Amazing people, growth opportunities, and meaningful work - Sales Associate HealthSherpa Employee Review

5.0
Apr 24, 2019
Recommend
CEO approval
Business Outlook

Pros

I don’t often write reviews, but I have had an exceptional work experience at HealthSherpa this past year. I originally started in a contract position but was given the opportunity to prove myself and move up within months, and they also paid to get me licensed as an agent. I’m now a permanent employee and committed to growing with this company. Another plus is I really like my manager and have real mentorship, which is rare. One big reason I love working here is because the company is full of kind, genuine people and we have great banter throughout the day - we are constantly problem-solving together while still having fun and cracking jokes. Great perks in the office, too, like fancy cold brew coffee on-tap and catered lunches. No joke - the CEO will bring you a fresh coffee if you ask. Last thing I’ll add, the work you are doing makes a difference, and you feel good about the impact the company is making in the health insurance world. The CEO and leadership are experts and regularly work with / give recommendations to the government, and they are often heard. It feels good to help people get affordable care, and working for a small mission-driven company that is moving mountains is a very fun and challenging experience.

Cons

The busy season is November 1st through December 15th, so be prepared for longer hours during that time of year, and a bit less intensity the rest of the year. Stress levels can sometimes run high during Open Enrollment, so self care is a must.

Explore other reviews about HealthSherpa

5.0
Oct 7, 2025
Recommend
CEO approval
Business Outlook

Pros

The best training sessions I've ever had for a company. The trainer is so knowledgeable, kind, fun and made training wholesome. Once we got to the flow it was a breeze, there was a lot of help. Little less micromanaging and metrics I must say

Cons

Most CSR roles, start from Seasonal with limited opportunities for full time long-term, but you can always rehire.

avatar
HealthSherpa Response
9mo
Thank you for sharing your experience! We’re so glad to hear you enjoyed the training and felt supported once you got into the flow– that means a lot to our team. We also appreciate your feedback on seasonal roles and opportunities for longer-term growth; it’s helpful input. Thanks again for being part of the team!
4.0
Mar 19, 2026
Recommend
CEO approval
Business Outlook

Pros

Nice people and not heavy work load. Health insurance is completely paid by company.

Cons

Dealing with false advertising Medicare calls. You get some Legit calls that actually need and want help but more are becoming bait and switch. Started out decent but becoming more like other brokers with same food card and money back tactics. No room for growth on Medicare side.

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