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    Thomas (TJ) Jankowski, Canadian serial entrepreneur and five-time CEO, Toronto. Bios, headshots and the subjects he comments on.

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    Bios

    50 words

    Thomas (TJ) Jankowski is a Canadian serial entrepreneur and five-time CEO based in Toronto, with five exits and $4B in P&L. He was CEO of Medimap, Chief Digital and Growth Officer at Coinsquare, EVP and Chief Digital Officer at Postmedia, and Chief Digital Officer at Flight Network. ICD.D. Phocuswright 35 Under 35. He writes at thomasjankowski.com.

    100 words

    Thomas (TJ) Jankowski is a Canadian serial entrepreneur and five-time CEO based in Toronto, with five exits and $4B in P&L. He ran Medimap, Canada's largest healthcare marketplace, as CEO (2022 to 2025); before that he was Chief Digital and Growth Officer at Coinsquare, EVP and Chief Digital Officer at Postmedia, and Chief Digital Officer at Flight Network, which he helped scale into more than thirty countries. He holds the ICD.D designation, an HBA from the University of Toronto and an MA from the University of Sunderland, and was named to Phocuswright's 35 Under 35 in 2015. He writes on AI, travel and healthcare at thomasjankowski.com.

    250 words

    Thomas (TJ) Jankowski is a Canadian serial entrepreneur and five-time CEO based in Toronto, with five exits and $4B in P&L. From 2022 to 2025 he was CEO of Medimap, Canada's largest healthcare marketplace, which shows patients live walk-in clinic wait times and availability. Under his leadership Medimap partnered with CANImmunize, NVIDIA and AWS, and the City of Winnipeg chose it to help take low-acuity patients out of emergency-room queues.

    Before Medimap he was Chief Digital and Growth Officer at Coinsquare, where he worked on the exchange's expansion into Europe; EVP and Chief Digital Officer at Postmedia, where he led product, digital technology and research and development and opened a digital development lab in Kitchener-Waterloo for the B2B business; and Chief Digital Officer at Flight Network, which he helped scale into more than thirty countries. Earlier he spent years at NCR in IT strategy and founded four startups, among them his own IT consultancy, mostly predictive modelling and machine learning work. He has mentored founders at StartUp HERE Toronto and sat on the boards of Spark Centre and Synergy Lab.

    He holds the ICD.D designation from the Institute of Corporate Directors, an HBA from the University of Toronto and an MA from the University of Sunderland, where his 2007 thesis studied neo-nomads. Phocuswright named him to its 35 Under 35 in travel in 2015.

    He writes on AI, travel and healthcare at thomasjankowski.com, on what agents, platforms and regulation change for the people who run these businesses. He is available for interviews, expert comment and conference talks.

    Headshots

    Thomas Jankowski headshot, 16:9
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    Thomas Jankowski headshot, 4:3
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    Thomas Jankowski headshot, 1:1
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    Download the high-resolution headshot (1793x1910 JPEG)

    Expertise

    AI agents

    • What happens when consumer agents meet the platforms they shop on. Meta launched Muse for billions of users on September 8, 2026; twelve days later Amazon locked it out of its store. Read
    • The real operating cost of running fleets of agents. Steve Yegge's agents, given ten weeks, filed roughly 450 legal artifacts, from a constitution to case law, to govern themselves. Read
    • Advertising inside AI assistants, and what the data trade looks like. OpenAI went from ads in ChatGPT on February 9, 2026 to a Meta-style pixel and conversions API by September. Read
    • Who pays for AI compute, and how the labs finance it. Anthropic is paying rival xAI roughly $1.25 billion a month to rent the Colossus 1 data center. Read

    OTAs and travel distribution

    • How distribution changes when the booker is an agent, not a person. He spent five years scaling Flight Network into more than thirty countries before agents entered the funnel. Read
    • Airline loyalty programs as financial businesses. More than 80% of IAG Loyalty's revenue comes from external partners buying Avios, about two-thirds of it from financial services. Read
    • Trust and reviews in travel marketplaces. GetYourGuide's Creator Reviews have one of its 33,000 travel partners book an activity free and review it within 24 hours. Read
    • Airline data as an asset class for AI. Google bought Spirit's internal data at a bankruptcy auction for $10 million, outbidding Mercor at $7.5 million. Read

    Health-tech

    • Getting patients to the right care: navigation, wait times and routing. As Medimap's CEO he reported Ontario walk-in waits of 40 to 70 minutes across the province (Global News, 2024). Read
    • AI scribes and clinical documentation. Ontario's Auditor General found all twenty approved AI-scribe vendors produced inaccurate notes in the procurement test. Read
    • AI in billing, coding and claims. BCBS plans paid an estimated $942 million more over two years for inpatient care that grew more complex on paper. Read
    • Prior authorization and AI-driven denials. CMS's WISeR pilot pays private review contractors up to 20 percent of the Medicare spending they avert. Read
    • EHR concentration and the agent layer. KLAS puts Epic at 42.3% of acute-care market share, and still gaining. Read

    Speaking topics

    • When the customer is an agent. What travel and retail distribution look like once AI agents do the searching and booking, and who keeps the margin.
    • AI in the clinic, before it reaches the exam room. What procurement tests, billing data and prior-authorization pilots already show about clinical AI in Canada and the US.
    • Running agents in production. The governance, compute and vendor bill that comes with moving from one assistant to a fleet.
    • Five CEO seats, four industries. Operating lessons from marketplaces, media, fintech and healthcare: growth, digital transformation and boards.

    Recognition

    Industry stages
    Travel industry conferences for Flight Network, 2014 to 2017: Phocuswright (North America and Europe), World Low Cost Carrier Conference, EyeforTravel Travel Distribution Summit, ITB Berlin, Travelport Symposium
    TorontoCIO executive roundtables on machine learning, AI and data governance, 2018
    Canada Healthcare Innovation Summit for Medimap, 2023

    As seen in

    The Globe and Mail · CBC News · CTV News · Global News · Financial Post · Toronto Sun · Calgary Herald · Winnipeg Free Press · BetaKit · Bitcoin Magazine · Yahoo Finance · Canadian Affairs · Canadian Healthcare Technology · Vancouver Tech Journal · News Media Canada · Media in Canada · Techcouver

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