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Skyward Specialty Insurance

Engaged Employer

Skyward Specialty Insurance reviews

4.5

95% would recommend to a friend

(151 total reviews)

Andrew Robinson

99% approve of CEO

95% positive business outlook

Skyward Specialty Insurance has an employee rating of 4.5 out of 5 stars, based on 151 company reviews on Glassdoor which indicates that most employees have an excellent working experience there. The Skyward Specialty Insurance employee rating is 24% above average for employers within the Insurance industry (3.6 stars).

Reviews by job title

151 reviews
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.

3.0
Aug 24, 2025
Recommend
CEO approval
Business Outlook

Pros

Travel to premier destination to reward employees

Cons

High stress and incompetent management.

5.0
Aug 18, 2025
Recommend
CEO approval
Business Outlook

Pros

-great leadership and managers -great work/life balance -competitive pay/benefits -very inclusive and maintains constant engagement with employees

Cons

-health insurance could be more affordable -no other cons

Viewing 7 - 9 of 151 Reviews

Glassdoor has 161 Skyward Specialty Insurance reviews submitted anonymously by Skyward Specialty Insurance employees. Read employee reviews and ratings on Glassdoor to decide if Skyward Specialty Insurance is right for you.