documenting findings clearly
  • Ability to translate business needs into problem statements and test plans
  • Strong collaboration skills across technical and non-technical teams
  • Willingness to follow established processes with consistent accuracy

Benefits

  • Salary range: $73,000–$89,000
  • Full medical coverage
  • Paid time off and company-recognized holidays
  • Wellbeing support and employee assistance resources
  • Training, mentorship, and cross-functional growth opportunities
  • Flat management structure with direct access to decision-makers
  • Access to learning resources, courses, and internal knowledge sharing

If you like the idea of being the “make it real” person for automation pilots, this is in your lane.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Data Entry Clerk – Remote

Two sentences that grab attention and tell remote job seekers why this role matters.
If you’re the kind of person who can spot a tiny data mistake from a mile away, this job is for you. You’ll help keep fuel, sales, and inventory data clean and accurate so operations run smoothly across multiple locations.

About Las Vegas Petroleum
Las Vegas Petroleum operates in the fuel distribution and travel center space, supporting gas stations, convenience stores, and truck stops. They focus on reliable service and operational accuracy as they grow across multiple markets.

Schedule

  • Remote (United States)
  • Full-time (schedule details not listed)

What You’ll Do

  • Enter and maintain data tied to fuel supply, sales, and inventory across locations
  • Review and verify data for discrepancies and correct issues quickly
  • Generate reports that support internal decision-making
  • Update databases with new and relevant information while maintaining accuracy
  • Coordinate with other departments to support information flow
  • Support administrative tasks and assist with cash reconciliation as needed

What You Need

  • Prior data entry experience or similar role
  • Strong attention to detail and accuracy
  • Proficiency with Microsoft Office, especially Excel
  • Strong organization skills and ability to prioritize tasks
  • Clear communication skills and team mindset
  • Ability to work independently and handle sensitive information discreetly

Benefits

  • Weekly pay
  • Competitive hourly wage
  • Growth and advancement opportunities
  • Medical, dental, and vision insurance
  • Retirement plan (401k, IRA)
  • Paid time off (vacation and sick pay)

If you want a steady remote role where accuracy actually matters, this is a solid one to move on.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Data Entry & Content Review Specialist – Remote

This is a 1099, fixed-term contractor role focused on validating biomedical article metadata and linking citations correctly. It’s detail-heavy, accuracy-driven work with a clear throughput target, and it comes with federal credentialing requirements, including in-person badge pickup in Bethesda, MD.

About CloudFactory
CloudFactory is a mission-driven company supporting AI and data quality work at scale through a global network of experts. Their focus is turning messy data into reliable, usable information that powers real-world AI and research systems.

Schedule

  • Remote (USA)
  • 1099 Independent Contractor
  • Fixed-term project: Estimated Feb 1, 2026 – Oct 1, 2026
  • System access typically available 24/7 (flexible work hours)

What You’ll Do

  • Validate structured metadata for biomedical journal articles in specialized systems
  • Identify and record research funding acknowledgments and grant identifiers
  • Link related citations (errata, retractions) and dataset DOIs (ex: GenBank, Dryad, Figshare)
  • Apply correct citation status indicators and filter non-citable items per data standards
  • Maintain productivity targets of about 35 citations/hour while meeting accuracy expectations
  • Work independently and manage your own workflow while passing periodic quality audits

What You Need

  • High school diploma required (Bachelor’s in Life Sciences/Library Science preferred)
  • Experience with data entry, metadata review, or structured data validation
  • Ability to read and interpret scientific journal articles and publisher sites
  • Comfort working with XML-formatted citations and structured data systems
  • Professional-level English reading comprehension
  • Provide your own computer + high-speed internet
  • PIV card reader required (you supply it)
  • Able to meet milestones across the Feb–Oct term

Benefits

  • 1099 contractor role (benefits typically not included)
  • Background check cost is covered by the company (per posting)

Must-Know Requirements Before You Apply

  • Tier 1 federal background check required (no felony convictions or pending legal proceedings listed as the standard)
  • Fingerprinting required (in-person, about 30 days; covered)
  • Mandatory in-person credentialing in Bethesda, Maryland to pick up a federal work badge once approved (estimated Jan 25–Feb 15, 2026)

Quick gut-check (because this one can backfire if you gloss over it):
If you can’t realistically travel to Bethesda, MD for the badge pickup, don’t apply. Everything else is workable. That one is non-negotiable.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Senior Claim Benefit Specialist – Remote

This is a higher-responsibility claims role: you’re adjudicating complex claims, handling appeals and reconsiderations, doing rework calculations, and acting like the “go-to” when things get messy. The big catch: you need a New York Independent Adjuster License.

About CVS Health
CVS Health delivers health solutions through its nationwide footprint and digital channels, supporting millions of members with a focus on more connected, convenient care and service.

Schedule

  • Full-time, remote
  • 40 hours/week
  • Application window closes 02/27/2026

What You’ll Do

  • Review and adjudicate complex and sensitive claims per plan guidelines
  • Apply medical necessity guidelines and verify coverage and eligibility
  • Identify discrepancies and apply cost-containment measures
  • Handle phone and written inquiries for pre-approvals, pre-authorizations, reconsiderations, and appeals
  • Ensure compliance requirements are met and payments align with policies
  • Identify and report overpayments, underpayments, and other claim irregularities
  • Perform claim rework calculations
  • Make outbound calls to collect missing details for claims and reconsiderations
  • Support the team by distributing daily work assignments to junior staff
  • Train, coach, and mentor claim benefit specialists as a subject matter expert

What You Need

  • New York Independent Adjuster License (required)
  • Experience in a production environment
  • Ability to manage multiple assignments accurately and efficiently
  • High school diploma required
  • Associate degree or equivalent work experience preferred

Benefits

  • Medical plan options
  • 401(k) with matching contributions
  • Employee stock purchase plan
  • Wellness programs, counseling, and financial coaching
  • PTO, flexible schedules, family leave, dependent care resources, tuition assistance (varies by eligibility)

Pay

  • Typical range: $18.50 – $42.35/hour (final offer depends on experience, education, geography, and other factors)
  • Eligible for bonus/commission/short-term incentive programs depending on role and plan

Quick reality check: if you don’t already have that NY Independent Adjuster License, this one is basically a “not yet” job, not a “maybe” job. If you do have it, tell me what claims world you’re coming from (medical, auto, workers comp, self-funded), and I’ll help you angle your resume bullets so you don’t look like a generalist.

Happy Hunting,
~Two Chicks…

APPLY HERE.

Billing Associate I – Remote

If you like detail-heavy work and want a solid entry-level lane into billing and revenue cycle, this role is about reviewing and repricing bills using state and federal guidelines to create savings for clients.

About One Call
One Call helps injured workers get the care they need when they need it by supporting care coordination and related services. They operate as a remote-first company with a mission-driven culture built around teamwork, speed, and customer care.

Schedule

  • Full-time
  • Remote (work from home)
  • Ongoing applications (no deadline listed)

What You’ll Do

  • Review bills submitted by payors and partners through One Call’s retrospective billing program
  • Apply state and federal guidelines, fee schedules, and customer-specific rules to reprice bills and generate savings
  • Stay current on billing protocols, regulations, and internal procedures that impact processing
  • Research billing errors and initiate/resolution actions
  • Respond to internal and external customer inquiries in a timely way
  • Maintain process documentation for assigned tasks
  • Communicate with internal departments to resolve discrepancies
  • Flag trends and improvement opportunities to support efficiency and accuracy
  • Handle sensitive information and maintain confidentiality

What You Need

  • High school diploma or GED
  • Knowledge or ability to learn billing rules/regulations (state and federal)
  • Strong attention to detail and organization
  • Solid verbal and written communication skills
  • Comfortable navigating systems and working on a computer all day
  • Ability to manage multiple tasks, meet productivity expectations, and stay focused
  • Proficiency with Microsoft Office
  • Ability to work independently and within a team

Benefits

  • Remote-first flexibility
  • Generous time off (minimum 18 PTO days, plus 8 company holidays and 2 personal days)
  • Medical, dental, vision, and pet insurance
  • 401(k) with matching
  • Company-paid life insurance and short/long-term disability
  • Colleague Assistance Program (counseling and financial services)
  • One Call Foundation support for unexpected hardships

Pay

  • Salary range listed: $17.50–$25.35/hour
  • Entry-level associate role (typically less than 1 year of office and/or billing experience)
  • Works under close supervision and follows standard procedures

This is the kind of job where accuracy is the whole game. If you’re the “let me double-check that” type, you’ll fit.

Happy Hunting,
~Two Chicks…

APPLY HERE.