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Garretson

Director of Finance (Chicago)

Garretson, Chicago

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Location: Chicago preferred; Remote fine (Candidates based in the U.S.)

About Garretson

Garretson is a fast-growing organization at the intersection of legal, technology, and financial services. As we expand, we seek a Director of Finance to establish strong financial foundations, oversee financial operations across multiple entities, execute financial management and compliance of litigation settlement funds and support our long-term growth strategy.

Role Overview

The Director of Finance will lead financial management, billing, revenue operations, and strategic financial planning to ensure operational efficiency and scalability. Opportunity for part-time or full-time position .

Key Responsibilities

  • Oversee and update financial records, ensuring accuracy and compliance.
  • Prepare consolidated financial statements and reporting across all entities.
  • Implement and maintain financial controls for transparency and risk management.

Billing & Revenue Operations

  • Establish and manage billing processes for existing and new clients.
  • Develop standardized invoicing and revenue tracking for Statuo, Jaine, and other entities.
  • Ensure timely collections and reconciliation of accounts receivable/payable.

Financial Planning & Analysis; Strategy & Fundraising

  • Develop financial models and projections to guide business growth and investment decisions.
  • Track and optimize cash flow, budgeting, and liquidity management.
  • Work with leadership to prepare financial materials for investor discussions and fundraising.
  • Support due diligence and financial structuring for potential acquisitions and funding rounds.

Qualified Settlement Fund Accounting and Management

  • Establish and manage settlement fund accounts with several different banking institutions.
  • Accounting and tax reporting management of Qualified Settlement Funds pursuant to IRS code 468B.1.
  • Evaluate and report on the settlement funds under management on a monthly, quarterly and annual basis.
  • Coordinate with third party payment distribution services and tax accounting entities.

Shared Services & Compliance

  • Streamline shared financial services, including payroll, HR, and benefits setup.
  • Implement accounting best practices and ensure regulatory compliance.
  • Collaborate with external counsel and auditors on financial governance.

Qualifications & Experience

  • 8+ years of experience in finance, accounting, or controller roles.
  • Background in law firms, professional services, SaaS, or legal tech is a plus.
  • Proficiency in QuickBooks, Rippling (or other PEO), and financial reporting software is a plus.
  • Strong analytical skills with the ability to develop and manage financial models.
  • Self-starter who thrives in a fast-paced, high-growth environment with multiple stakeholders.

Compensation & Structure

  • Compensation aligned with experience and industry benchmarks.

Seniority level

  • Seniority level

    Director

Employment type

  • Employment type

    Full-time

Job function

  • Job function

    Finance and Sales

  • Industries

    Legal Services

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