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Skyward Specialty Insurance

Engaged Employer

Great Company to Work For - Anonymous employee Skyward Specialty Insurance Employee Review

5.0
Jan 28, 2022
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

I find the culture at Skyward to be among the best I've seen. Skyward has a flat organization structure meaning anyone can have direct and consistent exposure to members of the Executive and Senior Leadership Teams. This has helped create a culture of collaboration and teamwork unlike any other. If you need assistance or another resource to excel in your role, all employees at Skyward are just a phone call away and willing to help. In addition, management is always available to coach, mentor, and develop talent. Additionally, I get a sense of fulfillment from my role. I know that I'm adding value to the organization, and I can see that value making a difference. Also, management has given me ample opportunities to branch out and experience firsthand different parts of the business that I am not familiar with but interested in learning about (e.g., meeting with brokers and other business partners). I think it’s very important to note management is committed to delivering top results and has re-underwrote or exited underperforming books of business. This makes me feel confident about the longevity of the company.

Cons

I believe the compensation package is on the low end compared to peers, but I know management is taking action.

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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