Does HealthSherpa pay their employees well?

According to anonymously submitted Glassdoor reviews, HealthSherpa employees rate their compensation and benefits as 4.2 out of 5. Find out more about salaries and benefits at HealthSherpa. This rating has decreased by 2% over the last 12 months.

How satisfied are employees working at HealthSherpa?

90% of HealthSherpa employees would recommend working there to a friend based on Glassdoor reviews . Employees also rated HealthSherpa 4.4 out of 5 for work life balance, 4.4 for culture and values and 3.2 for career opportunities.

What are the top reviewed jobs at HealthSherpa?

Consumer Advocate (6) , Agent Support (3) , Customer Service Representative (3) , Agent Support Representative (2) , Customer Service Representative (CSR) (2) , Medicare Sales Agent (2) , Medicare Specialist (2) , Senior Software Engineer (2)

What are the pros of working at HealthSherpa according to real employee reviews?

"The culture here is amazing." ((in 6 reviews)); "Amazing benefits" ((in 6 reviews)); "flexible, understanding, easy to work with, great management" ((in 5 reviews)); "Great people" ((in 4 reviews)); "The work we do is enjoyable and we get to help people from all over the United States" ((in 3 reviews))

What are the cons of working at HealthSherpa according to real employee reviews?

"Hourly pay is a little on the low side but you do get bonus per enrollment" ((in 3 reviews))

What are employees saying about HealthSherpa layoffs in 2026?

Explore Glassdoor’s employee reviews to understand what current and former employees are saying about HealthSherpa layoffs and their outlook for job security at HealthSherpa in 2026.

What are the top reviewed HealthSherpa locations?

Sacramento , San Francisco , New York , Soda Springs , Appleton , Michigan Center , Oklahoma City , Huntersville , San Antonio , Nashville , Colorado Springs , Denver

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HealthSherpa reviews

Values-Aligned Work in Tech - Anonymous employee HealthSherpa Employee Review

5.0

Apr 11, 2023

Anonymous employee

Recommend

CEO approval

Business Outlook

Pros

HealthSherpa is the first company I’ve worked for in over a decade to treat me like a person and compensate me well. The benefits package is very strong and I don’t have to worry about not being able to afford co-pays or having crazy high premiums. My manager is kind and cares about me and my growth. The work I do feels aligned to my values; I don’t feel like I had to sell my soul to work in tech. I have peace of mind at work even on stressful days.

Cons

I worry a bit about job security with mass tech layoffs. No one is immune.

HealthSherpa Response

We appreciate you taking the time to leave us a review! We are happy to hear that you are enjoying working at HealthSherpa and the benefits we offer.

Explore other reviews about HealthSherpa

5.0

Oct 7, 2025

Customer service representative

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.

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

Insurance agent

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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Jobs at HealthSherpa

Seasonal Bilingual Agent Support Representative (Remote - Virginia)

Seasonal Agent Support Supervisor (FL, OH, TN, TX, UT, VA)

Seasonal Agent Support Representative (Remote - VA)

Seasonal Agent Support Representative (Remote - TN)

Seasonal Agent Support Representative (Remote - OH)

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