Trial Attorney

Trial Attorney


With over 100 years of history, stability, and a proven track record of success at Sentry, we're currently in need of a dedicated and driven person just like you. We're currently hiring for a Trial Attorney to represent the interests of Sentry in defending claims made by providers pursuant to Florida P.I.P. laws.

The ideal candidate will work remotely in the Orlando, FL or Jacksonville, FL area and have a minimum of 2 years of trial experience, preferably in insurance defense, and a proven track record of defending insurance carriers in the challenging environment of Personal Injury Protection Litigation.

What You'll Do

As a Trial Attorney with Sentry, you'll draft pleadings, handle depositions, attend hearings, argue  motions, and negotiate settlements in the interest of Sentry. In addition, you'll:

  • Handle a full caseload of minimal to moderate complex matters representing Sentry
  • Communicate and report to the internal Client and Claims associates on progress of litigation, strategy, and evaluation
  • Assist Claims associates as requested in resolving cases against Sentry by settlement and/or trial
  • Develop and maintain all strategies from pre-trial through post-trial and conduct appeals when appropriate
  • Participate in training Claims personnel regarding litigation and the law as requested
  • Review case law and statutory changes to maintain current knowledge of the law and to report on emerging legal trends

What it Takes

  • Strong academic background and a Juris Degree (JD) from an American Bar Association-accredited law school
  • 2+ years of experience as a practicing litigation attorney licensed in Florida
  • Experience with P.I.P. litigation required; additional experience with tort / bodily injury litigation strongly preferred
  • Active license to practice law in the state of Florida
  • Proven ability to present complex concepts analytically and logically
  • Successful experience in dealing with people where conflict and controversy exists
  • Ability to self-manage in a remote work environment

What You'll Receive

We take great pride in making Forbes' list of America's Best Midsize Employers since 2017. A lot of different factors go into that honor, many of which contribute to your job satisfaction.  At Sentry, your total rewards go beyond competitive compensation.   Below are some benefits and perks that you'll receive.

  • Generous  Paid-Time Off  plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your  first eight percent , plus immediate vesting to help strengthen your financial future.
  • Group Medical, Dental, Vision and Life  insurance  to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense  Reimbursement Accounts  to ease taxes on health spending.
  • Extensive  Work-Life Resources  to lend a helping hand.
  • Sentry Foundation  gift matching program  to encourage charitable giving.
  • Continue your education and career development through Sentry University (SentryU).

How You'll Apply

If you are interested in joining Sentry's team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you'll need to create an account. Please complete your application and upload your resume online.

About Sentry

All of us at Sentry-more than 4,000 associates-have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We're proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.

Our headquarters is in Stevens Point, Wisconsin, with claims and service offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we're one of the largest and financially strongest mutual insurance companies in the United States. We're rated A+ by A.M. Best, the industry's leading rating authority.

Get ready to own your future at Sentry. Opportunities await.

Equal Employment Opportunity

It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Zach Wierzba

(see application details) 

Salary Range
$62,000.00 - 106,000.00
per Year
Salary range estimated by
North Adams, MA 01247, US
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