David Isaacson counsels public and private companies of all sizes and across all industries to help address the full range of legal, financial and administrative issues relating to their compensation and benefit plans. He provides counseling services that align legal strategies with practical approaches to achieve successful outcomes for each client.

David’s practice primarily focuses on health and welfare benefit plan and tax-qualified retirement plan compliance, including issues related to:

  • Health and welfare plan design and documentation
  • Affordable Care Act (ACA) 
  • Wellness program compliance
  • Consumer Driven Health Care initiatives (including health savings accounts and health reimbursement arrangements)
  • Health Insurance Portability and Accountability Act (HIPAA) privacy and security compliance
  • Negotiations with plan service providers
  • Employee benefit plan issues that arise in corporate transactions
  • ERISA fiduciary obligations and governance procedures around investments and other plan asset issues
  • Tax-qualified retirement plans, including 401(k), 403(b), 457, profit-sharing, cash balance and traditional defined benefit pension plans

Education

  • University of Illinois College of Law (J.D., magna cum laude, 2013)
    • University of Illinois (B.A., cum laude, 2010)
      • Philosophy, Communication

    Bar Admission

    • Illinois, 2013

    Court Admissions

    • U.S. Tax Court, 2016
    • U.S. District Court, Northern District of Illinois, 2013

    Professional Affiliations

    • American Bar Association
    • Chicago Bar Association

    Recognition

    • Named one of Best Lawyers: Ones to Watch® in America in Employee Benefits (ERISA) Law, 2021-2025
    Publications
    All Publications
    New Year, New Dependent Care FSA Limits: Don’t Forget to Amend Your Plan!
    Key Takeaways The One Big Beautiful Bill Act allows employers to raise the dependent care FSA exclusion limit starting Jan. 1, 2026. This is the first time since 1986 and offers meaningful additional tax savings for employees. Employers must amend plan documents to implement the higher limit. Without a formal update, plans will not be able to offer the increased contribution cap in 2026. Plan amendments must be executed by Dec. 31, 2025 to adopt the new limit. Plan sponsors should complete written amendments and follow the appropriate governance process before year end. The One Big Beautiful Bill Act (OBBB) allows employers to increase the maximum annual exclusion limit for dependent care flexible spending accounts (DCFSAs) beginning Jan. 1, 2026 – the first
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    A Quick Look at Benefits and Executive Compensation Provisions in the One Big Beautiful Bill
    On July 4, 2025, President Donald J. Trump signed into law the One Big Beautiful Bill (OBBB). For employers, the most notable benefits-related provisions include expanded flexibility for health savings accounts (HSAs) and new restrictions on premium tax credit eligibility – changes that may reduce the risk of triggering an employer shared responsibility penalty under the Affordable Care Act (ACA). While the OBBB does not change the tax incentives for retirement savings, nor does it cap the exclusion amount for employer-sponsored health insurance, it introduces several developments worth employer attention. A summary of key provisions follows. HSAs Extension of Telehealth Safe Harbor for HSA Participants. The OBBB permanently extends the COVID-era safe harbor allowing coverage of telehealth and other remote care services
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