From Local Stores to Global Marketplaces: Jessica Lesesky’s Story

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Jessica shares her background in retail and e-commerce, including her experience with marketplaces and brand partnerships. She discusses the role of Shutterfly in helping people preserve their memories and highlights the practical use case of Make My Book, an AI-powered service.

The conversation explores the growing demand for outsourced services and the desire for more human engagement in a digital world. Jessica emphasizes the importance of getting back to basics in retail and focusing on core customer experiences. The discussion also touches on the Watson Weekend show and the changes in consumer behavior and e-commerce over the years.

In this conversation, Jessica shares insights on consumer behavior, the importance of change for brands, the impact of technology on retail, the evolution of marketplaces, the value of sellers in marketplaces, the complexity of data analysis, the rise of retail media, lessons from re-platforming, the importance of focus and differentiation, and the challenges and outlook for 2024.


  • Shutterfly helps people preserve their memories and offers practical AI-powered services like Make My Book.
  • There is a growing demand for outsourced services and a desire for more human engagement in a digital world.
  • Retailers should focus on core customer experiences and get back to basics before chasing new technologies.
  • Practical use cases for AI can improve operational efficiency and provide value to retailers. Consumers are adaptable and willing to embrace new behaviors and technologies if they provide value and simplify their lives.
  • Brands that are willing to change and adapt quickly are more likely to succeed in the dynamic retail landscape.
  • Technology has significantly lowered the barrier to entry for entrepreneurs, but it has also created challenges for legacy brands with outdated technology.
  • Marketplaces need to have a well-thought-out strategy that adds value to both customers and sellers in order to be successful.
  • Retailers should focus on analyzing data from various channels to understand the customer journey and make informed decisions.
  • Retail media is becoming an important source of revenue for retailers, but not every retailer can build a successful media company.
  • Re-platforming projects require careful planning, a small and agile team, and a focus on prioritizing improvements that have the most impact.
  • Retailers should focus on their high-powered SKUs and complementary products or services to increase basket size and improve the customer journey.
  • The retail industry faces challenges such as consumer debt, inflation, and increased competition, but there are opportunities for growth through diversification and partnerships.
  • Jessica has a hidden talent for rapping and enjoys karaoke.


00:00 Introduction and Background

03:14 Role and Impact of Shutterfly

05:07 Make My Book: A Practical AI Use Case

07:31 The Demand for Outsourced Services

10:32 The Craving for Human Engagement

12:07 Identifying Consumer Needs and Best Practices

15:03 Getting Back to Basics in Retail

18:31 The Watson Weekend Show

20:06 Building Trust and Providing Value

21:14 Changes in Consumer Behavior and E-commerce

21:59 Consumer Behavior and Adaptability

23:21 The Importance of Change for Brands

24:18 The Impact of Technology on Retail

26:10 The Evolution of Marketplaces

28:34 The Value of Sellers in Marketplaces

30:33 The Complexity of Data Analysis

32:37 The Rise of Retail Media

36:03 Lessons from Re-platforming

39:02 The Importance of Focus and Differentiation

41:29 Challenges and Outlook for 2024

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