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Remote Health Insurance Jobs in Chesterfield, VA

Accounting Fly

Remote Senior Accountant

Richmond, VA · Remote

$70K - $85K/yr

Remote Senior Accountant - Small Business Tax & Accounting Job ID: 1045542 Date Posted: August 26 ... Monthly health insurance stipend, 401(k) with employer match, internet reimbursement, and a home ...

WB Agency

Sales Agent (Insurance)

Richmond, VA · On-site +1

$70K - $100K/yr

State insurance license (Life/Health) or ability to obtain one. * Strong communication ... Combination of fieldwork (meeting clients at their location) and remote/office-based work. * May ...

Planright

Sales Agent (Insurance)

Richmond, VA · On-site +1

$70K - $100K/yr

State insurance license (Life/Health) or ability to obtain one. * Strong communication ... Combination of fieldwork (meeting clients at their location) and remote/office-based work. * May ...

Camesiagency

Entry Level Sales Specialist

Richmond, VA · Remote

$80K - $130K/yr

... Health insurance license; licensing support and guidance provided. * Reliable computer, high-speed internet connection, and a quiet workspace for client calls. What We Offer * 100% remote work with a ...

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Showing results 41-60

All JobsHealth Insurance JobsRemote Health Insurance JobsRemote Health Insurance Jobs in Chesterfield, VA

Remote Health Insurance information

See Chesterfield, VA salary details

$59.4K

$78.1K

$98.9K

How much do remote health insurance jobs pay per year?

As of Sep 2, 2026, the average yearly pay for remote health insurance in Chesterfield, VA is $78,053.00, according to ZipRecruiter salary data. Most workers in this role earn between $70,400.00 and $80,800.00 per year, depending on experience, location, and employer.

What are remote health insurance jobs?

Remote health insurance jobs involve working in sales or providing customer service to policy-holders. As a work-from-home insurance agent, you sell healthcare policies to customers. You communicate with each customer by phone or internet to define their coverage needs, then help them select an insurance plan that has the benefits to meet those needs. Your duties can include assisting clients as they complete paperwork to obtain coverage and answering questions from new or existing policy-holders.

What are some common challenges of working in a remote health insurance role, and how can they be managed?

A common challenge in remote health insurance roles is maintaining effective communication with both clients and team members, as much of the work relies on virtual interactions. To manage this, professionals often use secure digital platforms and regularly scheduled video meetings to stay connected. Another challenge is staying updated with changing regulations and insurance policies, which requires proactive participation in ongoing training and close collaboration with compliance teams. Time management and self-motivation are also crucial, as remote work requires balancing multiple tasks independently throughout the day.

What are the key skills and qualifications needed to thrive as a remote health insurance specialist, and why are they important?

To thrive as a Remote Health Insurance Specialist, you need a solid understanding of health insurance policies, claims processing, and regulatory compliance, often supported by a relevant degree or insurance license. Familiarity with CRM software, claims management systems, and digital communication tools is typically required. Strong attention to detail, problem-solving skills, and effective virtual communication set top performers apart. These skills ensure accurate claim handling, regulatory adherence, and excellent customer service in a remote work environment.

What is the difference between Remote Health Insurance vs Remote Medical Claims Processor?

AspectRemote Health InsuranceRemote Medical Claims Processor
Required CredentialsInsurance licenses, knowledge of health policiesMedical billing certifications, claims processing knowledge
Work EnvironmentHome-based, insurance companies or brokersHome-based, healthcare providers or insurance companies
Industry UsageInsurance industry, health plansHealthcare providers, insurance companies
Common Search/ComparisonRemote health insurance vs remote medical claims processor

Remote Health Insurance professionals focus on selling, managing, or advising on health insurance policies, often requiring licensing and industry knowledge. Remote Medical Claims Processors handle the review and processing of medical claims, typically needing billing certifications. Both roles are home-based and serve the healthcare and insurance sectors, but they differ in responsibilities and credentials.

More about Remote Health Insurance jobs

What job categories do people searching Remote Health Insurance jobs in Chesterfield, VA look for?

The top searched job categories for Remote Health Insurance jobs in Chesterfield, VA are:

What cities near Chesterfield, VA are hiring for Remote Health Insurance jobs?

Cities near Chesterfield, VA with the most Remote Health Insurance job openings:

Remote Health Insurance jobs near you
Infographic showing various Remote Health Insurance job openings in Chesterfield, VA as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 18% Part Time, 3% Temporary, and 5% Contract. Highlights an 92% Physical, 1% Hybrid, and 7% Remote job distribution, with an average salary of $78,053 per year, or $37.5 per hour.

Remote Senior Accountant

Accounting Fly

Richmond, VA • Remote

$70K - $85K/yr

Full-time

Medical, Retirement, PTO

Re-posted 17 days ago

Job description

Job Title: Remote Senior Accountant - Small Business Tax & Accounting
Job ID: 1045542
Date Posted:  August 26, 2026
Employment Type: Full-time
Hiring Company: Confidential
Location: US Remote 
Applicants must be located in the United States and available during EST business hours.
Base Salary: $70,000–$85,000 per year (USD) 
Commensurate with experience.
Role Summary
 We are a growing CPA firm—not a corporate accounting department—looking for an experienced public accountant who loves working with small business owners. This isn't just about processing transactions; it's about taking ownership of client relationships and helping entrepreneurs succeed. If you've "been in the trenches" of a CPA firm and enjoy a mix of tax, high-level bookkeeping, and advisory work in a flexible, remote setting, you’ll fit right in.
Key Responsibilities
  • Tax Delivery: Independently prepare business (1120S, 1065) and individual (1040) returns and assist with proactive year-round tax planning.
  • Full-Cycle Accounting: Manage monthly bookkeeping, payroll, sales tax, and financial reporting for a dedicated group of clients.
  • The "Detective" Work: Take the lead on complex cleanup projects, turning disorganized records into clean, actionable financials.
  • Client Connection: Serve as the primary point of contact for your clients, answering their questions and leading them through onboarding with a helpful, expert touch.
  • Advisory Support: Assist with budgeting and financial analysis to help clients understand their "numbers" better.

Qualifications/Requirements
  • The Right Experience: 4+ years in a CPA firm or public practice (Corporate-only experience is not a fit for this role).
  • Tax Skills: You can prepare small business and individual returns from start to finish without hand-holding.
  • Tech Savvy: Advanced QuickBooks Online skills and experience with professional tax software (e.g., Drake, Lacerte, or UltraTax).
  • The Mindset: You enjoy "messy" books, love solving problems, and communicate clearly with non-accountants.
  • Certification: Already a CPA/EA or actively working toward your license.

Compensation & Growth
This isn't a dead-end staff position; you are helping build a firm alongside the owner in a culture that values quality over quantity. We focus on doing excellent work for the right clients rather than churning through volume.
  • Flexibility & Balance: Truly remote work with a trust-based, flexible PTO policy and sustainable "busy season" hours.
  • Full Benefits: Monthly health insurance stipend, 401(k) with employer match, internet reimbursement, and a home office setup budget.
  • Investment in You: We cover full CPA/EA exam materials and fees, provide an annual CE allowance, and offer direct mentorship.
  • Modern Culture: Collaborative environment with zero hierarchy and access to the latest cloud-based software and technology.
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About Accountingfly

Sourced by ZipRecruiter

In 2016, Accountingfly determined that fully-remote recruiting was the future of accounting staffing, offering huge benefits for employers, job-seekers, and our own business. We decided to focus our recruiting business on those companies offering only remote work opportunities—and it was the best decision we ever made. While our competitors struggle to adapt to the remote world, we lean on years of experience to provide unmatched remote accounting recruitment expertise. We’ve seen and done it all, successfully filling a wide variety of remote roles and making career dreams come true for talent at every level.

Industry

Accounting services

Company size

1 - 10 Employees

Headquarters location

Pensacola, FL, US

Year founded

2011

Social media

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