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

How Shopify Is Building The Future of AI Commerce with Andrew McNamara

Shopify's Director of Applied ML, Andrew McNamara, reveals how the new Sidekick Pulse and SimGym features are revolutionizing e-commerce for merchants of all sizes. With 15 years of experience building AI assistants—dating back to pre-Siri days—Andrew breaks down how Shopify is using "LLM as a judge" to ensure quality and why "vibe entrepreneurship" is the future of business.

Andrew explains how Sidekick has evolved from a simple chatbot into a proactive "AI Co-founder" that can democratize data for small business owners. He shares behind-the-scenes details on Sidekick Pulse, which performs deep research to surface actionable insights (like finding shipping errors that cost sales), and Simgym, a powerful simulator that uses AI shoppers to A/B test store changes before they go live.

We also dive into the technical side of how Shopify evaluates these models using statistical rigor and why the ability for merchants to build admin apps with a single prompt is a game-changer for productivity.

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Topics Covered

The 15-year evolution of AI assistants from rule-based systems to LLMs
How Sidekick Pulse proactively finds and fixes business-critical errors
Simgym: Using AI shoppers to simulate A/B tests without risking live traffic
The "LLM as a Judge" framework Shopify uses for product quality control
"Vibe Entrepreneurship" and reducing technical barriers for founders
Building custom Admin Apps in seconds using natural language prompts
Real-world examples from Andrew's own maple syrup store
The difference between general chatbots (Copilot) and specialized agents (Sidekick)
How "App Gen" allows merchants to create custom workflows instantly

Episode Timestamps

00:03 - Introduction to Andrew McNamara and his 15-year history with AI

01:01 - Comparing early AI assistants (BlackBerry/Samsung) to modern LLMs

06:45 - How Sidekick democratizes data analytics for small merchants

11:25 - Deep Dive: Sidekick Pulse and proactive business research

15:43 - Using "LLM as a Judge" to replace human evaluation at scale

18:41 - Generating custom Admin Apps with a single prompt ("App Gen")

21:58 - Andrew's personal experience running a Shopify store

25:31 - The concept of "Vibe Entrepreneurship" as a North Star

26:30 - Using AI to edit online store themes and layouts in real-time

37:39 - Simgym: Simulating buyer behavior to predict experiment results

42:06 - Why simulation is critical for both small and large enterprise merchants

48:04 - The culture of technical depth and passion at Shopify

51:34 - Why Andrew has dedicated his entire career to building assistants

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About Andrew McNamara

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

Shopify is the leading global commerce company, providing trusted tools to start, grow, market, and manage a retail business of any size. It powers millions of businesses in more than 175 countries and offers a unified platform for physical and digital commerce.


Resources Mentioned

Shopify Sidekick (AI Commerce Assistant)
Sidekick Pulse (Proactive Research Agent)
Simgym (AI Shopper Simulator)
Microsoft Copilot & Bing Chat
"LLM as a Judge" Evaluation Framework

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