Commercial Counsel

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance. Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

As Staff Attorney, you’ll report directly to the VP of Legal & Compliance and serve as a key legal resource across the organization. Your primary focus will be commercial contract review and negotiation on behalf of all business partners at Pie, managed through our contract lifecycle management platform, LinkSquares. You’ll own the full contracting workflow — from intake through execution — while building strong relationships with internal stakeholders who rely on your guidance to move work forward.

You’ll also lead Pie’s legal collections function, supporting accounts receivable recovery through demand letters, coordination with outside counsel, and resolution of disputed accounts. This role will likely expand to include corporate compliance and governance support, as well as other legal matters across the organization.

How You’ll Do It

Contract Review and Negotiation

Draft, review, and negotiate commercial agreements, vendor contracts, NDAs, and service agreements on behalf of all business partners at Pie.

Serve as the primary point of contact for contract intake and workflow management in LinkSquares, our 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 their 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.

Collections

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.

Corporate Governance and Compliance Support

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 (ex. website terms of service, workers comp policy terms and conditions, etc.)

The Right Stuff

4+ years of relevant legal experience, in-house or at a law firm advising companies on commercial matters.

J.D. from an ABA-accredited law school; active bar licensure in at least one U.S. state required; California licensure preferred.

Demonstrated experience drafting, reviewing, and negotiating commercial contracts; familiarity with contract lifecycle management tools required. Experience with LinkSquares a plus.

1 year of experience with collections, accounts receivable, or creditor rights matters required.

Demonstrated litigation experience strongly preferred — including familiarity with court filings, discovery, and managing outside litigation counsel.

Excellent written and verbal communication skills — used to translate legal concepts for non-lawyers without losing the substance.

Strong organizational skills and the ability to manage a high volume of matters simultaneously.

Sound judgment and the confidence to make independent decisions, escalating when appropriate.

Collaborative by nature, with the ability to build trusted relationships across the organization.

Proficiency with Microsoft Office (Outlook, Word, Excel, PowerPoint) and Google Suite (Gmail, Docs, Sheets, Drive); familiarity with SharePoint helpful.

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range$150,000—$185,000 USD

Compensation & Benefits

Competitive cash compensation

Comprehensive health plans

Generous PTO

Future focused 401k match

Generous parental and caregiver leave

Our core values are more than just a poster on the wall; they’re tangibly reflected in our work

Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information

Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

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Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

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