Full-Time

Senior Underwriter

Small Commercial Workers’ Compensation/Commercial Auto

Posted on 9/30/2025

Pie Insurance

Pie Insurance

501-1,000 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$95k - $120k/yr

Remote in USA

Remote

Category
Finance & Banking (1)
Required Skills
Risk Management
Requirements
  • High School diploma or GED required.
  • Bachelor's Degree or equivalent experience with some college coursework is preferred.
  • 3+ years of insurance experience required, preferred commercial lines experience.
  • 3+ year of commercial auto underwriting experience is required, 5+ years is preferred.
  • Aptitude for building and maintaining strong partner relationships through excellence in service, engagement & follow through in conjunction with our Business Development and Partner Experience teams.
  • Excellent interpersonal and communication skills with the ability to convey underwriting rationale both internally and externally.
  • Serve as a subject matter expert and resource for underwriting strategy, appetite, and decision-making.
  • Provide technical guidance and mentorship to other underwriters and support team members.
  • Excellent problem-solving skills to be able to manage complex tasks and work through solutions with little guidance and direction.
  • Excellent awareness of your own tasks, and how it impacts the team and deliverables.
  • Intermediate to advanced knowledge of commercial auto from business auto to trucking.
  • Ability to balance the outstanding execution of processes while handling a high volume of transactions.
  • Demonstrated ability to take initiative on escalated issues and rush requests.
  • Always seeking better ways to streamline processes and maximize efficiencies.
  • Verifying businesses using various resources and databases like Google, Yelp, LinkedIn, Facebook and similar sites.
  • Willing to work in an iterative development environment with an ever-changing landscape filled with possibilities and questions.
Responsibilities
  • Leverage commercial auto underwriting expertise to assess medium to complex risks to underwrite and bind new coverage.
  • Quickly and effectively assess each submission using 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 partner customer relationships.
  • Prioritize and resolve partner customer inquiries for documentation or support.
  • Provide technical assistance to the support teams 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.
  • Participate in review and evaluation of risk portfolio, making recommendations on book management issues.
  • Consistently meets production targets and contributes to team goals through efficient workload management and timely task completion.
Desired Qualifications
  • Five or more years of commercial auto underwriting experience is preferred.
  • Bachelor degree or higher in a related field is desirable.
  • Proven track record of building and maintaining partner relationships and delivering exceptional service is desirable.
  • Experience with underwriting in a fast-paced, remote environment is desirable.

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

501-1,000

Company Stage

Series D

Total Funding

$620.3M

Headquarters

Washington DC, District of Columbia

Founded

2017

Simplify Jobs

Simplify's Take

What believers are saying

  • 271% direct written premium growth drives fastest U.S. workers' comp expansion.
  • Audra Foglietta's Chubb expertise boosts financial performance as new CFO.
  • $615M funding since 2017 and 2,800 agency partnerships fuel nationwide scale.

What critics are saying

  • 14% layoffs in 2023 erode morale and trigger talent exodus to GEICO.
  • Funding drought exhausts cash runway without new VC investment.
  • Next Insurance steals market share with broader bundled policy offerings.

What makes Pie Insurance unique

  • Pie Insurance uses data analytics for precise small business workers' comp pricing.
  • Offers 3-minute online quotes and up to 30% savings in 40 states.
  • A.M. Best A-rated coverage revolutionizes traditional insurance processes.

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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

-14%

1 year growth

-14%

2 year growth

-15%
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.

Insurance Innovation 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.

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