Rodrigo Loureiro
Inventor, builder, investor, cyclist | Steward of a Christmas tree farm in Unison, Virginia | Founder CEO and Former Global CIO & CISO
ABOUT ME
Inventor, builder, investor, cyclist
AI and software | Gravel roads | A Christmas tree farm in Unison, Virginia
I spend my time on the things I would do for free. AI comes first. I trained as a statistician, with a BSc and an MSc in Statistics and Operations Research from the University of Lisbon, where I first studied neural networks in the early 1990s. Three decades later I am back at it: building a language model from scratch, reading the training and interpretability research, and applying it to AI security.
Security teams run dozens of tools, yet boards still can’t get a straight answer to one question: how exposed are we? I had to answer it with the markets watching. As Laureate’s first CISO I was on the executive team that took a private company public, at $4.2B in revenue, and I built the security program that let it stand up to public-market scrutiny, taking our security maturity from 1.2 to 3.8 in three years across a university network in 29 countries. After Laureate I turned that playbook into software, first inside my advisory firm, CyberVerse Advisors, then as Cyber Connective Corporation. I patented it (US 12,437,077), joined Microsoft for Startups and won seven-figure backing from a strategic partner. AI agents are the newest blind spot, and that’s where I’m taking it.
That playbook rests on more than three decades of building and running technology and security at scale. I started as a programmer in 1988, was Chief Technology and Information Security Officer for CGI’s Financial Solutions Group, and went on to become Laureate’s Global CIO, with a technology budget in the hundreds of millions.
Today I build software with AI: a personal-finance dashboard, a cycling coach and a retirement simulator, each with language models doing the analysis. I also invest my own capital, ride the gravel roads of western Loudoun, lead the nonprofit Cycling Unbound, and am the steward of a Christmas tree farm in Unison, Virginia.
I hold two US patents and co-authored two leadership books, the USA Today bestseller ‘Game On – Leaders Who Last’ and ‘Mission Matters’.
I am open to board and advisory roles, especially where AI and cyber risk meet, and to research collaboration.
University of Lisbon, Portugal: BSc and MSc in Statistics and Operations Research (with Honors), 1988 to 1994
Fluent in Portuguese, English, French and Spanish
What I work on
AI and large language models | AI security | Software development | Investing and personal finance tools | Statistics and operations research | Cycling training science | Land stewardship | Board and advisory work
I build software with AI: a cycling coach that reads my training data, tools that track and model my finances, and a simulator that asks whether the money will outlast me.
CURRENTLY
Working through how large language models function from first principles: building one from scratch, reading the training and interpretability research, and applying it to AI security. Taking my patented cyber risk scoring software into AI agents, the newest blind spot. And building with AI: a cycling coach, personal finance tools and a retirement simulator.
I invest my own capital in public markets and in private cybersecurity and AI companies, and I build my own tools to do it.
At home I am the steward of a Christmas tree farm in Unison, Virginia, and I work on preserving the village and the land around it.
Cycling Unbound is a Virginia 501(c)(3) nonprofit. We ride the historic gravel roads of western Loudoun and Fauquier, document their history, and work to keep them unpaved, open to everyone and safe to share.
Weekly open rides and a library of mapped routes at cyclingunbound.org.
PREVIOUS PROFESSIONAL EXPERIENCE
Laureate Education, Inc., Laureate International Universities •
Baltimore, MD (Global) Worldwide leader in higher education, with $3.3B in revenue from 27 accredited campus-based and online universities offering undergraduate and graduate degree programs to 875,000 students in 7 countries.
Joined Laureate Inc, as its first CISO, built, grew, and fostered growth within the IT/CISO team from 1 to 200 staff. Developed corporate information security strategy, facing a critical problem with lack of cybersecurity that had resulted in coverage termination by the cybersecurity insurance carrier. Within 24 months, improved the corporate IT/CISO posture, for example enabling purchase of a $50M policy for cyber risks for operations with the same insurance carrier that had previously deemed Laureate too risky on a cyber perspective, contributing to a successful IPO in 2017.
Multiple successes in driving all aspects of program lifecycle, from initial concept and requirements through design, development, sales, and implementation.
Previous
CGI, Inc. • Montreal, Quebec, Canada (Global) CGI is a global IT consulting, systems integration, outsourcing, and solutions company. Services provided include application services, business consulting, business process services, IT infrastructure services, IT outsourcing services, and systems integration services. CGI has customers in a wide array of industries and markets, with many in financial services.
CHIEF TECHNOLOGY & INFORMATION SECURITY OFFICER, FINANCIAL SOLUTIONS GROUP 2005 to 2015
Created and managed technology and INFOSEC strategy for CGI’s Financial Solutions Group, providing technical and security direction for all financial solutions, which included Trade, Originations, Servicing, Collections, and Gateway solutions. Led a team of 25 Senior Technical Architects via 4 direct reports.
Led business unit focused on building and deploying software for clients as CGI transformed from client single sales to selling software as a service hosted in CGI’s datacenter, selling 10-year contracts of reoccurring revenue. Security was the greatest challenge; software that was deployed in the client’s datacenter was now in CGI’s datacenter. Built and trained the team to make the environment in CGI’s datacenter secure. Developed programs that withstood audits by Bank of America (BOA), Citibank, Barclays, JP Morgan, and Chase.
Expert at building a technical information security program and also “selling” it to the client, to convince them to trust CGI. Performed complete architectural design and performance tuning for large-scale platform and web-facing infrastructure, which included J2EE and Oracle with BPEL, BPM, and EAI components. Information Security Governance: Rolled out an enterprise security program and technology roadmap for security solutions and security technology to address marketplace security requirements such as PCI-DSS and ISO27000.
Developed cloud security technology policy and standards to ensure safe deployment and offering of large information technology solutions in secure datacenters complying with the latest regulations and best practices Provided account management for the largest telecom operator in Brazil, including cultivating client relationships, identifying sales opportunities, and worked with the largest banking institutions, including JP Morgan Chase, Wells Fargo, Moody’s, and BOA.
Writing
AI capital spending: where the demand is real and where it is fragile
The five largest cloud companies are on course to spend about $805 billion on capital projects in...
Rebuilding a Mac without carrying the clutter over
Setting up a new Mac from nothing is how I get rid of clutter. It is also slow, because most of...
Mapping a 93 km gravel loop from Unison
The route started as a 77 km loop and finished at 93.1 km with 1,556 metres of climbing. The extra...
Reading all eleven pages of a 1992 conservation easement
The 35 acres I steward in western Loudoun County are under a permanent open-space easement...
Will the money outlast you? What retirement calculators skip
Most retirement calculators ask for a balance, a yearly withdrawal and an expected return, and...
A finance dashboard that never sees my password
I track net worth, holdings and spending in a dashboard I built myself, and the first requirement...
A personal operating system for AI agents
An AI assistant starts every session knowing nothing about you. You can paste in context each...
Training with power: what the numbers are for
A power meter reports one thing: how many watts you are putting into the pedals right now....
What a statistics degree from 1994 still explains about AI
I studied neural networks in Lisbon in the early 1990s, as coursework inside a master's in...
Running language models on my own hardware
One Mac on my home network does nothing except run language models. It answers on a local address,...
Why the gravel roads of western Loudoun are worth keeping unpaved
Most weeks I ride the unpaved roads between Unison, Bloomfield and the Fauquier line, and most...