Finding and paying for parking can be frustrating. Alex Israel, the CEO of the tech company Metropolis, is applying AI to the problem. Metropolis uses AI and computer vision to identify cars and then charge them for parking without drivers needing to report to a kiosk. Founded in 2017, the company now runs the largest parking lot network in the U.S., operating 4,200 locations across North America and processing over $5 billion in annual payments. But it has also realized concerns about AI tracking, fielding complaints around its fines and debt collection techniques. In January, a yearslong investigation in Tennessee found that Metropolis had engaged in deceptive practices, including misleading pricing and surprise fees, leading to a $9 million settlement. (The company denied wrongdoing and says the settlement was “the byproduct of a years-old acquisition of another company.”)

“We live in a seamless online world, yet the physical world remains outdated,” Israel says. “Parking is the entry point to every city, and for autonomous and connected mobility to scale, the infrastructure must be intelligent.” In November, Metropolis announced a $1.6 billion fundraising round, which it intends to use to scale into gas stations, drive-thrus and other retail spaces.