Staff Attorney Trial Specialist

Job Description

Job Description

Position will be headquartered in Orlando but also involves some travel to our Ormond Beach office.

Staff Attorney – Trial Specialist

Help Shape the Future of First-Party Property Litigation

Are you the attorney other trial lawyers call when the stakes are highest?

Security First is looking for an experienced, strategic trial attorney to elevate our litigation team through mentorship, courtroom excellence, and innovative trial strategy. This isn't a high-volume litigation position—it's an opportunity to influence outcomes, develop attorneys, and help build one of the strongest in-house litigation teams in Florida.

If you enjoy trying complex cases, coaching other attorneys, and helping shape litigation strategy from start to finish, apply today!

What You'll Do

As our Staff Attorney Trial Specialist, you'll serve as the organization's litigation strategist and trial mentor. You'll work alongside talented Staff Counsel Attorneys to strengthen trial preparation, refine courtroom strategy, and help deliver exceptional outcomes for our policyholders and the company.

In this role, you will:

• Lead trial strategy discussions for complex First Party Property litigation.
• Coach and mentor Staff Counsel Attorneys in trial advocacy, witness preparation, evidentiary issues, and courtroom presentation.
• Serve as second chair during trials across Florida, while occasionally acting as lead trial counsel.
• Evaluate trial readiness and identify opportunities to strengthen cases before they reach the courtroom.
• Partner with Claims professionals and Litigation Specialists to develop winning litigation strategies.
• Assist with mediation strategy and settlement evaluations.
• Create and deliver engaging trial training programs and best practices.
• Share your knowledge to help develop the next generation of exceptional trial attorneys.

What You Bring

We're looking for someone who combines courtroom confidence with a passion for coaching others.

Qualifications include:

• Juris Doctor from an accredited law school
• Active member of The Florida Bar
• Minimum 12 years of trial experience
• Extensive experience handling First Party Property litigation
• Strong courtroom presence and exceptional communication skills
• A collaborative leadership style and passion for mentoring attorneys
• Strategic thinking and the ability to simplify complex legal issues
• Ability to travel throughout Florida as needed for trials

Why You'll Love Working Here

We're serious about our work—but we also believe work should be enjoyable.

Our offices were designed with our team members in mind and includes:

• State-of-the-art fitness center
• Complimentary chef-prepared lunches monthly
• Beautiful walking trail around our offices
• Team Member appreciation events throughout the year
• Hybrid work environment that supports collaboration and flexibility
• Food truck events featuring local favorites
• Professional development, mentoring, and continuing education
• Competitive benefits package including medical, dental, vision, paid time off, 401(k), and more

At Security First, you'll find a collaborative culture where people genuinely enjoy working together and where your expertise is valued.

The Kind of Person Who Thrives Here

You are someone who:

• Enjoys leading through influence rather than direct supervision and takes pride in helping others succeed.
• Loves being in the courtroom.
• Enjoys mentoring and developing attorneys.
• Thinks strategically—not just tactically.
• Builds strong relationships across departments.
• Leads with integrity, professionalism, and humility.
• Believes great teams produce great results.