From the Inner City of St. Louis, Missouri to the C-Suite: President/CEO Stanford Oliver’s Uncommon Journey as a Successful Leader

The Most Influential Black CEOs to Follow, 2023

The renowned Roman poet Virgil once espoused the notion that “Fortune sides with him who dares.” While it is undoubtedly true that an inclination for bold innovation is a crucial component of success, it is not the sole determinant. The gist of success varies from person to person and is contingent upon individual experiences and circumstances. Stanford “Stan” Oliver, the esteemed President/CEO and Founder of DigiFlight, Incorporated, outlines his definition of true success and his vision of exceptional leadership.

“There is no substitute for work. Worthwhile results come from hard work and careful planning.” – John Wooden

During his early 20s, Stan coached AAU basketball and got his first taste of triumph. He sought guidance from his role models, Coach John Wooden and Martin Luther King Jr. by reading their written works and listening to their speeches numerous times. Through this effort Stan learned principles of leadership and motivation, and ultimately arrived at a profound definition he shared with his players, children, and others. According to him, one should not gauge their success based on outperforming others. While it is indeed possible to learn valuable lessons from illustrious figures such as Michael Jordan, LeBron James, Serena Williams, or Steve Jobs, one should not rely on their accomplishments to define personal success. According to his current definition, it is about finding inner tranquility, stemming from a sense of fulfillment attained by giving one’s best effort to maximize their God-given talents.

When asked to outline his chronicle as an efficacious leader thus far, Stan reflects on his ‘uncommon journey’ from growing up in the underserved area of St. Louis, Missouri, to his current position in the C-Suite of a rapidly expanding technology firm that supports national security.

As the President/CEO and Founder of DigiFlight, Incorporated, he has guided the company toward more extraordinary feats during uncertain and chaotic times. His vision has led to the development of a winning strategy and process that has ensured the firm’s path to success. It has also propelled the innovation engine that is revolutionizing and redefining company procedures and processes. To this end, he builds and nurtures strategic relationships with officials and partners across the industry, government, and academic sectors. Additionally, he is responsible for maintaining financial stability, a crucial factor in fostering growth and prosperity.

Stan has consistently adhered to the insight of John Wooden, who famously said, “There is no substitute for work. Worthwhile results come from hard work and careful planning.” Embracing this philosophy, he has always emphasized hard work and meticulous planning, recognizing them as essential elements in realizing his ambitions. His tenacity, diligence, and grit have distinguished him among “The Most Influential Black CEOs to Follow, 2023.”

Life Before DigiFlight, Inc.: Outstanding Achievements and Milestones

Before DigiFlight, Stan’s impressive military background includes two decades of service as an Army Aviator and Blackhawk Helicopter Pilot, during which he held various command and staff positions, including the Army Staff, 101st Airborne Division, 1st Armored Division, U.S. Army European Command, 10th Mountain Division, U.S. Army Security Assistance Command, and the U.S. Army Test and Evaluation Command. He graduated from the Armed Forces Staff College and the Command and General Staff College, acquiring significant expertise in Army Aviation Operations, Defense Acquisition, Cybersecurity, Information Technology, and IC Operations. With justified pride, Stan shares:

“My greatest achievement was spending 20 years serving my country with some great Americans and founding DigiFlight on my retirement.”

From Olympic Dreams to IT Entrepreneurship: The Serendipitous Journey

Stan, a St. Louis, Missouri resident, had harbored a childhood dream of becoming a professional boxer. He trained as an AAU boxer and aspired to qualify for the 1976 Olympic trials. However, he turned his attention to the IT industry when he failed to make the cut. Stan felt drawn to the field, inspired by the success of Bill Gates and Steve Jobs, who founded Microsoft and Apple.

Nevertheless, the young Stan chose to chart his course. In 1976, he enrolled in the engineering school at the University of Missouri-Rolla and earned a degree in Mechanical Engineering in 1981. He then joined the Army as an Army Aviator and retired in 2002 and set out to achieve his entrepreneurial pursuits. This was when DigiFlight came into existence.

Stan recounts: “I have always had a passion for technology. As an Army Blackhawk helicopter pilot, I got the opportunity to fly an advanced digitized aviation platform. It was state-of-the-art at the time. Over the years, the Army modernized other platforms, tanks, artillery, command and control systems, and unmanned aerial systems. In other words, the military became IT-centric. Here I was as a soldier in the middle of a technology revolution, and I loved it.”

Overcoming Challenges as a Leader: The Role of Mentorship

Stan embodies Jim Collins’s statement, “Greatness is not a function of circumstance. Greatness, it turns out, is largely a matter of conscious choice and discipline.” As a leader, the President/CEO and Founder of DigiFlight faced numerous setbacks. He mainly felt the constant need for close mentors who could have guided establishing and improving his leadership style. Nevertheless, he turned to reading books on leadership and experimenting with various approaches to gain the necessary lessons. Many of the great leaders of history, such as Steve Jobs, Dwight D. Eisenhower, Douglas MacArthur, Martin Luther King Jr., and John F. Kennedy, served as virtual mentors and inspirations for him.

Furthermore, growing up as a black man during the 60s and 70s in the inner city and later in the military presented additional challenges and disadvantages. However, these incidents pushed him to work harder and develop his leadership skills, ultimately contributing to his growth.

Today, he recognizes the significance of mentorship and thus, he mentors young people in his community.

“Greatness is not a function of circumstance. Greatness, it turns out, is largely a matter of conscious choice and discipline.” – Jim Collins

DigiFlight, Incorporated: Innovating to Stay Ahead in a Competitive Industry

DigiFlight, Incorporated is a technology firm that provides cybersecurity, enterprise IT, and aerospace solutions to support national security. Its clientele includes the U.S. Intelligence Community, the Department of Defense, the Federal Reserve, and the Department of Homeland Security. The company is known for being a leader in providing Attack Helicopter training to U.S. Army combat aviation units, foreign military partners, and the U.S. National Guard. This mission requires state-of-the-art IT infrastructure to train organizations on the AH-64E v6 Apache Attack Helicopter, the world’s most advanced attack helicopter. It is interoperable with joint advanced communication systems across the joint military force.

DigiFlight leverages advanced technologies, processes, and people to solve the most formidable problems in cybersecurity, enterprise IT, and aerospace industries. For example, it used virtual and mixed reality to develop an advanced attack helicopter simulation platform to train future aviators. The company also provides cybersecurity support to protect organizations in the 16 Critical Infrastructure Sectors, such as Oil & Gas, Finance, and Insurance. Its Foreign Military Sales portfolio includes providing FMS support to over 60 Foreign Military partner nations for all Army Aviation and Missile Platforms that the Army offers to its Foreign Partners.

The industry has its own set of boons and banes. One must embrace fluidity both to transform and when required to stay afloat. Stan explains how his company sails through this challenge:

“Our competition is constant and fierce. But we have a culture of innovation and entrepreneurship that helps us stay ahead. We are always on an innovation journey.”

With a focus on staying abreast of the latest advancements in technology and a commitment to meeting the evolving needs of its customers, DigiFlight is poised to remain at the forefront of the cybersecurity, enterprise IT, and aerospace industries.

Navigating Setbacks: A Lesson in Resilience and Business Management

Setbacks are an inevitable part of any professional journey. Even the most experienced and skilled individuals face obstacles that can test their resilience and determination. For Stan, one of the most shattering reversals he encountered was during the economic downturn of 2009. The company almost ran out of cash and needed adequate capital to sustain the business. This challenge continued for three to four years, during which the company had to borrow money from non-traditional lenders at great expense. It was the only way to allow DigiFlight to survive.

Through this experience, Stan learned that having enough capital to manage through uncertain times is essential for business sustainability. It was a valuable lesson in resilience and business management. He appreciates that setbacks are not failures but opportunities to learn, adapt and improve.

Innovative Contributions and Transformations in IT Services and IT Consulting

“DigiFlight has contributed significantly to cybersecurity for the U.S. Intelligence Community, the Department of Defense, and the Department of Homeland Security,” notes the founder. DigiFlight has solved some of the most complex cyber problems through threat intelligence and integrated technologies.

Moreover, DigiFlight has developed innovative test and evaluation concepts for testing advanced technologies across the test and evaluation lifecycle. Through these contributions, the company has established itself as a leader in the industry, leveraging advanced technologies, processes, and people to unravel the most problematic snags in the field.

In the view of Stan, the IT services and IT consulting industry has undergone significant transformations over the past 15 years. The emergence of cloud computing, the rise of big data, the proliferation of mobile devices, the development of artificial intelligence, the growth of the internet of things, and the emergence of blockchain technology are some of the most dramatic changes that have taken place. These advancements have revolutionized the industry, leading to new opportunities and challenges for professionals in the field.

As the industry continues to evolve, embracing innovation and pushing the boundaries of what is possible is essential. DigiFlight is committed to continue as an industry leader to resolve the hardest glitches and drive transformational change in the field.

Strategies for Motivating Himself and His Team Every Day

Stan, a successful leader, recognizes the importance of daily motivation for himself and his team. He begins each day with an optimistic mindset, seeking ways to make a positive impact in the world and the lives of others. This approach stimulates his mind and drives his personal motivation.

When it comes to his team, Stan keeps them motivated through a mission-focused approach that emphasizes pioneering efforts and missions in cyber and aerospace. This emphasis on meaningful work and cutting-edge innovation keeps his team driven and excited to tackle new challenges. He encourages them with constant ideation and supports his team to remain sharp to achieve their goals.

A CEO’s Struggle with Maintaining Work-Life Balance

The President, CEO, and Founder of DigiFlight Incorporated acknowledged that balancing his personal and professional life is hard. Despite his love for work, he sometimes overworks. He shares that his typical day starts with exercise at 6:00 AM, followed by breakfast and reading several pages of his current book at 7:30 AM. Work begins around 8:30 AM, with huddles with different product teams or leaders and strategic partnership meetings. Although he tries to end his day at 5:00 PM, it has not happened in about a year due to the company’s significant growth path. It focuses on revolutionizing aviation training and cyber. Recently, his workday has been extended until 9:00 PM.

Regarding finding balance, Stan enjoys attending events at the Kennedy Center or Shakespeare Theater in Washington, DC, or sporting events, with basketball being his favorite. During these events, he also makes it a point to spend time with his grandson or one of his three daughters. The adept businessman recognizes the importance of making time for personal pursuits and relationships outside of work.

“The people who are crazy enough to think they can change the world are the ones who do.” – Steve Jobs

DigiFlight’s Roadmap to Future Success

DigiFlight, a leading provider of attack helicopter training for Army Combat Aviation Units and Foreign Military Sales Partners, has set its sights on becoming the leader in training for all Army rotary wing platforms in the next three years. With an ambitious projection of 70% growth over the next fiscal year, DigiFlight is poised for success in the years ahead.

In addition to its training offerings, the brand is also expanding into the cybersecurity space. Stan shares that a component of its cybersecurity has spun out into a new firm, Camelot, in March 2023. Camelot specializes in protecting the 16 critical infrastructure sectors, while DigiFlight focuses on safeguarding government systems and data, including weapon systems security. With this strategic move, DigiFlight is positioning itself for continued success and growth in the years to come.

From Personal Goals to Inspiring Words: DigiFlight’s CEO Shares His Vision

Stan has set his sights on positively impacting underserved communities in urban, rural, and tribal America. To achieve this, he plans to form a nonprofit organization that will use a Marshall Plan-like approach, focusing on cultivating the next generation of STEM professionals. As an advocate for progress and equality, Stan believes these communities deserve more attention. Thus, he is determined to make a difference.

Drawing inspiration from Steve Jobs, who famously said, “The people who are crazy enough to think they can change the world are the ones who do,” Stan has a message for aspiring black professionals and leaders:

“My message for aspiring black professionals is to follow your dreams and remember failure will happen, but it is your best teacher. Learn from it and never quit.”

With these inspiring words, Stan hopes to motivate and empower others to pursue their goals and positively move the world.