The head of Travis Kalanick's restaurant tech startup is leaving after 5 years

• Guido Gabrielli is leaving restaurant tech company Otter after five years, per a company email viewed by BI.
• Otter's new head is Ashvin Kumar, who most recently worked at fintech Affirm.
• Otter is a nearly $70 million a year business, Travis Kalanick wrote in an email to staff.

One of Travis Kalanick's key businesses just named a new leader, according to a company email reviewed by Business Insider.

Guido Gabrielli is leaving Otter, the restaurant tech arm of City Storage Systems, per the company email sent by Kalanick.

He is replaced by entrepreneur Ashvin Kumar, who comes from Affirm.

Gabrielli is "moving on to a new chapter in his career of substance," Kalanick wrote about Otter's head, who joined the company from Uber. "He has been a part of CSS since the early days, with us for 5 years and has taken Otter from a scrappy upstart to the almost $70mm/yr business it is today."

Otter's global businesses include order management for platforms such as DoorDash, a virtual-menu arm, a revenue-recapture business that claws back money owed to restaurants, and a point-of-sale system. In early May, Gabrielli told Otter staff that the company had 100,000 restaurants paying for at least one service, BI previously reported.

The company's technology is used by customers of CSS's other arm, CloudKitchens, which renovates warehouses into ghost-kitchen facilities for mom-and-pop restaurateurs and big companies such as Chick-fil-A.

Otter has, at times, struggled with glitchy software and customer support. Last year, a CloudKitchens operator invited to speak at an all-hands meeting complained about the system, BI previously reported. In response, Gabrielli sent a Slack message to the full company promising better customer service.

Otter has also seen some personnel stumbles. The company ran a controversial sales boot camp that went off the rails before it was shut down last year, BI reported. And, like many peers, Otter has cut staff in multiple layoff rounds after the pandemic.

Kumar comes from Affirm, where he was a vice president working on special projects. Before his stint at the fintech company, he founded the social auction app Tophatter, which shut down in 2022.

"I've known Ashvin since the late 2000's Silicon Valley entrepreneur community. I couldn't be more excited about having him take the helm," Kalanick wrote in the company email.

In fall 2021, Kalanick raised $850 million for CSS from investors, including Microsoft, at a $15 billion valuation. Since then, the company has faced similar headwinds to the rest of the tech and real-estate industries, including higher interest rates and slower customer-demand growth than during the pandemic boom.

Through CSS, Kalanick wants to reinvent the business of food, just as he upended transportation by cofounding Uber.

BI reached out to Gabrielli, Kumar, and a representative for CSS about the leadership change. None responded to the request for comment, sent outside normal business hours.

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