Building Agents @Shopify | VP of Machine Learning Engineering | Bringing AI to entrepreneurs | Bush Pilot | Maple Syrup Producer settingnorth.com

Joined January 2010
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Every Sidekick decision comes back to one question: will this help more merchants successfully start and grow their businesses? Grateful to be on this journey with them.
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Let me know if you want to meet up in Seoul! So much going on at Shopify in this space. Let’s chat.
🇰🇷 Here’s what’s on deck for us @icmlconf in Seoul next month: Our Expo Talk on how we distill LLMs into smaller, faster, and more accurate models than their teachers. A live demo of Tangent, our autonomous ML pipeline research agent. A workshop on the generative turn in search and rec at 81M shopper scale. And booth presentations from every ML team at Shopify. Come see what we’re building. 👇🏻
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Looking forward to working with you!
joining @Shopify as an Applied ML Engineering Intern on the Sidekick team this fall, out of Toronto Sidekick, led by @Drewch, is Shopify’s AI co-founder for merchants. couldn’t think of a better place to work on AI that helps millions of merchants build and grow their businesses big thanks to @alspee for being incredibly kind and helpful throughout the process, and to @Drewch for the conversations that made this possible time to ship every hero needs a sidekick :)
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Andrew McNamara retweeted
Love the new Home page on @Shopify! Sidekick is the most powerful, best-designed AI assistant out there. Putting it front and centre for merchants will dramatically increase their chances of success.
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Andrew McNamara retweeted
Recently Shopify Flow introduced a version history page, but did you know that you can ask Sidekick about your versions, and even ask for a diff of what changed?
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Wedding favour bottling day
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Quick flight to BBQ dinner
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Andrew McNamara retweeted
the beauty of shopify is that it makes trying feel normal i remember being 13, trying to start a clothing dropshipping store with my best friend. we had absolutely no idea what we were doing but somehow it felt possible wish we had sidekick then haha
Shopify launched to the public 20 years ago today
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Andrew McNamara retweeted
Shopify launched to the public 20 years ago today
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Andrew McNamara retweeted
I'm on pat leave right now — and in the 2 hours I joined work yesterday for reviews, I was able to knock out 5 PRs for different small issues I found with some stuff we're building. River has changed everything, and we're _just_ starting to see the fruits of that labour.
Recently @tobi shared the philosophy behind River, our Slack-native AI agent, and how it has become a teaching workshop for all of @Shopify. Below River lies the Aquifer. Principal Engineers @burkelibbey & Javier Moreno share the engineering story of how River came to be, and the substrate it runs on:
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I’ve completed my New Year’s resolution 7 months early, I built a home gym. What will I do the rest of the year.
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“No one could employ me in Canada so I started my own business and that worked out” — @tobi
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Does anyone at toronto tech week homecoming have a wireless charger?
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Haha got one!
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Andrew McNamara retweeted
May 26
SimGym is one of the coolest things we’re doing @shopify 🤖🛍️ @Drewch @aaronglazer = dream team 😤
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Too good

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Been having tons of success in our agents with what @AnthropicAI called the “advisor” tool.
May 18
I’ve had very good results running autoresearch with local qwen 3.6 26b model as long as I had a simple vibed pi “advisor” extension that allowed it to periodically ask GPT 5.5 for ideas. I think this direction has a lot of merit.
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Andrew McNamara retweeted
May 16
a common joke around the Shopify office is that Sydney never died, just went to business school and become sidekick
Bing Sydney's dad (@MParakhin) is longer at Microsoft, they've lost the plot.
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Andrew McNamara retweeted
Fun fact: all the Sydney infrastructure, data management was replaced with a different approach after I left, but the new direction didn’t pan out, so, it is being switched back. Theoretically will be easier to resurrect Sydney now, if it were deemed a good idea.
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Love seeing @Shopify Sidekick used in the wild with @WellingtonBrew staff!
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Andrew McNamara retweeted
A very clear-eyed analysis of where AI-mediated commerce actually stands right now, based on early Shopify data. The part that I would claim is most interesting is not the headline conversion numbers, although those are striking. It's the journey compression pattern. More than half of AI-referred sessions start directly on a product detail page, compared to 20% for organic search. Agents are essentially speedrunning the discovery and consideration phases inside conversations. shopify.com/enterprise/blog/…
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