Hoping for the best but not holding my breath - Recruiting Pie Insurance Employee Review

2.0
May 27, 2024
Recommend
CEO approval
Business outlook

Pros

Most employees are hardworking and genuinely good people. The mission of supporting small businesses is noble and something most people truly care about when choosing Pie. There are high expectations and a high bar for talent which has led to highly talented people joining the company…unfortunately it doesn’t seem as though they can retain them. Remote work, pay is decent, good intentions I guess.

Cons

Where to start… Leadership is a mess. There’s been a ton of turnover before and after layoffs in 2023. Whether voluntary or not, not a great sign to see CFO, Chief Claims Officer, Chief Product Officer, Chief Analytics Officer, Chief Accounting Officer all leave recently. There’s a general feeling of burnout across the business, starting before layoffs and then intensifying after. Morale has been low for quite some time. People are unhappy and there’s a huge lack of trust in leadership. Not uncommon after a layoff but seems like not much is being done to improve or turn things around. Ultimately, seems like leadership tries to cover things up to make it seem like things are just fine when in reality the company and most employees are working out of fear in hopes to not be on the next RIF list.

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Pie is mission-driven and focused on modernizing an outdated industry, giving employees the chance to build products that genuinely help small businesses.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