Full-Time

Total Rewards Manager

Pie Insurance

Pie Insurance

201-500 employees

Tech-driven workers' comp for small businesses

Compensation Overview

$115k - $145k/yr

Remote in USA

Remote

Remote role; must reside in United States (territories excluded).

Bachelor's

Category
People & HR (1)
Required Skills
Claude
Workday HRIS
Human Resources Information System (HRIS)
Excel/Numbers/Sheets

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Requirements
  • Bachelor's Degree or equivalent experience with some college coursework
  • 5+ years compensation and equity analysis experience.
  • 3+ years of benefits administration experience.
  • Knowledge of laws and regulations as they apply to base compensation and incentive compensation programs, company policies, and operations.
  • SHRM Certified Professional (SHRM-CP) or Senior Certified Professional (SHRM-SCP) and certified compensation professional credentials.
  • Advanced communication (written, verbal and presentation) skills, to deliver complex information effectively and align people with the needs of the project/team.
  • Advanced problem solving skills, to be able to manage complex situations with multiple layers, and resolve to solution anticipating needs now and into the future.
  • Advanced awareness of workflow, and project tradeoffs to make decisions based on needs now and into the future.
  • Experience using G-Suite and collaboration tools.
  • Excel, HRIS (Workday), compensation tools.
  • Experience using AI tools (Claude) and other AI tools specific to Total Rewards a plus
Responsibilities
  • Serve as the Compensation Partner to deliver strategic compensation support to the organization: Provide consultation and guidance to key stakeholders (Director of People Operations, Chief People Officer, CEO, and CFO) as well as other leaders and People Partners regarding compensation strategy, programs, and communications.
  • Partner with People Partners and Talent Acquisition for all compensation activities related to their functions.
  • Assist with ad-hoc requests and reporting needs.
  • Compensation analysis: Ensure salary and equity structures remain market competitive as the market changes throughout the year.
  • Work with People Partners to recommend any necessary off-cycle increases and market adjustments.
  • Audit for pay gaps and ensure equitable pay.
  • Maintain Pie’s job architecture: Prepare and/or review job descriptions reflecting job responsibilities, activities, duties, and requirements and recommend appropriate alignment within our job architecture.
  • Ensure consistent application of job architecture throughout the organization thereby protecting equitable practices in job levels and compensation
  • Assist in maintaining systems to ensure accuracy of compensation data, job profiles, bonus targets, equity, etc.
  • Contribute to overall compensation strategy: Partner with external compensation consultant(s) on executive compensation practices, reviews, and recommendations.
  • Assist with equity strategy, planning, and execution.
  • Co-owns the implementation of the annual compensation and performance cycle program execution.
  • Administer benefits programs: Manages benefit programs, partnering with peers, vendors, consultants, and auditors to do so.
  • Recommend changes to benefits programs.
  • Implements and administers benefits programs.
  • Administer leave programs.
  • Own all benefits processes, systems, and reporting: Manage payroll contributions and match processes.
  • Oversee all benefits-related reporting.
  • Verify and maintain accuracy of data.
  • Ensure compliance with applicable laws, regulations, and policies.
Desired Qualifications
  • Experience using AI tools (Claude) and other AI tools specific to Total Rewards 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

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.