employer cover photo
employer logo
employer logo

Skyward Specialty Insurance

Engaged Employer

Challenge: Guess how many reviews are written by an executive - Anonymous employee Skyward Specialty Insurance Employee Review

1.0
Sep 9, 2014
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

"This type of company is not for everyone and the opportunities are limitless." Really!? Limitless - only if you are fine with "opportunities" to take on more work, more stress for little to no compensation and absolutly NO gratitude. The more work load is because this company can not keep employees so everyone else has to do the job of 2 or 3 employees. "There are several negative reviews about HIIG but all from employees who couldn't keep up with the pace and didn't make the cut." If you call "couldn't keep up with the pace and didn't make the cut" actually leaving HIIG for much better pay (30%+) plus significant bonuses and better working environment, then I'll take that as a compliment. "If you like to be challenged, then HIIG is the place for you." The only challenge here is staying out of the way of the CEO & his minions. These people are ruthless and will throw you under the bus quick. Don't think for a second your boss will go to bat for you when you are not to blame for a situation. "If you like to work at a job doing the same thing over and over, then don't fool yourself and think you could work at HIIG" Whatever! Don't fool yourself, this is not a great place to work. There is no appreciation for the countless hours put in and life events missed to be loyal to a company that will treat you with no respect. The executives make BANK! The people that actually do the work don't. I have heard HIIG described best this way: Once you leave HIIG you are like a beat down dog. You are scared to do anything, because you will likely get in trouble. At my new job, we can drink coffee without a lid (gasp!). The executives actually get their own coffee. The office is quite because eveyone is working and not scared to speak. When the CEO walks by, no one looks away or feels like they are being mentally undressed. You can go to the restroom without someone wondering how long you have been away from your desk.

Cons

No need to elaborate but I have to write twenty words for this to publish. Save your sanity, don't work here.

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.

See reviews by: Helpful|Rating|Date|All