The Future of Onsite Search With Charlie Cole

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The Future of Onsite Search With Charlie Cole

Charlie Cole

Charlie Cole is the President of XGEN AI, a composable AI platform for eCommerce. As a seasoned eCommerce executive, he has over two decades of experience leading digital transformations for global brands. Before XGEN AI, Charlie served as the CEO at Tribute Technology and FTD and held leadership positions at Samsonite and TUMI, where he drove significant digital growth.

 

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Here’s a glimpse of what you’ll learn:

  • [1:02] Charlie Cole’s career trajectory from digital marketing to becoming President of XGEN AI
  • [8:07] The rapid evolution of marketing — from Yahoo Mail ads to TikTok 
  • [11:40] Charlie talks about XGEN AI’s platform for eCommerce search
  • [19:57] How generative AI overcomes traditional search limitations
  • [25:22] The potential for a conversational, AI-powered shopping assistant
  • [29:59] Charlie shares his favorite moments from the Shoptalk convention
  • [33:01] How to make the most out of Shoptalk and other industry events

In this episode…

Online commerce search has long frustrated both brands and consumers. Whether it's typing in a detailed query and getting zero results or sifting through hundreds of irrelevant products, traditional search engines can’t keep up with consumers’ evolving shopping habits. As search behavior evolves and expectations rise, how can brands deliver a shopping experience that feels intuitive, personal, and helpful?

According to digital executive and eCommerce operator Charlie Cole, generative AI presents unique opportunities for search personalization. These tools can understand natural language, learn from user behavior, and surface relevant results — even for complex, descriptive queries. Charlie urges companies to invest in technologies that apply AI image recognition, contextual search, and predictive merchandising. By focusing on genuine customer needs and creating frictionless, conversational experiences, brands can drive loyalty and revenue.

In the latest episode of The Digital Deep Dive, Aaron Conant speaks with Charlie Cole, the President of XGEN AI, about revolutionizing eCommerce search with generative AI. Charlie discusses the future of search marketing, how to capitalize on industry events like Shoptalk, and how XGEN AI’s platform powers innovative search solutions.

Resources mentioned in this episode:

Quotable Moments:

  • “I really want to create a business where the only reason I joined is because I know the tech kicks ass.”
  • “Generative AI can actually fulfill the promise of improving your customer experience on a one-to-one basis.”
  • “No one just wants jeans… we've all been extensively trained to use these site searches.”
  • “I want XGEN to be the best applier of generative AI to the eCommerce front end.”
  • “We've been talking to websites like we've been talking to six-year-olds for about 20 years.”

Action Steps:

  1. Invest in AI-powered search and recommendation tools: Upgrading your eCommerce stack with generative AI can drastically improve the customer experience and conversion rates. Traditional search engines miss nuanced queries, while AI tools understand intent and deliver relevant results.
  2. Encourage natural, descriptive customer search behavior: Prompting users to search the way they speak unlocks deeper buying intent and higher engagement. Generative AI thrives on longer, more specific queries that signal stronger purchase readiness.
  3. Evaluate tech through an operator’s lens: Choose software that solves real-world problems you’ve experienced as a user or operator. This practical approach ensures your investment delivers measurable outcomes instead of empty promises.
  4. Use data to guide predictive merchandising: Combine customer history with contextual and image-based AI to surface fresh, relevant products. This expands cart size and deepens brand relationships without relying solely on past behavior.
  5. Stay open to emerging vendors and tech solutions: Exploring new tools, even from lesser-known companies, helps you stay ahead of innovation curves. Many transformative technologies begin at the edges of industry events and grow through early adoption.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Eric Sheinkop

Eric Sheinkop is the CEO of The Desire Company, a platform that connects brands with industry experts to create high-quality, conversion-focused video content. With a background in entertainment marketing, Eric co-founded Music Dealers, a pioneering music licensing platform that partnered with global brands like Coca-Cola, McDonald’s, and Disney. He is also an author, speaker, and thought leader in content strategy, recognized in Billboard’s 30 Under 30 and Crain’s Tech 50 list.

 

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Here’s a glimpse of what you’ll learn:

  • [01:44] Eric Sheinkop’s background in music and brand partnerships
  • [6:08] The types of content for driving conversions and FTC regulations on influencer content
  • [13:53] How to create cohesive and high-quality content
  • [19:53] Leveraging video content for retail media networks
  • [24:13] The challenges of AI-driven shopping experiences
  • [28:16] How AI shopping assistants will disrupt brand-consumer relationships

In this episode…

In today’s fast-moving digital landscape, brands face the challenge of creating high-quality, scalable content that converts. While influencer marketing and UGC once seemed like the answer, new FTC regulations and diminishing returns have left brands searching for a more effective approach. How can businesses generate content that builds trust and drives sales — without constantly reinventing the wheel?

According to brand partnerships and content strategy thought leader Eric Sheinkop, expert-driven content — featuring real professionals who use the brand’s product in their field — builds consumer trust and confidence at the point of sale. By investing in evergreen, professionally produced videos optimized for various digital platforms, brands can increase conversion rates, reduce returns, and enhance the customer experience. Eric also emphasizes the importance of aligning content strategy with new FTC regulations to ensure compliance and credibility while maximizing digital marketing efforts.

Tune in to this week’s episode of The Digital Deep Dive as Aaron Conant chats with Eric Sheinkop, CEO of The Desire Company, about the next evolution of digital content. Eric shares how AI-driven shopping assistants can reshape brand loyalty, how to create cohesive, story-driven content, and the new FTC regulations on influencer and UGC content. 

Resources mentioned in this episode:

Quotable Moments:

  • "Brands are spending millions; retailers are spending hundreds of millions on their site experience. So they don’t want to flood it with garbage."
  • "Influencer content disappears in 24 hours, but brands need evergreen content that continuously works across multiple channels."
  • "The FTC put out all new laws — not recommendations, laws — against UGC and influencer endorsements. Brands have to be incredibly careful."
  • "Not all videos are created equal. You need to understand what type of content is right for your shopper at various parts of the funnel."
  • "At what point is it just going to be AI talking to AI, and the consumer is completely out of the retail equation?"

Action Steps:

  1. Reevaluate your content strategy: Ensure your brand’s content is designed for conversion, not just awareness. Influencer and UGC content can drive traffic, but expert-driven content increases sales.
  2. Stay compliant with FTC regulations: The new laws around influencer marketing require transparency. Review your brand’s content to avoid costly violations.
  3. Invest in evergreen content: Unlike influencer content that quickly disappears, high-quality video assets can be repurposed across platforms for long-term ROI.
  4. Optimize video for different platforms: Create variations of content tailored for Amazon, direct-to-consumer websites, social media, and retail media networks.
  5. Prepare for AI-driven shopping experiences: As AI shopping assistants become more common, brands must focus on creating content that builds consumer trust and stands out in algorithm-driven searches.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Andrea Leigh

Andrea Leigh is the Founder and CEO of Allume Group, an eCommerce knowledge-sharing network. She is also the co-host of The CPG Guys podcast. With over 20 years of eCommerce experience working with thousands of brands, she is an educator, speaker, and writer involved with various organizations, including The Digital Shelf Institute and Path to Purchase Institute. Andrea spent 10 years as a Senior Executive at Amazon, where she led over 15 categories, helped launch Amazon’s automated pricing system and other programs, and managed Amazon Prime in Canada.

 

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Here’s a glimpse of what you’ll learn:

  • [4:32] Andrea Leigh shares how she helps brands navigate Amazon vendor negotiations
  • [9:39] The four-step FIRM framework for winning Amazon negotiations
  • [15:25] How to prepare for Amazon vendor negotiations 
  • [25:51] Can paid media spend be used as a negotiation tool?
  • [29:27] Tips for negotiating with Amazon’s AI chatbots 
  • [32:58] How potential tariffs will impact Amazon negotiations

In this episode…

Amazon vendor negotiations differ from standard, relationship-based retailer negotiations. With Amazon prioritizing data, algorithms, and automation, brands often feel overwhelmed and unsure of how to approach the process. How can you leverage your strengths to arrange favorable trade terms?

As an early Amazon adopter, Andrea Leigh has developed the FIRM framework — find your data, isolate your leverage, relax and go slow, and make requests — to help brands take a strategic, data-driven approach. After discovering and harnessing your data sources, you should identify the unique value you bring to Amazon, leverage delaying tactics to strategize further, and request concessions in areas that benefit the retailer. Andrea also recommends aligning trade terms with retail media planning to communicate your investments. 

In this episode of The Digital Deep Dive, Aaron Conant sits down with Andrea Leigh, the Founder and CEO of Allume Group, to talk about navigating Amazon vendor negotiations. Andrea shares common mistakes brands make in the process, what to expect from Amazon’s evolving negotiation process, and how to mitigate tariff-related cost increases.

Resources mentioned in this episode:

Quotable Moments:

  • "Amazon subscribes to interest-based negotiation; aligning with that approach can lead to better outcomes."
  • "The more interests you put on the table, the higher your likelihood of mutual success in negotiations."
  • "Most brands struggle in the preparation phase; without data, you’re negotiating blind."
  • "Slowing down the negotiation process can prevent costly mistakes and give you leverage."
  • "Your negotiation with Amazon isn’t just about trade terms; it’s your joint business plan for the year."

Action Steps:

  1. Prepare your data early: Gathering insights on trade terms, profitability, and operational efficiencies before negotiations begin will give you a stronger position and reduce stress. Keeping a well-organized record of past negotiations ensures continuity, especially if team members change.
  2. Identify your leverage points: Understanding what value you bring to Amazon — whether it’s growth potential, retail media investment, or supply chain efficiency — can help you push back on unfavorable terms. Using competitive benchmarking can strengthen your case further by showing how your brand stacks up in the marketplace.
  3. Slow down the negotiation process: Avoid agreeing to terms too quickly. Take time to assess Amazon’s requests, ask for clarification, and propose counter-offers. If needed, use strategic delays like requesting additional data or breaking negotiations into smaller steps to stay in control.
  4. Make strategic asks: Negotiation is a two-way street; brands should push for operational improvements, additional data access, or co-op relief alongside financial discussions. Finding "easy gifts" that Amazon values but cost you little can help build goodwill without major concessions.
  5. Align trade terms with broader business goals: Don’t view Amazon negotiations in isolation. Consider how they fit into your overall strategy, including media spend, supply chain investments, and long-term profitability. Ensuring alignment across internal teams like finance and marketing will create a unified approach to negotiations.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Tim Wilson

Tim Wilson is the Chief Revenue Officer at ProductWind, which offers influencer-as-a-service products to help brands win online. He’s an experienced sales and business development professional focused on helping the world’s largest advertisers understand how eCommerce and digital marketing impact their brands. Before ProductWind, Tim was an Affiliate Partner at Pattern, guiding partnerships and driving global eCommerce sales for brands.

 

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Here’s a glimpse of what you’ll learn:

  • [3:27] The problem with modern industry conferences: why most speakers don’t share valuable insights
  • [6:22] Tim Wilson shares the leading eCommerce trade shows and how to maximize their value
  • [11:42] Tim’s observations on AI-powered tools at industry events
  • [14:52] How the current financial landscape will impact eCommerce brands
  • [18:36] The risks of haphazard AI adoption
  • [26:47] Strategies for launching products during times of economic hesitation
  • [31:11] Why brands should train platform algorithms and data strategically

In this episode…

Navigating eCommerce conferences can be a frustrating experience. While networking opportunities are abundant, many presentations fail to provide authentic, actionable insights, leaving attendees wondering if these events are worth the investment. How can professionals maximize their time at these gatherings and extract real value beyond surface-level discussions?

Digital commerce expert Tim Wilson believes in building strong relationships and strategically leveraging AI-driven tools. He suggests that professionals should focus on unstructured networking opportunities, such as impromptu meetups and informal discussions, rather than relying on scripted presentations. Additionally, he emphasizes the importance of training retail algorithms well in advance of major sales events to ensure optimal product visibility. 

In this episode of The Digital Deep Dive, Tim Wilson, the Chief Revenue Officer at ProductWind, joins Aaron Conant to discuss maximizing networking opportunities in the eCommerce space. Tim shares product launch strategies, the importance of data security in AI, and how the financial landscape will impact eCommerce brands in the future.

Resources mentioned in this episode:

Quotable Moments:

  • “Getting to know somebody and talking to somebody has infinite upside. And really, the downside is quite small.”
  • “The best way to win Prime Day isn’t to load up on Prime Day.”
  • “When you go to a lot of these conferences, the information that’s shared is generally pretty well available.”
  • “If you’re there to sell or pitch, first of all, the presentation usually sucks.”
  • “Most people won’t admit that they’re confused, so it’s important to speak in a way they understand.”

Action Steps:

  1. Maximize networking at conferences: Prioritize informal conversations and spontaneous meetups over scripted presentations to gain deeper industry insights. Building relationships with peers can provide long-term value and open doors to unexpected opportunities.
  2. Train retail algorithms ahead of key sales events: Increasing engagement on product listings before Prime Day or Black Friday helps establish momentum with the algorithm. This ensures stronger organic rankings and higher visibility when competition peaks.
  3. Be cautious with AI tools and data privacy: Avoid inputting proprietary company information into AI models that may use or share the data externally. Understanding AI’s limitations can help prevent security risks and unintended data exposure.
  4. Adapt to evolving product launch strategies: Economic uncertainty and tariff fluctuations require brands to be flexible with their go-to-market plans. Monitoring cost structures and market conditions closely can help mitigate risks and optimize timing.
  5. Position yourself as an educator in leadership discussions: Senior executives may not fully grasp the intricacies of digital commerce, making it crucial to explain concepts clearly. Framing insights as opportunities rather than challenges can make decision-making more effective.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Nii Ahene

Nii Ahene is the Founder and Managing Director of Net Influencer, a publication offering insights into the influencer marketing industry. Previously, he co-founded CPC Strategy, which was acquired by Tinuiti, where he served as Chief Strategy Officer. Nii is also an angel investor in 5G, CPG, and B2B SaaS companies.

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Here’s a glimpse of what you’ll learn:

  • [3:44] Nii Ahene recounts the early days of eBay and how he recognized the shift toward online shopping
  • [6:19] The evolution of retail media and how Amazon changed product search behavior
  • [10:04] How brands should consider retail media investments
  • [16:44] Boosting product rankings and driving discovery on retail media networks
  • [25:36] Nii addresses the shift in product searches from Google to Amazon and TikTok
  • [32:57] The overreliance on AI for eCommerce
  • [43:09] Nii’s interest in the creator economy and its impact on the eCommerce space

In this episode…

Retail media has exploded in recent years, with hundreds of networks vying for ad dollars. While some brands see significant returns, others struggle to justify their investments. With so many options and increasing pressure from retailers, how can brands determine which retail media networks truly drive incremental growth?

Nii Ahene, an expert in eCommerce and digital marketing, emphasizes the importance of first-party data and strategic investments. Nii advises brands to evaluate whether a retail media network drives new customer acquisition or simply shifts existing demand. He suggests focusing on platforms where consumers actively research products and ensuring ad spend aligns with offline and online sales impact. Additionally, brands should integrate retail media with broader shopper marketing efforts, leveraging digital advertising to drive in-store purchases.

In this episode of The Digital Deep Dive, Aaron Conant speaks with Nii Ahene, the Founder and Managing Director of Net Influencer, about the evolving landscape of retail media. Nii shares insights on data-driven ad spending, the consolidation of retail media networks, and TikTok’s growing role in product discovery.

Resources mentioned in this episode:

Quotable Moments:

  • "Retail media thrived because consumers shifted product searches from Google to Amazon, making ads essential for visibility."
  • "Brands must evaluate retail media spend critically; incrementality, not fear, should drive investment decisions."
  • "Retailers need to offer more than ads; leveraging first-party data for off-platform targeting is the real opportunity."
  • "Amazon’s retail media began as a solution for product discoverability, but it’s evolved into a defensive tax."
  • "The creator economy reminds me of early eCommerce. New opportunities for brand discovery are emerging fast."

Action Steps:

  1. Critically assess retail media investments: Instead of blindly following industry trends, brands should evaluate whether retail media spending actually drives incremental growth. This allocates marketing budgets to strategies that create real value rather than just maintaining visibility.
  2. Leverage first-party data for targeted advertising: Retailers should develop partnerships to use customer data for off-platform marketing, such as social media and video ads. This enhances brand reach and engagement beyond traditional retail media networks, leading to better conversion rates.
  3. Prioritize digital discoverability over paid ads only: Brands should invest in content strategies, influencer partnerships, and organic search optimization to drive discovery. A balanced approach ensures long-term brand visibility rather than reliance on ever-increasing ad spend.
  4. Align retail media spend with offline sales impact: Many brands generate most of their revenue from brick-and-mortar stores yet allocate digital budgets without considering offline effects. Integrating digital and physical retail strategies ensures marketing efforts drive total brand growth.
  5. Stay agile with new eCommerce and AI tools: Emerging technologies can significantly enhance efficiency in retail media, email marketing, and product page optimization. Regularly evaluating and adopting the right tools keeps brands competitive in an increasingly data-driven landscape.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Aaron Conant

Aaron Conant is the Co-founder and Chief Digital Strategist at BWG Connect, a leading platform for executive strategy and networking sessions. In conjunction with BWG Strategy, BWG Connect has built an exclusive network of over 125,000 senior professionals and hosts over 2,000 virtual and in-person networking events annually. With over a decade of experience in digital commerce, Aaron provides advisory services to brands on Amazon sales strategies, retail media, DTC platform selection, and SEO. Before starting BWG Connect, Aaron was the Head of eCommerce Sales and Business Development at Perrigo and a Research Scientist at Pfizer. He is also the host of The Digital Deep Dive.

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Here’s a glimpse of what you’ll learn:

  • [1:38] When should brands invest in Amazon Streaming TV ads?
  • [3:10] How to adjust budgets and ad strategies based on the current economic climate
  • [4:55] The importance of meeting customer expectations in fulfillment and delivery
  • [6:52] Joint business planning (JBP) misalignment between media and business teams and its impact on profitability
  • [8:31] How AI and automation have transformed DSP and retail media

In this episode…

Many brands invest in digital advertising and retail media to drive growth, but understanding when and how to allocate budgets effectively is crucial. Developing a strategic approach to Amazon Ads, logistics, and AI automation can help businesses scale while maintaining profitability. What key insights are industry leaders leveraging to stay ahead in the evolving eCommerce landscape?

Five eCommerce and media experts share strategies for maximizing your company’s digital footprint. Adam Epstein explains that Amazon Streaming TV ads are most effective for brands that have optimized their sponsored ads and DSP strategies, making them a powerful tool for expanding awareness. Todd Hassenfelt highlights the importance of subscribe and save programs in securing customer loyalty during economic uncertainty, advising that brands allocate their budgets across multiple digital channels. Avi Moskowitz emphasizes that brands don’t need hyper-fast shipping — just the ability to set and meet clear delivery expectations. Nate Pinkston and Lauren Livak reveal how misalignment in joint business planning (JBP) between retail media and business teams can create inefficiencies, leading to missed opportunities and budget mismanagement. Kashif Zafar has leveraged AI in DSP, retail media, and programmatic ads.

In this special compilation episode of The Digital Deep Dive, host Aaron Conant revisits his most insightful conversations with industry experts. The episode covers key strategies for brands looking to refine their advertising, fulfillment, and automation efforts. With eCommerce continuing to evolve, these experts provide actionable takeaways to help businesses navigate digital growth, optimize ad spend, and enhance the customer experience.

Resources mentioned in this episode:

Quotable Moments:

  • “Streaming TV ads aren’t for everyone. If you haven’t maximized your sponsored ads and DSP, awareness strategies might be premature.”
  • “Retail media is booming, but brands must analyze private label competition and price gaps before allocating budgets strategically.”
  • “Fast shipping isn’t always the answer; what matters most is setting clear delivery expectations and meeting them consistently.”
  • “Disjointed JBP strategies lead to inefficiencies; retail media and sales teams must align to avoid budget misallocations.”
  • “AI and automation are revolutionizing retail media, making programmatic advertising more efficient across Amazon, Walmart, and Instacart.”

Action Steps:

  1. Optimize your Amazon ad strategy: Maximize sponsored ads and DSP before investing in awareness campaigns, like streaming TV ads, to ensure effective budget allocation.
  2. Leverage retail media strategically: Analyze private label competition and price gaps within your category to make informed decisions on media spend distribution.
  3. Enhance fulfillment consistency: Set clear and realistic delivery expectations for customers and prioritize meeting those promises rather than focusing solely on speed.
  4. Align retail media and sales teams: Integrate joint business planning (JBP) strategies between retail media and sales teams to prevent inefficiencies and budget mismanagement.
  5. Adopt AI-driven advertising solutions: Utilize AI automation in programmatic advertising to optimize budget allocation, improve targeting, and enhance performance across multiple retail platforms.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Meghan Corroon

Meghan Corroon is the Co-founder and CEO of Clerdata, a marketing intelligence platform that drives sales. As a data scientist, she has completed data science research for several national governments in Africa. Before co-founding Clerdata, Meghan was the Technical Director for the University of North Carolina at Chapel Hill’s Bill and Melinda Gates Foundation portfolio evaluation.

 

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Here’s a glimpse of what you’ll learn:

  • [4:16] The shift to incremental retail media measurement
  • [8:08] How to evaluate retail media performance
  • [12:43] Meghan Corroon explains the problem with self-reported retail media performance data
  • [16:41] Justifying retail media ad spend to leadership 
  • [23:27] How the halo effect impacts retail media investments
  • [26:08] Strategies for driving results across multiple retail media platforms

In this episode…

Retail media has evolved from a “growth at all costs” strategy to a demand for measurable ROI, forcing brands to rethink their ad investments. With nearly 700 retail media networks, companies struggle to allocate their budgets. As executives face increasing pressure to justify spending, incrementality measurement has emerged as a crucial tool for identifying retail media’s impact on sales and profitability. How can brands optimize their ad spend while ensuring data neutrality?

Data-driven professional Meghan Corroon helps brands assess the effectiveness of their retail media investments. Instead of relying on self-reported metrics from ad platforms — often skewed by conflicts of interest — companies should use third-party measurements to make data-driven decisions. Meghan explains how the halo effect influences buying habits across multiple retailers, emphasizing that retail media approaches must extend beyond just traditional performance metrics. By shifting to a neutral, evidence-based approach, brands can identify high-performing networks and reallocate budgets to maximize returns.

Tune in to this episode of The Digital Deep Dive as Aaron Conant hosts Meghan Corroon, the Co-founder and CEO of Clerdata, to discuss the future of retail media measurement. Meghan shares insights on optimizing retail media spend, evaluating ad performance, and navigating the growing complexities of retail media. She also highlights how brands can balance performance marketing with long-term profitability in an increasingly data-driven landscape.

Resources mentioned in this episode:

Quotable Moments:

  • "Retail media spend isn’t endless; brands need neutral measurement to prove value and optimize their investments."
  • "The biggest shift in 2024? Measurement and accountability replaced ‘growth at all costs’ in digital marketing."
  • "Self-reported ad data isn’t neutral; brands need independent insights to make informed decisions."
  • "Halo effects are real, but they’re not 60%; brands need data to separate hype from reality."
  • "Retail media success isn’t about spending more — it’s about spending smarter with the right data."

Action Steps:

  1. Adopt neutral retail media measurement tools: Brands should move beyond self-reported ad platform data and invest in third-party measurement solutions to accurately assess the impact of their retail media spend. This ensures unbiased insights and helps optimize budget allocation based on actual performance rather than sales-driven metrics from media networks.
  2. Leverage halo effects for smarter spending: Identify where retail media ads are influencing purchases across multiple retailers. By understanding cross-platform impact, brands can refine their strategies to maximize efficiency, ensuring that ad dollars drive incremental revenue beyond the immediate platform where they were spent.
  3. Prioritize performance-driven budget allocation: Treat retail media investments like a stock portfolio — shift ad spend toward the highest-performing platforms and tactics. By continuously testing and adjusting investments based on neutral data, brands can drive efficiency and ensure every dollar spent contributes to overall profitability.
  4. Bridge the gap between marketing and finance teams: Equip executives and finance leaders with clear, data-backed insights on retail media performance. By presenting evidence of incrementality, brands can justify ad spend, reclassify expenses when needed, and secure necessary budgets for continued investment in high-performing media channels.
  5. Refine ad strategies for different retail networks: Not all retail media networks perform equally. Brands should analyze category-specific effectiveness across platforms like Amazon, Walmart, and Best Buy to determine the best-performing ad types and placements. Adjusting the mix of PPC, DSP, and upper-funnel media can significantly improve return on ad spend.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Justin Leigh

Justin Leigh is the CEO of Workflow Labs, an automation software for eCommerce management. Before founding Workflow Labs, he was the Founder and CEO of Ideoclick, an online marketing services company. Justin began his career as a Product Manager at Amazon and a Senior Product Manager at Microsoft.

 

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Here’s a glimpse of what you’ll learn:

  • [3:51] The rising costs of operating an eCommerce business and its impact on profitability
  • [9:01] Amazon’s evolving strategies that are impacting sales
  • [15:46] How AI-driven automation helps manage catalog updates, content, and compliance
  • [21:19] Efficiency tools brands should implement into their eCommerce sites
  • [24:53] Justin Leigh shares how Amazon’s review system has altered customer trust and brand perception
  • [29:43] Future trends in eCommerce and the importance of tech-driven efficiency

In this episode…

With Amazon updating its platform regularly and operational costs rising, brands struggle to maintain profitability. Where should brands focus their efforts to achieve sustainable growth?

According to eCommerce entrepreneur Justin Leigh, brands spend too much time focusing on mundane tasks like catalog and content updates. This prevents them from strategizing customer engagement efforts and adapting to trends and platform changes. Justin recommends leveraging AI-driven automation tools to identify and correct site inefficiencies, monitor sales and pricing, and maintain compliance. 

In today’s episode of The Digital Deep Dive, Aaron Conant hosts Justin Leigh, the CEO of Workflow Labs, to discuss automating your Amazon business. Justin shares how Amazon’s new review system has eroded customer trust, the platform’s algorithmic changes that have impacted sales, and his recommended automation tools.

Resources mentioned in this episode:

Quotable Moments:

  • "Can you grow a profitable business online? A lot of folks are starting to ask themselves that question."
  • "The profitability of these businesses mattered. You know, this business segment became a big enough channel."
  • "If you can't manage and grow this segment profitably, you haven't accomplished very much as a brand."
  • "eCommerce and Amazon shifted the cost of managing your products onto the brands and manufacturers."
  • "The cost of sales just has to come down while getting better in terms of accuracy and efficiency."

Action Steps:

  1. Reevaluate your tech stack: It's crucial to regularly assess the tools and platforms you're using to ensure they provide maximum value and align with current business objectives.
  2. Automate mundane tasks: By leveraging automation for daily operations like catalog management and content updates, businesses can reduce costs and redirect human efforts toward strategic growth opportunities.
  3. Focus on foundational eCommerce tasks: Maintaining a strong operational foundation ensures your products are accurately represented and available, which is essential before implementing more complex strategies.
  4. Invest in strategic agency partnerships: Agencies can provide valuable insights and support that in-house teams may lack, especially under staffing constraints.
  5. Prioritize customer engagement and brand trust: Building a strong brand connection with customers can mitigate the overreliance on ratings and reviews, which can be misleading or manipulated.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Jana Weinstein

Jana Weinstein is the Director of Social Commerce at Blue Wheel, an omnichannel marketing and operational agency. As a sales leader, she specializes in TikTok Shop, business development, go-to-market strategies, and creator and affiliate marketing. Before Blue Wheel, Jana was the Director of Partnerships for TikTok Shop at Pattern® and managed TikTok Shop partnerships at TikTok.

 

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Here’s a glimpse of what you’ll learn:

  • [3:47] Jana Weinstein talks about the TikTok ban and its impact on creators and businesses
  • [6:56] The challenges of capitalizing on emerging social commerce
  • [11:17] How to launch products and build a presence on TikTok Shop
  • [17:30] AI and tech tools for launching and managing brands on TikTok Shop
  • [21:50] Partnering with agencies to scale on TikTok Shop
  • [28:12] The investment and pricing strategies required to launch on TikTok Shop
  • [33:08] Advice for breaking into social commerce

In this episode…

TikTok's role in social commerce has rapidly evolved, presenting both opportunities and challenges for brands. Recent uncertainties, including a Supreme Court ruling on a potential ban, have raised questions about the platform's future. Despite these challenges, TikTok's innovative approach to engaging content has made it a dominant player in the space. How can brands leverage TikTok Shop to boost revenue?

Social commerce expert Jana Weinstein emphasizes the importance of long-term strategies over short-term gains. Large enterprises often struggle to adapt to TikTok’s fast-paced environment due to complex approval processes, while smaller brands excel by responding to trends quickly. Jana highlights the need for personalized approaches, from testing various products with creators to aligning promotional tactics with TikTok’s unique ecosystem. She also warns against relying on heavy discounts, instead encouraging brands to focus on creating engaging content and exclusive offerings to sustain growth.

In this week’s episode of The Digital Deep Dive, Aaron Conant chats with Jana Weinstein, Director of Social Commerce at Blue Wheel, about TikTok's impact on social commerce. Jana shares insights from her experience launching TikTok Shop in the US, the role of AI in scaling content, and the platform’s influence on competitors like YouTube and Meta.

Resources mentioned in this episode:

Quotable Moments:

  • "Social commerce is definitely the wave of the future and something that brands really need to lean into."
  • "The platform is growing so quickly, and things are changing. We shift our strategies, and, sometimes, it's dramatic."
  • "If you're not going to truly lean into the social, then social commerce isn't the right space."
  • "Brands have to be ready for what's next. You have to continue to build on that momentum."
  • "It's our job as the agency to be the social commerce expert and own that for the brand."

Action Steps:

  1. Embrace creator collaborations: Partnering with creators is essential for brands entering social commerce platforms like TikTok. Creators are crucial for reaching and engaging with a broad audience, and their endorsement can significantly increase brand visibility and sales.
  2. Leverage campaign periods: Participate in high-value campaign periods offered by social platforms, such as TikTok's tentpole events. These moments bring increased attention and boost awareness and sales without resorting to deep discounts.
  3. Focus on consistent content creation: Regularly posting engaging content is necessary to remain relevant on platforms like TikTok. Consistency helps in maintaining audience interest and leveraging the platform's algorithm to increase visibility.
  4. Understand and adapt to market trends: Stay informed about trending content and consumer preferences on social platforms. Reacting quickly to these trends enables brands to maintain relevance and capitalize on viral opportunities.
  5. Test and learn with product offerings: Use social platforms to experiment with various products and identify which resonates best with audiences. This approach allows brands to refine offerings based on direct consumer feedback and preferences.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

Benjamin Davis is the Founder and CEO of TryNow, which has pioneered the “try before you buy” model to improve conversion rates for eCommerce brands. Under his leadership, TryNow has raised approximately $24 million in funding. Before TryNow, Benjamin founded an apparel brand and worked in private equity. 

 

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Here’s a glimpse of what you’ll learn:

  • [1:32] How TryNow reduces CAC through “try before you buy” solutions
  • [4:18] Benjamin Davis explains the “try before you buy” concept
  • [10:34] The impact of “try before you buy” on cart value
  • [17:04] Why you shouldn’t focus on return rates when implementing the “try before you buy” model
  • [24:24] How various eCommerce categories are adopting “try before you buy” methods
  • [28:16] What are the barriers to widespread “try before you buy” adoption?

In this episode…

eCommerce brands are so focused on minimizing returns that they often don’t consider how to enhance the online customer experience fundamentally. Consumers want the same experience online as they have in-store, like trying on clothes before purchasing them. How can you unify the online customer experience to increase conversions?

Benjamin Davis has pioneered the “try before you buy” method, which allows customers to sample items before purchasing them and decide which ones to keep or return. Rather than analyzing each customer’s return rate, brands can encourage them to sample multiple items to increase purchase rates and profit per order. This model also drives lifetime value since brands demonstrate trust in their consumers by allowing them to try products before charging them.

Tune in to this episode of The Digital Deep Dive as Aaron Conant hosts Benjamin Davis, the Founder and CEO of TryNow, to talk about implementing a “try before you buy” solution. Benjamin discusses this model’s impact on cart value, how D2C categories are adopting this solution, and how TryNow reduces CAC.

Resources mentioned in this episode:

Quotable Moments:

  • "We can't take gross sales to the bank; everything is net."
  • "Paying in the face of doubt and uncertainty is the problem we solve."
  • "Why isn't everyone doing this? We've just gone GA in April, so it's all happening."
  • "No one goes broke making a profit."
  • "Solutions that make the online experience closer to in-store will be the game changer."

Action Steps:

  1. Implement a “try before you buy” model: This approach allows customers to try products at home before purchase, reducing barriers to purchase and increasing the likelihood of multiple items being sent, which can increase overall sales. By mimicking the in-store experience, this model addresses online shopping apprehension and improves conversion rates, especially in industries like fashion and cosmetics.
  2. Enhance fraud prevention measures: Collaborate with payment networks and card brands to ensure robust fraud prevention, which is essential when allowing products to be sent without upfront payment. By securing transactions, brands can confidently offer “try before you buy” solutions, minimizing risks associated with potential fraud.
  3. Focus on profit per order instead of return rates: Shifting the focus from reducing return rates to improving net revenue per customer can lead to more profitable outcomes. By encouraging larger initial orders and increasing the chance of multiple items being kept, brands can enhance profitability even if return rates increase.
  4. Leverage customer feedback for product improvement: Engage directly with customers to gather insights on why products are returned and aim to improve product offerings accordingly. Understanding the customer's perspective helps address fit and satisfaction challenges, leading to reduced return rates and better product-market fit.
  5. Explore new verticals for “try before you buy”: While fashion and cosmetics are the most common applications, other sectors like electronics or home goods can also benefit from this model. Identifying and targeting new potential markets can open up opportunities for growth and expansion by tapping into segments where this purchasing flexibility can drive significant customer interest.

About BWG Connect...

BWG Connect provides executive strategy and networking sessions that help brands from any industry with their overall business planning and execution. We network and knowledge share together to better understand and adapt to the newest trends, strategies, and pain points shaping growth in the digital space. BWG Connect, in conjunction with BWG Strategy, has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.

In addition, we have had 1x1 conversations with over 5,000 brands and have a real-time pulse on what digital strategies are successful and why. This in-depth knowledge allows our team to operate on the cutting-edge and provide our clients with best-in-class guidance on how to win in the digital world. We have provided free consultations and strategy sessions for companies of all sizes, from start-ups to Fortune-100, to enable growth, resolve issues and make curated service provider introductions that can impact your digital footprint.

We have held to the philosophy of providing high-level insights and actionable knowledge with no sales pitches in order to provide to our network the ability to listen, learn and act to improve themselves as well as their organizations. Our ultimate goal is to be the resource out there to help digital executives find the research they need to excel in the modern marketplace.

If you are interested in getting involved with any of our current or past events, you can find them here. If you are looking for help & would like to set up some time to chat with our team, you can schedule a time or reach out directly to Aaron@bwgconnect.com or Tiffany@bwgconnect.com.

BRINGING TOGETHER INFLUENTIAL EXECUTIVES AND SENIOR PROFESSIONALS

What is BWG Connect?

BWG Connect provides executive strategy & networking sessions that help brands from any industry with their overall business planning and execution. BWG has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.
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