Claims Training & Development Facilitator - Jacksonville, FL at Stillwater Insurance Group

Join our collaborative team where effort and work ethic get noticed. Enjoy a positive, friendly, energetic work environment with accessible leadership, where you will have the opportunity to learn the insurance industry and valuable skills while we invest in your future career with us.

Why Stillwater? Stillwater Insurance Group is a mid-sized national insurance provider offering a variety of home, auto and commercial insurance products in 50 states. We are headquartered in Jacksonville, Florida, with additional offices in New York and Omaha, Nebraska. We offer an up-beat and supportive environment for a new team-member who brings a positive attitude, reliable work habits, attention to detail and an interest in learning. Our employees consistently describe Stillwater as a great company with great people where honesty and integrity are high priorities. Coaching and development, recognition and growth opportunities are some of the benefits of working in our small team environment. 

Are you passionate about empowering others through education and training? We’re looking for a Claims Training and Development Facilitator to design, deliver, and enhance training programs for our growing team of claims professionals. This role plays a key part in onboarding new team members and ensuring continued excellence across Auto, Property, Casualty, and Liability lines.

As a strategic partner in our Claims department, you'll develop and facilitate dynamic training sessions, ensure regulatory and procedural compliance, and foster a culture of continuous learning and improvement. If you’re a collaborative leader who thrives on helping others succeed, we’d love to hear from you.  This is an in-office position in Jacksonville, FL.  

Principal Responsibilities: 

• Facilitate onboarding and systems training for all new claims employees, including Auto, Property, Casualty, and Liability lines.
• Develop and deliver refresher training to strengthen technical and procedural proficiency across all claim types.
• Collaborate with management to identify performance gaps and tailor training sessions to address opportunities for improvement.
• Participate in the design, development, and implementation of new training materials, manuals, and job aids.
• Conduct specialized training on coverage interpretation, liability assessment, claim documentation, and negotiation techniques.
• Provide educational sessions to ensure compliance with state regulations, unfair claims practice acts, and internal claims handling standards.
• Partner with third party claims services to ensure consistency in process execution, documentation standards, and customer communication expectations.
• Monitor training effectiveness through evaluations, feedback, and performance metrics to ensure continuous improvement.
• Serve as a subject matter resource for questions related to Auto, Property, Casualty, and Liability claim handling.

MINIMUM JOB REQUIREMENTS: 

• Bachelor’s degree (BA) from a four-year college or university, or two years of related experience and/or training, or equivalent combination of education and experience.
• Proven experience as a trainer, facilitator, or educator, preferably in a claims or insurance environment. 
• Exceptional presentation, communication, and interpersonal skills. 
• Active State Adjuster licenses.
• Professional designations such as Associate in Claims (AIC), CPCU, FCLS, PCLS, or CIFI preferred but not required.
• Minimum of five to seven years of prior claims experience in the following lines: Auto, Property, Casualty, and Liability 
• Prior multi line claims experience is preferred. 
• Strong knowledge of claims systems, coverage analysis, and claims processes.
• Excellent written and oral communication skills.
• Ability to engage and motivate a diverse group of learners. 
• Strong organizational, problem-solving, and analytical abilities.
• Ability to manage multiple priorities and work both independently and collaboratively.
• Ability to create and deliver training content that resonates with different learning styles. 
• Ability to assess and analyze training effectiveness and make data-driven improvements. 
• Time management and organizational skills to handle multiple training programs simultaneously. 
• Proficiency with Microsoft Office Suite and training software (LMS systems, e-learning tools). 

KNOWLEDGE, SKILLS, ABILITIES AND OTHER QUALIFICATIONS:

• Analytical Skills: Synthesizes information, uses experience to complement data, and designs effective workflows.
• Training Development: Designs and delivers engaging, results-oriented training that improves technical performance.
• Change Management: Communicates change effectively, supports staff through transitions, and evaluates results.
• Quality Management: Promotes accuracy, compliance, and continuous improvement.
• Judgment: Exhibits sound decision-making, supports rationale for actions, and involves appropriate stakeholders.

Apply today to start your journey of being celebrated and valued with Stillwater Insurance Group.

Offer for employment contingent upon the acceptable responses from both a background investigation and a pre-employment drug screen.

 Stillwater Insurance Group is a drug-free workplace and an equal opportunity employer.