Remote insurance jobs with unlimited PTO
Remote jobs whose ads offer unlimited or flexible paid time off. Updated every morning. Today: 30 jobs, 4 posted in the last 7 days.
Today's remote insurance jobs with unlimited or flexible PTO
Entry-level jobs first. Read the company and the full ad for free.
- Continue to employerAssociate Underwriter, NortheastCoalition, Inc.
- See the jobCoalition, Inc.
- See the jobResilience
- See the job
- See the jobLadder
- See the job
- See the jobCoalition, Inc.
- See the jobCoalition, Inc.
- See the job
- See the jobStrongpoint Partners
- See the jobThe Ride Platform
- See the jobResilience
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As of 8 November 2026, Psst lists 30 remote insurance jobs with unlimited or flexible PTO from 14 companies. 4 of them (13%) are entry-level, asking for 2 years of experience or less; none say outright that no experience is needed. 97% are open only to people living in the US, and 0 can be done from anywhere. Where the pay is listed, the typical job pays about $130K a year (middle of the advertised range, in US dollars).
Where you can live
| Location | Jobs |
|---|---|
| US | 30 |
| Canada | 1 |
Experience asked
| Level | Jobs |
|---|---|
| No experience needed | 0 |
| Up to 1 year | 1 |
| Up to 2 years | 2 |
| Entry-level (years not stated) | 1 |
| Some experience | 11 |
| Senior | 15 |
About remote insurance jobs with unlimited or flexible PTO
Companies hiring the most
Skills and tools asked most
compliance (70%), documentation (57%), excel (17%), negotiation (13%), sql (10%), python (10%).
How to get one
Apply soon after a job appears: 4 of today's remote insurance jobs with unlimited or flexible PTO were posted in the last 7 days. Psst alerts send new ones the morning they appear.
Questions
How many remote insurance jobs with unlimited or flexible PTO are there today?
On 8 November 2026 Psst found 30, collected that morning from company career pages. Every one is open to people in the US, Canada, the UK or Australia.
How much do remote insurance jobs with unlimited or flexible PTO pay?
In the US, the typical job here advertises about $130K a year (middle of the range, 22 jobs with pay listed). Pay depends on seniority and company.
How long do remote insurance jobs with unlimited or flexible PTO stay open?
Half of today's ads have been open 25 days or less at the company's career page. Older ads are more likely to be filled or forgotten.
Do I need a paid membership to apply?
No. Read the job for free, then sign in with Google to continue to the employer. A free account is enough.
What does Psst Premium add?
Premium shows every search result with pay and “posted today” filters, and the jobs Psst found today before they go public tomorrow. It includes first-day job email alerts matched to your saved criteria: up to 25 new matches per digest, at most one job email a day when matches are available. Set your preferences and confirm your email to activate them. Premium also helps you prepare for a specific job: review skill gaps, tailor your resume, draft a cover letter and application answers, then track your next step with the Apply Kit. Company Radar emails you new remote jobs from up to 25 companies you follow, and your tracker syncs to every device with “Still open?” and follow-up reminders. The Interview Room lets you practise interview questions for a specific job, with AI feedback on your answers. Resume and cover letter downloads (PDF and Word) are included. Try it for 7 days with the Reply Sprint ($4.99, one payment that never renews), or choose $14.99/month or $79/year, plus applicable tax. Your first resume download is free with a confirmed job alert. Anyone can build and tailor a resume for free.
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Example with made-up details. The score is the builder's own check, not an ATS rating or a promise of an interview.