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 over thirty eight years of experience, Jake Haller is a household name in the timeshare and vacations club industry. He has served as the VP Marketing, Director of Marketing, OPC Manager, CMP, Concierge and operated telesales Operations for many major players in the vacation industry such as Shell Vacations Club, Starwood Vacation Ownership, Cendant 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 is a high-impact executive with more than a decade of leadership in the timeshare event marketing industry, recognized for building scalable operations, elevating performance, and leading transformation across complex, multi-market environments.
She began her career on the front line as a marketing agent and quickly distinguished herself as a standout producer with exceptional business judgment and leadership presence. That foundation powered her rise into Operations Manager at Winning Ways, where she helped drive the company’s early expansion across California, Oregon, Nevada, Washington, Arizona, and the U.S. Virgin Islands. In that role, she built critical administrative and operational infrastructure from the ground up—systems, workflows, and standards that strengthened execution, improved consistency, and supported long-term growth.
In 2024, Suzette advanced into a dual executive role as Chief Innovations Officer and Director of Project Management, leading enterprise initiatives that modernized internal processes, improved cross-functional alignment, and accelerated company-wide performance. In 2025, she assumed leadership of Human Resources and Compliance, where she directs culture, workforce strategy, and multi-state compliance—aligning people, performance, and policy to reduce risk and increase organizational capability.
Suzette is a SHRM-Certified Professional (SHRM-CP), reflecting validated expertise in talent strategy, organizational design, and compliance leadership. Outside of work, she enjoys traveling the world with her family.
CASSIDY ROCKE, Operations Manager
Cassidy Rocke serves as the Operations Manager at Winning Ways, where she oversees all facets of backend operations. From event coordination and partner relations to payroll, contract negotiation, onboarding, and guest communication, Cassidy ensures every moving part of the company runs smoothly and efficiently. Her role is integral to the daily function and long-term success of the business.
With deep roots in the industry—both of her parents having long-standing careers in timeshare marketing—Cassidy was affectionately dubbed a “Timeshare Baby” and began her own journey in 2016. Since joining Winning Ways in 2018, she has played a key role in the company’s evolution, championing technological upgrades, process improvements, and the expansion of new programs that have enhanced both performance and culture.
Cassidy’s leadership style blends transformational and coaching approaches. She believes in adapting her guidance to the individual needs of her team members, helping them grow while maintaining focus on operational excellence and business goals. Known for her foresight, she anticipates challenges before they arise and addresses them proactively. To her, success is where preparedness meets opportunity. She prides herself on being a knowledgeable industry resource and a hands-on leader willing to step in wherever needed.
Cassidy holds dual Bachelor’s degrees in Industrial & Organizational Psychology and Human Resource Management from the University of Phoenix, where she graduated with a perfect 4.0 GPA, made the Dean’s List, and finished two years ahead of schedule. Her academic background gives her a strategic lens on company dynamics, organizational change, and employee engagement—insights she uses to navigate both people and processes with clarity and purpose.
Driven by core values of integrity, transparency, growth, and excellence, Cassidy is passionate about building strong workplace culture and helping others reach their full potential. Outside of work, she is a proud dog mom and a creative spirit with a love for photography, travel, and exploring new places. Whether she’s attending comedy shows, music festivals, or adventuring through new cities, Cassidy brings her trademark curiosity, energy, and appreciation for life to everything she does.
BRADLEY EARLE, Director of Marketing
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, Assistant Director of Marketing
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 7 years, he has been promoted 5 times and has now been acknowledged as a Top Producer and Assistant Director 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.
DAVID FERGUSON, National Trainer
With over 20 years of experience in the vacation ownership industry, David has built a reputation as a dynamic and results-driven professional. Throughout his career, he has worked with some of the most recognized names in the industry, including Disney Vacation Club and Wyndham, where he consistently earned numerous sales performance awards for his leadership, customer focus, and his ability to drive exceptional results.
David’s passion for helping guests vacation more and giving new agents the tools they need to be successful is matched only by his dedication to personal growth and family. Outside of work, he enjoys traveling, staying active in the gym, and spending quality time with his two daughters.
ROMARIO ALVAREZ, Pro Travel Manager
Romario began his illustrious career in our industry here at Winning Ways in the summer of 2019, at the age of 18.
Quickly and confidently, Romario made his way up and into leadership.. Where today, he is not just a pillar in the Industry. But he proudly holds the record for post Corona Sales volume in a year, with having generated $1.2 Million in 2023..
Additionally, his hard work & dedication has lead to him being rewarded the title of Travel Team Manager. His consistent contributions to hitting targets has made him trustworthy of leading a team on any given weekend, make sure we’re hitting targets, & helping expand to old & new markets across the country. He has definitely made a huge impact in the industry, even though he is barely getting started!
Romario has a very unique ability, that simply put, just isn’t seen very often.. And his performance is accurately regarded as the Company’s “Gold Standard.”
Romario’s life & financial successes are directly attributed to his profound devotion to succeed. Winning Ways is honored to be the Company, where he has earned such levels of success. And moreover, is eagerly awaiting his exciting future!
JUSTIN POOLE, Director of Strategy
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.