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. 

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. 

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.

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. 

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. 

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. 

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. 

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. 

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.

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.

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.

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.

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. 

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.

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. 

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. 

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. 

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.

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. 

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.