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Skyward Specialty Insurance

Engaged Employer

Skyward Specialty Insurance reviews

4.5

95% would recommend to a friend

(151 total reviews)

Andrew Robinson

99% approve of CEO

95% positive business outlook

Skyward Specialty Insurance has an employee rating of 4.5 out of 5 stars, based on 151 company reviews on Glassdoor which indicates that most employees have an excellent working experience there. The Skyward Specialty Insurance employee rating is 24% above average for employers within the Insurance industry (3.6 stars).

Reviews by job title

151 reviews
5.0
Jul 5, 2026

Outstanding company culture

Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

The company and culture at Skyward Specialty Insurance is outstanding and by far my favorite over the course of my career.

Cons

My only con would be that although the benefits package overall is good, the medical coverage this year was not as favorable as in past years.

5.0
May 7, 2026

Great company

Recommend
CEO approval
Business Outlook

Pros

Employee engagement, Work-life balance, pro-tech company, pro-people place to work and grow.

Cons

Medical insurance isn’t great and it’s expensive. No PPO option in 2026.

Viewing 1 - 3 of 151 Reviews

Glassdoor has 161 Skyward Specialty Insurance reviews submitted anonymously by Skyward Specialty Insurance employees. Read employee reviews and ratings on Glassdoor to decide if Skyward Specialty Insurance is right for you.