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Olive AI CFO, product chief, other top execs have left two months after 450 job cuts


Rohan D'Souza - Olive AI
Rohan D'Souza has left Olive AI Inc., where he was chief product officer.
Olive AI Inc.

Leadership ranks at Olive AI Inc. are thinning with the recent departures of the CFO, chief product officer and other top executives who joined in the early days of unicorn status two years ago.

The Columbus health IT company announced last Friday that CFO Ali Byrd and Chief Product Officer Rohan D’Souza were stepping down, a spokeswoman confirmed via email this week. Jeremy Friese, president over health insurer markets, also told the company earlier this month that he plans to leave.

Executive ranks have been shrinking two months after Olive cut 450 jobs throughout the organization. None of the departing leaders were based at the Columbus headquarters, having been hired after Olive adopted a nationwide distributed workforce model in the pandemic. Five of the seven remaining C-suite leaders listed on the company's website are in Columbus.

The company has not shifted its flexible work-from-anywhere model known as "the grid," the spokeswoman said.

"We are grateful for all that Ali and Rohan have contributed to the growth of Olive, and the work of their respective teams will continue to be a priority," the company said in a prepared statement. "We are thankful for the remarkable impact (Friese) has made on Olive since joining the company. We remain committed to delivering automation and intelligence to bridge the divide in healthcare."

Byrd, with more than 25 years of software industry experience, joined when Olive first achieved unicorn status at a $1.5 billion valuation in a $225.5 million venture capital round in December 2020. He worked from New York City.

Olive is searching for a CFO, the spokeswoman said. Friese's role was consolidated into that of Chief Customer Officer Geoff Martin, who works from Chicago.

Dr. YiDing Yu, Olive chief medical officer, adds the title of chief product officer taking on D'Souza's duties. Based in Boston, she had joined along with Friese when Olive acquired Verata, the prior-authorization artificial intelligence startup Friese founded, for $120 million. That was days after the December 2020 unicorn round. Friese formerly was a physician executive at the Mayo Clinic.

Yu "has a proven track record of delivering world-class products to market," the spokeswoman said. She remains chief medical officer as well.

Online publication Axios first reported on the executive departures, citing unnamed sources who said Byrd and D'Souza were fired abruptly. The company did not comment on that characterization.

In July 2021 Olive was valued at $4 billion after raising a $400 million venture capital round, the largest in state history. The company making AI-powered software to automate many hospital administrative tasks has raised a cumulative $848 million in venture capital since its 2013 founding.

Only one leader remains from three hired in October 2020 as the leaders of a new cybernetics division, creating AI-powered "workers" to augment and empower human healthcare administrative staff.

Working from Seattle, D'Souza started as the division's general manager and company executive vice president. Last July he was promoted to the new role of chief product officer to split off some operating duties from Olive founder and CEO Sean Lane.

Hired with D'Souza was Tony Brancato, vice president of products for cybernetics, working out of Los Angeles, and Mike Biselli, vice president of emerging technology partnerships, who is in Denver.

Biselli last July was named senior vice president and "evangelist," according to his LinkedIn profile. Brancato left in July and recently announced on LinkedIn that he's joined a stealth-mode fintech as head of product.

Shoshana Deutschkron was named chief marketing officer the same day as Byrd in 2020. With more than two decades in tech, Deutschkron left Olive this April and the following month announced she had joined Portland startup Wheel as chief marketing officer. Jen Martin, who joined in 2020, was promoted to chief marketing office this June at the Columbus office.

Other executives who indicated on LinkedIn they have left Olive in September:

  • Casey Langwith, who was promoted in February to senior director of operations. She has announced she founded a health startup that's in stealth mode in Santa Monica, California.
  • Michael Burnett, executive vice president of operations since 2019, based in Boston. He has not listed a new position. Three months ago he posted on LinkedIn about the debut of a suite of Olive products for hospital insurance claims and billing departments.

Based in downtown Columbus, Olive still plans to renovate the former Anthem building at 6700 N. High St. in Worthington as a new headquarters, the spokeswoman confirmed via email. After the job cuts, the company had scaled back the scope of the first phase of renovations for the 231,000-square-foot office on 20 acres.


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