Leadership

Matt O’Mara, is a visionary entrepreneur and the President and Founder of Whimsy, a leading intermodal trucking company in the Chicago area. With humble beginnings as a truck driver, Matt’s keen eye for opportunity and unwavering dedication have propelled him to the forefront of the industry.

Before embarking on his entrepreneurial journey, Matt gained invaluable experience navigating the complex world of transportation. During that time he identified a gap in the Chicago intermodal market, inspiring him to venture out on his own and lay the foundation for what would later become Whimsy Trucking.

In 1996, Matt took a leap of faith and established Whimsy with only a handful of trucks and drivers. Despite the company’s modest start, Matt’s passion for excellence and commitment to client satisfaction quickly garnered attention in the industry. Over the past 30 years, he has cultivated an extensive network of connections both within and beyond Whimsy, forming strategic alliances that have been instrumental in the company’s growth.

Today, Whimsy has evolved into a thriving enterprise, thanks in large part to Matt’s exceptional leadership and unwavering determination. Under his guidance, the company has experienced significant expansion and has become a prominent player in the Chicago intermodal industry. Matt’s success serves as a testament to his innovative spirit, strong work ethic, and dedication to fostering lasting relationships with clients, partners, and employees alike.

As the President and Founder of Whimsy, Matt O’Mara continues to drive the company forward, always striving for improvement and seeking out new opportunities for growth. His inspiring journey from truck driver to industry leader is a powerful reminder that with hard work, determination, and an entrepreneurial spirit, anything is possible.

Gigi O’Mara, the dynamic Director of Finance and Human Resources at Whimsy, is an integral force behind the company’s success. Since joining the team in 2000, Gigi has been instrumental in shaping the organization’s core values and mission, while working alongside her husband and business partner, Matt O’Mara.

As a firm believer in the power of experience and the importance of constant evolution, Gigi identifies Whimsy’s niche in the intermodal industry as its expertise in equipment chassis, yards, and reach stackers. Her unwavering commitment to customer satisfaction and employee welfare has helped solidify the company’s core values and drive its continued growth. Gigi has been a female trailblazer in a fast-paced male dominated industry who takes great pride in sharing her wealth of knowledge with future Whimsy leaders.

In her role as Director of Human Resources, Gigi focuses on managing the company’s human capital, fostering a supportive and rewarding work environment for its amazing team. She manages the company’s resources, ensuring that Whimsy remains financially stable while fostering a supportive and rewarding work environment for its employees. Gigi’s efforts are aimed at nurturing a positive and productive workplace culture while maintaining Whimsy’s commitment to both customers and employees alike.

Gigi’s dedication to Whimsy’s mission, combined with her extensive experience and deep understanding of the industry, has been invaluable to the company’s expansion and success. As a key figure in the organization, Gigi continues to drive Whimsy forward, reinforcing its reputation as a leading player in the intermodal trucking industry and maintaining its commitment to setting the bar for “Best in Class Transportation”.

Robert (Bob) Zoufal, Chief Operating Officer at Whimsy, brings over 30 years of experience in the Chicago intermodal business to the table. A 1985 graduate of Loyola University of Chicago School of Business, Bob holds degrees in Marketing and Business Administration.

As a dedicated leader, Bob believes in prioritizing customers and upholding integrity through hard work, honesty, and thoroughness. He is committed to sharing his intermodal industry knowledge with peers, customers, and employees, fostering a collaborative and successful environment.

Outside of work, Bob serves on the Board of Advisors for Catholic Charities of Chicago. He enjoys spending quality time with his family, attending Cubs and Blackhawks games, and playing golf. Bob resides in the Wrigleyville neighborhood with his loving wife, Jan.

Diana Minkova, Safety Director at Whimsy since 2017, has over 14 years of safety management experience in the Transportation Industry.

With a keen eye on detail, Diana partners with terminal managers and drivers to develop, encourage, and maintain the highest level of safety and compliance, Increase productivity, and improve company’s overall safety culture. Diana in responsible for developing and maintaining proper safety policies and procedures to ensure compliance with all DOT, FMCSA and OSHA local and federal regulations and standards regarding transportation and workplace safety. Diana develops and conducts training for drivers and monitors performance, mentors managers and supervisors in safety management practices, conducts audits, inspections and evaluations, oversees all accidents, including reporting, investigations, documentation and prevention.

Diana acts as the first point of contact for employees, drivers, and supervisors, expertly troubleshooting HR-related issues and takes great pride in her role as a coach, mentor, and trainer for drivers, providing them with the knowledge and support they need.

Her dedication and guidance throughout the years have been paramount to the continuous growth, impeccable compliance and safety standards, and beloved culture at Whimsy.