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Pie Insurance

Tech-driven workers' comp for small businesses

Underwriter - Workers' Compensation

Full-Time
$80k - $100k/yr+ Discretionary bonuses
Mid
Bachelor's
Remote in USA
RemoteRemote within the United States, excluding territories; up to 10% travel may be required.

About the job

Requirements
  • A high school diploma or GED is required.
  • A minimum of 3 years of underwriting experience or equivalent experience is required.
  • Intermediate to advanced knowledge of workers' compensation class codes is required.
  • Ability to sell the product while simultaneously discerning risk characteristics within the direct-to-business market.
  • Ability to execute processes effectively while handling a high volume of transactions.
  • Experience verifying businesses using resources and databases such as Google, Yelp, LinkedIn, Facebook, and similar sites.
Responsibilities
  • Assess medium to complex risks using workers' compensation or commercial insurance underwriting expertise to underwrite and bind new and renewal coverage.
  • Decide each request using underwriting guidelines and known risk exposures, loss frequency, and loss severity.
  • Achieve profitable growth through appropriate risk evaluation while building and maintaining payroll partner customer relationships.
  • Prioritize and resolve payroll partner customer inquiries for documentation or support.
  • Provide technical assistance to the payroll partner sales team and customers regarding policy and endorsement provisions and underwriting acceptability for designated insurance coverages.
  • Maintain industry knowledge of commercial insurance underwriting and changes in market and account positions.
  • Develop and maintain knowledge of forms, coverages, ratings, and manuals for the specific line being underwritten.
  • Participate in review and evaluation of the risk portfolio and make recommendations on book management issues.
  • Take on other tasks, responsibilities, and projects as needed.
Desired Qualifications
  • A bachelor's degree or equivalent experience with some college coursework is preferred.
  • Experience with Insurity, HubSpot, and Salesforce is preferred.
  • Experience underwriting insurance for payroll partners is valuable.
  • Strong expertise in the California workers' compensation market is preferred.

About the company

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

Denver, Colorado

Founded

2017

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Simplify's Take

What believers are saying

  • January 2026 milestones showed 55,000 policies in-force and continued geographic expansion.
  • Pie says 2026 priorities are responsible growth and deeper agent partnerships, strengthening retention.
  • More than $615 million funding and A.M. Best A rating support carrier credibility.

What critics are saying

  • May 2023 layoffs cut 14% after management said profitability required no additional investment.
  • Pie Development v. Pie Insurance keeps trade-secret claims alive around its founding.
  • If capital markets stay shut, Pie’s cash runway and growth stall before profitability.

What makes Pie Insurance unique

  • Pie’s 2026 agent network tops 5,000 agencies, embedding distribution others lack.
  • Its 2026 Connecticut expansion and 55,000 policies-in-force show scaled underwriting breadth.
  • Data science, AI pricing, and reinsurance specialization remain Pie’s core moat.

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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

↑ 13%

1 year growth

↑ 3%

2 year growth

↑ 1%
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.