Neutral - Anonymous employee Pie Insurance Employee Review

3.0
29 Dec 2024
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

-Compensation -Unlimited PTO (but let's be real, unlimited PTO is a cost saving effort, when someone leaves the company, the company does not have any days to pay out on, so cool on paper, sucks when you move on) -Direct leadership (most of them anyway) I don't think this is a terrible place to work, I think we are going through an intense period of growing pains that I hope we survive and make it out the other side.

Cons

-no concrete operating procedures. Everything is done on a case by case basis, and two people with the same issue/problem to resolve are told to do two different things. Or a procedure may be developed, but it's half-baked with no input from the people directly affected by it. -Of course, can't not talk about the RIFs. A RIF is always a con, I've lived through them before in prior employers and it's rarely something that can be completely avoided. I think the issue is the communication around it, which is usually none or minimal. We are told all is going well, then there's a small RIF in a department or two and you only know about it because of people posting on LinkedIn. -was made to believe when I hired on I would have a ton of opportunities for career growth within a year or two, I've had none. -all the bureaucratic red tape to get people hired. My last job could be awful with the bureaucratic red tape all over the place, while some checks and balances should be in place, there shouldn't be so much that it makes things next to impossible to accomplish. -Everything is a priority, so nothing is.

Explore other reviews about Pie Insurance

5.0
23 Oct 2025
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

Pie is mission-driven and focused on modernizing an outdated industry, giving employees the chance to build products that genuinely help small businesses. The organization embraces modern technology and design thinking, encouraging innovation, experimentation, and new ideas. Leadership is accessible and human, and the company invests in connection and community even in a remote environment.

Cons

Because Pie is growing fast, change is constant—if you need rigid structure or slow, steady routines, it may feel overwhelming at times.

2
3.0
26 May 2026
Recommend
CEO approval
Business outlook

Pros

I worked with many talented, thoughtful engineers who cared about building reliable systems and supporting each other. The remote environment was generally workable, and there were meaningful technical problems to solve across backend services, APIs, data quality, production support, and customer-facing workflows. I also appreciated opportunities to take ownership, mentor teammates, and work on systems that had real operational impact.

Cons

Priorities and organizational direction could shift quickly, which sometimes made it harder to plan long-term technical work or understand how career growth would be evaluated. Communication around larger company changes could have been clearer and more timely. Career progression, role expectations, and decision-making sometimes felt uneven across teams.

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