Underwriting Assistant – Remote

Join a leading specialty insurance company and support underwriting teams with critical transaction and policy operations. This remote role offers a balance of detailed work, collaboration, and career growth in a respected industry leader.

About Crum & Forster
Crum & Forster (C&F), established in 1822, is a specialty and commercial insurance provider with a financial strength rating of “A+” (Superior) by AM Best. With more than 2,000 employees across the U.S., C&F is recognized as a Great Place to Work® (2024) for its commitment to people, diversity, equity, and inclusion. As part of Fairfax Financial Holdings, C&F combines strong financial backing with a culture of innovation and service.

Schedule

  • Fully remote position (based in Southfield, MI)
  • Full-time role within Surplus & Specialty division
  • Salary range: $34,400 – $64,600 annually (depending on experience)

What You’ll Do

  • Provide pre-quote support, validating underwriting data (auto classification, GL classification, losses, etc.)
  • Assist with documentation review and producer communication prior to binding coverage
  • Process bind orders, issue policies, and ensure data accuracy in internal systems
  • Manage post-bind activities including endorsements, cancellations, reinstatements, and inspections
  • Report policy data to regulatory agencies and resolve any criticisms
  • Support underwriters by booking premiums and maintaining policy documentation
  • Collaborate with cross-functional teams to streamline processes and resolve issues
  • Contribute to special projects and continuous improvement efforts

What You Need

  • 1–3 years of insurance operations experience (surplus lines preferred)
  • Strong knowledge of policy issuance and post-bind operations
  • College degree preferred
  • Proficiency in Microsoft Word, Excel, and internet-based systems
  • Excellent math, data analysis, and problem-solving skills
  • High attention to detail and accuracy in reviewing, entering, and processing transactions
  • Ability to thrive in a fast-paced environment with shifting priorities
  • Strong communication and teamwork skills

Benefits

  • Competitive compensation package
  • 401(k) with generous employer match
  • Employee Stock Purchase Plan with company match
  • Comprehensive health, dental, and vision coverage
  • Generous Paid Time Off and wellness-focused programs
  • Tuition reimbursement, professional training, and certification support
  • Volunteer opportunities, donation matching, and employee-driven giving programs

Applications are being accepted now—this is your chance to build a career with a respected insurer known for excellence and innovation.

Be part of a team where your detail-oriented work helps drive success.

Happy Hunting,
~Two Chicks…

APPLY HERE

Provider Enrollment Coordinator – Remote

Support a world-class healthcare system by managing the enrollment and credentialing process for providers. This remote role blends administrative precision, payer coordination, and team collaboration in a mission-driven environment.

About Mass General Brigham
Mass General Brigham is a not-for-profit healthcare system built on the legacy of New England’s most prestigious hospitals. We advance patient care, research, teaching, and community service while shaping the future of medicine. Every role here is part of a team dedicated to changing lives.

Schedule

  • Fully remote role
  • Full-time position
  • Hourly rate: $19.42 – $27.74 (depending on experience)

What You’ll Do

  • Prepare, collect, and submit enrollment and re-enrollment applications to insurance carriers
  • Manage CAQH IDs, update systems, and ensure compliance with payer requirements
  • Enter enrollment details into online portals and track approval status
  • Submit re-enrollment/revalidation paperwork on payer schedules
  • Coordinate with Revenue Cycle Operations, Credentialing, and other departments on enrollment issues
  • Provide support to providers and staff regarding enrollment processes
  • Maintain usernames, passwords, and provider records securely in enrollment systems
  • Handle additional projects and ad hoc duties as assigned

What You Need

  • Bachelor’s degree preferred (or directly related experience in lieu of degree)
  • 1–3 years of experience in healthcare (provider enrollment, credentialing, or billing preferred)
  • CPCS certification a plus
  • Knowledge of managed care and provider credentialing processes helpful
  • Strong analytical and problem-solving abilities
  • Excellent communication and organizational skills
  • Proficiency in Microsoft Office (Word, Excel)
  • Ability to work independently, manage multiple priorities, and adapt in a fast-paced environment

Benefits

  • Competitive hourly pay with differentials and premiums as applicable
  • Comprehensive medical, dental, and vision benefits
  • 401(k) retirement plan with employer contributions
  • Paid time off, recognition programs, and career advancement opportunities
  • Inclusive, supportive culture that values growth and collaboration

Applications are open now—become part of a team where administrative excellence supports better patient care every day.

Your detail-oriented work can help power the future of healthcare.

Happy Hunting,
~Two Chicks…

APPLY HERE

Assistant Billing Manager – Remote

Advance your career in healthcare billing while supporting one of the most respected hospital systems in the world. This role combines leadership, analysis, and hands-on billing responsibilities in a collaborative, mission-driven environment.

About Mass General Brigham
Mass General Brigham is a not-for-profit healthcare system built on the legacy of two of New England’s leading academic medical centers. We advance patient care, research, teaching, and community service. Our teams drive medical innovation while delivering compassionate care, making every role vital in improving lives.

Schedule

  • Fully remote role (based in Somerville, MA)
  • Full-time position with opportunities for growth
  • Salary range: $62,400 – $90,750 annually (depending on experience)

What You’ll Do

  • Assist the Billing Manager with client relationships and revenue cycle activities
  • Review and distribute reports, research billing inquiries, and manage charge reconciliation
  • Support procedure code dictionary maintenance and other master files
  • Research and respond to patient/customer service inquiries
  • Analyze monthly rejection details and resolve edits in EPIC work queues
  • Review accounts for write-off and document collection efforts
  • Assist with onboarding, training, and supporting new staff

What You Need

  • High School Diploma or equivalent required; Associate’s degree preferred
  • 2–3 years of billing or revenue cycle experience
  • Strong knowledge of medical billing practices and payer requirements
  • Proficiency with billing software and electronic health record (EHR) systems (EPIC experience preferred)
  • Excellent leadership, analytical, and problem-solving skills
  • Strong interpersonal communication and ability to work under pressure with accuracy

Benefits

  • Comprehensive medical, dental, and vision coverage
  • 401(k) retirement plan with employer contributions
  • Generous paid time off and recognition programs
  • Career advancement opportunities across the healthcare system
  • Premiums, bonuses, and differentials where applicable

Applications are being accepted now—take the next step in your career with a healthcare system known for excellence and innovation.

Your leadership in billing can help change lives.

Happy Hunting,
~Two Chicks…

APPLY HERE

General Virtual Assistant – Remote

Step into a versatile virtual role where you’ll handle tasks that keep businesses organized and running smoothly. This fully remote opportunity offers flexibility, training, and long-term growth potential.

About Wing
Wing is on a mission to redefine the future of work by helping companies build world-class teams and put their operations on autopilot. We provide global support services with an inclusive, supportive culture designed for long-term success.

Schedule

  • Fully remote, US-based position
  • 20–40 hours per week, US work hours
  • Flexible workload depending on client needs

What You’ll Do

  • Organize and store documents, files, and company data
  • Perform data entry: lead lists, meeting minutes, payroll info, and research notes
  • Research products, purchase goods, and secure samples
  • Support marketing and sales campaigns via CRM systems
  • Manage invoicing, payments, and expense tracking
  • Prepare trend and comparative analysis reports
  • Monitor projects and coordinate internal communication
  • Manage team calendars, book travel, and schedule meetings
  • Answer calls, set appointments, and follow up on inquiries
  • Manage inboxes and email correspondence
  • Handle ad hoc administrative tasks

What You Need

  • 6 months to 1 year of experience as a Virtual Assistant
  • High school diploma or equivalent
  • Excellent phone, email, and instant messaging communication skills
  • Strong organizational and time management abilities
  • Proficiency with MS Office and spreadsheets
  • Knowledge of cloud services, VoIP, and online calendars (e.g., Google Calendar)
  • Tech-savvy, proactive, and eager to learn
  • Age 18+

Technical Requirements

  • USB headset with noise cancellation
  • Working webcam
  • Computer: minimum 1.8 GHz processor and 4GB RAM
  • Reliable wired internet: 25 Mbps main / 10 Mbps backup

Benefits

  • Salary: $2,400–$3,600/month (based on experience)
  • Performance incentives
  • Paid training and upskilling opportunities
  • Holiday and overtime pay
  • 100% work-from-home
  • Job security and stability
  • Supportive team culture with career growth opportunities
  • Fun and inclusive work environment

Applications are being accepted now—don’t wait to secure your place in a fast-growing remote-first company.

Build your career as a trusted virtual professional with Wing.

Happy Hunting,
~Two Chicks…

APPLY HERE

Digital Marketing Specialist – Remote

Step into a fast-paced digital marketing role where you’ll help build campaigns, manage branding, and drive engagement for a company reshaping the future of work. This is a fully remote opportunity with growth potential and immediate start.

About Wing
Wing is redefining the future of work by helping companies worldwide build world-class teams and automate operations. We are a one-stop shop for scaling organizations, powered by an inclusive, innovative culture and a global team.

Schedule

  • Fully remote, US-based role
  • 20–40 hours per week, US work hours
  • Flexible workload depending on level of experience

What You’ll Do

  • Manage and update accounts, graphics, videos, and reviews
  • Develop and execute multi-platform marketing campaigns
  • Ensure branding consistency across all channels
  • Build and manage customer engagement events or promos
  • Oversee lead generation, influencer outreach, and affiliate partnerships
  • Track KPIs, adjust bids/budgets, and review keyword performance
  • Conduct SEO strategies and content research
  • Create reports and monitor campaign effectiveness
  • Support general administrative and ad hoc marketing tasks

What You Need

  • Bachelor’s degree or professional certification in marketing/business
  • 2+ years in social media or 1–2 years in digital marketing
  • Strong content writing/copywriting skills with a portfolio of work
  • Proficiency with Adobe Photoshop, Illustrator, Sketch, InDesign, or similar tools
  • Strong knowledge of CMS platforms and SEO
  • Excellent written and verbal English (B2+ level)
  • Organizational and time management skills
  • Technical setup: USB headset with noise cancellation, webcam, and reliable internet (25 Mbps main / 10 Mbps backup)

Benefits

  • Salary: $3,200–$5,000/month (based on experience level)
  • Performance incentives
  • Paid training and upskilling opportunities
  • Holiday and overtime pay
  • Job stability and career growth opportunities
  • 100% remote, inclusive team culture
  • Fun and supportive work environment

Hiring now—don’t miss the chance to grow your digital marketing career with a company leading the shift toward remote-first work.

Your next career step starts here.

Happy Hunting,
~Two Chicks…

APPLY HERE

Employee Benefits Underwriting Analyst – Remote

Use your analytical skills to deliver strategic benefits solutions for clients across the U.S. This fully remote role offers growth, collaboration, and the chance to make a measurable impact.

About Alera Group
Founded in 2017, Alera Group has grown into one of the largest independent insurance and financial services firms in the U.S. We help clients succeed in Employee Benefits, Property & Casualty Insurance, Retirement Services, and Wealth Solutions. With a nationwide network, we combine local service with national expertise. Propel, an Alera Group company, is seeking talented colleagues ready to drive results.

Schedule

  • Fully remote position
  • Preference for candidates in Eastern or Central time zones
  • Full-time role with competitive salary: $50,000–$80,000 annually (based on experience)

What You’ll Do

  • Develop onboarding materials, renewal projections, benchmarking reports, and contribution models
  • Roll over and adapt client templates for plan year changes
  • Produce utilization, financial, and experience reports for high-value clients
  • Prepare funding analyses and comparative models for optimized plan design
  • Negotiate with carriers to secure competitive rates and products
  • Communicate insights through calls, emails, and presentations
  • Support training, workflow tracking, and compliance updates

What You Need

  • 3+ years of experience in the Employee Benefits industry
  • Bachelor’s degree, ideally in a mathematical field
  • At least 1 year in an Excel-intensive role
  • Proficiency with pivot tables, complex formulas, and data visualization
  • Knowledge of tools like ImageRight, BenefitPoint, Springbuk, Deerwalk, or Domo a plus
  • Strong organizational, verbal, and written communication skills
  • Analytical mindset with accuracy and decisiveness

Benefits

  • Medical, dental, life, and disability insurance
  • 401(k) with employer contributions
  • Generous paid time off
  • Comprehensive benefits package supporting balance and growth

Interviews are happening now—don’t miss this opportunity to apply your expertise in a role with national impact.

Shape the future of employee benefits with Alera Group.

Happy Hunting,
~Two Chicks…

APPLY HERE