Search is moving from keywords to context, and ads have to move with it. Andrew Desmarais on AI product discovery and retail media done right.

Sponsored listings have a bad reputation for a reason: most of them ignore who is actually looking. Andrew Desmarais works on a platform built around the opposite idea, where a paid placement is treated as a search result that has to earn its position rather than buy it. We get into how AI is changing what shoppers type and ask, why long-tail and conversational queries break traditional keyword matching, and what happens to product discovery when an AI agent is doing the shopping. He also gets into the less glamorous side, which is proving return on the spend. Useful if you own search, retail media, or a discovery experience that is starting to feel dated.

WHAT WE GET INTO

How AI changes what product search has to understand

Keywords versus context, and why the shift matters now

Serving ads that feel made for the shopper instead of bolted on

Making sponsored placements complement organic results instead of fighting them

Off-site recommendations and where retail media goes beyond your own site

Long-tail and conversational queries that keyword engines never handled well

What AI agents change about the shopping journey

Measuring return so retail media survives the next budget review

What the conference floor says about where the industry actually is

ABOUT ANDREW DESMARAIS

Andrew Desmarais works on the commercial team at Constructor, the AI product search and discovery platform built specifically for ecommerce. Founded in 2015, Constructor uses natural language processing, machine learning, and generative AI across search, browse, recommendations, quizzes, and AI shopping assistants, and now offers a retail media suite with personalized sponsored listings. Its customers include Sephora, Petco, Bonobos, Birkenstock, and Target Australia.

WHAT YOU WILL LEARN

- Why keyword-matching engines struggle with the way people search now

- How to run sponsored placements without eroding trust in your results

- Where personalization makes an ad genuinely useful rather than intrusive

- What to prepare for as AI agents start doing product discovery for shoppers

- How to measure retail media return in a way that holds up internally

QUOTE OF THE EPISODE

"Search is changing from keywords to context."

CONNECT WITH ANDREW

LinkedIn: https://www.linkedin.com/in/andrew-desmarais-aba202176/

Constructor: https://constructor.com

CONNECT WITH THE SHOW

The Last Click: https://www.thelastclick.co/

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-last-click/id1896943826

Spotify: https://open.spotify.com/show/033B9FZX57M6cuTn52LXel

The Last Click on LinkedIn: https://www.linkedin.com/company/thelastclick/

Chris Parsons on LinkedIn: https://www.linkedin.com/in/chrisaparsons/

Chris and Scotty discuss their upcoming conference in Boston, covering topics like personalization, earned media, loyalty, and sustainability. They share insights on AI, content, and the impact of industry trends on consumer behavior. The conversation highlights the importance of actionable takeaways from conference sessions.

Takeaways

• Personalization in e-commerce
• The role of content in discovery and personalization

Chapters

• 00:00 Pre-Conference Excitement
• 00:50 Conference Travel and Setup
• 05:20 The Promise of Personalization
• 11:15 Transition to Earned Media
• 13:18 Defining Loyalty and Community
• 16:16 Sustainability and Fireside Chats
• 18:46 The Quest for Actionable Insights

Insights from the journey of Crocs, Biosteel to Warroad and beyond.

Morning everyone!
Today, I had the pleasure of chatting with Andrew Nichols, a seasoned leader in brand management and growth. Andrew's journey spans various industries—from consumer packaged goods to e-commerce and sports nutrition. His insights on brand evolution and market positioning are incredibly valuable for anyone looking to navigate the complexities of modern business.

Andrew began his career at Unilever, gaining a solid foundation in consumer goods. However, his journey took a turn as he ventured into e-commerce, where he helped brands understand the importance of technology in scaling their operations. His diverse experience includes roles at Sony Electronics, the Canadian Olympic Association, and managing Crocs Canada for nearly a decade.

"Every time that we've engaged, you are with a brand and you're really defining that brand and taking it from a level where it's like it's kind of hit this early maturity state and you're finding ways to take it to the next level."
— Chris Parsons

Andrew shared fascinating insights about his time at Crocs, a brand that has undergone multiple revivals in its popularity. He was instrumental in transforming Crocs’ e-commerce strategy, shifting from a marketing website to a robust e-commerce platform that could compete with giants like Amazon.
He emphasized the importance of channel strategy, highlighting how brands often struggle when they don’t define their retail approach. Andrew's role involved ensuring that partners understood their unique positions in the market and helped create a balanced demand across various channels.

Transitioning to Biosteel, Andrew applied his expertise to position the brand as a go-to option for athletes. What’s striking about Biosteel's approach is how it built brand loyalty through authenticity. Andrew noted that their growth was driven by athletes choosing Biosteel over competitors, which naturally enhanced brand awareness.

"We were born on the backs of an athlete need and we built that brand under the pretense that if you know, you know."
— Andrew Nichols

Currently, Andrew is the President and Chief Revenue Officer at War Road Hockey Company. He reflects on how his past experiences shape his leadership style today, emphasizing the importance of leveraging existing relationships and understanding market dynamics.

As we wrapped up our conversation, it was clear that understanding consumer behavior and maintaining a flexible strategy are key to thriving in today’s competitive landscape.

Reflecting on Andrew’s journey reminds us that success often comes from a blend of experience, adaptability, and a deep understanding of the audience. If you’re navigating brand dynamics, take a page out of Andrew’s book—embrace change and listen to your customers.

For more insights from Andrew's journey and to hear the full conversation, check out the complete episode!

Discover how the Retail AI Council is shaping the future of retail with AI solutions.

At E-Tail, the energy is palpable as industry leaders gather to discuss the future of retail technology. Chris Parsons sat down with Doug Weich, the driving force behind the Retail AI Council, to explore the challenges and opportunities retailers face as they navigate the rapidly evolving AI landscape.

The Retail AI Council is a unique initiative built by retailers for retailers. Doug emphasizes their mission: "helping retailers leverage AI effectively." In a world where technology is advancing at breakneck speed, retailers often struggle to keep up. This council provides a collaborative space where retailers can discuss their needs without the pressure of being sold to.

What's refreshing about the Retail AI Council is its focus on community rather than competition. Doug explains, "We’re not consultants or analysts; we’re here to facilitate connections and promote collaboration." This approach allows retailers to share insights and solutions, ultimately helping them find the right technology that fits their specific challenges.

As Doug highlights, the process of finding the right AI solutions can be daunting. With hundreds of booths at events like E-Tail, "it’s tough for a small team to navigate and find the right fit." The council aims to ease this burden by fostering conversations among retailers, allowing them to share experiences and recommendations organically.

The conversations within the Retail AI Council create a safe space for sharing. Doug notes how "honesty and transparency come out" when veterans in retail discuss their pain points and creative solutions. This level of collaboration is essential for driving innovation in the industry.

For those looking to connect and collaborate, joining the Retail AI Council is straightforward and free. Doug invites all retailers and industry partners to participate, saying, "There’s a big red join button at retailaicouncil.com, and it’s free for everyone." This initiative is powered by its members, ensuring that the council's direction aligns with the actual needs of the retail community.

As the retail landscape continues to evolve, organizations like the Retail AI Council are crucial in helping retailers adapt and thrive. Stay tuned for more insights and conversations from the frontlines of retail technology! https://www.linkedin.com/in/dougweich/

Discover how Kate Farms is transforming nutrition for those in need.

Hey there,

Today, we delve into the inspiring journey of Kate Farms, a company founded with a mission born from necessity. Chris Parsons sits down with Catherine from Kate Farms, who shares the profound story of how the company came to be and its evolution in the world of nutrition.

Kate Farms was established by Richard and Michelle, driven by the challenges they faced with their daughter Katie, who was born with cerebral palsy. Exclusively tube-fed from an early age, Katie struggled to thrive on existing products.

"When she was five, she weighed 16 pounds, and this number just is imprinted in my mind... two parents desperate to save her," Catherine reflects.

Determined to make a difference, they collaborated with a dietitian and vegan chef to create a plant-based, organic, and allergen-free formula that has become the cornerstone of Kate Farms’ offerings.

Fast forward to 2016, Kate Farms transitioned from retail to focus on the medical channel, after realizing that families like Richard and Michelle were seeking their products in bulk. This pivot marked a significant shift in their business model, led by CEO Brett Matthews.

Catherine, who joined the team in January 2018, highlights the broader mission that has emerged: "We've learned that there are many people beyond the medical channel that need access to good nutrition."

The company has since launched new product lines, including everyday nutrition for kids and adults, and has expanded its distribution dramatically—recently securing a spot in 6,800 stores across major retailers like Walmart and CVS.

Navigating the complexities of pricing and distribution has been a significant learning curve for the team. Catherine shares the challenges they face with maintaining quality while adapting to the competitive landscape:

"How do we think about the margin structure? Ultimately, we want to maintain the same standards and high quality."

As Kate Farms continues to grow, their commitment to providing nutritious options for those in need remains unwavering. Catherine’s story is a testament to the power of perseverance and innovation in the face of adversity.

Reflecting on this journey, it’s clear that Kate Farms is just getting started. For more insights, dive into the full conversation with Catherine on The Last Click.

Elina Vilk , President and Chief Business Officer at David's Bridal, discusses the convergence of retail and technology, the importance of design thinking in customer experience, and the innovative tools and technology implemented by David's Bridal to reduce stress and anxiety for customers and vendors in the wedding planning process.

Takeaways

• Convergence of Retail and Technology
• Design Thinking in Customer Experience
• Innovative Tools for Reducing Stress in Wedding Planning

Why do the most resilient brands focus on making people feel seen rather than just optimizing for clicks?

In this episode of The Last Click, host Chris Parsons sits down with Stephen Bailey, Chief Marketing Officer at John Fluevog Shoes. With over 20 years of retail experience, Stephen shares why the real growth lever in modern commerce isn't just automated pipelines or data dashboards—it's humanness, community, and radical trust.

Discover how John Fluevog built a cult-like customer base, why patience is a key strategy for brand longevity, and how modern retail leaders can successfully balance AI and data analytics with genuine human empathy.

🎯 Key Takeaways & Topics Covered:

• Community Beats Transaction: How treating customers like a community rather than sales targets builds lasting trust.

• Human Service as a Competitive Advantage: Why in-store expertise and empathy create irreplaceable value.

• Patience & Consistency: Why real brand loyalty takes discipline and resisting short-term quarterly metrics.

• Data + Context: Analytics tell you what is happening, but human context explains why.

• Balancing Tech & Human Touch: Leveraging AI for operational efficiency while empowering teams to drive meaningful customer connections.

⏱️ Timestamps / Chapters:

• 00:00 – Introduction and Guest Credibility
• 00:26 – Stephen's Background and Community Focus
• 02:04 – The Fluevog Community and Advocacy
• 03:34 – Creating a Tightly Knit Customer Base
• 06:38 – Building Advocacy Through Patience and Service
• 07:51 – The Power of Face-to-Face Interactions
• 08:51 – Product Knowledge vs. Human Connection
• 09:21 – Patience as a Key to Brand Longevity
• 10:37 – Using Technology to Profile and Personalize
• 13:26 – Balancing AI and Human Touch
• 15:23 – The Impact of Mass Market Expansion on Culture
• 16:24 – Shifting from Wholesale to Direct Channels
• 18:55 – Maintaining Brand Integrity and Trust
• 22:40 – Creating Unique Customer Experiences
• 26:32 – Leadership and Empathy in Retail
• 30:35 – Final Thoughts and Nuggets of Wisdom

🔗 Resources & Guest Links:

• Guest: Stephen Bailey (CMO, John Fluevog Shoes)

• John Fluevog Shoes: fluevog.com

• The Last Click Platform: thelastclick.co

Stephen has spent the last 20 years on client side, charged with telling the world about John Fluevog's unique soles for unique souls. Fluevog is a 56 year old, independent, Canadian footwear brand that now has 20 company owned stores in Canada, and the US and the world's greatest and largest fan base of Fluevogers. For Fluevog, and a hand picked selection of other incredible brands he works primarily on branding, communications, ecommerce, partnerships, retail strategy and all of the best omnis. Stephen lives in Vancouver with his lovely wife & their two horrible teenagers, and enjoys soccer, coaching and writing in the third person.

The conversation covers the journey of an entrepreneur navigating burnout, career shifts, and the challenges of retail. It also delves into the introduction of a linen essentials brand, the co-founding of a mahjong business, and the entrepreneurial culture in British Columbia. Additionally, it explores the impact of the pace of work and the need for change management in the modern workplace. The conversation delves into the impact of AI on productivity and the reservations associated with its use. It also explores the mental load and existential concerns faced by individuals, as well as the importance of business layering and risk assessment. Additionally, it discusses community building, authentic marketing, and the courage required in decision-making and business evolution.

Vivian McCormick

https://shopwilet.com/

Takeaways

• Navigating burnout
• Entrepreneurial challenges AI and its impact on productivity
• The importance of human connection in business

Chapters

• 00:00 Introduction and Community Giving
• 01:23 Navigating Burnout and Career Shift
• 05:23 Introduction to Willet and Linen Essentials
• 07:04 Linen Essentials and Sleep Comfort
• 09:53 Starting Willet and Identity Shift
• 12:53 Co-founding mijs and Mahjong
• 14:45 Entrepreneurial Culture in BC
• 17:30 The Messy Middle of Retail
• 21:38 Pace of Work and Change Management
• 24:50 The Impact of AI on Productivity and Reservations
• 29:57 The Mental Load and Existential Concerns
• 32:10 Business Layering and Risk Assessment
• 38:03 Community Building and Authentic Marketing
• 43:22 Courage in Decision-Making and Business Evolution

Paul Rivias from Exchange Solutions discusses the importance of data-driven loyalty programs and personalized offers in retail. He emphasizes the need for smart discounting and the impact of AI on customer experience.

Takeaways

• Data-driven loyalty programs
• Smart discounting
• Impact of AI on customer experience

Chapters

• 00:00 Introduction and Professional Background
• 01:26 Exchange Solutions and Loyalty Perspective
• 02:24 Loyalty Platform and Data Utilization
• 03:50 Personalized Offers and Insights
• 05:13 Evolution of AI in Retail
• 07:02 E-commerce and Personalization
• 10:21 Margin Awareness and Retail Math
• 13:06 Smart Discounting and Offer Decisioning

The conversation covers the importance of fostering relationships in the industry and the evolving landscape of AI in retail. It also delves into the changing landscape of retail technology, the future of events and conference formats, challenges and opportunities in AI adoption, content, community, and commerce in the AI era, and the future of paid AI advertising.

Scott Silverman from CommerceNext

Takeaways

• Importance of fostering relationships
• The evolving landscape of AI in retail

Chapters

• 00:00 Building Strong Relationships in the Industry
• 02:13 The Changing Landscape of Retail Technology
• 04:38 The Future of Events and Conference Formats
• 06:04 Challenges and Opportunities in AI Adoption
• 09:11 Content, Community, and Commerce in the AI Era
• 11:31 The Future of Paid AI Advertising