Doug McMillon Wal-Mart Store, Inc., Chief Executive Officer Doug McMillon speaks at the Wal-Mart shareholder meeting in Fayetteville, ArkWal Mart Annual Meeting, Fayetteville, USA

Wal-Mart Stores Inc.’s image as “a good old boys network” lingered long after the 1992 death of its founder Sam Walton.

This began to change as, in 2014, the baton to head the company was passed to Doug McMillon, the 47-year-old chief executive officer of Wal-Mart International, signaling a generational shift at the retailer. McMillon, who spent his entire career at Wal-Mart, wasn’t exactly new blood but he represented a youthful face for the company.

One of McMillon’s biggest challenges has been moving Wal-Mart into the digital age. He’s said he operates with a certain level of paranoia, no doubt referring to competitor Amazon.

Wal-Mart in September acquired Jet.com, for $3.3 billion, whose technology uses an algorithm to give customers discounts as they build baskets online. The ceo said Jet’s team was culturally aligned with Wal-Mart and he tapped Jet’s founder Marc Lore to run Wal-Mart U.S. e-commerce.

Lore has since been behind a string of Wal-Mart acquisitions including ShoeBuy.com, Moosejaw and Modcloth. Wal-Mart bought Bonobos in June for $310 million, installing its founder and ceo Andy Dunn to run the growing collection of digitally native vertical brands.

Now, walmart.com sells $2.99 tank tops and the company’s specialty sites sell $750 shoes and $800 parkas. McMillon hasn’t ruled out offering higher-priced products on the flagship Wal-Mart site in the future.

And the acquisitions are expected to continue. There has been significant talk in the market that Wal-Mart may purchase Birchbox, but the retailer isn’t commenting.

Lore is believed to be as obsessed with beating Amazon as McMillon is. Prior to launching Jet.com, Lore cofounded Quidsi, the parent of Diapers.com, which he sold to Amazon in 2010. He’s said to be miffed by Amazon’s decision to close Quidsi in March.

Wal-Mart is testing technology such as digital endless shopping aisles and machine learning to hep merchants with pricing.

Both McMillon and Lore are closely watching Store No. 8, the Wal-Mart-supported innovation center dedicated to transforming the store experience through robotics, virtual and augmented reality, machine learning and artificial intelligence. No quick fix, Store No. 8 has a three- to seven-year horizon.

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