Full-Time

Director Actuary

Pie Insurance

Pie Insurance

201-500 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$180k - $240k/yr

+ Discretionary bonuses + 401(k) match

Remote in USA

Remote

Remote team members must live and work in the United States, excluding territories.

Bachelor's

Category
Finance & Banking (1)
Required Skills
Python
SQL
Machine Learning
Data Engineering
Data Analysis
Snowflake

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Requirements
  • A Bachelor's Degree is required.
  • 10+ years of progressive insurance actuarial experience is required.
  • 6+ years of people leadership experience.
  • Ability to communicate effectively across organizational levels and present perspectives and requests clearly, directly, and openly.
  • Ability to collaborate across multiple cross-functional groups and understand different points of view and needs.
  • Ability to translate business segment strategy into functional plans and guide execution.
  • Ability to apply integrative thinking to solve underlying business needs.
  • Ability to surface issues early, manage stakeholder expectations, and anticipate problems.
  • Active use of artificial intelligence tools to accelerate analysis, drafting, and team productivity.
  • Ability to exercise independent judgment, bring well-reasoned actuarial positions to senior leadership, and defend them under scrutiny.
Responsibilities
  • Lead Corporate Actuarial functions for workers' compensation and other property and casualty lines of business.
  • Manage a growing team of actuaries responsible for reserving, reinsurance, pricing, ratemaking, analytics, and systems integration.
  • Enhance enterprise risk management capabilities, apply predictive models, research workers' compensation industry trends, and develop and deliver presentations to senior-level audiences.
  • Ensure consistent use of methods and assumptions across lines of business during loss-trend deep dives and recurring work.
  • Guide team members in developing loss-trend storylines for workers' compensation and other lines of business.
  • Manage regular reporting deliverables, including competitor commentary and pure premium relativity.
  • Establish relationships and collaborate with cross-functional areas to prioritize team work and support development of insurance trends.
  • Collaborate with actuaries and business units to execute actuarial data-driven initiatives.
  • Develop high-quality, reproducible predictive and descriptive tools for business use.
  • Review innovative models and recommend regulatory approaches to innovation.
  • Monitor portfolio key performance indicators, including frequency and severity trends, and proactively inform senior management.
  • Collect, aggregate, and analyze data from multiple internal and external sources.
  • Write and maintain code to build and maintain data pipelines for production models.
  • Use and develop advanced actuarial techniques to discover patterns, insights, and trends in company data.
  • Produce rate-level indications using advanced actuarial ratemaking methodology.
  • Work with reinsurers and the reinsurance broker to optimize the reinsurance program and create reporting, including bordereau materials, for reinsurance partners.
  • Work with external partners such as A.M. Best, auditors, and external consultants as needed.
  • Partner with the Data team to identify and establish actuarial data requirements.
  • Provide regular status updates to senior leadership.
  • Identify issues and recommend mitigation strategies.
  • Ensure key stakeholders are identified and regularly informed of project status.
  • Lead the development and documentation of actuarial department processes.
  • Support, mentor, and coach team members and provide professional development, continuous feedback, and career-development opportunities.
  • Partner with the People Partner on performance-improvement and coaching plans.
  • Identify hiring needs and serve as hiring manager for recruiting analysts.
  • Address conflict-management and team-member-relations needs with the People Team.
  • Partner with the People Partner throughout the team-member lifecycle, including hiring, onboarding, performance management, team-member relations, and offboarding.
Desired Qualifications
  • Experience using Snowflake, SQL, Python, and other programming languages.
  • Fellow of the Casualty Actuarial Society.

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.