Corporate Trainer and OD Leader

Are you passionate about developing people and driving organizational growth through learning and development?

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.

We’re seeking a Corporate Trainer and Organization Development Leader to design, deliver, and enhance training programs that strengthen employee capabilities and support strategic business objectives. This role is key to fostering a culture of continuous learning, improving performance, and advancing organizational development initiatives.

As a trusted partner across the organization, you will create impactful learning experiences, facilitate leadership and professional development programs, and support change management efforts that align with company priorities. If you thrive on helping individuals and teams succeed, we’d love to hear from you. This is an in-office position based in Jacksonville, FL.

Principal Responsibilities

• Design and Facilitate Training Programs: Develop and deliver engaging onboarding, technical, and professional development sessions for employees at all levels.
• Support Organizational Development Initiatives: Partner with leadership to implement programs that enhance team effectiveness, leadership capability, and organizational culture.
• Conduct Needs Assessments: Identify skill gaps and performance challenges; recommend targeted learning solutions to address them.
• Create Learning Materials: Develop manuals, job aids, e-learning content, and blended learning resources aligned with corporate standards.
• Drive Change Management: Facilitate workshops and communication strategies that support organizational transitions and process improvements.
• Measure Training Impact: Use assessments, feedback, and performance metrics to evaluate effectiveness and recommend enhancements.
• Collaborate Across Departments: Work closely with HR, leadership, and all business units to ensure training aligns with strategic goals.
• Promote Continuous Learning: Encourage a growth mindset and provide resources that support ongoing employee development.

Minimum Job Requirements

• Bachelor’s degree in human resources, Organizational Development, Education, or related field (or equivalent experience).
• 5-7 years of proven experience in corporate training, facilitation, and organizational development.
• Strong presentation, communication, and interpersonal skills.
• Ability to engage diverse learners and adapt content to different learning styles.
• Experience with instructional design and adult learning principles.
• Proficiency with Microsoft Office Suite, LMS platforms, and e-learning tools.
• Strong analytical and problem-solving skills; ability to manage multiple priorities.
• Familiarity with change management and OD frameworks preferred.

Knowledge, Skills, And Abilities

• Training Development: Designs and delivers impactful learning experiences that drive performance.
• Organizational Development: Supports cultural initiatives, leadership development, and team effectiveness.
• Analytical Thinking: Uses data to assess needs and measure program success.
• Change Management: Communicates and facilitates organizational transitions effectively.
• Collaboration: Builds strong partnerships across departments to achieve shared goals.

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 .