MANAGEMENT BIO
JAKE HALLER, Co Owner Managing Partner
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, Chief Innovations Officer | Project Management Director
Suzette Eslabon started in the timeshare industry as an OPC in 2010 and swiftly transitioned to become the Operations Manager for Winning Ways. She played a major role in the early stages of the company expansion wearing multiple hats in the administrative department to service California, Oregon, Nevada, Washington and USVI. Suzette held down the fort in all of Winning Ways’ operations for over a decade until she transitioned to Chief Innovations Officer and Project Management Director in 2024. Outside of work- she 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 & Northern California
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, Southern 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, Southern 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.
VENUE CAPTAINS:
JONATHAN WELLINGTON
Jonathan Wellington is an experienced professional with an impressive 16 years of dedicated service in the timeshare industry. Having played a pivotal role in the company’s growth, Jonathan has successfully built and managed a team that spans from Northern California to Southern California.
With a deep passion for his work, Jonathan consistently demonstrates unwavering commitment and devotion. His strong work ethic and determination are evident in the exceptional results he consistently delivers. Jonathan’s enthusiasm for his job is infectious, as he invests all his knowledge and skills to ensure the success of his team and the overall growth of Winning Ways.
Jonathan Wellington is a highly valued member of the Winning Ways family, and his contributions have made a significant impact on the company’s success. With his passion and dedication, he continues to elevate the standards of excellence in the timeshare industry.
ROMARIO ALVAREZ
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.
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!
DAVID FERGUSON
David has an extensive sales background. He’s been in the vacation ownership industry since 2004 working for companies such as Wyndham resorts and Disney Vacation Club as senior agent for 12 & ½ years. He’s been awarded numerous sales achievement awards and is a licensed real estate agent. He started working as an agent with Winning Ways in 2019 and has a true passion for taking care of guests. David has consistent top tier production as a senior agent and within his roles as a Venue Captain, mentor and talent acquisition agent he helps a lot of new Winning Ways agents achieve success as well.
David enjoys spending time with his 2 daughters and he loves to travel. He’s been to 7 countries and plans to visit many more.
ANTHONY ROQUE
Beloved Son and Family member.. Anthony started his career in hospitality 7 years ago when he was 18 years old. He then found his calling, here in Marketing. Anthony began as an OPC agent in 2022. Being the Quick Learner he is, he soon became one of the Company’s Top Producers, and now has worked his way up the ladder, and into leadership. Anthony is very respected amongst his peers and subordinates, and is eagerly awaiting all the great next steps that are in front of him. Winning Ways is Proud to say, this is Anthony’s Home, and is looking forward to his continued success.
BRANDON THOMAS
Brandon, a rising name in the timeshare industry, swiftly advanced to the position of Venue Captain despite his recent entry into the field in December 2023. His journey began when he caught the attention of Bradley Earle at Winning Ways’ esteemed event, Coastal Christmas, in San Diego. Initially starting as a greeter, Brandon’s dedication and enthusiasm propelled him to the role of OPC, and eventually to VC, showcasing his strong leadership within the greater San Diego region. Beyond his professional achievements, Brandon finds relaxation riding his motorcycle through San Diego’s scenic canyons during his leisure time.
KRYSTAL ORTIZ, EVENTS MANAGER
With over a decade of diverse experience spanning sales, marketing, and event coordination, Krystal brings a wealth of expertise to our team at Winning Ways. Krystal has excelled as an Event Coordinator at Winning Ways USA, Prior to this role, Krystal thrived as a Business Account Executive at Spectrum, achieving sales targets by prospecting, and driving sales of a range of communication solutions to small and medium-sized enterprises with a keen focus on customer relationships and territory growth.
Previously, Krystal demonstrated exceptional leadership as a Multi-Store Manager at Verizon, overseeing sales teams and ensuring outstanding customer experiences across multiple locations. Her career journey also includes roles such as Sales/Marketing Representative at Bluegreen Vacations, where she consistently exceeded sales quotas, and Supervisor at C&C Market Research Co., where she honed organizational and operational skills.
Krystal is known for her strategic approach to event management, strong negotiation skills, known for her leadership in driving sales, nurturing team success, and delivering exceptional customer satisfaction/experience.
Beyond her professional achievements, Krystal is an avid traveler who cherishes exploring new destinations and cultures, spending quality time with friends and family, enjoys attending concerts and seeking out new experiences.