Find & Apply For Training and Development Manager Jobs in Naples, Florida

About John R. Wood Properties John R. Wood Properties is a luxury real estate brokerage serving Southwest Florida and an affiliate of Christie's International Real Estate, with offices in Naples, Marco Island, Bonita Springs, Fort Myers, and Punta Gorda. JRW exists to enrich the lives of the people we serve, and our culture rests on three beliefs: We Show Up A Plus, We Do the Right Work, and We Steward the Reputation. The Opportunity We are looking for a Director of Learning & Development to build and own the agent development function at JRW. This role moves the company from ad hoc, reactive training to intentional pathways built around where each agent actually is in their business and career, and it is accountable for real behavior change, not just attendance. You will work alongside our broker team and Agent Services, designing everything from short, focused sprints to bespoke programs for agents serving our luxury clientele. Every program is built on the Ninja Selling foundation already in place across the company, protecting agents' production time rather than competing with it. What You'll Do

• Design agent pathways using defined agent avatars and production quartiles, partnering with managing brokers so programs reflect what they see in their offices.
• Build six-to-eight week sprints around specific habits, like prospecting and lead follow-up, and track the activity change that comes out of each one.
• Coordinate program timing with the broker team's coaching calendar so training reinforces what brokers are already doing.
• Partner with Agent Services on luxury training for agents serving high-net-worth clients, reflecting our Christie's and LPI positioning.
• Own content end to end: identify gaps, build new classes and materials, and run each through a dry-run review before it goes on the calendar.
• Measure what matters: survey every class, track behavior change (calls made, appointments set), and connect results to transactions and volume per agent.
• Work with our market research team so agents can turn data into stories they use with clients, and keep training current with the technology agents actually use.
• Take part in broker-level meetings to stay connected to recruiting, retention, and coaching conversations. Your First 90-120 Days
• Get to know the company: meet the broker team and agents, and find where the real gaps are versus the assumed ones.
• Build early relationships with agents ahead of the seasonal ramp-up.
• Get oriented on the technology initiatives already underway so future training builds on what is in motion. What We're Looking For Required
• Demonstrated experience building training content and programs from the ground up, ideally in real estate or another agent- or advisor-based industry.
• Experience segmenting an audience by production level, career stage, or similar, and designing targeted programs for each group.
• Comfort owning full-cycle content creation, from spotting the gap to building and delivering the material.
• Strong facilitation and presentation skills, credible in front of a room of experienced, high-producing agents.
• Comfort learning new technology platforms independently.
• Ability to travel independently among our Southwest Florida offices, including periodic overnight travel.
• Bachelor's degree, or an equivalent combination of education and directly relevant experience. Preferred
• Familiarity with Ninja Selling, or a genuine willingness to adopt it.
• Experience designing training for agents or advisors serving high-net-worth clients.
• Experience with Christie's International Real Estate or a comparable luxury brand.
• Florida real estate license, or willingness to obtain one.

Work Environment This is an in-person role, not a remote position. Content development can happen off-site, but you will be on the ground at our offices regularly for sales meetings, sprint kickoffs, and live training, with heavier travel during your first 90-120 days. Candidates elsewhere in South Florida should expect frequent, planned time in Southwest Florida. The role involves presenting to groups for extended periods, regular travel by car between offices, and occasionally moving materials up to 20 pounds. How You'll Know You're Succeeding

• Transactions and volume per agent trending upward year over year.
• Strong adoption and completion of sprint and pathway programs, with documented behavior change.
• Positive survey feedback following major programs.

At least one bespoke luxury training track built and delivered with Agent Services in your first year.

Pay:

From $120,000.00 per year

Benefits:

401(k) 401(k) matching Dental insurance Health insurance Health savings account Life insurance Paid time off Tuition reimbursement Vision insurance Application Question(s): Can you travel among our Southwest Florida offices (Naples to Punta Gorda) 50-60% of the time? Are you able to work on-site in Southwest Florida (This role is not remote) Do you have at least 5 years of experience designing and delivering training programs for adult professionals? Have you built a training program from the ground up, rather than only delivering existing content? Which industries have you trained in? Are you familiar with Ninja Selling? Do you hold a Florida real estate license In 2-3 sentences, describe a program you built and how you measured whether participants changed their behavior

Education:

Bachelor's (Preferred)

Work Location:

In person