Ray Skillman was born circa 1942 and raised in Owensboro, Kentucky. He is the eldest son of William R. Skillman Sr. and Jean Pardon Skillman. His mother Jean Pardon Skillman (1917–2001) and father William Sr. (deceased 1995) lived in Owensboro, and Ray was one of three children in the family. He grew up in the Owensboro area on the Ohio River, attending local schools and completing his high-school education there.
Skillman’s childhood environment was strongly shaped by automobiles and racing. His father introduced him to car races in the 1950s, sparking a lifelong interest in cars. By his mid-teens, Ray Skillman was already working on cars himself: at age 16 he bought his first vehicle – a 1950 Ford Business Coupe – and even upgraded it with a Chevrolet V8 engine.
Ray Skillman – Key Facts
| Fact Category | Details |
|---|---|
| Full Name | Ray Skillman |
| Birth Year | Circa 1942 |
| Birthplace | Owensboro, Kentucky, USA |
| Early Interest | Developed passion for cars through his father and racing exposure |
| First Car | Bought a 1950 Ford Coupe at age 16 and modified it with a V8 engine |
| Career Start | Began selling used cars in 1960 as a teenager |
| First Business | Founded Skillman Auto Sales in Owensboro, Kentucky |
| Industry Entry | Expanded into franchises like Fiat (1971) and Mazda (1974) |
| Major Move | Relocated to Indiana in 1979 to expand dealership operations |
| Company Founded | Skillman Automotive Group formally established under his leadership in 1988 |
| Business Scale | Operates ~16 dealerships across 10 locations in Indiana |
| Brands Represented | Chevrolet, Ford, GMC, Buick, Hyundai, Kia, Mazda, Mitsubishi |
| Revenue Growth | Grew business from ~$240M (2009) to ~$1B+ (2023) |
| Ray Skillman Net Worth | Not publicly disclosed; wealth derived from dealership ownership, sales, service, and financing operations |
| Leadership Style | Known for disciplined cost control, customer-first philosophy, and long-term growth strategy |
Ray Skillman’s Automotive Career
Ray Skillman is an Indiana-based automotive entrepreneur who founded the Skillman Automotive Group in the late 1970s. Starting in 1960 as a teenager selling used cars in Owensboro, Kentucky, he built a company that would become one of the state’s largest dealer groups.
Over more than five decades, Skillman guided steady expansion into new- and used-car sales, collision repair, and financing, culminating in a network serving Indianapolis and surrounding suburbs. By the 2020s the group included about 16 showrooms at ten area locations, and it was ranked among Indianapolis’s top private companies with roughly $1 billion in annual revenue.
Early Career in the Car Business and Industry Entry
Skillman’s career began in Kentucky. He bought his first car, a 1950 Ford Coupe, at age 16 and, upon finishing high school, opened a used-car lot in Owensboro.
From 1960 until 1979 he operated Skillman Auto Sales, gradually expanding by adding new franchise lines. In the early 1970s he acquired a Fiat import franchise in 1971 and later added a Mazda franchise in 1974.
Founding and Growth of Skillman Automotive Group
In 1979 Skillman relocated to Indiana to partner with Charlie and Chuck Stuart in a new Oldsmobile dealership north of Greenwood. He quickly broadened the enterprise by adding GMC and Mitsubishi franchises.
By 1988, after Charlie Stuart retired, Skillman bought out the Stuart family partners and took full ownership of the venture. This period effectively marked the founding of the Skillman Automotive Group under Ray Skillman’s leadership.
The group’s early years included bringing Skillman’s own family into management, his son Bill Skillman and son-in-law Cory Delp both became partners as the business accelerated its growth.
Expansion Strategy and Dealership Network Development
Under Skillman’s direction the group expanded through strategic dealership acquisitions and brand diversification. For example, during the late-2000s recession the group bought at least five underperforming dealerships from competitors.
These moves helped Skillman Automotive Group grow into a 13-showroom chain at seven locations by 2010. In subsequent years the network continued to grow: by 2013 it covered 17 franchise brands in 13 central-Indiana sites, and by the mid-2020s it operated roughly 16 franchises across ten locations.
Through this expansion the company came to represent major manufacturers such as Chevrolet, Ford, GMC, Buick, Hyundai, Kia, Mazda, and Mitsubishi. Each dealership is typically full-service, offering new and used sales alongside on-site service, parts and financing departments to meet local customer needs.
Business Achievements, Revenue Growth, and Market Presence
Skillman Automotive Group’s sales and revenue grew substantially under Ray Skillman’s tenure. The group’s total revenue was about $240 million around 2009, rising to roughly $606.7 million by 2012, making it #64 on Ward’s 2013 Megadealer 100 list.
By 2020 annual revenue was approaching $876 million, and by 2023 it had roughly reached $1 billion. Alongside revenue growth, vehicle sales and headcount also increased: for example, more than 25,000 new and used vehicles were sold in 2012, and employee count rose from about 900 in 2013 to over 1,100 by 2023.
These results placed the Skillman group among the largest dealer organizations in the state. In industry rankings, Automotive News listed Skillman Auto Group as the 84th-largest U.S. dealership group by 2020, and local business media ranked it as the 10th-largest private company in the Indianapolis area by revenue in 2023. The group’s stores have won multiple manufacturer awards, including GMC Dealer of the Year and Mazda Gold Cup, in recognition of their sales and service performance.
Leadership Style and Business Philosophy
Throughout his career Ray Skillman has been known for a conservative, detail-oriented management style. Colleagues note that he emphasizes strict cost control and thoughtful planning.
He has articulated the company mission in customer-focused terms, stating “all of our efforts are directed toward our goal of earning customers for life.” Under his leadership the organization adopted the slogan “Stack ’em deep and sell ’em cheap” to convey its value-oriented sales approach. Skillman remains highly visible in daily operations, and he has built a corporate culture focused on training staff and delivering world-class service in every department.
Current Operations, Business Activities, and Industry Influence
As of the early 2020s Ray Skillman was still actively steering the company he founded. Industry listings continue to identify Ray Skillman as the group’s president.
Under his oversight the Skillman Automotive Group continues to invest and expand. In 2025 the company submitted plans to relocate two Indy-area dealerships, Kia and Hyundai franchises, from the city’s west side to a new complex in Whitestown, with construction slated to begin for a spring 2026 opening.
This project marks the group’s first move into the fast-growing northern suburbs. In total, Skillman Auto Group now operates dealerships across Greater Indianapolis including communities such as Greenwood and Franklin, serving as a major employer and advertiser in the region.
Its estimated $1 billion annual revenue and 1,112 employees as of 2023 reflect the lasting scale of Skillman’s enterprise. Through consistent leadership and continued facility investments, Ray Skillman’s career has firmly positioned him as a leading figure in Indiana’s automotive retail industry.
Ray Skillman Net Worth
As of 2026, Ray Skillman’s net worth is not publicly disclosed, and no figure has been officially verified by major financial authorities. His income comes from his ownership of the Ray Skillman Automotive Group, an Indiana-based network of franchised auto dealerships.
The group sells new and used vehicles from brands including Chevrolet, Buick, GMC, Ford, Hyundai, Kia, Mazda and Mitsubishi. It also operates parts and service departments (including a Classic Cars collector-car division) and provides customer financing for vehicle purchases. These automotive sales, service and financing operations constitute the sources of Skillman’s revenue.
FAQs
Who is Ray Skillman?
Ray Skillman is an American automotive entrepreneur and the founder of the Skillman Automotive Group. He is known for building one of Indiana’s largest dealership networks over several decades.
What is Ray Skillman known for?
He is best known for developing a large-scale automotive dealership business in Indiana. His company operates multiple franchises representing major vehicle brands.
Where is Ray Skillman from?
Ray Skillman was born and raised in Owensboro, Kentucky, United States. He later moved to Indiana to expand his business career.
When did Ray Skillman start his career?
He began his career in the car business around 1960 as a teenager selling used vehicles. This early start laid the foundation for his long-term success in the automotive industry.
What businesses does Ray Skillman own?
Ray Skillman owns the Skillman Automotive Group, which includes multiple dealerships offering new and used vehicles, service, and financing. The group represents several major automotive brands.
