Full-Time

Underwriter

Workers' Compensation

Pie Insurance

Pie Insurance

201-500 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$80k - $100k/yr

+ Bonus

Remote in USA

Remote

Must live and work in the United States (territories excluded).

Bachelor's

Category
Finance & Banking (1)
Required Skills
Sales

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Requirements
  • High School diploma or GED required.
  • Minimum 3 years of underwriting experience or equivalent is required
  • Intermediate to advanced knowledge of workers’ compensation class codes
  • Ability to sell our product while simultaneously discerning risk characteristics within the direct to business market
  • Ability to balance the outstanding execution of processes while handling a high volume of transactions
  • Verifying businesses using various resources and databases like Google, Yelp, LinkedIn, Facebook and similar sites
  • Some travel could be required in this position, up to 10% travel
Responsibilities
  • Leverage workers’ compensation or commercial insurance underwriting expertise to assess medium to complex risks in order to underwrite and bind new and renewal coverage
  • Quickly and effectively decide each request through the use of Pie’s underwriting guidelines and known risk exposures and loss frequency and severity
  • Achieve profitable growth through appropriate risk evaluation while building and maintaining outstanding payroll partner customer relationships
  • Prioritize and resolve payroll partner customer inquiries for documentation or support
  • Provides technical assistance to the payroll partner sales team and customers regarding policy and endorsement provisions and underwriting acceptability for designated insurance coverages
  • Maintain strong industry knowledge on commercial insurance underwriting expertise and changes in market/account positions. Develop and maintain full knowledge of all forms, coverages, ratings, and manuals for the specific line being underwritten
  • Participate in review and evaluation of risk portfolio, making recommendations on book management issues
  • Take on other tasks, responsibilities and projects as needed
Desired Qualifications
  • Experience with Insurity, HubSpot and Salesforce preferred
  • Verifying businesses using various resources and databases like Google, Yelp, LinkedIn, Facebook and similar sites
  • Experience underwriting insurance for payroll partners is very valuable
  • Strong expertise in the California workers' compensation market is preferred
  • Bachelor's degree or equivalent experience with some college coursework is preferred

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.