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Skyward Specialty Insurance

Engaged Employer

Worst Company - Worst Career Move - Executive Assistant Skyward Specialty Insurance Employee Review

1.0
Sep 10, 2014
Recommend
CEO approval
Business Outlook

Pros

Lower level staff are friendly and form family like bonds to shelter and give shoulders to each other for all the abuse from management.

Cons

NO RAISES OR BONUSES (even if promised, don't kid yourself) SUB PAR SALARIES (once you look around at the job market you will soon notice that in your role you could be making 30-40% more at a real company) NO CAREER GROWTH (they do not promote from within. If you do get "promoted" it will be a lateral move with no pay increase) HORRIBLE BENEFITS NO 401K MATCHING (CEO claims that it is in the works, do not count on it) CLOCKING IN & OUT (lower level employees are forced to clock in and out even for lunch breaks, management constatnyl monitoring your hours and punches) PETTY RULES & POLICIES (no headphones at your cubicle, no mugs or open containers at your desk, no cell phones out unless you are executive level or higher, employees in offices can not have their blinds raised, the list goes on and on and keeps growing) HALF CUBICLES (no real privacy, the office structure is so that superiors can constantly monitor you) HORRIBLE PTO (no sick days, you only get 10 holidays and 14 PTO days which your sick days are also pulled from. You only gain additional PTO days after being there for 3 years!! They also no longer let you take unpaid PTO days and goodluck taking off during the holiday season.) HORRID CEO (it is a dictatorship. the CEO is constantly feared by all staff. Executives, Presidents, and Vice Presidents will throw any and all employees under the bus to save themselves.)

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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