Benefits at Pie Insurance

Financial + Retirement


401(K) matching

Company equity

Performance bonus

Office Perks

Commuter benefits

Company-sponsored outings

Company-sponsored happy hours

Onsite gym

Onsite office parking

We offer team members a parking subsidy.

Relocation assistance

Free snacks and drinks

Some meals provided

Home-office stipend for remote employees

All Pie-oneers receive both a one time lump sum stipend when they join Pie as well as a monthly stipend to help them cover any work from home expenses like internet and phone bills.

Health Insurance + Wellness

Dental insurance

Disability insurance

Flexible Spending Account (FSA)

Health insurance

Life insurance

Pet insurance

Vision insurance

Mental health benefits


Volunteer in local community

Flexible work schedule

Pie provides employees with a flexible work schedule that includes Core hours.

Open door policy

Open office floor plan

Pair programming

Remote work program

Pie-oneers can work where they are most productive, whether that's in the office or from home.

OKR operational model

Child Care + Parental Leave

Family medical leave

Employees who have been with the company for 12 months are eligible for 12 weeks of family medical leave.

Generous parental leave

We provide up to 16 weeks of parental leave for the primary caretaker. Pie also provides 16 weeks of leave for the secondary caretaker.

Return-to-work program post parental leave

Vacation + Time Off

Generous PTO

Generous PTO policy

Paid volunteer time

Paid holidays

Paid sick days

Unlimited vacation policy


Highly diverse management team

Hiring practices that promote diversity

Professional Development

Online course subscriptions available

Promote from within

Lunch and learns

Search the 13 jobs at Pie Insurance

Recently posted jobs

2 Days Ago
Fintech • Insurance • Machine Learning • Other • Analytics • Automation
The Vice President of Legal at Pie will oversee all legal matters, providing strategic legal guidance, managing a team of legal professionals, and collaborating with executive leadership to protect and advance the company's legal interests. Responsibilities include developing and executing legal strategies, managing legal operations, leading a legal team, ensuring compliance, and mitigating legal risks.
Fintech • Insurance • Machine Learning • Other • Analytics • Automation
The Underwriter for Workers' Compensation at Pie is responsible for assessing medium to complex risks and underwriting new and renewal coverage. They will utilize their underwriting expertise and knowledge of workers' compensation to make underwriting decisions and maintain relationships with payroll partner customers.
7 Days Ago
Fintech • Insurance • Machine Learning • Other • Analytics • Automation
The Finance Business Partner will support Pie's business leaders in analyzing, managing, growing, and optimizing their functions. Responsibilities include providing financial management support, conducting strategic projects, budgeting and forecasting, reporting, and driving continuous improvement.