Welcome to our career site
Build Your Future with Century Benefits — Where Careers and Care Come Together.
Century Benefits is an independent insurance agency located in the heart of Portland, Oregon. Not only being a one-stop shop for all insurance needs, we have created a strong focus on Medicare over the years.
Our mission at Century Benefits is to simplify insurance for all of our clientele by providing the best options suitable for their needs, educating about the policy/policies and how to best maximize their benefits.
Benefits and Perks
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Generous PTO
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Company Sponsored Events and Outings
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Professional Development Opportunities
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Health, Dental and Vision Insurance Benefits
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Great Location to Fit any Commute Style
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401k Matching for your Retirement
Hear it from us
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Before Century Benefits, I bounced between HVAC and customer service, searching for the right fit. What drew me in was the culture—it’s the best work environment I’ve ever experienced. Training was solid. Sometimes I wanted to move faster, but it was clear, practical, and boosted my confidence. Even in a large class, I felt truly seen and supported. That support changed everything. I’ve struggled with self-doubt and giving up too soon, but here I’ve learned that progress—even small—is still growth. For the first time, I stuck with something. That alone is a huge win. This job isn’t easy, but if you believe in yourself and put in the work, you’ll go further than you imagined. Shoutout to Spiller, Heatherington, Jason, Ronnie, and especially CEO Andrew.
Dalton Young
Agent
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Before Century Benefits, I was a barista looking to grow my income and build a real career. I wanted to use my people skills in a more professional, long-term role and this opportunity gave me exactly that. Training was intense at first, but the support and resources made all the difference. The culture is positive, encouraging, and genuinely fun. I wasn’t sure I had the personality for sales, but I’ve learned, grown in my communication, and increased my income right away. Hitting and exceeding goals has been a huge confidence boost. My advice: stay open, be coachable, and use every bit of feedback. Everything here is designed to help you succeed.
Alison Seal-Shelton
Agent
Current job openings
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Portland-Medicare Sales ExecutivePortland Office
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Vancouver-Medicare Sales ExecutiveVancouver Office
About Century Benefits
Century Benefits is a fast-growing startup in health insurance, focused on improving lives through expert guidance and top-tier coverage. Founded in 2015, we offer a fun, supportive work environment and a client-first approach. With proprietary tech, we make finding the right plan simple and personalized.