Full-Time

People Operations Generalist

Pie Insurance

Pie Insurance

201-500 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$80k - $100k/yr

Remote in USA

Remote

Remote in the United States; territories excluded; requires reliable internet.

Bachelor's

Category
People & HR (1)
Required Skills
Human Resources Information System (HRIS)

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Requirements
  • High school diploma or equivalent experience is required.
  • A Bachelor's Degree is preferred.
  • HR Certification is preferred.
  • 5 years HR administrative, Rewards, Benefits, or Generalist experience.
  • Experience with enterprise HRIS is a plus.
Responsibilities
  • Navigate Employee Relations and Compliance: Compliance Expertise: Stay up to date on the latest changes to legislations, locally, state, and federally; especially noting diversity-related policies and regulations
  • Ensure compliance with labor laws and regulations, maintain employee records, and update People policies.
  • Notify and advise People Team leaders of employee relations trends and/or compliance issues with laws and regulations.
  • Provide guidance to leaders on employee relations, performance management, and separation decisions, ensuring proper documentation and compliance.
  • Assist with performance evaluations, setting goals, and providing feedback.
  • Data & Reporting Support: Workforce Analytics: Analyze workforce data to identify diversity gaps and trends.
  • Generate reports and provide insights on People related metrics.
  • Data Management: Ensure data hygiene in HRIS and Drive, ensuring best practice for data integrity.
  • Systems Support & Process: Support optimal system functionality through active troubleshooting; maintain tenant health.
  • Advise on best practices and functionality to best utilize tech-stack for People team initiatives and programs.
  • Support People Operations process improvement efforts through process design updates and testing.
  • People, Process and Programs Support: Employee Engagement & Programming: Create initiatives to promote inclusive workplace culture.
  • Collaborate with leadership to integrate diversity goals into business strategy.
  • Collaborate with cross-functional teams to provide feedback on key programs (PP > EoYR, Engagement Survey, etc.).
  • Benefits & Leave Admin: In collaboration with Sr. Total Rewards Manager: Advise team members on leave options.
  • Support organization benefit program design and roll-out.
  • Team Member Lifecycle: Support onboarding programming to align with business strategy and initiatives.
  • Manage headcount process ensuring data alignment, accurate job descriptions, and process continuity.
Desired Qualifications
  • Bachelor's Degree preferred.
  • HR Certification preferred.
  • Experience with enterprise HRIS is a plus.
  • Adept at using HRIS, preferably Workday.
  • Experience with project management software, such as JIRA and various collaboration tools including Google Docs and Slack messaging.
  • Experience or ability to learn People Systems tech-stack for key programs (CultureAmp, Continu, Tilt).

Pie Insurance provides workers’ compensation insurance for small businesses. Its product uses data-driven technology to underwrite and price policies, delivering fast, online access with quotes in about three minutes. The platform processes, underwrites, and issues workers’ comp coverage, with nationwide availability across 38 states and Washington, D.C., offering potential savings of up to 30% and straightforward terms for small business owners.

Company Size

201-500

Company Stage

Series D

Total Funding

$620.3M

Headquarters

Washington DC, District of Columbia

Founded

2017

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Simplify Jobs

Simplify's Take

What believers are saying

  • January 2026: Pie said 2025 policies-in-force topped 55,000, up 25% year over year.
  • Pie expanded to Connecticut in 2025, reaching 40 states plus Washington, D.C.
  • Pie’s partner network passed 5,000 agencies, widening low-cost distribution.

What critics are saying

  • May 2023 layoffs cut 66 employees; Pie still chased profitability without fresh capital.
  • The 2025 Pie Development lawsuit keeps John Swigart and Dax Craig under trade-secret scrutiny.
  • A carrier pricing misstep or loss-ratio spike would crush Pie’s surplus and broker trust.

What makes Pie Insurance unique

  • Pie prices workers’ comp with granular data, selling direct and through 5,000 agencies.
  • Its online quote-and-bind flow takes three minutes, targeting small-business owners.
  • Ford Pro Insure uses Pie’s underwriting, servicing, and claims stack for commercial fleets.

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Benefits

Competitive cash compensation

Equity

Comprehensive health plans

Generous PTO, including paid sick leave

Future focused 401k match

Generous parental & caregiver leave

Growth & Insights and Company News

Headcount

6 month growth

41%

1 year growth

27%

2 year growth

25%
Yahoo Finance
Feb 8th, 2024
Pie Insurance Integrates with Ivans Download

Pie Insurance integrates with Ivans Download.

Business Wire
Nov 30th, 2023
Pie Insurance Secures $11 Million Series A Funding to Rapidly Expand SMB Workers’ Compensation Insurance Offering

Pie Insurance (www.pieinsurance.com) today announced the completion of an $11M Series A funding round. The round was led by Greycroft, and included pa

FF News
Oct 2nd, 2023
Pie Insurance Appoints Audra Foglietta As Chief Financial Officer

Pie Insurance (“Pie”), an insurtech company specializing in commercial insurance for small businesses, today announced the appointment of insurance executive Audra Foglietta as the company’s new chief financial officer (CFO). Foglietta joins Pie during a pivotal period of growth—Pie is the fastest growing workers’ comp insurer in the U.S.1, achieving a 271 percent increase in direct written premiums, surpassing the growth of all other insurers.Foglietta brings a wealth of financial leadership and strategic expertise to Pie, having spent more than twenty years at Chubb, the world’s largest publicly traded property and casualty insurance company. Most recently, Foglietta served as Chubb’s executive vice president and CFO of Global Operations and Technology, in addition to previously serving as CFO of Westchester Specialty, the company’s excess and surplus division. Foglietta has a proven track record of driving financial performance and operational efficiencies in the public insurance sector. Her expertise includes global business transformations, corporate finance, financial planning and analysis, business analytics and operations.“I’m honored to join Pie as its CFO and be part of an organization that is redefining the small commercial insurance landscape and growing at an impressive rate,” said Audra Foglietta, incoming CFO at Pie. “Pie’s commitment to technology and innovation combined with its dedication to serving the unique needs of small businesses resonated with me

Reinsurance News
Oct 2nd, 2023
Pie Insurance names Audra Foglietta Chief Financial Officer

Pie Insurance, an insurtech company specialising in commercial insurance for small businesses, has appointed Audra Foglietta as the new Chief Financial Officer.

II Reporter
Aug 25th, 2023
Pie Insurance Expands Leadership Team with Appointments of Four Industry Experts

Carla Woodard, Jaime Gilliam-Swartz, Arash Sadati and Kris Bagchi join Pie's leadership team as Vice Presidents.