The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Engineering & DevTools/The Engineering Leadership Podcast
The Engineering Leadership Podcast artwork

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

The Engineering Leadership Podcast · 2026-05-12 · 37 min

0:00--:--

Topics in this episode

Engineering managementgenerative AIengineering leadershipelcscaling eng teams

Episode notes

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. ABOUT ANDREW MCNAMARA Andrew McNamara is Director of Applied Machine Learning at Shopify, where he leads the team behind Shopify Sidekick, an AI co-founder that gives merchants access to the e-commerce expertise they need to run and grow their business.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Scaling TensorFlow, Navigating Startup Pivots, ML Edge Infrastructure and AI Inference Strategy w/ Rajat MongaEngineering Founders · on Engineering management85 / 100
  • AI Is Ready for Government. Is Government Ready?The So What from BCG · on generative AI84 / 100
  • Building Skills-Powered Organizations in the AI Era with Ravin JesuthasanChange Management Review Podcast · on generative AI81 / 100
  • How CX Leaders Can Win With AI with Greg MeliaBusiness Transformation Pitch with The CX Goalkeeper · on generative AI77 / 100
  • RBC's Kelly Bradley on Disclosure, Disruption, and Developing TalentHBS Managing the Future of Work · on generative AI77 / 100
  • The Future of Microsoft Partnerships in the AI Era with Jay McBainIAMCP Profiles in Partnership · on generative AI75 / 100

More from The Engineering Leadership Podcast

All episodes →
  • Determining bets, using customer insights to pivot, and gaining developer buy-in & trust w/ Tomas Reimers #26483 / 100
  • Utilizing AI internally to iterate faster and empower smaller teams to upskill w/ Vivek Raghunathan #26396 / 100
  • The Product Paradigm Shift: How Livekit Navigated High Stakes Scaling Challenges to Build the Future of Voice-First AI Interfaces w/ Russ d’Sa #26276 / 100
  • Building an empowered career w/ Jean Hsu & Cate Huston #26163 / 100
  • Redefining profit, centering human flourishing, and building an incorruptible mission-driven roadmap w/ Eric Ries #26075 / 100
Explore the best B2B Engineering & DevTools podcasts →
All The Engineering Leadership Podcast episodes →