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Skyward Specialty Insurance

Engaged Employer

Don’t be fooled - Anonymous employee Skyward Specialty Insurance Employee Review

1.0
Oct 21, 2021
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Almost none, and what little pros exist only benefit management or aren’t worth putting up with the other garbage.

Cons

The most helpful thing to know is that after the rebrand, the new CEO requested that employees bury bad reviews on Glassdoor with the filler garbage you see after April 2020. Notice they were all written pretty close to the same time frame. The new CEO seemed like a nice guy, but company in general has normalized so many toxic behaviors and situations that I’m not sure he will ever fully understand what’s broken. The entire upper management team has cultivated the most toxic and degrading environment I’ve ever seen or been in. Insecurities are expected to be coddled and there is zero chance something isn’t another persons fault. They will never hesitate to throw you under the bus to save face, and they never acknowledge or take responsibility for their own mistakes. If you’ve unknowingly done something that upset them, or they feel you could improve in certain areas, they will tell every person in their path - except the employee directly. Regarding the actual work, let’s be real it’s insurance, but there is zero room at Skyward to want growth or advancement. Implementing goals only goes so far on a one way street, and people stopped caring about them almost instantly. There are no growth or development opportunities, and one misstep trying to reach your goals and taking action is met with a slap on the hand at best. .

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Skyward Specialty Insurance Response
4y
We are sorry you did not enjoy your experience with Skyward and we would be pleased to have an opportunity to discuss it with you as we can always learn and grow from everyone’s feedback. We are proud of the incredible work and accomplishments our Skyward Team achieves every day and we are steadfastly committed to provide an environment where our employees’ growth and happiness is reflected in their performance, contribution and engagement. The changes we have made under the new leadership are significant, but our work continues and we improve every day. This year alone, we created added flexibility with remote and hybrid work schedules, new and improved medical, dental, and lifestyle support benefits, increased salaries and bonus incentives, and established a company-funded and employee-led Foundation for charitable giving. Skyward is growing and there is internal movement within the organization. We added 114 new A+ Team Members year-to-date and have promoted 40 people into positions of increased responsibility. As our culture changes and shifts, we understand that some may not be prepared to make the change with us. We acknowledge that the performance-based culture we are instilling may not be for everyone, but the one thing that we will not waver on is on our Company’s GREAT Values which specifically speak to bettering ourselves and supporting that same spirit in each other. Overall, the overwhelming feedback from employees indicates we are headed in the right direction. Your experience sounds like it has been different. Please reach out directly to me if you would like to share more information so that I may be of assistance. Tom Schmitt, Chief People Officer

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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