Does Skyward Specialty Insurance pay their employees well?

According to anonymously submitted Glassdoor reviews, Skyward Specialty Insurance employees rate their compensation and benefits as 4.4 out of 5. Find out more about salaries and benefits at Skyward Specialty Insurance. This rating has decreased by 2% over the last 12 months.

How satisfied are employees working at Skyward Specialty Insurance?

95% of Skyward Specialty Insurance employees would recommend working there to a friend based on Glassdoor reviews . Employees also rated Skyward Specialty Insurance 4.6 out of 5 for work life balance, 4.5 for culture and values and 4.3 for career opportunities.

What are the top reviewed jobs at Skyward Specialty Insurance?

Underwriter (6) , Underwriting Assistant (6) , Assistant Underwriter (4) , Business Analyst (4) , Claims (4) , Senior Underwriter (4) , Accounting (3) , Anonymous (3) , Claim Director (2) , Executive Assistant (2) , Intern (2) , Internship (2) , Manager (2) , Project Manager (2) , Recruiter (2)

What are the pros of working at Skyward Specialty Insurance according to real employee reviews?

"Great culture and vision." ((in 19 reviews)); "Good people and flexible" ((in 11 reviews)); "My management always pitches in and helps us as well when we are a little overwhelmed at times." ((in 10 reviews)); "Leadership is approachable and knowledgeable." ((in 8 reviews)); "Very employee friendly" ((in 6 reviews))

What are the cons of working at Skyward Specialty Insurance according to real employee reviews?

"Can’t wear jeans, system and upper management" ((in 7 reviews)); "Systems need improvement and benefits need to be better." ((in 7 reviews)); "Insurance is constantly evolving and changing but those changes should be explained to employees." ((in 3 reviews)); "No bonuses." ((in 3 reviews)); "no work life balance" ((in 3 reviews))

What are the top reviewed Skyward Specialty Insurance locations?

Houston , Kennesaw , Atlanta , Dallas , Birmingham , Rolling Meadows , Sacramento , Chicago , New York , Scottsdale , Oklahoma City , Washington , Missouri City , Hartford , Pittsburgh , Fort Myers , Orlando

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

Ratings by demographic groups

Race / Ethnicity

Gender

Sexual orientation

Disability

Parent or family caregiver

Veteran status

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

Jun 20, 2025

Employee Experience

Clinical consultant

Recommend

CEO approval

Business Outlook

Pros

Skyward has a strong positive company culture defined by its commitment to work life balance, inclusion and diversity, transparency and accountability, and a spirit of collaboration and respect. Leadership is approachable and knowledgeable. Their sense of balance and support throughout the workplace is truly uncommon.

Cons

The VPN system can be a bit clunky at times, which impedes the ability to onboard 100% remotely. Improvements would allow for full work within the VPN and sharing of all screens would make a noticeable difference. But this is not an impediment to the daily workflow.

5.0

May 20, 2025

Amazing Company & team

Anonymous employee

Recommend

CEO approval

Business Outlook

Pros

Working with this company has been great, Great team, culture and atmosphere around the company.

Cons

I do not have any cons to report

2.0

Apr 5, 2025

Benefits

Anonymous employee

Recommend

CEO approval

Business Outlook

Pros

Overall decent. Good people and flexible

Cons

Poorly organized and management not promoted in order of knowledge.

Viewing 10 - 12 of 151 Reviews

Jobs at Skyward Specialty Insurance

Senior Underwriter OR AVP - Medical Stop Loss (Captives)

Senior Underwriter or AVP, Medical Stop Loss (Core)

Analyst, Global Agriculture Reinsurance

Assistant Vice President OR Senior Underwriter, Global Agriculture Reinsurance

Sr. Underwriter OR AVP - E&S General Liability