If you are looking for a work at home job that comes with health insurance, you are not alone. It is honestly one of the most common things people ask about when they start researching remote work!
The good news is that these jobs definitely exist, and there are more of them than most people think. You just have to know where to look and what to look for.
A lot of companies that shifted to remote work during the pandemic never went back to the office, and they kept benefits packages like these intact as well. That means there are real jobs out there with real health coverage, and you could maybe land one sooner than you think.
That is exactly what this post covers, so that you can go into your job search with a clearer picture of what is out there if health insurance is an important part of deciding to work for a company.
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Remote Jobs Hiring Now With Health Insurance Benefits
Carnival Cruise Line – Personal Vacation Planner · FL, GA, TX, and NC only · Full-time; Monday–Thursday 10AM–7PM EST, Friday 9AM–6PM EST, occasional Saturdays. Make outbound calls to warm leads including past guests and interested cruisers to sell vacation packages and build long-term customer relationships. Requires a high school diploma or GED, 1 year of sales experience, strong communication skills, and CRM proficiency. $15.00 per hour for first 10 pay periods, then $16,500 base salary plus commission; average annual earnings $65,000–$70,000; top performers earn $100,000+. Benefits include medical, dental, vision, 401(k) with match, employee stock purchase plan, PTO, 8 paid holidays, 2 floating holidays, tuition reimbursement, and complimentary and discounted cruises.
Cigna/Accredo – Customer Service Representative · Must reside within 50 miles of Memphis TN, Tempe AZ, Warrendale PA, or Whitestown IN · Full-time; Monday–Friday 10AM–7PM CST after training · Handle 75–100 inbound calls per day from patients with rare and complex conditions to coordinate specialty medication shipments and answer questions. Requires a high school diploma or GED and at least 6 months of customer service experience; healthcare or pharmacy background a plus; hardwired internet required. Pay not disclosed. Benefits include medical, dental, vision, 401(k), and career advancement opportunities.
Smith.ai – Virtual Receptionist · United States · Part-time to full-time; minimum 25 hours per week, flexible scheduling including one required Monday shift; 24/7 operation · Answer inbound calls for a variety of businesses, take messages, book appointments, collect payments, screen new clients, and transfer calls. Requires strong typing skills (minimum 40 WPM), a personal desktop or laptop with at least 8GB RAM, a USB headset, and a reliable broadband internet connection; background check required. $15.00 per hour starting rate; $16.00 per hour for fluent English/Spanish bilingual agents. Benefits include paid training and healthcare for agents working 30+ hours weekly.
ABC Legal Services – Court Support Specialist · United States — remote positions available in Montana, North Dakota, Oklahoma, Michigan, South Carolina, Mississippi, Kentucky, and Puerto Rico · Full-time, Monday–Friday · Contact courts by phone and email to track and retrieve legal documents, update records in an internal system, and relay case status updates to process servers and clients. Requires a high school diploma or GED, strong communication skills, and comfort with Microsoft Office, Teams, and PDF handling; legal or call center experience preferred. $15.00 per hour. Benefits include health, dental, and vision insurance, 401(k) with match, PTO, 7 paid holidays, 4 floating holidays, life insurance, FSA, and pet insurance.
Alorica – Customer Service Representative · United States · Full-time · Help customers resolve questions and issues, document call details, and connect them with relevant products and services. Requires a high school diploma or GED, 6+ months of customer service or sales experience preferred, and a hardwired internet connection; equipment provided. Pay not disclosed. Benefits include health, dental, and vision coverage with HSA options, PTO, 401(k), paid training, tuition reimbursement, and employee discounts.
Beyond Finance – Client Retention Specialist · United States (48 contiguous states) · Full-time, including weekends · Take inbound calls from enrolled debt relief clients who are struggling with their program, and help them understand their options and stay on track toward becoming debt-free. Requires experience in retention, sales, or collections; strong communication, de-escalation, and CRM skills required; high school diploma or equivalent needed. $19.00–$20.00 per hour plus commission. Benefits include health, dental, and vision coverage, generous PTO, paid holidays, parental leave, and 401(k) matching.
Allstate – Licensed Insurance Sales Representative. Multiple U.S. states including AL, CT, FL, GA, LA, MO, NC, NM, VA, and more (see listing for all open locations). Full-time. Handle inbound and outbound calls with active insurance shoppers to recommend and sell Allstate coverage — no cold calling required. Requires an active Property & Casualty or Personal Lines insurance license or willingness to obtain one before start date. Pays $18.00 per hour base plus uncapped commission (average total $52,730–$76,480/year); benefits include health, dental, vision, and 401(k) starting day one.
Insurify – Digital Insurance Agent. AL, AZ, CA, CO, CT, FL, GA, IL, IA, KS, MD, MA, MI, MN, MO, MT, NH, NJ, NM, NY, NC, OH, OK, OR, PA, RI, SC, TN, TX, UT, VT, VA, and WA. Full-time. You'll help customers compare and choose insurance policies by phone using a consultative sales approach across multiple carriers and products. Requires a valid state Property and Casualty insurance license and 2 or more years of auto and home insurance sales experience. Pays $40,000 to $53,000 base annually plus performance-based compensation. Benefits include health, dental, 401k with match, and paid family leave.
Instrumentl – Customer Enablement Manager · United States · Full-time · Build training programs, onboarding materials, and communication campaigns to help nonprofit customers get the most out of a grant management platform. Requires 2+ years in customer success, onboarding, or training in a SaaS environment; strong communication skills and familiarity with tools like G Suite, Zoom, Intercom, and Canva required; nonprofit or fundraising background a plus. $70,000–$85,000 per year plus equity. Benefits include 100% covered health, dental, and vision insurance for employees (50% for dependents), generous PTO, parental leave, 401(k), company laptop, and home office stipend.
Signet Jewelers – Virtual Jewelry Expert · United States · Full-time, permanent; flexible availability required including nights, weekends, and holidays · Help customers find jewelry through chat, phone, and text by offering style advice, product information, and concierge shopping services. No specific degree required; strong customer service, sales, and communication skills needed; tech comfort with Zoom, Teams, and multiple screens required. $17.00 per hour to start; Spanish bilingual differential available. Benefits include comprehensive health, dental, vision, and prescription insurance, 401(k) with match, PTO, paid holidays, tuition reimbursement, and paid training with all equipment provided.
Trupanion – Inbound Sales Specialist · United States (select states) · Full-time; 40 hours per week including evenings and weekends, Pacific Time hours · Help pet owners choose the right insurance coverage for their cats and dogs through warm inbound calls and emails. Requires 2+ years of high-volume sales or inbound call center experience and 1+ years of customer service; must obtain Property and Casualty licensing (training and study time provided); hardwired internet connection required. $20.00 per hour plus uncapped monthly performance bonuses; $1,500 sign-on bonus for already-licensed candidates. Benefits include full medical, dental, and vision at no cost to employee, 4 weeks PTO, 9 float holidays, RSU stock grants, free pet health insurance, and paid volunteer time.
Principle Choice Solutions – Customer Service Representative · United States (remote; must live within 1 hour of a hiring location) · Full-time; shifts between 10AM–9PM CST including evenings, weekends, and holidays · Answer inbound calls to help Veterans with questions, document interactions, and resolve issues. Requires a high school diploma or GED, U.S. citizenship, a REAL ID or U.S. passport, strong communication skills, and reliable high-speed internet; 1 year of call center experience preferred. $23.28 per hour ($18.35 base + $4.93 health and wellness benefit). Benefits include health, dental, and vision insurance, PTO, 11 paid holidays, 401(k) with employer match, tuition assistance, and paid training with all equipment provided. Background check required.
Renaissance Learning – Support Agent I · United States (Pacific Time Zone preferred) · Full-time · Help K–12 education software users troubleshoot technical issues and get the most out of their products via phone, chat, and email. Requires strong customer service and communication skills and the ability to learn complex software quickly; experience with Salesforce, JIRA, or SaaS support a plus. $34,900–$40,200 per year. Benefits include medical, dental, vision, telehealth, HSA/FSA, 401(k) with match, paid vacation and sick time, 12 paid holidays, 20 weeks parental leave (14 paid), tuition reimbursement, and life and disability insurance.
ParentSquare – Manager, CSM (SMB) · United States · Full-time · Lead a team of customer success managers and design digital-first engagement strategies to support thousands of small school district clients. Requires 3+ years in customer success or account management in SaaS and 2+ years in people leadership; SMB experience preferred. $85,000–$105,000 per year. Benefits include employer-paid health insurance including dependents, 401(k) match from day one, paid parental leave, stock options, health and wellness reimbursements, increasing PTO, and 16 paid holidays including your birthday.
Holland America Line – Outbound Personal Cruise Consultant. United States (excluding AR, CA, CT, DE, HI, ME, MN, NH, NY, OK, OR, SD, VT, WA, WV, WY). Full-time, Monday–Friday, 8-hour shifts between 7AM–6PM PST, weekends as needed; training begins July 20, 2026. Make outbound calls and send emails to warm leads to help guests plan and book cruise vacations. Requires at least 1 year of sales experience; strong communication and CRM skills needed. First-year earnings average around $50,000; top performers reach $80,000+. Benefits include health coverage, 401k, employee stock purchase plan, travel perks, and tuition assistance.
Instrumentl – Inbound Sales Development Representative. United States. Full-time. Call nonprofits and universities to introduce grant management software, book demos for the sales team, and track prospect details in a CRM. No degree required; looking for early-career candidates or career switchers with strong communication skills and comfort making high-volume outbound calls. On-target earnings $60,000–$75,000 per year. Benefits include fully covered health, dental, and vision insurance, 401k, generous PTO, parental leave, and a home office stipend.
GlossGenius – Customer Support Expert. United States (continental). Full-time, Monday–Friday 10AM–6:30PM EST or Monday–Friday 12–8:30PM EST or Tuesday–Saturday 12–8:30PM EST. Answer calls, emails, and texts to help small beauty and wellness business owners get the most out of a salon and spa software platform. Requires 1+ year of customer-facing experience and comfort using AI tools; SaaS experience preferred. $55,000–$60,000 per year. Benefits include health and dental insurance, 401k, parental leave, home office stipend, fertility benefits, and a yearly professional development stipend.
Looking For More?
If so, FlexJobs is a good way to find them if you create an account and do a search. Their job board isn't free, but I've been a member and found it to be really useful for me because all the job leads fit the following criteria:
- All jobs are either remote or flexible in nature
- Scam-free (all jobs vetted by humans before posting)
- No ads or junk on their site, so you can browse distraction-free
- Hundreds of jobs posted every day across tons of categories
- Respected, long-standing, and truly useful
They let you try them out for 14 days for $2.95. So there is not much risk if you just want to create an account and see if you find anything you may want to apply for.
Anna Thurman is a work at home blogger and mom of two. She has been researching and reviewing remote jobs for over 15 years. Her findings are published weekly here at Real Ways to Earn.