So much potential - Anonymous employee Pie Insurance Employee Review

2.0
Mar 25, 2025
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Fully remote, unlimited PTO, great healthcare plan, the attempts at transparency are appreciated, some great co-workers and middle management.

Cons

Job security is nonexistent. Small layoffs are occurring almost monthly that don't take into account how critical the roles may be. I've seen positions eliminated that were shocking. The disconnect in upper management is staggering at times. The push to become profitable is so strong it feels dire even though we've been told it isn't. Co-founder is leaving the company. You typically don't jump ship when things are going great. Pie has a major culture issue at the moment and there appears to be zero attempt at solving it. The highest C-suite turnover I've ever seen in my career. Since I've joined Pie the CFO, CTO, CAO, Chief Claims Officer, Chief legal officer, and Chief Commercial Officer have all left the company either on their own or through reorgs. I'd be willing to bet Pie gets acquired/sold within 12 months.

Explore other reviews about Pie Insurance

5.0
Oct 23, 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Pie is mission-driven and focused on modernizing an outdated industry, giving employees the chance to build products that genuinely help small businesses.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
May 26, 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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