Great benefits, crappy engineering culture - Software Engineer HealthSherpa Employee Review

1.0
Mar 1, 2022
Recommend
CEO approval
Business outlook

Pros

Healthsherpa goes the extra mile to provide great health insurance benefits. Probably the best health insurance you will see in your lifetime.

Cons

They have successfully created a typical silicon valley she/he bro developer shop that is roughly akin to a hipster coffee shop with beards 'high-five'n each other for creating problems, then high five'n each other for monkey patching data in production. When you are high-five'n yourself for 'caching' data and then ask someone else to figure out why memcached is called 29000 times per request because you are too busy being awesome, that's when you have arrived into the hipster twilight zone of mediocre engineering that healthsherpa is neck deep into. The spaghetti code is intertwined to everything and any suggestion to clean it up is cast to a side task that you shouldn't have last longer than a day. If you want to do software engineering, you won't be doing it here because the engineers that helped to create the mess use their 6 years of code muckery and experience in the code base to help perpetuate the myth of their awesomeness. No software engineering principals need apply, no encapsulation, modularization, separation of concerns, or polymorphism. But hey, if you are a hipster who likes to hive-five people into believing you are achieving something, they might give you a promotion! Look how many high five's today, oh you must be a sr developer! lol

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HealthSherpa Response
4y
Thank you for sharing your experience at HealthSherpa. We're sorry you've had a negative experience, despite our best efforts: this is not the experience we want people to have at HealthSherpa. We appreciate the courage it takes to share this feedback, which we value and will learn from. We strive to find the right balance between technology quality and development speed. While we recognize that while we haven't always gotten it right, we've made large strides in our engineering quality and culture over the past year, and work hard to recognize and reward problem solving instead of problem creation. There's still a ways to go, but we're incredibly proud of the progress our team has made on our journey to carve out domain boundaries, shift our architecture to a modular monolith, and create reusable systems that help make development a joyful experience. I'd also encourage you to share any ideas for improvement with your teammates—we've implemented many changes that employees have shared with us. Our teammates' feedback and ideas are critical to making our work culture and product stronger, and we'll work on creating more avenues that make it easier to provide that feedback. Our development process, team, practice, culture, and technical quality are continuously improving due to this focus on excellence, and we're quite looking forward to the future!

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
8mo
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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