- Duke University
1980-1984 - Emory University
1992-1994
MAJOR ACHIEVEMENTS
At Caesars Entertainment (2016-2020), Ottolenghi led a company-wide pivot to digital, overseeing seven enterprise cloud migrations and an innovation programme credited with lifting EBITDA by approximately 67 per cent over three years.
Earlier, as Global CIO at Las Vegas Sands, he established a cyber-defence function and introduced unified IT standards that delivered a ten-fold improvement in the value of technology investments.
EMPLOYMENT
Ottolenghi began his career in 1985 by founding Computer Innovations, a retail technology venture that reached $3.3m in sales within three years. After completing his MBA, he joined Holiday Inn Worldwide in 1994 as Director of Emerging Technologies, where he pioneered the hotel sector’s first web-based reservation system.
In 1996 he became Chief Technology Officer at Carlson Wagonlit Travel, architecting the industry’s inaugural internet-based booking platform and generating a $50m profit over five years. He went on to co-found AgentWare in 1999, developing a meta-search engine later licensed to Kayak.
From 2003 to 2007, Ottolenghi served as CEO of INTENT MediaWorks, introducing legal peer-to-peer content distribution and advising the US Senate on software innovation. He then established PLAT4M, a SaaS consultancy whose travel-tech solutions cut client transaction costs by 30 per cent and enabled revenue turnarounds for Fortune 500 companies.
His entry into large-scale gaming came in 2013 with Las Vegas Sands, where, as Global CIO & Chief Innovation Officer, he unified global IT operations, secured regulatory approvals in Nevada and Singapore and led the response to a major cyberattack.
In 2016, Ottolenghi moved to Caesars Entertainment as EVP & CIO, embedding big data, IoT and mobile initiatives across the enterprise. Under his leadership, customer personalisation strategies unlocked multi-million-dollar revenue gains and reduced technology spend by almost one-third.
He then joined Stride in 2021 as EVP & CCO, modernising the ed-tech provider’s platforms for scalability and security. In 2024, he became Chief Transformation & Commercial Officer at Lee Enterprises, leveraging an AWS partnership to introduce generative-AI content tools and reposition the media group for digital growth.
In June 2025, Ottolenghi was appointed CEO of VIP Play. Tasked with integrating sportsbook technology, optimising operational efficiency and guiding future US market expansion, he now leads the company’s strategy to deliver intelligent, secure and highly personalised gaming experiences.
