Jessica O'Brien

O'Brien, Jessica Senior Counsel

O'Brien, Jessica Senior Counsel

Practice Focus

Jessica O’Brien is senior counsel in Tressler’s Insurance Services Practice Group in Orange County. She concentrates her practice on coverage matters, including bad faith and extra contractual liability litigation involving a variety of tort issues.  She has a particular interest in trucking and motor carrier, construction defect and sex and human trafficking exposures. Jessica evaluates and analyzes insurance coverage matters, conducts risk assessments for insurance carriers and prepares coverage opinions and position letters. She also manages coverage litigation. Jessica has consistently obtained favorable results for her clients by settling a range of insurance coverage and liability disputes.

Professional Background

Most recently, Jessica spent over five years as in-house counsel for a top ten auto and casualty insurance carrier, where she specialized in coverage analysis, drafting coverage position letters and reservations of rights, while actively managing complex liability and bad faith litigation in personal, commercial and professional liability lines of Insurance. Jessica regularly prepared staff for depositions and trial testimony and advised internal departments on case law changes in tort and insurance coverage fields affecting business conduct.

Prior to working in-house, Jessica spent six years representing individuals and corporations struggling with income tax debt, advocating on their behalf in front of the IRS and various State Departments of Revenue. Owner/Operator Truck Drivers were her "bread and butter" in that era. Jessica reveled in being able to bring her clients relief from the strain of overwhelming legal issues. 

Memberships & Affiliations

  • The Chicago Tax Club
  • Illinois Bar Association
  • Michigan Bar Association
  • Kentucky Bar Association
  • Kentucky Defense Counsel
  • Federation of Defense & Corporate Counsel 

News

Community Involvement

Jessica volunteers as an under six soccer coach for her local parks and recreation department. She considers helping her ‘minions’ progress as athletes and people one of the most fulfilling parts of her life at present. 

Personal Life

Jessica is married to her loving husband, Michael. They share two beautiful dog children, Rosie Bug and Kiki.