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

"Not sure how they decide to spend their money; 2 layoffs in 2 years but they continue to hire and have executives travel around the country." ((in 10 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

37% 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

Jun 28, 2023

Benefits

Customer success

Recommend

CEO approval

Business Outlook

Pros

Great benefits that are mostly covered by company

Cons

After the most recent RIF not much security has been provided

Pie Insurance Response

Thank you for sharing your feedback regarding the benefits at Pie. We're pleased to hear that you found our benefits package to be a positive aspect of your time with us. Our aim is to provide comprehensive benefits that support our employees' well-being and enhance their work-life balance. Regarding your concerns about job security following the recent reduction in force, we understand that changes can create uncertainty. At Pie, we work hard to be as transparent as possible about all areas of the business, and will continue to keep all Pie-oneers well-informed of our strategies. Thank you again for sharing your perspective.

5.0

Feb 19, 2021

Amazing opportunity!!!

Business development manager

Recommend

CEO approval

Business Outlook

Pros

Pie is such an exciting company to work for because we are BUILDING it from the ground up. This leads to an extremely fulfilling day where input and feedback is not only encouraged but 100% necessarily as we look to be a tremendous company.

Cons

If you are not comfortable with radical change, this wont be a good spot. If you enjoy dropping donuts in the field, this is also not a job for you.

Pie Insurance Response

Thank you for the great feedback!

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 49 - 51 of 161 Reviews

Jobs at Pie Insurance

Principal People Partner

Vendor Management & Sourcing Specialist

Principal People Partner

Staff Business Systems Analyst