Executive · Board Advisor · Keynote Speaker
Les Ottolenghi
Former Fortune 500 CIO and four-time CEO who helps boards and leadership teams turn AI and cybersecurity from risk into measurable growth.
30+
Years leading enterprise technology
$186B
Market value created across his career
30x
Peak equity value acceleration
25+
Board and advisory roles
How I work with leaders
What I do.
Four ways to bring operator-level experience into the room, from a single keynote to a seat at the table.
01
Keynote speaking
Straight talk on AI, cybersecurity, and transformation for boards, leadership offsites, and industry conferences. Every talk is built from three decades of real results, not recycled slides.
02
Board & executive advisory
Independent counsel for CEOs and boards facing technology risk, AI governance, and large-scale change. Les has sat on audit committees and briefed boards on cyber threats, so he knows which questions matter.
03
AI strategy & transformation
From scattered pilots to an operating model that pays for itself. Where AI earns its place, what to build versus buy, and how to bring the organization along.
04
Cybersecurity leadership
Security as a business capability, not a cost center. Les built the gaming industry’s largest cybersecurity program and has stood up three successful security organizations.
Speaking
Selected talks.
RESULTS THAT SHOW UP ON THE BALANCE SHEET
Proof.
Lee Enterprises Built a modernization plan that delivered $30M+ in added EBITDA and a 20% cut in operating costs within 10 months. The stock price doubled in three months.
Chief Commercial & Transformation Officer
Lee Enterprises, SmartSites Launched a first-of-its-kind AI website platform that returned 9x on product and marketing spend and grew digital subscribers 40%.
Chief Commercial & Transformation Officer
Stride, Inc. Led the technology and digital roadmap behind a 283.7% rise in stock value in under three years, plus a 43% jump in operating income.
Chief Commercial Officer & CIO
Caesars Entertainment Turned Caesars into a digital business: roughly 67% EBITDA growth, doubled revenue growth, and about $100M in technology savings.
EVP & Chief Information Officer
Las Vegas Sands Created the company’s first cyber defense organization, protecting $11B in gross revenue and turning back a potentially crippling attack.
Chief Information & Innovation Officer
Codere (NASDAQ: CDRO) Helped steward a turnaround that freed up 20% more working capital and beat EBITDA expectations.
Board Member
WHERE LES HAS LED
About
I don’t just advise. I’ve operated.
I spent three decades running technology and the business inside large, regulated, high-stakes companies — as CIO at Caesars and Las Vegas Sands, Chief Commercial Officer at Stride and Lee Enterprises, and a four-time CEO — before moving to the board side of the table.
I built one of the travel industry’s first metasearch engines, one of the first web-based hotel reservation systems, and a first-of-its-kind AI publishing platform. Today I’m Founder of FuzeBox AI and CEO of VIP Play.
Every engagement starts the same way: I listen first, then say the uncomfortable thing. The result is a strategy the leadership team actually owns and a story the board can back.
MBA, Emory Goizueta (Woodruff Scholar) · BA, Duke · CIO 100 Award · Constellation Business Transformation 150 · 2018 Olympic Torch Bearer
Ways to engage
Three ways to work together.
Start with a single talk or bring Les in for the long haul. Every format comes with the same candor.
Keynote
60 min
on stage or virtual
- Talk tailored to your audience
- Pre-event briefing call
- Audience Q&A
- Executive workshop
- Follow-up advisory
- Board briefing
Advisory
2 spots open
Monthly
retainer
- Standing sessions with the CEO or CIO
- AI and security program review
- Executive workshop each quarter
- On-call for the hard decisions
- One board briefing per year
- Formal board seat
Board & fractional
Ongoing
seat or fractional CIO
- Independent or advisory board seat
- Technology and risk committee
- Fractional CIO / CTO cover
- Leadership hiring and coaching
- Unlimited advisory access
- Quarterly strategy review
FAQ
Common questions.
What topics does Les speak on?
AI and trust, cybersecurity as a business capability, leading large-scale transformation, and what boards actually need to know about technology. Recent keynotes include the Chief AI Conference, Ai4, and CES. Every talk is tailored to the room.
Does he speak virtually as well as in person?
Yes. Les delivers keynotes, panels, and workshops both on stage and virtually, with the same prep call either way.
How far ahead should we book?
Eight to twelve weeks is ideal for conferences. Board briefings and executive sessions can often happen sooner, so reach out even if your date is close.
What does an advisory engagement look like?
A monthly retainer with standing sessions for the CEO or CIO, quarterly workshops, and on-call access for high-stakes decisions. Scope is set in a short discovery call.
Is Les available for board roles?
Yes. Les has served on public, private, and PE/VC-backed boards, including Codere (NASDAQ: CDRO), with experience on audit and nominating and governance committees.
Which industries does he work with?
Gaming and hospitality, media and publishing, education, travel, sports entertainment, and financial services, along with PE- and VC-backed growth companies.
Latest insights
From the blog.
Booking for 2027
Bring an operator into the room.
Keynotes, board briefings, and advisory for leaders who need AI and cybersecurity to be a strategy, not a headline.