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Skyward Specialty Insurance

Engaged Employer

Best place to work! - Senior IT Project Manager Skyward Specialty Insurance Employee Review

5.0
Dec 15, 2025
Recommend
CEO approval
Business Outlook

Pros

Supportive Leadership: The management genuinely listens to ideas and empowers employees to drive meaningful change. Senior leadership is approachable and invested in your success. Collaborative Environment: Teamwork is highly valued—cross-department collaboration is the norm, not the exception. Everyone shares knowledge and supports one another. Strong Work-Life Balance: Flexible schedules and a culture that respects personal time make it easy to maintain a healthy work-life balance. Career Growth: Plenty of opportunities for professional development, training, and internal advancement. Hard work and initiative are regularly recognized with promotions or new responsibilities. Innovative Projects: Skyward embraces new technologies and encourages experimentation, which makes the work both challenging and rewarding. Inclusive Culture: Diversity is celebrated, and there are strong efforts to foster an inclusive, welcoming environment for all employees.

Cons

Fast-Paced Environment: While exciting, the pace can be intense at times, requiring adaptability and strong time-management skills. Growing Pains: As the company expands, occasional changes in processes or role definitions can occur. However, management is transparent and communicates changes well. High Expectations: The bar for performance is set high, but this also creates lots of opportunities to shine for motivated professionals.

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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