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Different makes a difference

Skyward Specialty, named a “Best Place to Work in Insurance” for 2023, is not like mainstream insurance companies, in a good way. In fact, we’re different from most others in our industry in just about every way. We have the spirit of a start-up with the security of nearly a billion dollars in written premium. If you are looking to make a difference in our customers’ lives and in your career, you have come to the right place. Build your career at Skyward Specialty and here’s what you can expect.

Lively Collaboration

We are committed to bettering ourselves and supporting that same spirit in each other, and we have fun doing it.

Professional Treatment

If you’re hired here, you’re already an accomplished professional. As such, you will be treated with trust and respect to allow you to perform at your highest level and to put your expertise into play.

Entrepreneurial Spirit

We do not aspire to become a big wooly mammoth of an insurance company. We are scrappy, nimble, creative and ready to rock.

Strategic Career Growth

We are a learning organization where employees are given the latest tools and technology to expand their skill sets. With our learning platform, SkyHigh™, employees are empowered to strategically grow their career skyward.

Specialty Focus

We are not trying to be everything to everybody. We are focused on being the best and ruling the markets we serve. 

Impassioned Inclusion

We avidly seek a rich diversity of thought, backgrounds and perspectives. Every one of us makes everyone else better.

winning and compassionate

Skyward Specialty was named a “Best Places to Work in Insurance” for 2023 by Business Insurance. 

We share this recognition with all of our employees who are instrumental in our success. Together we have built a compassionate and winning culture that has become the hallmark of our organization and the extraordinary environment we have built. We are building the Company we always wanted to work for! 


Learn more about our people and our culture in the 2023 Annual People Report. Our comprehensive report is a celebration to our commitment to transparency, diversity, and the well-being of our amazing team.

what makes us special

  • Culture
    • Read our full Annual People Report – Click Here
    • Skyward Specialty was named a “Best Places to Work in Insurance” by Business Insurance
    • Employees have the flexibility to work in the environment that best suits their needs – hybrid/remote workforce
    • We have five Employee Resource Groups focused on providing an inclusive, safe environment for employees to thrive as their
      authentic selves
    • Our voluntary turnover for 2023 was 7% record low, well below the industry average
    • The Company offers six mental health half-days typically aligned with Company-observed federal holidays
    • All employees have a half-day PTO to exercise their right to vote
    • Part of our PTO offering includes a SAID Day to encourage employees to observe and celebrate their heritage, culture and causes of personal importance
  • Wellbeing & Balance
    • The Company observes seven holidays, and three additional holidays for employees to use at their discretion which include: one floating holiday, a community service day and a SAID Day
    • Additionally, we provide six half days that align with the other Company holidays for mental wellness – these days are also designated as “No Meeting Mornings”
    • All full-time employees receive a minimum of 120 hours of PTO annually
    • Our generous parental leave policy includes an additional four weeks of 100% paid pregnancy leave and two weeks of child bonding leave for parents including adoptive parents
    • The Company has multiple Family Assistance Programs providing assistance for employees seeking adoption and fertility treatment
    • All employees can take advantage of our charitable matching program – doubling their giving impact – and also participate in volunteer events sponsored by the Company
  • Compenstation & Benefits
    • We offer inclusive benefits covering medical, dental, vision and Company paid short-term and long-term disability
    • Every employee is eligible to participate in our Employee Stock Purchase Plan, where they can purchase stock at a 15% discount
    • The Company offers generous retirement 401k match up to 5% offered to all employees
    • Our competitive and fair compensation practices align with experience, skill and performance
    • In addition to competitive base pay, we offer performance-based incentives to all employees so they can share in our successes
      as an organization
  • We are proud of our dispersed workforce – 98% of employee schedules are remote/hybrid
  • Very proud of our “Dress for your day” dress code
  • We offer an Employee Referral Program – Paid $48,000 in 2023
    • 46% of 2023 new hires were referred by current Skyward Specialty employees
  • We seek to look internally for Internal promotions and expanded opportunities encouraged
  • The Company offers an 11-week internship program through the Skyward Specialty Summer Internship Program
  • Each employee participates in regular informal performance evaluations throughout the year as well as a comprehensive annual review
  • Browse our career opportunities here
  • Career Development
    • Our cascading OKR process ensures alignment across the organization to allow employees to more fully understand how their work impacts the organization
    • We’ve increased internal promotions or expanded roles by 152% since 2021
    • Employee Resource Group (ERG) leadership opportunities
    • We offer Management 101 training to all managers – more than 90% of all leaders have participated in this training
    • We offer a structured Mentorship Program for employees looking to grow their career and develop new skillsets by partnering
      with a mentor
    • ASCEND, an ERG focused on developing professionals, provides resources and opportunities for employees to grow their career
      at Skyward Specialty and beyond
  • Continuing Education
    • SkyHighTM learning portal provides more than 4,000 eLearning on-demand courses for continuing education and training opportunities to foster growth and development “in the flow” of work
    • We offer a best-in-class Certification Program to all employees that offers resources and financial assistance to expand their professional expertise; depending on the certification additional pay incentives and/or bonuses are available
    • All employees can benefit from our Tuition Reimbursement policy which offers $3,000 annually for employees seeking college-level coursework to assist with tuition, textbooks and course-related fees

See Current Openings

Check out positions that are open now, but also be sure to check back often. We are a fast-moving Company, and we’re building a top-tier team to drive that growth.

Do you think bigger than what is common for the insurance industry? Are you highly motivated to build something great? If so, then this could be the beginning of something great, for you and Skyward Specialty. See what we’re building and where you fit in below. 

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