Full-Time

Senior Strategic Financial Modeler

Posted on 5/21/2025

Pie Insurance

Pie Insurance

501-1,000 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$160k - $200k/yr

+ Bonus

Remote in USA

Remote

Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Category
Finance & Banking (2)
,
Required Skills
Data Science
Excel/Numbers/Sheets
Financial Modeling
PowerPoint/Keynote/Slides
Requirements
  • Bachelor’s Degree in Finance, Business, Economics, Accounting or related field is required.
  • 10+ years of total relevant experience in the areas of insurance Finance or Accounting is required.
  • 7+ years of experience in Financial Planning and Analysis (FP&A) is required.
  • Strong insurance accounting knowledge including both GAAP and Statutory is highly recommended.
  • Exceptional modeling skills with strong experience building three-statement models, building models from scratch, and building dynamic scenarios for scenario analysis.
  • Strong finance acumen and with a high attention to detail.
  • Highly analytical skills and natural curiosity for how the “why” behind company metrics and KPIs; digs in until they have the understanding.
  • Advanced proficiency in Excel and PowerPoint.
  • Excellent interpersonal, oral/written communication skills, with the ability to build trusted relationships with business stakeholders.
Responsibilities
  • Build from scratch the three-statement financial projection model (balance sheet, income statement and cash flow) by legal entity for both GAAP and Statutory projections.
  • Own capital modeling for the business - BCAR, RBC, and Hazardous Financial Condition.
  • Perform variance analysis on key elements of results (gross written premium, net earned premium, losses, cash, capital, balance sheet drivers that impact the model).
  • Create presentation materials for various audiences including senior leadership and the Board, to display forecast, plan and actual results.
  • Maintain rolling near- and long-term forecasts for use by Pie management, Pie’s Board, and to inform communications with investors, ratings bureaus, reinsurance partners, and regulators.
  • Coordinate with FP&A business partners and their business leaders on incorporating 5-year business plans into the models.
  • Lead the implementation and continuous improvement of financial modeling processes, ensuring scalability and adaptability to evolving business needs.
  • Mentor and train junior team members on advanced modeling techniques and best practices.
  • Collaborate with IT and data engineering teams to automate data flows and model updates, increasing efficiency and accuracy.
  • Read and understand reinsurance contract terms and understand accounting for reinsurance for all policies in force.
  • Build out the forecast model for the treatment of reinsurance, pulling the thread through to all three financial statements.
  • Develop and maintain robust scenario analyses to assess the impact of various reinsurance structures.
  • Builds out the modeling and forecasting for Gross to Net Written and From Gross to Net Earned, taking into account UPR and IFP impacts.
  • Build loss and LAE forecasts based on AY and PY; understands loss triangle modeling.
  • Perform variance analysis and explain drivers of variance to a peg (e.g. CAY and PAY development and drivers of that development by state/segment).
  • Work with our actuarial, claims and data science teams to understand trends and drivers of Pie’s insurance losses and integrate those insights into our forecasting processes.
  • Build modeling/forecast for DAC and explain variances.
  • Partner with accounting and product teams to optimize DAC capitalization and amortization strategies.
  • Build ad-hoc models for analyzing and aiding strategic decision-making.
  • Build out the MD&A financial narratives to help the board and investors understand Pie’s business.
  • Provide financial modeling and analysis support for fundraising, reinsurance negotiations, and potential future acquisitions.
  • Lead the integration modeling for M&A activities.
  • Present complex financial concepts and recommendations to executive leadership.
Desired Qualifications
  • 3+ years of building financial models specific to insurance companies is preferred, including modeling RBC and BCAR.
  • Insurance industry experience is required (P&C experience is a plus).
  • Demonstrated experience influencing cross-functional teams and mentoring junior staff.
  • Track record of driving process improvements and implementing automation in financial modeling and reporting.
  • Strong preference to base decisions on data and ROI.
  • Experience in managing work-streams end-to-end along with working across multiple functions and teams.
  • Google Suite, Looker, Intacct, Adaptive and Workday experience or experience with related tools is a plus.

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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