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Masters of Scale

When AI agents do your shopping, everything changes, with Shopify’s Jess Hertz

Tuesday, 1 September 2026 · 2 min read · Listen to the episode ↗

In this episode, Jess Hertz from Shopify explores how AI is revolutionizing entrepreneurship by lowering barriers to starting a business. She highlights the effectiveness of AI tools like Sidekick in enhancing merchant sales and improving conversion rates. Hertz also discusses the shift in workforce dynamics due to AI, emphasizing the need for individuals with diverse skill sets. With Shopify's robust infrastructure, the platform supports a wide range of merchants, driving significant growth and retention.

Jess Hertz discusses the transformative impact of AI on entrepreneurship, noting that it has significantly lowered the barrier to entry for starting a business. Approximately 10 percent of new shops on Shopify make their first sale within a day of signing up, showcasing the platform's effectiveness in facilitating quick market entry.

As COO, Hertz implemented a new sales team compensation plan aligned with merchant outcomes, reinforcing Shopify's philosophy that the company's success is tied to that of its merchants. This approach has contributed to Shopify achieving its fifth consecutive quarter of over 30% growth, with nearly 90% of quarterly revenue generated from merchants who have been on the platform for more than a year.

Hertz highlights the role of AI in boosting merchant sales, particularly through tools like Sidekick, which have led to significant improvements in conversion rates. While the complexity of commerce transactions poses challenges, it also serves as a competitive advantage for Shopify, which provides a robust infrastructure that helps merchants navigate this complexity.

The discussion also addresses the evolving nature of the workforce in the context of AI, with a shift from T-shaped individuals to X-shaped individuals who possess expertise across multiple areas. Hertz believes that this diverse skill set will be essential for enhancing productivity as AI becomes more integrated into business operations.

Additionally, Hertz points out that AI is particularly beneficial for niche products, with 75% of AI-attributed orders in the last quarter coming from categories outside the top 100. Shopify's infrastructure is designed to effectively support a wide range of merchants, contributing to high retention rates for those achieving significant gross merchandise volume.

Hertz reaffirms her commitment to Shopify's mission of fostering entrepreneurship and acknowledges the need to adapt to rapid changes in the business landscape. She views the current chaos as an opportunity to tackle complex problems and emphasizes the importance of maintaining a lightweight identity to enable continuous improvement.

This summary was generated from the episode transcript and can contain mistakes.