Shady tactics by new management - Anonymous employee Pie Insurance Employee Review

1.0
Aug 5, 2024
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

It paid well in the very beginning near 2021, and 2022.

Cons

Management at the company faced challenges, particularly regarding bonuses and consistent year-over-year raises/compensation. Leadership occasionally employed questionable tactics, and there were instances of inappropriate remarks (such as anti-lgbtqia+, and blatant misogyny) made by former C-level executives, who subsequently stepped down without ever offering a genuine apology. The company also experienced frequent layoffs, which appeared to be a strategy to maintain profitability by replacing full-time employees with lower-paid contracted staff. Additionally, there was a notable lack of transparency from the leadership, despite their claims of being forthcoming about their actions and decisions. Moreover, management frequently placed staff in "crunch" mode, over-promising to clients, and staff while setting unrealistic deadlines. This often resulted in employees being unable to fulfill projects in a timely manner, creating a challenging and stressful work environment. These are just to name a few.

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Pie is mission-driven and focused on modernizing an outdated industry, giving employees the chance to build products that genuinely help small businesses.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

See reviews by: Helpful|Rating|Date|All