Does Pie Insurance pay their employees well?

According to anonymously submitted Glassdoor reviews, Pie Insurance employees rate their compensation and benefits as 3.7 out of 5. Find out more about salaries and benefits at Pie Insurance. This rating has improved by 4% over the last 12 months.

How satisfied are employees working at Pie Insurance?

47% of Pie Insurance employees would recommend working there to a friend based on Glassdoor reviews . Employees also rated Pie Insurance 3.5 out of 5 for work life balance, 3.2 for culture and values and 2.8 for career opportunities.

What are the top reviewed jobs at Pie Insurance?

Business Development (6) , Senior Software Engineer (6) , Business Development Manager (4) , Inside Sales Representative (4) , Underwriter (4) , Customer Service Representative (3) , Engineer (3) , Underwriting Associate (3) , Account Specialist (2) , Business Development Associate (BDA) (2) , Claims Adjuster (2) , Customer Success (2) , Inside Sales (2) , Principal Engineer (2) , Senior Claims Adjuster (2)

What are the pros of working at Pie Insurance according to real employee reviews?

"Pie has a great culture" ((in 21 reviews)); "Great benefits that are mostly covered by company" ((in 19 reviews)); "Amazing people on the claims team" ((in 16 reviews)); "Leadership is accessible and human, and the company invests in connection and community even in a remote environment." ((in 9 reviews)); "IT team was great" ((in 5 reviews))

What are the cons of working at Pie Insurance according to real employee reviews?

"Constant layoffs left everyone feeling demoralized and overwhelmed." ((in 8 reviews)); "Audit and Billing have months of backlog and people are waiting on hold for hours due to management's bad decisions and lack of action." ((in 7 reviews)); "I had 4 managers in 2 years." ((in 4 reviews)); "•Aggressive communication from a recently appointed leader has fostered an uncomfortable atmosphere, where shaming and silencing of other claims leaders is prevalent." ((in 3 reviews))

What are employees saying about Pie Insurance layoffs in 2026?

Explore Glassdoor’s employee reviews to understand what current and former employees are saying about Pie Insurance layoffs and their outlook for job security at Pie Insurance in 2026.

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Pie Insurance

Pie Insurance reviews

3.2

47% would recommend to a friend

(161 total reviews)

John Swigart

59% approve of CEO

38% positive business outlook

Ratings by category

3.7

Compensation and benefits

3.5

Work/Life balance

3.3

Diversity & inclusion

3.2

Culture & values

2.8

Senior management

2.8

Career opportunities

Pie Insurance has an employee rating of 3.2 out of 5 stars, based on 161 company reviews on Glassdoor which indicates that most employees have a good working experience there. The Pie Insurance employee rating is in line with the average (within 1 standard deviation) for employers within the Insurance industry (3.5 stars).

Ratings by demographic groups

Race / Ethnicity

Gender

Sexual orientation

Disability

Parent or family caregiver

Veteran status

Reviews by job title

161 reviews

3.0

Jan 19, 2026

Good coworkers weak leadership

Senior software engineer

Recommend

CEO approval

Business Outlook

Pros

Kind, supportive coworkers. Solid employee benefits

Cons

Management had poor communication and leadership skills.

2.0

Oct 27, 2025

Poor Communication

Anonymous employee

Recommend

CEO approval

Business Outlook

Pros

Coworkers were the best despite the lack of direction. PTO.

Cons

The interview process was disorganized from the start long waits, poor communication, and unclear expectations. Once hired, it became obvious that promotions and career growth are almost nonexistent. There’s no clear path for advancement, and management rarely provides constructive feedback or support. Communication between departments is chaotic, and decisions are often made without transparency or logic.

5.0

Oct 23, 2025

Great Culture, Smart People, and Real Innovation

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.

Viewing 7 - 9 of 161 Reviews

Jobs at Pie Insurance

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