At the core of our success is a team of visionary leaders who bring passion, experience, and a shared commitment to excellence. Our leadership team is dedicated to driving innovation, empowering our people, and delivering exceptional value to our clients. With diverse expertise and a unified purpose, they guide our company forward—strategically, ethically, and with unwavering focus on long-term growth.
JAKE HALLER, Owner, President & CEO
With almost thirty years of experience, Jake Haller is a household name in the timeshare and vacations club industry. He has served as the Director of Marketing for many major players in the vacation industry such as Shell Vacations Club, Ka’anapali Oceans Resort and Fairfield Resorts, to name a few.
Jake started his career in the business as an OPC. He understands that it doesn’t only take exceptional skills to be successful in the competitive industry of timeshare—but more importantly, one must know how to value relationships with customers and clients. With commendable hard work and resilience, Jake advanced himself to management roles, and later on, founded his own marketing companies. He strongly believes that being an OPC is a reputable career, and he strives to instill this philosophy not only to his team but to everyone. What makes Jake thrive is his high regard for honesty, integrity, and genuine customer service. These are the core values of Winning Ways. Jake also brings valuable contributions to the community as he is actively involved with fund raisers and charities. On his free time, he travels with his wife Victoria, and enjoy all sorts of adventures with son Jacob. Undeniably, the success of Winning Ways is deeply rooted to the inspiration that Jake Haller brings to his team on a daily basis. He is the solid anchor of the company that aspires to create the true essence of win-win.
VICTORIA HALLER, Co Owner Sales and Admin Support
Victoria Haller is the Sales and Administrative support of Winning Ways. She is a graduate of U.C. Davis and a licensed R.E. agent in the State of California. She brings to the table over twenty years of sales closing and executive management experience. She was instrumental in the success of Trendwest Resorts and Shell Vacations whom are all part of the Wyndham Vacation Ownership Family now. Victoria has been awarded over 20 sales and management achievement awards, with one of them being a lifetime member of the prestigious President’s Club. Her ambition, leadership skills blended with her charisma makes the ideal executive. Her remarkable ability to adapt to different kinds of situations and relate to all kinds of people contributes to her success.
Her passion is helping guests realize the importance of quality family time and assisting them in taking the initiative to actualize their dreams. Victoria enjoys hiking in the outdoors, exploring new destinations and running with her JRT.
SUZETTE ESLABON, HR & Compliance
Suzette Eslabon began her career in the timeshare industry as a marketing agent, quickly distinguishing herself through her drive, professionalism, and ability to adapt in a fast-paced environment. Her strong work ethic and leadership potential earned her a major transition to Operations Manager at Winning Ways, where she played a foundational role in the company’s early expansion. Suzette was instrumental in building and managing administrative operations across multiple territories, including California, Oregon, Nevada, Washington, and the U.S. Virgin Islands.
For more than a decade, Suzette served as the backbone of Winning Ways’ operations, navigating the complexities of a growing enterprise with remarkable consistency and dedication. In 2024, she took on a dual leadership role as Chief Innovations Officer and Director of Project Management, where she led strategic development, operational enhancements, and the implementation of forward-thinking initiatives that shaped the company’s trajectory.
In 2025, Suzette further expanded her leadership scope by becoming Head of Human Resources and Compliance. In this role, she now oversees the company’s organizational culture, talent development, regulatory adherence, and ethical governance—ensuring Winning Ways not only grows sustainably but also maintains the highest standards of integrity and accountability.
Outside of her professional responsibilities, Suzette enjoys traveling the world with her family.
CASSIDY ROCKE, Operations Manager
Both of Cassidy’s parents have long-standing careers in timeshare marketing, earning her the affectionate title of “Timeshare Baby.” She began her own journey in the timeshare industry in 2016 and joined Winning Ways in 2018. Cassidy quickly advanced from an admin support role to Operations Manager, thanks to her dedication and expertise. She leads with integrity, is passionate about growth and mentorship, and prioritizes efficiency and accuracy in her work. Outside of Winning Ways, Cassidy is a proud dog mom and loves to travel.
JUSTIN POOLE, Regional Manager, Pacific Northwest
Justin Poole is a dynamic leader with a track record of success in the business world. His journey began in 2014 when he embarked on a winning streak that would set the foundation for his impressive career. Starting in Palm Springs, CA, Justin quickly rose through the ranks and transitioned into a management role.
His leadership skills shone through as he grew the Southern California (SoCal) team, expanding its reach into Arizona, Las Vegas, and eventually taking over Northern California. Justin’s strategic vision and dedication to excellence propelled Winning Ways to new heights, even as the COVID-19 pandemic presented unprecedented challenges.
Never one to rest on his laurels, Justin has continued to push boundaries and explore new opportunities. He spearheaded the company’s expansion into the minivac realm, leveraging his extensive sales background to drive growth and innovation. Recently, he set his sights on the Pacific Northwest, where he is redeveloping infrastructure and building on the successes experienced in Southern California.
Throughout his career, Justin has remained laser-focused on the success of Winning Ways. His collaborative approach and direct involvement with Jake Haller, the company’s president, have fostered a strong partnership and a shared commitment to excellence. With over a decade of experience, Justin Poole continues to lead Winning Ways towards continued growth and success.
BRADLEY EARLE, Regional Manager, California
Proud Husband and Father of 4. Bradley is a 30 year Veteran Leader of our industry. His journey started in Sedona Arizona, where at the age of 18 he became an OPC and quickly thrived. He set or broke numerous performance records, until becoming a Director in Jan of the year 2000. Again he excelled, and as a Director, has been recognized nationally several times, for his achievements, leadership, and accomplishments. Bradley is a True Professional. A Genuine Leader. And is a Highly Respected and Trusted Staple of our beloved Industry.
VICTOR ALVAREZ, Regional Manager, California
Victor – also known as VDAD in the field, graduated from CSUF all while starting his timeshare career back in 2018 here with Winning Ways, when he was only 18 years old. His magnetic personality, determination, and capacity for leadership quickly set himself apart from the rest of the pack. Starting off as a greeter in Victor’s 6 years, he has been promoted 4 times and has now been acknowledged as a Top Producer and Regional Manager throughout this industry.
Victor is a very talented and highly respected individual, who has worked tirelessly to add new tangibles to the industry and he’s done so successfully.
Victor’s production foundations have created new baselines across the field.. Of which his peers and subordinates, are all proud to say they have found success following his guidance and direction..
Victor is happy to call Winning Ways his home and is very excited to recruit and build that next generation of OPCs and leaders here in Winning Ways.