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Skyward Specialty Insurance

Engaged Employer

Good Start-up Opportunity but Horrible Work Environment & Pay - Anonymous employee Skyward Specialty Insurance Employee Review

1.0
Feb 19, 2018
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Newer P&C carrier so opportunity to influence the future of the company with a CEO who has a proven track record of taking his prior company public and building it to an A+XV carrier. He is a proven multi-million dollar success story. If you can get on the inner circle, you will learn immense things from him. Opportunity to grow with a carrier who is building itself into a $1 Billion company.

Cons

Many job opportunities for women but If you are in favor of the #MeToo movement, don't work here. Very sexist communications & comments by many at the Executive level. Most in management are afraid of angering the CEO, who can be volatile and so few stand up to him. As a result, executives in every department have limited control. Very different than the multiple other carriers. Additionally, you must have very thick skin as the CEO will scream at the top of his lungs and demean people in public meetings.. If you don't like yelling, this is not the place to work. Corporate structure was constantly evolving... little stability. HR was a moving target. Lack of data analytics and cutting corners on various software made it more difficult to properly do job and turn a profitable book of business. Little things are demoralizing such as you can't eat or drink at your desk. If they ever did an employee engagement survey, the results would be abyssmal.

Explore other reviews about Skyward Specialty Insurance

5.0
Jul 5, 2026
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.

1.0
Apr 22, 2026
Recommend
CEO approval
Business Outlook

Pros

Compensation is fine and benefits are fine.

Cons

Management practices dictatorship. IT managers do NOT understand IT. They are technically very poor. Off shore contractors just fool them and they are willing to be ridiculed by them. They emphasize on overworking. Politics at its peak. Directors have rude behavior. They do not provide any training, just shooting in the air. Most of the calls happen after office hours. There are weekend releases so your Friday evenings and Saturday mornings are destroyed. No reward, no bonus. They have a system called Clockify where you have to justify every second of your work.

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