In September 2018, AutoNation announced it was looking for a new CEO and said Jackson would become executive chairman once a replacement was hired.
In early 2019, the company hired Carl Liebert, an industry outsider and COO of insurance provider USAA, to become CEO, and Jackson retired from that post.
Liebert started in the role in March 2019 but was let go in July 2019 when the company shifted gears and named its longtime CFO Cheryl Miller as CEO. Liebert turned out not to be a good fit, Jackson said at that time.
Miller's tenure at the top of AutoNation also was short-lived. She requested medical leave in April 2020, and AutoNation returned Jackson to the CEO seat to fill in for Miller while she was out. But she never returned, resigning from the company in July 2020.
At that point, with the coronavirus pandemic well underway, AutoNation said it had extended Jackson's contract to April 12, 2022. The company said it planned to begin a search for Jackson's successor in late 2021 or early 2022. Jackson's contract said he could leave sooner if a new CEO was hired before that April date.
Some industry analysts at that time said the executive shuffle was a concern among investors, and some management experts were critical that AutoNation was waiting to begin its search. But AutoNation said the timing wasn't right for a search then because of the pandemic.
The outspoken Jackson, known for being a voice for dealers, particularly with regard to his criticism of stair-step incentive programs, will leave AutoNation after first joining the company as CEO in October 1999. He previously headed Mercedes-Benz USA — making the same leap from automaker executive to dealership group chief that Manley is now making.
Early in his tenure with AutoNation, Jackson moved quickly to close most of the retailer's 29 AutoNation USA used-car megastores and convert the rest to new-car dealerships. He also killed plans for a national brand, though he kept the idea close and bided his time until the 2013 rollout of the AutoNation brand for all company dealerships, save for luxury-brand stores.
Jackson later extended that brand name to auctions, aftermarket parts and finance and insurance products, and he brought back AutoNation USA used-vehicle stores albeit with a smaller footprint and slower rollout than the retailer's efforts in the late 1990s. Jackson also helped raise $28 million for cancer research and treatment through AutoNation's Drive Pink initiative.
"I've always loved Jackson's blunt style, [and] his crystal ball in terms of predictions on things like the [annual industry sales rate] tended to be very accurate," Whiston said.
AutoNation, of Fort Lauderdale, Fla., ranks No. 1 on Automotive News' list of the top 150 dealership groups based in the U.S., with retail sales of 249,654 new vehicles in 2020. It retailed 241,182 used vehicles for the same period, ranking it No. 3 on Automotive News' list of the top 100 used-vehicle retailers.