Eileen Dennis Hinshaw is a visionary leader, trailblazing entrepreneur, and the driving force behind Cobol Cowboys, LLC. As COO and Co-founder, she has played a pivotal role in shaping the company’s mission to preserve, modernize, and sustain COBOL — a critical programming language that powers industries worldwide.
With a career built on innovation, adaptability, and a deep respect for technology’s foundational roots, Eileen has not only led operations with precision but also championed the next generation of IT professionals. Her strategic leadership, combined with a no-micromanagement approach, empowers a global network of consultants while ensuring that legacy systems continue to support the digital future.
Spinning the Globe, Riding the Dark Horse, and Honoring Future Trailblazers
In Eileen’s home, a world globe is more than just décor — it’s a symbol of connection. She often gives it a spin, sending out what she calls “vibes of connection and shared peace around the world.” That sense of global unity has shaped both her journey and her role in the technology industry.
Her childhood was filled with adventure, from a brief moment atop a grey Brahma bull in Oklahoma to riding runaway horses with cousins. But it was at age 10, on Barbie’s red, barrel-racing quarter horse, that she truly felt the exhilaration of mastering the ride. “I climbed on, held on, and repeated the ride,” she recalls. That early experience shaped how she approached challenges — gripping the reins, adapting quickly, and leaning into the momentum.
Today, Eileen sees COBOL as the industry’s “dark horse” — a force still running strong, defying expectations. “This is a horse I’m counting on to continue running robustly for many years to come,” she says. It’s a technology that, despite being overlooked by the mainstream, remains essential to global infrastructure.
Cobol Cowboys, the company she co-founded in 2013, is proof of that endurance. With a network of over 650 independent consultants worldwide, the organization has played a crucial role in maintaining and modernizing COBOL systems. The company gained global attention in 2017 when Reuters journalist Anna Irrera took its story viral, sparking conversations about the unsung role of COBOL programmers in today’s digital economy.
Eileen’s mission extends beyond preserving technology — she is also invested in inspiring the next generation. She reflects on Nanjanika, a young girl in Sri Lanka who has yet to choose her educational path. “Will this article reach her?” she wonders. Thanks to the digital pioneers of the past and the programmers of today, the answer is yes. With another spin of her globe, she salutes the past, present, and future cowgirls of the IT industry.
“The dark horse is still running — strong, steady, and essential to the world’s digital infrastructure.”
A Journey Rooted in Passion, Purpose, and Partnership
Eileen’s career is a testament to resilience, reinvention, and an unshakable commitment to helping others. Raised in an editorial environment, she was immersed in the rhythm of a newsroom from an early age. The scent of ink in the print shop, the hum of typesetting machines, and the sharp wit of journalists shaped her formative years.
While technology was revolutionizing industries, Eileen gravitated toward writing, marketing, and human resources. Yet, the advice of her mother lingered in her mind: “Technology will be your survival.” Navigating through a career that spanned editorial roles, training management, and marketing, she eventually found herself drawn back home to Texas.
Eileen’s passion for supporting others took center stage as she organized an international women’s conference, a moment that solidified her belief in the power of collective empowerment. “When women are free to do their work, everyone benefits,” she reflects.
Love and partnership would soon intertwine with her professional journey. Meeting Bill Hinshaw in North Texas, she found a kindred spirit — someone who, like her, valued purpose over prestige. Their connection, forged through deep conversations and shared values, led to marriage. “Over the past 23 years, we’ve saved each other on many levels,” she shares.
Eileen’s foray into the world of IT was unexpected but transformative. A website design course at Southern Methodist University became the gateway to understanding the intricate world of COBOL, the programming language that had quietly powered industries for decades.
Racing home from class one evening, she embraced Bill in gratitude, finally grasping the significance of his life’s work. When she asked why he continued returning to COBOL, his answer was simple yet profound: “To help others.” That ethos became the foundation of Cobol Cowboys, the company they built together.
With Bill in his 70s and Eileen in her 50s, they embarked on a journey that blended their expertise, grit, and shared vision. There were challenges — some as unpredictable as a rodeo — but the rewards far outweighed the trials. “The opportunity to start a company together was an enthusiastic commitment we made, and like most rodeos, we’ve had some rough rides — but the outcome has been well worth it,” she reflects.
“When we free our Cowgirl Spirit, we are free to empower humanity.”
Building a Legacy Through Hard Work, Adaptability, and Purpose
Eileen never set out to become the Chief Operating Officer of a technology consulting firm, but every step in her career prepared her for the role. She and Bill built Cobol Cowboys from the ground up, leaning into their strengths and defining a mission that would serve both their clients and the industry. “We let our roles evolve and we both committed to doing what we do best,” Eileen recalls.
The approach was intentional — drawing from her years of experience in editorial work, training, human resources, promotions, legal, and recruiting. “It’s a compilation of industry experiences, knowledge, and gleaning from those who’ve invested in me,” she says.
Eileen’s understanding of success was shaped early. As a teenager, she danced with a small company in Southern California, even performing for the televised opening of The Pasadena Tournament of Roses. She coached youth in sports and cheerleading, modeled for the early rebounders, and saw firsthand how discipline, creativity, and perseverance opened doors.
Eileen’s mother’s dedication reinforced this mindset, painting rodeo signs and murals to help cover the costs of lessons. “Many opportunities in my youth strengthened me for life’s unseen journeys ahead,” she reflects. That resilience became even more critical in her professional life.
Without a formal college degree, Eileen encountered roadblocks in an industry that often prioritizes credentials over experience. But she never let that define her limitations.
In both business and life, Eileen believes that one of the biggest challenges to overcome is herself. While it may be tempting to blame a lack of education, experience, or knowledge, she sees that as short-sighted. We all have access to a world of knowledge and education—if we choose to seek it.
For Eileen, success is rooted in staying positive, maintaining balance, surrounding herself with trustworthy individuals, and confidently bringing strong talent to the forefront. Prioritizing self-care to prevent burnout is essential when running a business. Ultimately, it all comes down to the discipline of making great choices and fostering the right mindset, rather than dwelling on past negative circumstances or blaming others. “I have continued to overcome this challenge by self-educating — reading, online studies, research, and constant observation,” she says.
Entrepreneurship offered Eileen the freedom to prove that success isn’t determined by degrees but by knowledge, adaptability, and determination. “As an adult, I consider ‘work’ a true gift. We love the work accomplished at Cobol Cowboys. When our clients and consultants are successful, we are successful,” she states, sharing a quote from one of their consultants: “The connection is a divine event that goes way beyond the code that we support.”
“Our consultants are the STAR in our brand!”
Balancing Leadership and Life with Purpose and Discipline
Eileen approaches her dual responsibilities — running a company and maintaining a fulfilling personal life — with a clear strategy: prioritize and set achievable boundaries. “It’s about knowing what needs immediate attention and what can wait,” she explains. By structuring her day with intention, she ensures both Cobol Cowboys and her personal life receive the attention they deserve.
Her mornings begin with a “round-up” over coffee with her husband, Bill, where they map out the day ahead. From there, she shifts into business mode — scanning news updates, responding to emails and texts from clients and consultants, and staying informed on the latest developments in COBOL and mainframe technology.
Daily interviews with potential clients, consultants, or media are a regular part of her schedule, as is managing payroll, invoices, and banking. Marketing and promotional efforts also demand her attention, alongside proofreading and finalizing contracts and agreements. Despite the demands of her role, Eileen remains steadfast in her commitment to balance. “Setting boundaries isn’t about saying no — it’s about making space for what truly matters,” she says.
“Commitment to my faith frees my spirit to enjoy a life of service to my husband, our family, our business . . . and to the world.”
Building a Legacy in COBOL and Beyond
Eileen takes immense pride in what she and her husband have built together. Founding Cobol Cowboys stands as one of her greatest achievements — a brand she conceptualized to capture both the expertise and resilience of those working in legacy systems. “‘Cobol Cowboys’ was a name I put forward, and it became a magnet for drawing clients and consultants,” she says.
The company’s tagline, ‘Not our first rodeo,’ resonates globally, underscoring the deep experience and reliability the team brings to the industry. Eileen’s impact on COBOL extends far beyond branding. Through her work, she has helped shape the past, present, and future of the language that powers critical systems worldwide.
“I believe together we will provide ongoing support and maintenance for years to come,” Eileen explains. Training and mentoring the next generation remains a cornerstone of her mission, ensuring COBOL remains a vital force in the tech landscape.
“Our work isn’t just about keeping COBOL alive — it’s about preparing the next generation to carry it forward.”
Leadership Without Micromanagement and the Power of Diverse Experience
Eileen believes in hiring professionals who have already proven themselves. At Cobol Cowboys, leadership is not about control but trust. “As COO, I do not micromanage. That’s a written promise made to our consultants,” she says. Instead, she offers consistency, fairness, and support — ensuring that both clients and consultants have what they need to succeed.
Her leadership style is deeply influenced by her diverse career path. From editorial and training to HR, promotions, legal, and recruiting, every role has contributed to her ability to lead with balance. “Diverse experience creates balance, internally and externally. It’s needed, from the top down,” Eileen explains.
For those aspiring to follow a similar path, she offers practical advice. Seek out employers who provide educational assistance, earn degrees and certifications that enhance career prospects, and never stop learning. Eileen also emphasizes the importance of self-confidence. “Be proud of who you are. Our differences and the way we present ourselves at every age are splendid.”
Beyond technical expertise, Eileen encourages aspiring leaders to study real-world case studies of IT business successes and failures. She also stresses the importance of strong communication skills. “Constantly improve your communication skills for public speaking and writing. Check out Toastmasters International,” she advises. For her, leadership is not about exerting control — it’s about empowering others to thrive.
“Trust, not control, is the foundation of great leadership.”
The Future of Operations Management: AI, COBOL, and the Next Generation
Operations management has transformed significantly, with artificial intelligence streamlining decision-making by providing instant data. Eileen recognizes AI’s growing role in operations but raises a critical question: “Will fewer levels of management be needed?” While automation is reshaping industries, she believes human expertise remains essential, particularly in IT.
Looking ahead, she sees a pressing need to cultivate the next generation of COBOL and mainframe professionals. “Cobol Cowboys is calling on young people to explore the IT field and understand the fundamentals of COBOL and the mainframes. They will one day be our future IT leaders and make multi-million-dollar decisions,” she says.
To stay ahead in an evolving tech landscape, Eileen prioritizes clear and fair communication with clients and consultants. She also stresses the importance of equipping the next generation with the tools to manage and modernize COBOL systems. With an estimated 220 to 800 billion lines of COBOL still in use worldwide — and 1.5 billion new lines written annually — understanding this technology is crucial. “To have new technology, the old must be maintained as it contains business knowledge to help the new technology,” she explains.
Encouragingly, colleges and universities are reintroducing COBOL courses, signaling a renewed interest in a language that remains the backbone of many critical systems. Eileen sees this resurgence as an opportunity. “There is a new and vibrant energy for young women and men to learn COBOL,” she says.
“The future of AI depends on the past — COBOL is the bridge that connects them.”
Conclusion
Eileen Dennis Hinshaw’s impact extends far beyond operations — she is a catalyst for change in the IT industry, inspiring both seasoned professionals and emerging talent to embrace the enduring relevance of COBOL. Under her leadership, Cobol Cowboys continues to bridge the gap between legacy systems and modern technology, proving that innovation is not just about what’s new but also about preserving what works.
As she spins the world globe in her home — sending out wishes for connection and shared progress — her mission remains clear: to keep COBOL running strong, mentor the next wave of IT leaders, and ensure that the backbone of digital infrastructure remains robust for generations to come.
