Staff Attorney Trial Specialist

Security First Insurance; Orlando (FL); On-site; USD 140,000 - 180,000; Full time

Benefits offered by this job

Fitness center access

Chef-prepared lunches

Walking trail

Team events

Hybrid work environment

Mentoring and development

Benefits package

Job summary

Security First Insurance in Orlando, FL, seeks a Staff Attorney – Trial Specialist with 12+ years of trial experience in first party property litigation to lead our litigation team. The role involves mentoring attorneys, shaping strategy, and handling high-stakes trials.

The position supports a hybrid work environment with periodic travel to the Ormond Beach office to coordinate statewide litigation efforts and ensure excellence in trial advocacy across the organization.

Qualifications

• Juris Doctor (J.D.) from an accredited law school.
• Active license to practice law in Florida and ability to maintain good standing.
• Minimum of 12 years of trial experience, including significant First Party Property litigation.
• Demonstrated success developing trial strategies and achieving favorable outcomes.
• Experience mentoring attorneys and leading legal teams.

Responsibilities

• Serve as a trial strategy leader, developing case themes and courtroom approaches.
• Mentor and develop attorneys and paralegals to excel in trial advocacy.
• Oversee a team of paralegals with workload management and coaching.
• Provide statewide trial support as second-chair and lead counsel when needed.
• Collaborate with claims professionals to evaluate risks and plan litigation strategy.
• Lead witness preparation, expert coordination, and strategic depositions.

Skills

Trial strategy

Mentoring

Leadership

Team development

Courtroom advocacy

Education

Juris Doctor (J.D.)

Florida Bar license

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,

Key Responsibilities

• Serve as a trial strategy leader, partnering with Staff Counsel Attorneys to develop case themes, evidence strategies, and effective courtroom approaches.
• Lead, mentor, and develop attorneys and paralegals, fostering excellence in trial advocacy, case preparation, and first party property litigation.
• Manage and oversee a team of paralegals, including workload management, performance coaching, training, and professional development.
• Provide statewide trial support by serving as second-chair counsel and, when needed, acting as lead trial counsel in first party property cases.
• Collaborate with attorneys, litigation specialists, and claims professionals to evaluate cases, identify litigation risks, and drive successful trial and resolution strategies.
• Conduct key trial-focused litigation activities, including witness preparation, expert coordination, and strategic depositions.
• Develop and deliver training programs, best practices, and advocacy resources that enhance trial readiness and litigation performance across the organization.
• Provide legal and strategic guidance on litigation trends, trial outcomes, settlement considerations, and emerging issues affecting first party property litigation.

Qualifications

• Juris Doctor (J.D.) from an accredited law school.
• Active license to practice law in Florida and ability to maintain good standing.
• Minimum of 12 years of trial experience, including significant experience handling First Party Property litigation and trying first party property cases.
• Demonstrated success developing trial strategies and achieving favorable litigation outcomes.
• Experience mentoring attorneys, leading legal teams, or developing litigation talent.

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.