Shopify’s Sidekick Just Leveled Up: AI That Runs Your Store (Proactively)

In this episode, Andrew McNamara—Director of Applied Machine Learning at Shopify—shares how AI is transforming commerce through Sidekick, Shopify's intelligent assistant for merchants. Drawing on 15 years of experience building AI assistants, Andrew explains how Shopify is moving beyond chatbots toward proactive, agentic systems.

The conversation explores new features like Sidekick Pulse and Simgym, which help merchants uncover hidden business issues, simulate buyer behavior, and test changes safely before going live. Andrew also introduces ideas like “LLM as a Judge” and “vibe entrepreneurship,” showing how AI can dramatically lower the barrier to building and running a business.
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‍Key Topics Covered

The evolution of AI assistants from rule-based systems to modern LLMs

How Sidekick democratizes data and analytics for small merchants

Sidekick Pulse and proactive AI-driven business research

Simgym: simulating AI shoppers to run experiments without live traffic

The “LLM as a Judge” framework for scalable quality evaluation

Generating custom Shopify Admin apps with a single prompt

“Vibe entrepreneurship” and reducing technical barriers for founders

Real-world lessons from Andrew’s own Shopify store
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Episode Timestamps

00:03 – Introduction to Andrew McNamara and his AI background

01:01 – Early AI assistants vs. modern LLMs

06:45 – How Sidekick democratizes data for merchants

11:25 – Deep dive into Sidekick Pulse

15:43 – Using “LLM as a Judge” for model evaluation

18:41 – Generating custom Admin apps with natural language (“App Gen”)

21:58 – Andrew’s personal experience running a Shopify store

25:31 – “Vibe entrepreneurship” as a guiding principle

26:30 – Editing online store themes with AI in real time

37:39 – Simgym and simulated buyer behavior

42:06 – Why simulation matters for merchants of all sizes

48:04 – Shopify’s culture of technical depth

51:34 – Andrew’s long-term passion for building AI assistants
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About the Guest

Andrew McNamara is the Director of Applied Machine Learning at Shopify, where he leads the development of Sidekick and other intelligent merchant tools. Previously, he served as Director of the Montreal Research Lab at Microsoft and was a key contributor to Bing Chat (Copilot). Andrew has over 15 years of experience building and deploying AI assistants at scale.
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About the Company

Shopify is a leading global commerce platform that provides tools to start, grow, market, and manage retail businesses of any size. Powering millions of merchants across more than 175 countries, Shopify enables unified physical and digital commerce through a single, trusted platform.

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