The Digital Deep Dive With Aaron Conant
This is the Digital Deep Dive Podcast, where we tackle the newest trends, strategies and pain points shaping growth across the digital landscape.
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Data-Driven Amazon Forecasting With Todd VanderStelt and Sam Hager
11/13/2025
Data-Driven Amazon Forecasting With Todd VanderStelt and Sam Hager
Todd VanderStelt is the Co-founder of MixShift, a firm that helps Amazon agencies, aggregators, and brands scale operations and reporting for their Amazon accounts. He is also the Managing Partner at Dash Applications, which delivers software to improve operations and sales for retailers and brands, and the Founder of TidalBore Group, a management consulting firm specializing in retail. Previously, Todd held leadership roles at Amazon, where he built forecasting tools and operational systems. Sam Hager is the Co-founder and CEO of MixShift. He began his career in the Amazon space, managing multimillion-dollar business books across advertising and agency services. Before MixShift, Sam was the Marketplace Strategist and Amazon Advertising Manager at Booyah Advertising. In this episode… Forecasting in the Amazon ecosystem is one of the most frustrating challenges for brands and agencies. With so many shifting variables — from ad spend to competition to inventory fluctuations — how can companies predict sales and plan budgets without wasting resources or missing opportunities? Amazon forecasting and automation veteran Todd VanderStelt and eCommerce strategist Sam Hager have developed a forecasting method for Amazon brands. They emphasize simplifying forecasting through a top-down model that uses a few key data inputs — ad spend, seasonality, and organic growth — to generate highly accurate predictions. Sam and Todd advise building forecasting tools that align teams around data, tie budgets directly to performance, and factor in real-world contexts, like promotions or unexpected press coverage, to make informed decisions. In this episode of The Digital Deep Dive, Aaron Conant talks with Todd VanderStelt and Sam Hager, Co-founders of MixShift, about building accurate and actionable Amazon forecasting models. Together, they explain why top-down forecasting outperforms traditional methods, how linking ad spend to revenue improves planning, and the future innovations transforming eCommerce analytics.
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Discoverability in the Age of LLMs With Spencer Millerberg
11/06/2025
Discoverability in the Age of LLMs With Spencer Millerberg
Spencer Millerberg is the Founding Partner of DetailPage, which helps brands optimize traffic and gain Amazon market share. He founded OneClickRetail, the original provider of Amazon market share data that was sold to Ascential. As an eCommerce and data analytics expert, Spencer has helped over 650 brands improve sales, margins, and search positions on eCommerce sites. In this episode… In today’s digital marketplace, visibility is everything. With AI tools like ChatGPT shaping how shoppers discover products, brands are facing a new kind of competition — one where search optimization meets machine learning. How can companies ensure their products are recommended when customers ask AI what to buy? According to eCommerce and data analytics expert Spencer Millerberg, the key lies in mastering both traditional and generative optimization. He urges brands to speak the customer’s language, not their internal catalog terms, and to keep content fresh to trigger algorithmic boosts. By understanding how AI prioritizes retailer and brand content, and by revisiting SEO regularly, brands can secure lasting visibility and growth. In this episode of The Digital Deep Dive, Aaron Conant welcomes Spencer Millerberg, Founding Partner of DetailPage, back to the show to discuss AI-driven discoverability. Spencer explains why retailer content dominates AI recommendations, how quarterly content updates improve search ranking, and why optimizing neglected B SKUs drives major growth.
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Current State of AI Content With Josh Fulmer
10/30/2025
Current State of AI Content With Josh Fulmer
Joshua (Josh) Fulmer is the Executive Creative Director of Lunge Marketing, a full-service eCommerce agency specializing in Amazon, Walmart, TikTok Shop, and Google Ads services. With over 18 years of design and brand strategy experience, he leads creative teams in developing engaging, inclusive visual narratives. Before joining Lunge, Josh served in the US Marine Corps, worked in the craft beer industry, and built a design consulting practice. In this episode… Content creation has become more essential and complex than ever. AI tools promise faster, cheaper results, but at what cost to brand trust and authenticity? How can brands balance speed and creativity while maintaining a consistent voice across every channel? According to content strategist Josh Fulmer, the key lies in using AI as an enhancer, not a replacement. He recommends developing clear content strategies grounded in audience research and user personas to ensure every asset serves a purpose. Brands should focus their budgets on creators and platforms that truly align with their target market, while maintaining consistent tone and messaging across formats. The goal is thoughtful integration, where technology supports creativity without diluting brand integrity. Welcome back to The Digital Deep Dive as Aaron Conant talks with Joshua (Josh) Fulmer, Executive Creative Director of Lunge Marketing, about AI’s impact on content creation. Josh discusses how brands can maintain consistency amid disruption, build smarter strategies through audience targeting, and balance automation with authentic storytelling.
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Retention Marketing and Maximizing Customer Potential With Aaron Schwartz
10/02/2025
Retention Marketing and Maximizing Customer Potential With Aaron Schwartz
Aaron Schwartz is the Co-founder and Co-CEO of Orita.ai, a software company that improves email deliverability. He is also an advisor and investor in various commerce tech companies, including Passport and EcoCart. Previously, Aaron built and managed the DTC brand Modify Watches and was the President of Loop. In this episode… Email remains a core channel for reaching customers, but brands often misuse it. As customer acquisition costs climb and competition intensifies, many brands resort to blasting their audiences with more campaigns, only to see engagement fall and customers unsubscribe. How can companies harness smarter strategies to keep customers engaged without burning them out? According to eCommerce veteran Aaron Schwartz, the answer lies in data-driven retention marketing. Over-sending emails may provide a short-term lift, but ultimately damages deliverability and customer trust. By tapping into customer behavior data, brands can determine when someone actually wants to hear from them, creating more meaningful engagement. Shifting from a marketer’s mindset to a consumer’s perspective — and using modern analytics instead of outdated rules of thumb — can transform email, SMS, and direct mail into profitable retention channels. In this episode of The Digital Deep Dive, Aaron Conant talks with Aaron Schwartz, Co-founder and Co-CEO of Orita.ai, about retention marketing best practices. Aaron discusses why brands must move past intuition and embrace data, how machine learning enables smarter segmentation, and why balancing timing with customer preferences drives higher ROI.
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The Reinvented Omnichannel Org of the Future With Lauren Livak Gilbert
09/25/2025
The Reinvented Omnichannel Org of the Future With Lauren Livak Gilbert
Lauren Livak Gilbert is the Executive Director of the Digital Shelf Institute (DSI), which shapes the future of digital and advances commerce through community, content, and education. In her role, she defines the strategy for creating a global industry commerce community to support brands, retailers, and future leaders in the complex digital environment. As a thought leader in digital and design, Lauren has over 10 years of experience driving impactful multichannel design content, transformative digital shelf solutions, and high-conversion web UX designs across multiple regions. Before DSI, she held numerous roles at Johnson & Johnson, where she owned the digital shelf for consumer products in North America. In this episode… The pace of change in digital commerce has forced brands to rethink their organizational structures. Traditional structures built solely for brick-and-mortar sales can no longer keep up with evolving customer expectations and constant platform updates. How can brands transform their organizations to stay relevant in the omnichannel marketplace? Seasoned digital commerce strategist Lauren Livak Gilbert urges brands to transform their overall operations instead of merely choosing where eCommerce belongs in the company. Presenting yourself to retailers as a single unified company, setting shared goals across teams, and using AI to automate tasks like forecasting and content creation are essential. Lauren also highlights the need for clean, standardized data and advises HR leaders to prepare the next generation of digital talent. These shifts position businesses to adapt quickly and thrive. In this episode of The Digital Deep Dive, Aaron Conant sits down with Lauren Livak Gilbert, Executive Director of The Digital Shelf Institute (DSI), to discuss building the reinvented omnichannel organization of the future. Lauren explains why shared goals drive higher eCommerce sales, how AI frees teams for strategic thinking, and why HR must rethink talent development.
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Leveraging TikTok Shops for Omnichannel Growth With Jana Weinstein
09/18/2025
Leveraging TikTok Shops for Omnichannel Growth With Jana Weinstein
Jana Weinstein is the Director of Social Commerce and Affiliate Strategy at Blue Wheel Media, an omnichannel marketing and operational agency, where she leads influencer, creator, and affiliate strategies across managed programs and creator-led initiatives. As a sales and growth leader, she specializes in TikTok Shop, business development, go-to-market strategies, and full-funnel social commerce performance. Before Blue Wheel, Jana was part of the founding team of TikTok Shop, where she launched the partner ecosystem and built enterprise agency partnerships. She also served as the Director of Partnerships for TikTok Shop at Pattern®. In this episode… While many brands recognize TikTok Shop’s potential to boost sales and discoverability, they often hesitate to get started on the platform. Concerns about content creation, budget limits, and measuring results can make it difficult to identify a starting point. How can brands start and scale on TikTok Shop? According to social commerce expert Jana Weinstein, TikTok Shop is worth the investment. She advises brands to begin by building an authentic, organic presence through simple, consistent content to train the platform’s algorithm. Paid media can boost visibility while affiliate programs generate revenue, provided brands cultivate strong creator relationships and gamify engagement. Achieving growth on TikTok requires an intentional long-term strategy rather than a quick viral hit. Tune in to this episode of The Digital Deep Dive as Jana Weinstein, Director of Social Commerce and Affiliate Strategy at Blue Wheel Media, returns to speak with Aaron Conant about why TikTok Shop is a long-term marketing investment. Jana shares three reasons to get started on the platform, TikTok’s recent growth and new opportunities, and how to navigate operations on TikTok Shop.
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Gen AI's Impact on ROI for Businesses and Agencies With Udayan Bose
09/11/2025
Gen AI's Impact on ROI for Businesses and Agencies With Udayan Bose
Udayan Bose is the Founder and CEO of NetElixir, a digital marketing agency designed to help the growth of eCommerce businesses, B2B companies, and retail brands through strategic solutions and an AI-powered platform. Udayan is also the Co-founder of The Udaan Trust, a nonprofit foundation of NetElixir that supports underprivileged young women in India to pursue their education goals and build successful careers. In this episode… AI is transforming the way businesses operate, but the question remains: How can AI create measurable value instead of being just another buzzword? As industries experiment with generative tools, the stakes are high for brands trying to keep up with rapid technological shifts. What does it take to integrate AI responsibly to drive growth and innovation? Digital marketer and AI researcher Udayan Bose says companies must rethink how AI fits into core strategies rather than treating it as an add-on. They can leverage machine learning and generative models to identify high-value customers, streamline complex workflows, and uncover new opportunities for revenue growth. The advantage comes from reinvesting efficiency gains into new roles, experimentation, and innovation. When paired with a human-centered, responsible approach, AI can reshape industries. In this episode of The Digital Deep Dive, Aaron Conant sits down with Udayan Bose, Founder and CEO of NetElixir, to discuss unlocking business value with generative AI. Udayan talks about the disruptive potential of applied AI, why responsible adoption balances efficiency with human innovation, and how to select agencies and invest in future-proof strategies.
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A Deep Dive on Microsoft Copilot and Productivity With Will Nelson - Part 2
09/04/2025
A Deep Dive on Microsoft Copilot and Productivity With Will Nelson - Part 2
Will Nelson is the Copilot Lead at Microsoft, where he leads federal executive engagements for Microsoft Copilot, focusing on AI applications. With a background in product operations, internal tooling, and early-stage tech companies, he has launched new products, built scalable systems, and bridged gaps between emerging tools and real-world outcomes. Before Microsoft, Will was a Founding Product Ops Intern at Pie Insurance, where he grew the commercial auto vertical from zero to $2 million in premiums. In this episode… Many organizations waste time in meetings, scatter knowledge across various tools, and engage in repetitive administrative tasks. Employees often feel bogged down by minutiae rather than focusing on high-value work that drives impact. How can integrating AI into daily office applications reduce inefficiency, free up human creativity, and improve team productivity? Microsoft Copilot embeds AI directly into familiar tools like Word and Teams. The technology includes meeting transcription, automated agendas, real-time translations, and post-meeting recaps that free teams from administrative burdens. AI integrator Will Nelson recommends using AI to clarify acronyms, generate podcasts from transcripts, and role-play for interviews or presentation prep. By leveraging AI as a facilitator rather than a replacement, businesses can focus on mission-critical work rather than minutiae. In today’s episode of The Digital Deep Dive, Will Nelson, Copilot Lead at Microsoft, returns to chat with Aaron Conant about how AI tools can enhance daily workflows. Will talks about streamlining project management, enhancing collaboration in Teams, and the importance of context in prompting.
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A Deep Dive on Microsoft Copilot and Productivity With Will Nelson - Part 1
08/28/2025
A Deep Dive on Microsoft Copilot and Productivity With Will Nelson - Part 1
Will Nelson is the Copilot Lead at Microsoft, where he leads federal executive engagements for Microsoft Copilot, focusing on AI applications. With a background in product operations, internal tooling, and early-stage tech companies, he has launched new products, built scalable systems, and bridged gaps between emerging tools and real-world outcomes. Before Microsoft, Will was a Founding Product Ops Intern at Pie Insurance, where he grew the commercial auto vertical from zero to $2 million in premiums. In this episode… Many organizations are racing to adopt AI but struggle to apply it securely, effectively, and at scale. Leaders worry about whether they need multiple tools, how to trust AI outputs, and how to prepare their teams for this shift. With so many platforms available, how can businesses identify where AI delivers the most value without adding unnecessary complexity? According to AI expert Will Nelson, Microsoft Copilot functions as an AI coordinator that integrates tools, data, and context to enhance outputs. This tool allows companies to conduct deep research and secure their data through tenant-based governance. Will maintains that organizations don’t need world-changing use cases to benefit from AI; even simple applications like meeting preparation and document summarization can significantly increase productivity. This can be accomplished through effective, specific prompting. In this episode of The Digital Deep Dive, Aaron Conant chats with Will Nelson, Copilot Lead at Microsoft, about how Microsoft Copilot enables organizations to adopt AI effectively. Will talks about the future convergence of large language models, how government agencies are adopting AI, and how to use synthetic data to train AI models.
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AI’s Missing Link: How Data Readiness Unlocks AI’s Full Potential With Joe Luchs
08/21/2025
AI’s Missing Link: How Data Readiness Unlocks AI’s Full Potential With Joe Luchs
Joe Luchs is the Founder and CEO of DatalinxAI, an AI-powered data refinery that simplifies customer data. As an expert in AI, AdTech, MarTech, and SaaS, he previously served as the Global Head of AWS and Amazon Ads at Amazon, where he led global partnerships and AI business development. Joe was also the Commercial Founder and Head of Revenue at Beeswax (acquired by Comcast) and held a leadership role at Oracle. In this episode… Organizations are beginning to implement AI for personalization, automation, and business intelligence. Yet, messy, unstructured, and inconsistent data hinder smooth implementation. How can businesses bridge the gap between cutting-edge AI models and the data readiness required to scale them? According to AI and data expert Joe Luchs, companies often spend years and vast resources on data prep before they notice ROI on AI models. He recommends using secure hybrid cloud architectures, embedding data compliance measures, and automating preparation processes to free up teams from tedious work. By focusing on high-quality data readiness, businesses can accelerate AI adoption, empower staff to focus on innovation, and deliver the hyper-personalized experiences consumers expect. In today’s episode of The Digital Deep Dive, Aaron Conant sits down with Joe Luchs, Founder and CEO of DatalinxAI, to discuss preparing data for widespread AI adoption and integration. Joe explains how consultancies have pioneered data readiness, the future of AI-driven brand experiences, and the dangers of leveraging AI without proper regulations.
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Walmart Holiday Prep: Content, Conversion, and Ad Strategies With Michael Lebhar
08/14/2025
Walmart Holiday Prep: Content, Conversion, and Ad Strategies With Michael Lebhar
Michael Lebhar is the Co-founder and CEO of SellCord, which helps brands scale and maximize sales on Walmart.com. He is also the Co-founder of Spawn Fitness, which manufactures high-quality workout equipment, and the CEO of Lebbro Industries Inc, a parent company for multiple eCommerce brands. With experience scaling and selling brands on Walmart Marketplace and stores, Michael has become a leading expert in online and in-store growth strategies. In this episode… Many brands hesitate to invest heavily in Walmart’s online marketplace, assuming it will generate only a fraction of their Amazon sales. With this mindset, brands often miss opportunities to grow their digital presence and secure retail shelf space. With the holiday season approaching, how can brands rethink their Walmart strategy to maximize online and in-store sales? According to Walmart marketplace strategist Michael Lebhar, early and committed investments in the platform pay off in the long run. He advises brands to tailor content optimization specifically for Walmart’s search algorithm, prioritize high-conversion keywords, and refine product listings before ramping up ad spend. During the holidays, brands can align promotional strategies with Walmart’s curated deals to capture seasonal traffic and boost long-term rankings. In the latest episode of The Digital Deep Dive, Aaron Conant invites Michael Lebhar, Co-founder and CEO of SellCord, back to the show to discuss holiday selling strategies for Walmart. Michael talks about content optimization, Walmart’s various advertising formats, and how to sustain post-holiday sales momentum.
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Conversational Search and the Changing Shopper Journey With Chris Perry
08/07/2025
Conversational Search and the Changing Shopper Journey With Chris Perry
Chris Perry is the Co-founder and Chief Learning Officer at firstmovr, a satellite Center of Excellence (COE) for eCommerce education and change management. He is also an Executive Educator and Keynote Speaker at the Path to Purchase Institute. With over 12 years of experience as an eCommerce leader and executive educator, Chris aims to empower leaders to embrace change with actionable knowledge, strategies, and KPIs. In this episode… The rapid evolution of eCommerce and the rise of AI-driven tools are disrupting the way consumers discover, evaluate, and stay loyal to brands. Traditional loyalty programs often fail to keep pace, and many brands still prioritize acquisition over retention. How can companies adapt their digital shelf strategies to capture human shoppers and stay relevant to AI-driven recommendations? Digital upskilling advocate and eCommerce strategist Chris Perry advises brands to focus on shopper-centric content optimization by creating long-tail assets that answer detailed consumer questions and appeal to AI agents like Rufus or ChatGPT. Navigating the digital shelf requires understanding how conversational queries differ from traditional keyword searches and proactively testing and reskilling to stay ahead of competitors as AI adoption accelerates. Tune in to this episode of The Digital Deep Dive as Chris Perry, Co-founder of firstmovr, returns to speak with Aaron Conant about navigating the AI-driven transformation of eCommerce. Chris shares real-world examples of AI-assisted product discovery, the importance of long-tail content for search visibility, and why early adoption and reskilling are critical for the future.
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The Blending of Retail Media, Sampling, and Performance Marketing With Jack Shannon
07/31/2025
The Blending of Retail Media, Sampling, and Performance Marketing With Jack Shannon
Jack Shannon is the Co-founder and CEO of Recess, a brand activation platform for top consumer brands, like PepsiCo, General Mills, and Milk Bar. With over 15 years of experience scaling innovative marketing solutions, he and his partner have scaled Recess from the ground up. Jack is also an investor in Venvee and Editframe. In this episode… As retail media networks proliferate and demand more brand dollars, many companies struggle to identify which channels deliver results beyond the major platforms like Amazon and Walmart. With hundreds of fragmented options, it's increasingly difficult to measure ROI, target consumers, and justify media spend. How can brands identify a scalable, performance-driven alternative that bridges physical and digital touchpoints? Experiential marketer and media strategist Jack Shannon advises brands to leverage performance-driven sampling and targeted real-world applications. This includes using mobile data to reach high-density shopper audiences in environments like gyms, schools, and apartment communities — places where people are naturally engaged. By blending audience targeting, digital amplification, and measurement tools like store lift analysis and loyalty data integration, experiential marketing can drive bottom-funnel metrics and long-term customer loyalty. In this episode of The Digital Deep Dive, Aaron Conant sits down with Jack Shannon, Co-founder and CEO of Recess, to discuss measuring and scaling experiential marketing. Jack talks about sampling as a form of performance media, how social amplification and real-world data drive meaningful outcomes, and how to reach offline audiences.
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Everyday AI for Everyday Productivity With Danny Silverman
07/24/2025
Everyday AI for Everyday Productivity With Danny Silverman
Danny Silverman is the Founder and Digital Strategy and Growth Consultant at Silverstream Strategic Consulting. As a digital commerce executive, he has over two decades of experience in eCommerce, marketing, and general management consulting. Throughout his career, Danny has scaled a digital commerce agency 10x in three years, led marketing efforts for a global SaaS platform, and navigated Amazon’s landscape since 2006. In this episode… Professionals often feel overwhelmed by the pace of innovation, especially when it comes to AI. While many know AI can save time and boost productivity, most still struggle with using it effectively in their daily business or personal workflows. How can you leverage AI tools to enhance creativity, decision-making, and strategic decisions? Digital strategist and eCommerce consultant Danny Silverman uses AI to challenge ideas, simulate expert feedback, and train personalized GPTs. He recommends organizing work by using separate chats, uploading materials to provide context, and clearly defining prompts. Danny also warns against AI hallucination and encourages users to always validate outputs, maintaining that AI should be a collaborator, not a crutch. Join Aaron Conant in this episode of The Digital Deep Dive as he welcomes Danny Silverman, Founder and Digital Strategy and Growth Consultant at Silverstream Strategic Consulting, back to discuss how professionals can maximize AI’s potential. Danny explains how to structure prompt interactions, how to build personal assistants, and the future of agentic AI.
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AI Driving Onsite Personalization at Scale With Darpan Saini
07/17/2025
AI Driving Onsite Personalization at Scale With Darpan Saini
Darpan Saini is the CEO of App0, a generative AI platform that builds intelligent, human-centered digital assistants for companies. Previously, he co-founded Cloud Lending Solutions, which streamlined lending operations for major financial institutions before its acquisition by Q2. Darpan is also a member of the ELFA Innovation Advisory Council, where he helps shape the future of FinTech. In this episode… Despite investing in website optimization tools, eCommerce brands are struggling to increase conversions. The user experience on most sites has plateaued, with little innovation in how shoppers search, explore, and make decisions. As customer behavior shifts toward AI-powered conversational tools, how can brands adapt their digital experiences to meet these expectations? With experience developing generative AI for eCommerce, Darpan Saini maintains that brands can transform static sites into intelligent, interactive experiences. Traditional optimization tactics, like minor UI tweaks or static product filters, offer diminishing returns. Instead, Darpan recommends investing in AI-powered quizzes, personalized product detail pages, and conversational search that can adapt in real time to each shopper’s needs. By enabling one-to-one personalization without needing user data histories, brands can convert more first-time visitors, reduce returns, and stand out in a crowded market. In this week’s episode of The Digital Deep Dive, Aaron Conant speaks with Darpan Saini, CEO of App0, about improving conversion rates through AI-powered shopping experiences. Darpan talks about the rise of voice commerce, how his company develops A/B testing to increase conversions, and offers advice for deploying AI-powered shopping assistants.
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Tariffs and Prices on Amazon With Scott Needham
07/04/2025
Tariffs and Prices on Amazon With Scott Needham
Scott Needham is the Founder and CEO of SmartScout, an Amazon FBA product research software. He is also the former CEO of BuyBoxer, which he built into a top 100 Amazon seller, managing over 120,000 products. Scott hosts the Smartest Amazon Seller podcast, which shares insights on navigating the Amazon marketplace. In this episode… As global tariffs shift and economic uncertainty looms, brands are under pressure to make informed pricing decisions and maintain margins. Many rely solely on internal data for scenario planning, making it difficult to benchmark against the broader market. Without visibility into industry-wide pricing trends, how can businesses decide whether to raise prices or maintain their threshold? After monitoring price movements across product categories, pricing and market intelligence expert Scott Needham noticed that only 3% of products available on Amazon experienced price increases during the initial tariff period. He emphasizes that brands need external market visibility to justify pricing structures internally. Additionally, brands can leverage TikTok Shop and influencer-led strategies as growth engines, especially in fast-moving categories like groceries and supplements. Join Aaron Conant in The Digital Deep Dive as he hosts Scott Needham, Founder and CEO of SmartScout, to discuss pricing strategies and market trends in a shifting eCommerce landscape. Scott shares how brands can use data to avoid reactionary pricing, Prime Day discounting strategies, and the future role of AI shopping assistants.
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LLM's, SEO, and the Future of Voice Commerce With Max Sinclair
05/29/2025
LLM's, SEO, and the Future of Voice Commerce With Max Sinclair
Max Sinclair is the Founder and CEO of Azoma (formerly Ecomtent), which generates AI-powered product content across eCommerce sites. Before founding Azoma, he spent six years at Amazon, where he launched Amazon Business in the UK, Amazon.sg in Singapore, and Amazon Grocery across the EU. Max is also the host of New Frontier: The AI for ecommerce podcast. In this episode… Traditional search engines are losing their dominance as consumers turn to AI-powered tools for product discovery. This shift challenges eCommerce brands to stay visible in a digital landscape driven by conversational interfaces and personalized recommendations. How can businesses optimize their online presence when search requires context, intent, and interaction? AI-driven search optimization expert Max Sinclair maintains that brands can remain competitive by aligning their content strategies with the mechanics of large language models. Appearing in AI search results involves more than traditional SEO; it requires crafting semantically rich content that aligns with customer personas, goals, and use cases. Max emphasizes the importance of visual elements, customer sentiment, and AI’s multimodal capabilities, allowing brands to improve visibility and relevance on emerging platforms like ChatGPT, Gemini, and Amazon’s Rufus. Tune in to this episode of The Digital Deep Dive as Aaron Conant hosts Max Sinclair, Founder and CEO of Azoma, to discuss the evolution of product search in the age of generative AI. Max talks about the rise of conversational and voice-based search, how direct checkout integrations could disrupt traditional online marketplaces, and his predictions for AI shopping assistants.
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STV Ads and Your Digital Media Budget With Justin Ruiss
05/15/2025
STV Ads and Your Digital Media Budget With Justin Ruiss
Justin Ruiss is the SVP of the Media Sector at BWG Global, a knowledge-sharing network hosting in-person and virtual industry events. In his role, he hosts Q&A forums with executives from various sectors, including social media, advertising, connected TV, streaming, and gaming. Before joining BWG Global, Justin was the Investor Relations Activations Developer at Cision and an Equity Analyst at The Benchmark Company. In this episode… Retail media, CTV advertising, and AI-powered search are evolving faster than many brands can adapt. Marketers are grappling with fragmented content strategies, fluctuating CPMs, and uncertainty around how to allocate budgets effectively across platforms. With performance expectations rising and consumer behaviors shifting, how can brands stay competitive without overspending? According to media and eCommerce analyst Justin Ruiss, now is an ideal time to invest in CTV due to oversupply, lower CPMs, and advanced targeting capabilities. He recommends increasing production budgets to create modular, high-quality content that can be repurposed across channels like TikTok, Amazon, and streaming platforms. Brands can also adopt centralized content planning and leverage tools like Amazon Marketing Cloud to drive enhanced targeting and performance while planning for economic volatility and regulatory changes. In this episode of TheDigital Deep Dive, Aaron Conant interviews Justin Ruiss, SVP of the Media Sector at BWG Global, about the future of digital media buying and AI in eCommerce. Justin explores CTV trends, the rise of agentic AI, and how brand guidelines shape content in gaming environments.
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A Strategic Look at Unified Commerce With Kelly Goetsch
05/08/2025
A Strategic Look at Unified Commerce With Kelly Goetsch
Kelly Goetsch is the Chief Operating Officer of Pipe17, which specializes in AI-powered composable order operations. Before joining Pipe17, he served as the Chief Strategy Officer at commercetools, where he played a pivotal role in scaling the company to over $100 million in annual recurring revenue. Kelly also co-founded MACH Alliance, a nonprofit industry organization advocating for Microservices, APIs, Cloud-native, and Headless (MACH) technologies. In this episode… Customers expect fast fulfillment and delivery across various selling channels, including social media and marketplaces. Traditional systems struggle to keep pace, leaving companies tangled in connectivity issues between their sales, inventory, and fulfillment networks. How can brands deliver seamless, cost-effective experiences while scaling across these fragmented digital touchpoints? With experience in AI-driven order management, Kelly Goetsch advises brands to adopt a connectivity-first model. This requires integrating a flexible routing layer that connects selling channels, back-office systems, and fulfillment partners, enabling dynamic order flow based on cost, speed, and product needs. Kelly also recommends embracing emerging sales platforms like TikTok and leveraging AI tools to align with how customers discover products, noting that companies must modernize their operations or risk falling behind in today’s competitive landscape. In today’s episode of The Digital Deep Dive, Aaron Conant speaks with Kelly Goetsch, COO of Pipe17, about reshaping order management for AI-driven shopping. Kelly explains how selling channels have evolved, marketing gaps in midsize brands, and how voice commerce has shaped emerging conversational shopping experiences.
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Shopify’s Push Into B2B With Denis Dyli
04/24/2025
Shopify’s Push Into B2B With Denis Dyli
Denis Dyli is the Founder and Principal of Uncap, a Shopify B2B eCommerce agency. He has led the company to become a Shopify Premier Partner, delivering over 350 eCommerce projects and replatforming more than 100 Shopify Plus stores. With over 15 years of experience in eCommerce development and strategy, Denis helps B2B and B2C sellers optimize their eCommerce platforms. In this episode… For DTC brands expanding into B2B, legacy platforms can create significant friction. Outdated technology, slow feature deployment, and mounting maintenance costs often hinder growth, especially when buyers expect seamless, digital-first experiences. How can companies modernize their B2B operations to stay competitive and meet evolving customer expectations? According to digital commerce expert Denis Dyli, DTC brands with Shopify Plus stores can activate B2B capabilities by enabling features like custom pricing, net terms, and B2B storefront templates. He recommends updating themes to support new Shopify accounts and tailoring the logged-in buyer experience to streamline ordering. By leveraging native functionality and apps like Gorgias and Klaviyo, DTC brands can create polished, scalable B2B portals without a complete replatform. In today’s episode of The Digital Deep Dive, Aaron Conant hosts Denis Dyli, the Founder and Principal of Upcap, to discuss the future of B2B eCommerce on Shopify. Denis talks about digital transformation in the B2B space, B2B companies that would benefit from Shopify’s capabilities, and the impact of tariffs on the digital commerce landscape.
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Bridging the Digital Organizational Gap With Danny Silverman
04/17/2025
Bridging the Digital Organizational Gap With Danny Silverman
Danny Silverman is the Founder and Digital Strategy and Growth Consultant at Silverstream Strategic Consulting. As a digital commerce executive, he has over two decades of experience in eCommerce, marketing, and general management consulting. Throughout his career, Danny has scaled a digital commerce agency 10x in three years, led marketing efforts for a global SaaS platform, and navigated Amazon’s landscape since 2006. In this episode… Recently, eCommerce teams have faced intense pressure from all sides, including organizational flattening, budget cuts, and mandatory AI integrations. Many leaders find themselves stuck in reactive mode, unable to assess strategy, structure, or performance. How can brands stay agile and make informed decisions without getting overwhelmed? Brands face three common barriers: misaligned go-to-market strategies, outdated marketing tactics, and fragmented organizational design. To regain control and drive profitable growth, seasoned eCommerce strategist Danny Silverman recommends beginning with candid, cross-level interviews to identify hidden challenges before conducting deep data analyses to reveal underlying trends. For mid-sized brands especially, he stresses the importance of empowering decision-makers with budget control and executive sponsorships while leveraging AI tools for content creation and operational efficiency. In this week’s episode of The Digital Deep Dive, Aaron Conant chats with Danny Silverman, Founder and Digital Strategy and Growth Consultant at Silverstream Strategic Consulting, about adapting organizational structures to an evolving digital landscape. Danny explains how Chief AI Officers are gaining traction amid AI integrations, how Amazon sellers can maintain profitability in a volatile economy, and how he diagnoses structural issues in an organization.
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A CIO's Perspective on Navigating the Evolution of Technology With Jon Harding
04/10/2025
A CIO's Perspective on Navigating the Evolution of Technology With Jon Harding
Jon Harding is the Senior Vice President and Global Chief Information Officer at Conair LLC, a multibillion-dollar consumer products company. In his role, he has driven major initiatives, including implementing a global SAP system and other eCommerce platforms. Before joining Conair, Jon held senior leadership IT roles at Kellogg Company, where he spearheaded enterprise system transformations across Europe and the US. In 2023, he was recognized as the New York CIO of the Year in the enterprise category. In this episode… Enterprise IT leaders are often expected to maintain flawless systems while simultaneously driving innovation. As digital tools evolve, companies must adopt new technologies while avoiding disruption and risk. How can organizations balance innovation with stability and strategic alignment? When managing IT transformation at the enterprise level, veteran technology executive Jon Harding recommends aligning tech initiatives with clear business outcomes rather than chasing the latest trends. This requires initiating early cross-functional collaboration in tech planning, focusing on change management, stakeholder buy-in, and long-term thinking. To integrate AI efficiently, Jon suggests prioritizing high-ROI use cases like customer support automation and content creation while maintaining governance and budget control. In this week’s episode of The Digital Deep Dive, Aaron Conant talks with Jon Harding, the Senior Vice President and Global CIO at Conair, about enterprise-level tech stack innovation and digital transformation. Jon shares change management strategies, vendor selection considerations, and the future of enterprise advisory work.
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Vendor Central's Accounting Shakeup With Hannah Blackburn
04/03/2025
Vendor Central's Accounting Shakeup With Hannah Blackburn
Hannah Blackburn is the Co-founder and Director of The Hawkers Club, a company that helps vendors and sellers solve their most pressing challenges and navigate eCommerce marketplaces, including Amazon and Target. In her role, Hannah advises online sellers and vendors on how to directly position their brands and value offerings as Amazon partners to increase profitability and revenue. Before co-founding The Hawkers Club, she joined Amazon as a brand specialist with an initial focus on vendor excellence and marketing before transitioning to stock management and profitability. Since she’s written the business logic powering some of the algorithms that run Amazon, Hannah knows how you can systematically make profitable decisions that Amazon’s algorithms reward. In this episode… Recent sweeping changes to how Amazon Vendor Central calculates and processes chargebacks, shortages, and overbilling have left many brands scrambling to adjust their internal processes and preserve cash flow. What do these updates entail, and how can vendors stay ahead of the curve? Former Amazon insider Hannah Blackburn explains that overbilling calculations have shifted from “distributor shipment” to “Amazon payables,” potentially reducing double billing and improving predictability if brands adapt quickly. Brands must now track and forecast co-op charges based on expected payments rather than shipments. Additionally, Amazon no longer accepts bulk aged shortages, so brands should track aging internally and file disputes for shortages immediately. Hannah maintains that staying proactive prevents long-term revenue loss under Amazon’s new conditions. In this episode of the Digital Deep Dive, Aaron Conant welcomes Hannah Blackburn, the Co-founder and Director of The Hawkers Club, back to the show to discuss Amazon’s evolving Vendor Central policies. Hannah talks about rising packaging chargebacks, updated dispute workflows, and how to protect future chargeback recoveries.
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The Future of Onsite Search With Charlie Cole
03/27/2025
The Future of Onsite Search With 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. 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.
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The Need for Content That Converts With Eric Sheinkop
03/20/2025
The Need for Content That Converts With 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. 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.
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Amazon Vendor Negotiations With Andrea Leigh
03/13/2025
Amazon Vendor Negotiations With 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. 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.
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Trade Shows, Networking, and New Product Launch With Tim Wilson
03/06/2025
Trade Shows, Networking, and New Product Launch With 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. 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.
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The Future of Retail Media With Nii Ahene
02/27/2025
The Future of Retail Media With 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. 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.
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The Future of eCommerce: A Compilation of Trends in Streaming TV Ads, Fulfillment, and More
02/20/2025
The Future of eCommerce: A Compilation of Trends in Streaming TV Ads, Fulfillment, and More
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. 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.
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Incremental Retail Media Measurement With Meghan Corroon
02/13/2025
Incremental Retail Media Measurement With 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. 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.
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