Full-Time

Senior Underwriting Manager

Underwriting

Pie Insurance

Pie Insurance

201-500 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$130k - $165k/yr

+ Discretionary bonuses

Remote in USA

Remote

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

Bachelor's

Category
Finance & Banking (1)
Required Skills
Data Analysis

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Requirements
  • High school diploma/GED required.
  • Bachelor's degree or equivalent experience preferred.
  • Minimum 8 years of commercial insurance experience required.
  • Minimum 4 years of progressive leadership experience in commercial insurance underwriting; experience leading managers or team leads is a plus but not required.
  • Disciplinary expertise sought out by peers and team members; strong technical underwriting judgment with the ability to handle complex risks independently.
  • Proven ability to manage operational execution across a team, balancing throughput, quality, and team development simultaneously.
  • Skilled at translating strategic direction into operational plans and guiding a team through execution — including during periods of change or ambiguity.
  • Strong data fluency: able to track team performance metrics, identify trends, and communicate findings clearly to leadership.
  • Effective cross-functional communicator; builds trust with internal partners and escalates appropriately without over-relying on the Director.
  • Advanced problem-solving skills with the ability to navigate multi-layered situations and anticipate downstream impacts.
  • Experience with performance management, coaching plans, and talent development.
  • Knowledge of insurance underwriting best practices, service metrics, and customer experience operations.
  • Progress toward or attainment of a professional designation (CPCU, ARe, or equivalent) is a plus and encouraged as a development milestone for those on a Director-track trajectory.
  • Proficiency in G-Suite tools and collaboration platforms (Slack preferred).
Responsibilities
  • Own team adherence to service levels, underwriting guidelines, and quality standards; proactively surface and resolve operational bottlenecks before they escalate.
  • Serve as the primary internal escalation point for complex submissions, risk evaluations, and underwriting judgment calls within the team.
  • Manage workload distribution and capacity across the team to maintain SLA performance during volume fluctuations or staffing changes.
  • Oversee training and SOP currency; ensure team members are up to date on appetite, product changes, pricing models, and industry developments.
  • Directly manages a team of underwriters that may include senior individual contributors, Team Leads, and/or other managers depending on organizational structure.
  • Coaches and develops team members with a focus on building independent decision-making, accountability, and technical proficiency — creating the conditions for others to operate with greater autonomy over time.
  • Partners with the People team and the Director throughout the full team member lifecycle, including performance management, coaching plans, hiring, and offboarding.
  • Identifies hiring needs and leads recruiting for high-quality underwriters; shapes team composition with a view toward future capability needs.
  • Identify, develop, and implement process improvements that drive efficiency, underwriting quality, and conversion within the team.
  • Gather feedback from underwriters and internal partners to surface operational gaps; bring forward well-scoped recommendations to the Director.
  • Provide reporting and performance data to the Director and leadership; use data to frame team results and highlight trends requiring action.
  • Support implementation of new underwriting tools, best practices, and product or pricing changes as directed by the Director and cross-functional partners.
  • Serve as an operational point of contact for partner agents on day-to-day underwriting matters, escalating relationship-level issues to the Director as appropriate.
  • Partner with Business Development to support retention and partner engagement at the team level.
Desired Qualifications
  • Workers' compensation underwriting experience strongly preferred.
  • Bachelor's degree or equivalent experience preferred.
  • Experience leading managers or team leads is a plus but not required.
  • Progress toward or attainment of a professional designation (CPCU, ARe, or equivalent) is a plus.
  • Slack 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.