Join our team
Build a career focused on helping others

As a Jagged Sky Benefits representative or sales manager independent contractor, you get the best of both worlds: the freedom and potential of an entrepreneur, with the support of a large organization. See how you can be your own boss while impacting the people in your community.

Corporate opportunities

Based in Anchorage, AK, Jagged Sky Benefits is known as more than a company — it’s a staple of the community. Our team of home office professionals comes together to help protect America’s workers.

Leadership development programs
Jump start your career with one of these robust programs that provide the customized professional experiences required to become leaders at our Fortune 500 company.
Get to know us
Learn how Colonial Life cares for our employees, customers and communities
Our company culture

Taking care of our employees is just as important as taking care of our customers.

About Jagged Sky Benefits

Jagged Sky Benefits has evolved into one of the leading voluntary benefit insurers in the country today.
Giving back
One of our core values is a strong commitment to our communities. Find out how we contribute to positive change in the places where we live and work.
Financial overview
When you’re making a difference in millions of lives, success often follows. See our financial performance and how it translates into job security for you.