Les Ottolenghi
Innovative Technology Executive
Les Ottolenghi is a globally recognized technology and business transformation leader whose expertise spans artificial intelligence, cybersecurity, digital transformation, and strategic innovation. With over two decades of experience leading Fortune 100 companies, startups, and global enterprises, Les combines visionary leadership with a passion for driving impactful change.
Innovative Technology Executive - AI Thought Leader - Digital Transformation Strategist
Professional
Experience
Described briefly my professional
background, skills, and accomplishments.
Chief Executive Officer at VIP Play, Inc.
Les Ottolenghi now serves as CEO of VIP Play, Inc., an AI-first sports entertainment company pioneering fan engagement and mobile sports wagering experiences. He brings deep expertise in leveraging artificial intelligence and digital transformation to build scalable platforms and modernize operations.
AI Innovation: Driving the development of AI-powered solutions that enhance fan interaction, personalize experiences, and optimize operations.
Strategic Partnerships: Building collaborations that integrate advanced technologies and expand VIP Play’s market presence.
Business Transformation: Leading initiatives that align cutting-edge innovations with growth strategies, creating new opportunities in sports entertainment.
Chief Tranformation and Commercial Officer at Lee Enterprises, Inc.
Les leads AI initiatives and strategic partnerships for Lee Enterprises, one of the largest news publishing organizations in the U.S., modernizing operations and delivering innovative content solutions.
- AI Innovation: Introduced AI tools to streamline workflows and improve content delivery.
- Strategic Partnerships: Developed collaborations that integrate advanced technologies.
- Business Transformation: Oversaw initiatives aligning technological advancements with business goals.
Executive Vice President, Chief Commercial Officer, and Former CITO at Stride, Inc.
At Stride, Inc., Les provided executive leadership in commercial strategy, partnerships, and technology innovation. His work focused on transforming education through technology and personalized learning solutions.
- Digital Learning Innovation: Oversaw the integration of AI-driven tools to improve learning outcomes and operational efficiency.
- Commercial Strategy: Led efforts to expand Stride’s reach through strategic partnerships and innovative business models.
- Technology Leadership: As Chief Information and Technology Officer (CITO), modernized the company’s infrastructure to support scalable growth and enhance digital offerings.
Chief Information Officer (CIO) at Caesars Entertainment Corporation
Les directed digital transformation efforts, integrating advanced technologies to enhance customer experiences and streamline operations.
- Digital Ecosystem: Implemented data analytics and IoT-based innovations.
- Cybersecurity Leadership: Established robust security frameworks to protect digital assets.
Senior Vice President and CIO at Las Vegas Sands Corporation
Les drove IT strategy for one of the world’s premier luxury hospitality brands, enhancing global operations and guest services.
- Global IT Leadership: Upgraded infrastructure and introduced digital innovation.
- Enhanced Guest Experience: Delivered solutions redefining luxury hospitality.
Co-Founder and CEO of Plat4m Technologies
Les co-founded a technology startup focused on providing innovative SaaS solutions tailored to address complex business needs.
- SaaS Innovation: Introduced scalable cloud-based technologies.
- Entrepreneurship: Fostered a dynamic and results-driven organizational culture
$186B Value Created
30x Share Price
1994 – Present
Recognitions &
Honors
Awarded for significant and
outstanding contributions to his
profession.
Constellation’s Business Transformation 150
Evanta Breakaway Leadership Awards
CIO 100 Award
Top Technology Community Leader
Top Tech Executive for Hospitality & Gaming
And many more across decades of achievements.
Speaking
Engagements
Les is a sought-after speaker who has
delivered keynotes and presentations at
major conferences, events, and universities.
Chief AI Conference
Defining Intelligence: How CAIOs Lead Strategy, Set the Narrative, and Win the Boardroom
Ai4
Ai Fan Engagement Software Solutions
TIBCO Now
Culture and Digital Transformation
GM Geek Week
Gartner CIO
Roundtable
Society of Motion
Picture and Television
Engineers
Wall Street Buy
and Sell-Side Analysts
Internet of Things
at CES
Microsoft Igloo Digital
Workplace Switch
Technology Association
of Georgia
across global forums
and institutions.
Board &
Advisory Roles
Les contributes to strategic decision-making
as an advisor and board member for several
organizations.
Advisor
FiscalNote, 802 Secure, Breadware, NeurRun, Certree
Board of Directors
Intent MediaWorks, Skyworks Aerial, Rich Robotics, AgentWare
Advisory Boards
Oracle Software, Salesforce Software, Sequoia Capital, Andreessen Horowitz, UNLV Lee Business School Information Systems Programs
Member
Duke Angel Network, Technology Association of Georgia
Additional
Highlights
Olympic Torch Bearer
With technology increasingly becoming a staple in our daily lives, UI/UX design has become an essential part of the digital world.
Cyberbullying Advocate
Produced an award-winning documentary screened across U.S. schools and reviewed by HBO, CNN, and the U.S. Congress.
Athlete
Competitive marathon, road race runner and avid skier.
Educational
Background
Described briefly my professional
background, skills, and accomplishments.
Master of Business Administration (MBA)
Emory University’s Goizueta Business School
Bachelor of Arts
Duke University