Rob Tyrie

SOME BACKGROUND

I'm a serial entrepreneur, writer, analyst and computer scientist. I founded Ironstone Advisory in 2019 after more than 40 years working in enterprise software and professional services. Today I focus on enterprise AI, software and business strategy, particularly in insurance, financial services and capital markets.

My career has moved between product, professional services, business development and building new markets. At Salesforce, I was a Senior Director and led Global Insurance Business Development. At BOLT Systems, I was Head of Professional Services. At NexJ Systems, I grew professional services from $1M to $15M and served as general manager of the insurance vertical.

EDUCATION AND TEACHING

I hold a BSc in Computer Science and Statistics from Western University. I completed post-graduate work at the University of Toronto and executive education at Rotman. I have also designed professional-services workshops and courses and worked as an instructor and course designer at Seneca College.

MY WORK

Through Ironstone, I work with leaders on AI governance, insurance advisory, software, cloud, capital, technology-stack assessment and innovation. I make assumptions, evidence and decisions visible so teams can understand the system, decide what matters and execute.

I'm also a co-founder of the Grey Swan Guild. I write on Medium and LinkedIn about AI, software, systems and the gap between useful technology and hype. I'm interested in what these tools can do, who they serve and how people can use them without surrendering judgment or agency. I would still like to see a world with no garbage.

OUTSIDE WORK

I'm a first-generation Canadian with roots in Europe and the Caribbean. I read, travel and make things with new technology. Travel is my drug of choice. Toronto is home, with a special affinity for New York, Tel Aviv and Jamaica. I support Toronto FC, the Toronto Raptors and the Toronto Blue Jays.

MOTTO

Conflabularum ergo sumus. We converse, therefore we are.

The idea is that human consciousness and cognition are not contained entirely within the individual. They also live in conversation: an inner monologue, a dialogue between people or an exchange across time through books, papers and other writing. It is also a riff on artificial intelligence, generative pre-trained transformers and Wittgenstein's challenge to Descartes.

COMPANIES I ADMIRE

Google (Android and Workspace), Perplexity, Veezoo, Basecamp, Metaculus, Notion, Finviz, Disney, Apple (Pixar), Progressive Insurance and USAA.

CITIES I GO BACK TO

Toronto, Ottawa, Vancouver, Montreal and Kelowna in Canada; Kingston, Jamaica; Tel Aviv, Israel; New York, Austin and San Francisco in the United States; and Saint-Adolphe-d'Howard, Quebec.

RESTAURANTS I LOVE

Alchemist in Barcelona; Grey Gardens, Sake Bar Kushi, Diners Corner and Little Sister in Toronto; Grand Central Oyster Bar, Eleven Madison Park, Le Bernardin and Quality Meats in New York; and Boulevard in San Francisco.