BIRMINGHAM, Ala. — Shipt has named former executive Raj Kapoor as its next CEO, putting a familiar leader in charge of the delivery company that grew from a Birmingham startup into a $550 million Target acquisition and a prominent name on the city’s skyline.
Kapoor will take over Oct. 18, succeeding Kamau Witherspoon, the company announced Wednesday. He previously served as Shipt’s chief operating officer from 2022 to 2025 and most recently was Target’s senior vice president of marketplace.
The incoming CEO will be based in the San Francisco Bay Area and travel regularly to Birmingham and Minneapolis. Shipt said Birmingham remains its headquarters, with additional hubs in those two cities.
The transition opens another chapter for a company whose local history involves two recognizable downtown buildings — and whose approach to grocery delivery differs substantially from the expensive warehouse-and-truck operations that sank some early online grocers.
Birmingham entrepreneur Bill Smith founded Shipt in 2014. The service launched that November with an initial enrollment opportunity for 1,000 customers in his hometown, according to contemporaneous reporting by TechCrunch.
Its approach connected customers ordering online with personal shoppers who collected their purchases from existing stores and delivered them. When Target announced its agreement to buy Shipt in December 2017, the service had more than 20,000 personal shoppers operating in more than 72 markets.
Target agreed to pay $550 million in cash, describing the acquisition as a way to combine its store network with Shipt’s technology and shoppers to expand same-day delivery. The arrangement kept Shipt operating independently as a wholly owned subsidiary.
Nearly nine years later, Shipt says its same-day delivery marketplace connects members with more than 120 retailers and reaches 80% of the U.S. population. Its business also includes Target Last Mile Delivery, which handles next-day parcel delivery for Target customers.
Witherspoon, who has led Shipt for more than four years, will remain through late October to assist with the transition. The company said he decided to leave after more than 15 years across the Target organization.
“My focus is simple: enhance convenience for our customers, empower our shopper and driver community, and strengthen business performance across our offerings,” Kapoor said in the company’s announcement.
Shipt’s downtown presence can create the impression that the company bought the buildings bearing its name. The documented transactions tell a more specific story: Its founder purchased part of one building, while Shipt leased space in the other.
Smith acquired the basement and six floors of the historic John Hand Building in 2014, according to the Birmingham Business Journal. Shipt began operating there that year and expanded into additional space as it grew.
The 21-story building, constructed in 1912, stands at 20th Street and First Avenue North, in the landmark grouping commonly called the “Heaviest Corner on Earth.” Shipt added its logo to the building in 2016.
In January 2019, Shipt announced a downtown expansion into the building then known as Wells Fargo Tower, at 420 20th St. N. The company signed a lease for 60,000 square feet and became an anchor tenant, with the tower taking the Shipt name. That transaction was a lease, not a purchase of the skyscraper.
At the time, Shipt said it would retain its John Hand Building offices as well. Its later move to the tower marked a shift in its downtown footprint: In February 2022, the John Hand Building’s rooftop Shipt sign was replaced with the name of Landing, Smith’s flexible-apartment company, Bham Now reported.
The buildings made Shipt’s growth unusually visible. A company launched inside a former banking landmark eventually put its name atop Birmingham’s tallest building.
The use of contractors is part of the explanation for Shipt’s business model, but it is not the only important distinction between Shipt and earlier grocery delivery ventures. Another is its reliance on stores that already stock and sell the merchandise.
Shipt classifies its personal shoppers as independent contractors and pays them by the order. Its shopper guidance says they receive all customer tips and are responsible for expenses including gasoline and mobile data. Shoppers must also have a valid driver’s license and automobile insurance.
That arrangement places some delivery expenses on shoppers rather than the company. It also distinguishes those workers from Shipt’s corporate employees, including the staff associated with its Birmingham headquarters.
The store-based approach addresses a separate cost problem: Shipt’s same-day grocery service uses retailers’ existing inventory and locations rather than requiring a new network of grocery warehouses for each market. Target explicitly cited the combination of its stores and Shipt’s shoppers when announcing the acquisition.
Webvan, one of the best-known failures of the dot-com era, took a different route. It built elaborate distribution infrastructure and planned rapid expansion before establishing enough demand to support the investment, according to a 2001 analysis published by the University of Pennsylvania’s Wharton School.
Soon after beginning service in 1999, Webvan announced a $1 billion agreement for 26 automated warehouses. Its model also relied on a fleet of customized delivery vans. It shut down and announced plans to file for bankruptcy in July 2001.
Wharton’s analysis contrasted Webvan with British supermarket chain Tesco, which tested online ordering on a smaller scale and filled orders from existing stores before committing to dedicated warehouses. The comparison shows that grocery delivery’s prospects depended on infrastructure, expansion decisions and customer demand — not simply whether delivery workers were employees or contractors.
Shipt’s Birmingham history also includes a gap between its early expansion ambitions and the corporate jobs it ultimately added.
In 2018, state and local officials announced an expansion plan calling for 881 new Birmingham jobs. Birmingham committed up to $1.7 million, and the broader package included state workforce assistance, potential tax credits and county incentives tied to hiring.
By August 2023, however, Shipt had fallen short of the promised hiring increase, according to an AL.com examination of the agreements. The company told the news organization it had nearly 850 corporate employees in Alabama at that time, most based at its Birmingham headquarters. That was a total workforce figure, not 850 newly created jobs.
AL.com reported that Shipt terminated its agreement with the Alabama Department of Commerce in March 2023 because it no longer expected to meet its employment commitments. The company received no Jobs Act cash incentives or tax credits under that agreement, although separate city, county and workforce-training programs had paid it money.
Those figures describe the company’s position in 2023, not a current employee count. Shipt’s latest leadership announcement confirms Birmingham’s continuing headquarters role but does not provide an updated local staffing figure.
Kapoor now returns to a company with a much broader reach than the Birmingham grocery startup Smith launched in 2014. Its next CEO will work primarily in California, but the company says its headquarters remain in the city where the business began.