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

Travis Kalanick
Travis Kalanick's food empire has a new head for its restaurant tech business. Theo Wargo/WireImage
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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, Kalanick said in the email.

He'll be replaced by the 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 was most recently a vice president at Affirm, 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 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 headwinds similar to the rest of the tech and real-estate industries, including higher interest rates and slower customer-demand growth than during the pandemic boom.

With CSS, Kalanick aims 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.

Do you have a CSS story to share? Reach out to this reporter using a nonwork phone on Signal and Telegram at 646 768 1627.

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Meghan Morris
Meghan is the bureau chief in Singapore. She oversees business, lifestyle, and news coverage and leads the company's local hiring and editorial strategy.Singapore's bureau works on global news during Asia's daytime. They also collect tales from around the region about entrepreneurs, Big Tech work culture, FIRE, relocation, consumer trends, and AI, focused on people-centric storytelling.Before moving to Singapore in 2024, Meghan worked in NYC and SF as a senior correspondent, writing deeply-reported business investigations. If you have sensitive information, please email her from a nonwork email or reach out on secure messaging app Signal at @MeghanEMorris.1 (PR pitches only by email.)She enjoys speaking about tech, finance, and news on television, at conferences, and on podcasts. Please email for booking.These are some of her favorite features she has written over the years:She spent the 2022-23 academic year doing Columbia University's Knight-Bagehot Fellowship, where she took courses in statistics, advanced corporate finance, family office management, and other classes at Columbia Business School. During her fellowship, she also led MBA seminars on due diligence and brought Pulitzer-winning authors to the business school.Before she joined Business Insider in 2018, she wrote about private equity real estate for three years at the industry's trade magazine, PERE. Meghan holds bachelor's and master's journalism degrees from Northwestern University.