# Building reliable and proactive agentic systems at scale: how Shopify’s reflexive AI culture was instrumental in their development of Sidekick w/ Andrew McNamara #258

Page: https://stenobird.com/podcast/the-engineering-leadership-podcast-743839/building-reliable-and-proactive-agentic-systems-at-scale-how-shopify-s-reflexive-ai-culture-was-instrumental-in-their-development-of-sidekick-w-andrew-mcnamara-258
Text version: https://stenobird.com/podcast/the-engineering-leadership-podcast-743839/building-reliable-and-proactive-agentic-systems-at-scale-how-shopify-s-reflexive-ai-culture-was-instrumental-in-their-development-of-sidekick-w-andrew-mcnamara-258.md
Podcast: [The Engineering Leadership Podcast](https://stenobird.com/podcast/the-engineering-leadership-podcast-743839)
Published: 2026-05-12T16:00:00+00:00
Episode link: https://sfelc.com/podcasts
Audio file: https://pscrb.fm/rss/p/afp-942744-injected.calisto.simplecastaudio.com/4d87e711-78c0-43f3-9633-fa05520e07f2/episodes/73aa4fd4-0a5e-4463-b5fd-d72c4e3fdb55/audio/128/default.mp3?aid=rss_feed&awCollectionId=4d87e711-78c0-43f3-9633-fa05520e07f2&awEpisodeId=73aa4fd4-0a5e-4463-b5fd-d72c4e3fdb55&feed=Z8Dl_qAv
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Duration seconds: 2232

## Resource

Andrew McNamara, Director of Applied Machine Learning @ Shopify, joins the ELC podcast to share insights on building agentic platforms at scale, like Sidekick, that must keep reliability for its users at the forefront. Andrew describes the building philosophy behind Shopify and what it means to cultivate a culture of prototype-first while prioritizing hiring early-stage talent. We cover Sidekick’s development journey and how user feedback impacted its product vision, why evaluation is so important for determining ground truth sets, and the benefit of user-driven use cases. Andrew also dissects how they went about making product design decisions, such as building proactive agents and identifying subagent specializations.

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