Justin Raymond
Founder & CEO @Flexday
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WORK HISTORY
Founder & CEO @Flexday
CA
Flexday is the platform for the fractional and short-term workspace category — modernizing how companies access office space and how landlords unlock new revenue from underutilized assets. We operate a two-sided marketplace serving 500+ enterprise and SMB clients and progressive commercial landlords across North America.Current: Agentic AI Re-platformingLeading the end-to-end product design and architecture of Flexday\'s AI-native operational transformation. Bringing in-house a fully integrated technology stack spanning:CRM — unified customer and landlord relationship intelligenceCMS — dynamic content and listing managementDashboarding — real-time operational visibility across the marketplaceFinancial Data Systems — transaction, billing, and revenue infrastructureOperational KPIs — live performance metrics powering decisions at every level of the businessThis re-platforming replaces fragmented third-party tooling with a coherent, agentic intelligence layer — enabling Flexday to operate with greater speed, precision, and scalability as we enter our next phase of growth.Platform & Marketplace Leadership-> Built and scaled a two-sided marketplace connecting commercial landlords with SMB\'s and enterprise clients-> Developed the fractional office product category and go-to-market model-> Established landlord partnership infrastructure enabling asset monetization with minimal operational burden-> Created supply side distribution partnership for North America-> Designed and executed demand side distribution strategy
EDUCATION
Springfield College
M. Ed.
Trinity College School - TCS
OSSD
McGill University
Bachelor of Education (B.Ed.)
SKILLS
ABOUT JUSTIN RAYMOND
I\'ve had the good fortune of arriving early to markets that turned out to matter — on-demand transportation, flexible workspace, and now AI-native business operations. Twenty-five years of founding and leading companies at inflection points has given me a clear bias: build for where the market is going, not where it is. Right now, I\'m leading the next chapter at Flexday — the platform for the short-term workspace category. We\'ve built a marketplace trusted by 500+ companies across North America. And we\'re now going deeper. The current focus: agentic AI replatforming. I\'m overseeing and leading Flexday\'s full operational transformation — bringing in-house a unified technology stack that integrates CRM, CMS, dashboarding, financial data, and operational KPIs into a single, AI-native intelligence layer. This isn\'t automation for automation\'s sake. It\'s about building a company that reasons, adapts, and executes at a level that wasn\'t possible two years ago. What I bring: Marketplace architecture — I\'ve built and scaled multi-sided marketplaces from zero, most notably at Hailo, where I grew Canada\'s largest taxicab network drivers, customers) and joined the Global Executive Team as North American President. Flexday is the continuation of that playbook — applied to commercial real estate.Entrepreneurial range with executive depth — I\'ve founded and led six companies across transportation, sustainability, and workspace. I\'ve also operated at the executive level inside global organizations (Transdev, the world\'s largest multimodal transportation company), carrying M&A and technology strategy mandates at the C-suite level.Product ideation through go-to-market execution — I don\'t just generate ideas. I build the systems, teams, and commercial engines behind them. From CellWand\'s carrier distribution agreements with AT & T, Verizon, Rogers and Sprint, to Flexday\'s landlord and enterprise partnership model — I close the loop between vision and revenue.AI × Business fluency — I\'m not a bystander to the AI transition. I\'m running it inside a live company. The decisions I\'m making today — on data infrastructure, product intelligence, and operational design — are the decisions that will define whether companies like ours lead or follow in the next decade. We are at an inflection point. The companies, leaders, and platforms that treat AI as a core operating layer — not a feature — will define the categories of the future. I intend to be one of them.
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