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Pie Insurance

Tech-driven workers' comp for small businesses

Commercial Counsel

Full-TimeUpdated on 10/3/2026
$150k - $185k+ Discretionary bonus + 401(k) match
Mid
JD
Remote in USA
RemoteRemote team members must live and work in the United States; territories are excluded.

About the job

Requirements
  • At least 4 years of relevant legal experience, in-house or at a law firm advising companies on commercial matters.
  • A J.D. from an ABA-accredited law school and active bar licensure in at least one U.S. state are required.
  • Demonstrated experience drafting, reviewing, and negotiating commercial contracts is required, along with familiarity with contract lifecycle management tools.
  • At least 1 year of experience with collections, accounts receivable, or creditor rights matters is required.
  • Strong written and verbal communication skills to translate legal concepts for non-lawyers without losing substance.
  • Strong organizational skills and the ability to manage a high volume of matters simultaneously.
  • Sound judgment and confidence in making independent decisions and escalating when appropriate.
  • Ability to build trusted relationships across the organization.
  • Proficiency with Microsoft Office (Outlook, Word, Excel, PowerPoint) and Google Suite (Gmail, Docs, Sheets, Drive).
Responsibilities
  • Draft, review, and negotiate commercial agreements, vendor contracts, non-disclosure agreements, and service agreements on behalf of Pie business partners.
  • Serve as the primary point of contact for contract intake and workflow management in the LinkSquares contract lifecycle management platform.
  • Identify legal risks and propose practical revisions that protect Pie’s interests without creating unnecessary friction for the business.
  • Partner with internal stakeholders across Technology, Finance, Operations, and other teams to understand contracting needs and provide responsive, business-oriented guidance.
  • Manage the executed contract repository, including tracking key dates, renewal windows, and obligations.
  • Handle subpoena responses as they arise.
  • Manage Pie’s legal collections process for unpaid premium accounts and past-due invoices.
  • Draft and send formal demand letters; coordinate with outside collection agencies or local counsel when legal action is warranted.
  • Track recovery progress and report outcomes to Finance and legal leadership.
  • Resolve disputed accounts and escalated matters within applicable legal frameworks.
  • Assist with corporate governance matters, including maintenance of corporate records, preparation of board and officer documentation, and related filings.
  • Support regulatory compliance initiatives across Pie’s multi-state insurance holding company structure as needed.
  • Assist with additional legal matters and special projects as the legal team’s needs evolve.
  • Assist with creating, updating, and maintaining company policies, such as website terms of service and workers’ compensation policy terms and conditions.
Desired Qualifications
  • California bar licensure is preferred.
  • Experience with LinkSquares is a plus.
  • Demonstrated litigation experience is strongly preferred, including familiarity with court filings, discovery, and managing outside litigation counsel.
  • Familiarity with SharePoint is helpful.

About the company

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

Denver, Colorado

Founded

2017

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Simplify's Take

What believers are saying

  • January 2026 milestones showed 55,000 policies in-force and continued geographic expansion.
  • Pie says 2026 priorities are responsible growth and deeper agent partnerships, strengthening retention.
  • More than $615 million funding and A.M. Best A rating support carrier credibility.

What critics are saying

  • May 2023 layoffs cut 14% after management said profitability required no additional investment.
  • Pie Development v. Pie Insurance keeps trade-secret claims alive around its founding.
  • If capital markets stay shut, Pie’s cash runway and growth stall before profitability.

What makes Pie Insurance unique

  • Pie’s 2026 agent network tops 5,000 agencies, embedding distribution others lack.
  • Its 2026 Connecticut expansion and 55,000 policies-in-force show scaled underwriting breadth.
  • Data science, AI pricing, and reinsurance specialization remain Pie’s core moat.

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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

↑ 13%

1 year growth

↑ 3%

2 year growth

↑ 1%
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.