Randie Thompson has extensive experience in employee benefits and ERISA law, with a specific focus in health and welfare benefit plans. She represents plan sponsors, fiduciaries and vendors in a wide variety of matters related to employee benefit plan compliance, design, administration and governance. 

Throughout her career, Randie has developed unique expertise in representing complex health plan arrangements, including self-funded single employer plans, multiple employer welfare arrangements (MEWAs - both professional employer organizations and association health plans), voluntary employees' beneficiary associations (VEBAs), Native American tribal health plans, and group purchasing organizations. Representing plans of all types and levels of complexity has provided Randie deep insights into the increasingly complex issues faced by her clients, including those more recently introduced by the Consolidated Appropriations Act of 2021.

At Conner & Winters, Randie advises clients on plan design, documentation, administration, compliance and reporting, including complex compliance analysis under ERISA's prohibited transaction rules. She also assists clients with completing government audits and investigations, oversees internal compliance reviews and provides fiduciary training. Randie's expertise extends from federal employee benefit statues and regulations under laws such as ERISA, IRC, HIPAA, COBRA, ACA, PHSA and FMLA to the increasingly complex area of state-specific benefit laws, including matters of ERISA preemption. 

Randie previously worked at Conner & Winters as a summer clerk and then as an associate attorney. Since that time, she has worked for other law firms, maintained a solo ERISA practice, worked as a health and welfare benefits compliance consultant for a global benefits consulting firm and served as in-house ERISA counsel for a Silicon Valley-based healthcare technology firm. 

Randie graduated with honors from the University of Tulsa College of Law and she also holds a Master of Laws (LL.M.) in Taxation from Georgetown University Law Center. Prior to law school, she earned her undergraduate degree from Dartmouth College.


  • Complex compliance analysis, including ERISA prohibited transaction and plan expense rules
  • Contract drafting and negotiation
  • Compliance and fiduciary training
  • Plan design, documentation, administration and governance
  • Employee communications
  • Governmental reporting, audits and investigations
  • ERISA, IRC, HIPAA, COBRA, ACA, PHSA, FMLA and state law compliance
  • ERISA preemption

Honors & Leadership

Honors & Recognitions

  • Editor, Tulsa Law Review


Alerts & Publications


University of Tulsa College of Law, J.D. with honors

Georgetown University Law Center, LL.M. in Taxation

Dartmouth College, B.A. in English Literature


  • Oklahoma, 1999
  • Colorado, 2002
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