June 20, 2024
From the Gridiron to the Boardroom: Insights from Kyle York on Transitioning to Sales Careers
On today’s episode, we had the pleasure of speaking with Kyle York from York IE. Kyle’s journey from high school football under the Friday night lights to becoming a successful entrepreneur offers invaluable lessons for former athletes and military veterans transitioning into sales careers.
Kyle reminisces about his days playing football at Bentley University and the profound impact sports had on his career trajectory. Growing up in a family where football was a given, with his father being an Allstate player and the family owning a sporting goods store, Kyle was destined for the gridiron. His athletic career, especially the intense, adrenaline-pumping Friday night games at Manchester West High School, shaped his tenacity and competitive spirit.
Transitioning from athletics to business was not without its challenges. Kyle shares how his experience at Bentley, both academically and athletically, prepared him for the corporate world. Despite initially resisting a sales career, viewing it as akin to “snake oil salesmanship,” he soon realized his natural affinity for it. His early roles at Whipple Hill, a small tech startup, taught him the value of hard work, self-reliance, and adaptability—traits honed on the football field.
Kyle’s journey underscores the importance of leveraging one’s background in sports or the military when entering the sales profession. The discipline, teamwork, and resilience required in these fields translate seamlessly into the fast-paced, goal-oriented world of sales. Kyle’s stint at Whipple Hill, followed by a pivotal role at Dyn, which eventually led to a successful acquisition by Oracle, illustrates the potential for growth and achievement in sales.
York IE, Kyle’s latest venture, exemplifies his commitment to supporting startups with comprehensive advisory services. He emphasizes the significance of a solid go-to-market strategy and the crucial role sales play in a company’s success. His advice to aspiring sales professionals is clear: be the CEO of your own career. Set long-term goals, work backward to identify necessary milestones, and execute with precision.
For athletes and veterans contemplating a sales career, Kyle’s insights are invaluable. The key is to harness the skills developed through sports or military service—discipline, resilience, and strategic thinking—and apply them to the sales landscape. Whether you’re starting as an SDR or aiming to lead a sales team, the principles remain the same: stay focused, be adaptable, and always strive for excellence.
In closing, Kyle’s story is a testament to the power of determination and the seamless transferability of skills from the athletic field to the corporate world. His journey offers a roadmap for anyone looking to transition successfully into a sales career, proving that with the right mindset and work ethic, success is within reach.
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