Careers – Jagged Sky Benefits

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.

Join Our Sales Team

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.

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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.

More About the Programs

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.

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About Jagged Sky Benefits

Jagged Sky Benefits has evolved into one of the leading voluntary benefit insurers in the country today.

Our Company

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.

See How We Give Back

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.

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