Best place I've ever worked - Anonymous employee HealthSherpa Employee Review

5.0
Apr 10, 2023
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

I've worked in a lot of places, HealthSherpa is hands down the best company I've ever worked for. I've worked here for over one year. Everyone is so respectful. I like everyone I work with. 100% fully remote and not ever going back to the office! Flexible schedule, the focus is on getting your work done and not how many hours you put into a day. They cover 100% of employee and family benefits, which is really nice. I like this benefit the most. They provide too much transparency at times but I guess it's better to know than not. They allow for employees to ask any questions without fear. I've never experienced that at other companies. They are currently going through some growing pains. This happens to start ups when they are making a transition from scrappy working 60+hours a week startup to more organized better balanced work/life startup. They've more than doubled in employee size in the last year and are still catching up to upgrading their systems, processes, and structure to match. No company is perfect and not everyone loves it here, this small handful of people sometimes makes it frustrating for the rest of us that love it here. I honestly think this is because they haven't worked at many start ups. They also don't leave, which means this place must be doing something right for them: pay, benefits, respectful co-workers, fully remote work, flexible schedules, etc.

Cons

Currently going through some growing pains to upgrade our structure, systems, and processes to match our size and the company we want to be. The complainers that just complain (don't leave) and do not bring any solutions forward. They almost ruin it for the rest of us.

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HealthSherpa Response
3y
Thanks for taking the time to leave us a review! We're happy to hear you're enjoying the remote work environment and the benefits that we offer.

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.

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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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