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For experienced and new agents at all levels
Weekly accountability in office or zoom
Goal setting and results plan
After-hours contract & business support
The most personalized coaching option
No up-front fees (paid from commissions only)
Limited availability
Your closest friends in the biz
Small groups of 3-5 agents
Closely-knit peer groups that hold each other accountable and help solve problems
Every group is a little different & meeting times, locations, etc. are determined by the group
No additional fees
Available to all KW Jax agents
8:55 am Monday-Friday
Phone call for all agents (the best five minutes of your day)
Kick off your two hours of lead-gen time with your office-mates with some words of encouragement and a time to ramp it up!
No additional fees
Available to all KW Jax agents
Master your contract knowledge
Ask questions and get help with your transactions
In office or on Zoom
No additional fees
Available to all KW Jax agents
Learn new ways to attract business & build trust
In office or on Zoom
No additional fees
Available to all KW Jax agents
The 30-day ultimate career kick-off for new agents
Class topics posted on the KW Jax calendar every month
Experienced agents and Ignite grads are welcome to visit any class
No additional fees for visitors
Available to all KW Jax agents
A changing market requires a change in approach. BOLD was created to help you shift your mindset and adopt the tactics and conversations proven to bring success in today's extraordinary business landscape.
In-person - Various Locations in the U.S. (and sometimes in Jacksonville)
Ask for more details
KW Jax and NEFAR host a variety of workshops and educational events designed to help you grow
Many events are free to join or low fees for NEFAR members
Some events contribute to agent continuing education requirements
Check out the KW Jax calendar or ask for more details
For more info on any of the coaching opportunities above, contact Ryan Winter.
Cell: 904-735-8994 (call or text)
Email: training175@kwjacksonvillerealty.com
your Coach: Ryan Winter
your Coach: Ryan Winter
Ryan Winter is a dynamic leader, educator, and strategic consultant with a passion for helping people grow—both professionally and personally. As the new Director of Career Development at Keller Williams Jacksonville, Ryan brings a unique blend of sales experience, operational leadership, and a heart for coaching others into thriving careers in real estate.
With over a decade of experience in leadership, technology implementation, contract management, and business development, Ryan has worked alongside C-level executives, real estate professionals, and entrepreneurs to design high-impact systems that drive clarity, accountability, and measurable results. He has served as a COO, licensed real estate broker, enterprise implementation lead, and fractional executive across a wide range of industries, including legal services, marketing, and proptech.
But Ryan doesn’t just thrive in the boardroom—he comes alive in the great outdoors. Whether he's flying a plane, riding a motorcycle through backroads, scuba diving offshore, fishing with his sons, or hiking new trails, Ryan pursues life with curiosity, courage, and a love for adventure. He believes that great leadership starts with grounded presence, clear vision, and a willingness to keep growing.
Ryan lives in St. Johns, Florida with his wife and three young boys, where they're often found camping, gardening, or chasing the next big fish
For Coaching Clients
For Coaching Clients
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