Show cover of The Digital Deep Dive With Aaron Conant

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.


The Responsible Intersection of AI and Tech With Andrew Schydlowsky
Andrew Schydlowsky is the Founder and CEO of TrackStreet, a cutting-edge SaaS platform that empowers brands by leveraging eCommerce data. He has been involved in eCommerce since 1998, starting with an innovative idea to sell sports nutrition products online. As a serial entrepreneur, Andrew founded Performance Unlimited, Inc., Soma Distribution, Inc., and Kala International, Ltd. He also established Soma Internacional, S.A. in Peru. His diverse experience includes roles as Chief Growth Officer for a retail chain and Corporate Trainer for Unisys in Beijing. In this episode… With the digital landscape evolving and new technologies emerging, brands must navigate rapid eCommerce growth and AI integrations. Where should businesses focus their energy to avoid being misled by shiny objects or overwhelmed by an influx of data?  With over 25 years at the helm of eCommerce, Andrew Schydlowsky affirms that brands can leverage technology and AI to make strategic business decisions but must recognize their risks and potential to derail progress. Before adopting any new tool or software, systemize your data and assess your tech stack regularly to ensure responsible use and long-term stability. By maintaining a clear vision for your business, you can evolve your business with the market while staying savvy about the implications and pitfalls of trends. Tune in to the latest episode of The Digital Deep Dive as Aaron Conant speaks with Andrew Schydlowsky, the Founder and CEO of TrackStreet, about the intricacies of eCommerce, technology, and AI. Andrew talks about leveraging AI to automate data and decision-making, the evolution of the digital landscape, and TrackStreet’s mission. 
46:06 6/13/24
Seller Fulfilled Prime Deep Dive With Matt Snyder
Matt Snyder is the Founder and CEO of Brands Excel, where he helps brands scale on Amazon. As a revenue generator, he has over 15 years of experience growing DTC, B2C, and B2B companies within the eCommerce space and Amazon’s marketplace. Matt focuses on building long-term growth by developing alternative sales channels and product lines that complement overarching omnichannel strategies. Before Brands Excel, he was the Vice President of Online Retail at Vari. In this episode… With eCommerce competition intensifying, brands are scrambling to fulfill customer requests and manage inventory costs. How can Amazon’s Seller Fulfilled Prime enable operational and cost efficiency? Seasoned eCommerce leader Matt Snyder leverages SFP in his business to streamline logistics, reduce costs, and improve the customer experience. Before investing in this fulfillment method, conduct a self-audit to ensure SFP aligns with your product types and business model. Seller Fulfilled Prime requires brands to meet specific performance metrics, including 93% on-time deliveries and precise product tracking, to maintain Prime status and customer trust. Matt suggests cultivating partnerships with SFP 3PL partners to manage logistics and complex fulfillment requirements. Tune in to the latest installment of The Digital Deep Dive as Aaron Conant meets with Matt Snyder, the Founder and CEO of Brands Excel, who shares the ins and outs of Seller Fulfilled Prime. Matt explains the impact of Amazon Marketing Cloud and AI on future eCommerce strategies, how to maintain profitability with SFP, and the benefits of inventory control.
47:53 6/6/24
Restoring Marketing Signals in the Post Cookie World With Mandar Shinde
Mandar Shinde is the CEO of Blotout, a Y Combinator restoring identity and data accuracy in a cookieless era. He also volunteers with ProductNation/iSPIRT, a nonprofit sourcing public goods for Indian product startups. In this role, Mandar helps enable data democratization with zero trust. As a data-driven entrepreneur, he has experience in privacy, analytics, blockchain, advertising, compliance, and cloud computing.   In this episode… The deprecation of third-party cookies threatens the stability of targeted marketing, and businesses are navigating uncharted territories. With the cornerstone of personalized advertising crumbling, how can companies navigate the landscape without relying on third-party data? Apple’s aggressive stance on data privacy has placed limitations on digital advertising, specifically after the advent of iOS 14, which allows users to opt out of third-party tracking. Data-driven eCommerce entrepreneur Mandar Shinde emphasizes adjusting your lifecycle and performance marketing strategies to align with the shifts in data regulations and online tracking. This involves conducting an internal assessment of your customer data collection, storage, and processing systems to ensure compliance and effective adaptation. Transitioning to first-party data collection by adopting CDPs and server-side tracking is a viable solution to privacy concerns in a cookieless environment. In today’s episode of The Digital Deep Dive, Mandar Shinde, the CEO of Blotout, joins Aaron Conant for a discussion about adapting to a cookieless landscape. Mandar talks about the imminent shifts and the necessary actions brands must take to ensure their digital presence and customer relationships remain strong.
51:37 5/30/24
A Chat on Entrepreneurship With David Sanborn
David Sanborn manages strategy and operations for GIZMO, a developer and manufacturer of consumer electronics. He is also the Co-founder of Kiid Coffee, a unique food brand that uses creative marketing to target nutritional gaps in children’s food. As an inventive entrepreneur, David has built and sold several brands, including Basics Brands, which he expanded into the pet retail space before selling it.  In this episode… Starting a brand from scratch, creating an unparalleled product, and selling it successfully are seemingly basic yet daunting challenges in today’s competitive eCommerce marketplace. What does it take to cut through a saturated market and carve out a space for your products? David Sanborn, a serial entrepreneur, has conquered the challenge of branding and innovation in the modern digital landscape. He maintains that strategic partnerships and mentors are invaluable resources for product development. These industry professionals can share ideas and strategies that can expedite launch and enhance innovation. Before launching your product, test its market fit to allow for customer feedback and ample refinement. Additionally, digital marketing is essential for brand awareness, so by integrating a mission-driven approach into your creative strategies, you can stimulate authentic consumer engagement and cement a long-term presence in the market.  In this episode of The Digital Deep Dive, Aaron Conant meets with David Sanborn of GIZMO to share innovative approaches to launching an eCommerce brand. David breaks down the intricacies of product development, the importance of market-fit testing, and how to stand out in a competitive market through creative marketing and genuine value creation.
39:23 5/23/24
Email Innovation: Driving Profitable Results Through Cutting-Edge Technology
Aaron Schwartz is the Co-founder and President of Orita, 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 spent seven years building and managing DTC brand Modify Watches and was the President of Loop. Daniel Brady (DB) is the CEO of Orita. As a neuroscientist turned data scientist, he has helped leading eCommerce brands organize their data sets. DB has also worked with CEOs, CTOs, and other leaders to build eCommerce companies.  In this episode… Customers are often overwhelmed by an inbox flooded with marketing emails, leading them to unsubscribe, much to brands’ dismay. Yet these brands are constantly grappling with finding the right balance in their communication frequency to keep customers engaged without driving them away. How can you maintain engagement in your email campaigns while saving money? Using machine learning, data scientists and brand builders Daniel Brady (DB) and Aaron Schwartz have revolutionized customer data usage and engagement. You can implement AI into your email and SMS campaigns to analyze consumer data and identify communication patterns. This allows you to discover optimal touchpoints and avoid inundating your customers with emails. Periodically auditing your email lists can improve deliverability and help maintain higher subscriber engagement. Ultimately, building and nurturing long-lasting customer relationships through email marketing engagement boosts brand loyalty and customer lifetime value. Tune in to the latest episode of The Digital Deep Dive as Aaron Conant welcomes DB and Aaron Schwartz of Orita to discuss enhancing your email marketing campaigns. Together, they share the financial benefits of leveraging AI to enhance email campaigns, how to select tech vendors, and how to optimize your tech stack. 
42:31 5/16/24
Navigating the Sunset of 3rd Party Cookies With David Cost
David Cost is the VP of Digital and eCommerce at Rainbow Apparel Co, an omnichannel fast-fashion retailer offering women’s, plus-size, and children’s clothing. In his role, he manages over 1,000 stores in the US, Puerto Rico, and the US Virgin Islands and has grown the eCommerce business over 9x.  David has developed new eCommerce technologies as a beta tester and early adopter for companies, including Oven Bits, BloomReach, and Instant Labs. He has also served on customer advisory boards for Salesforce and Shopify and has spoken at CommerceNext and other industry events.  In this episode… Third-party cookies are sunsetting, and although an official date hasn’t been set for their demise, brands must consider alternatives. How can you continue targeting customers in a post-cookies world? Website cookies include first-party, generated from the brand, and third-party, originating from outside sources. Third-party cookies only store information for seven days, whereas first-party cookies can retain data for up to 20 years. According to eCommerce executive David Cost, You can bypass third-party cookies by gathering relevant consumer information through a brand-exclusive data layer and sharing it with others. This allows you to create and optimize marketing messages to retarget customers and boost conversions. Leveraging first-party cookies also lowers customer acquisition costs, ensuring you can easily identify and retain your top purchasers. In the latest episode of The Digital Deep Dive, Aaron Conant welcomes David Cost, the VP of Digital and eCommerce at Rainbow Apparel Co, to discuss solutions for the demise of third-party cookies. David shares his thoughts on using AI to create first-party cookies, how product videos drive conversions, and why you need segmented first-party data.
41:57 5/9/24
Embracing Omnichannel Strategies With Andrea Moore
Andrea Moore is the Chief Digital Officer at NEST New York, a fast-growing, leading fragrance lifestyle brand. As a C-suite executive and omnichannel leader, she has experience launching, building, and scaling digital businesses to $100 million. Andrea is also an angel investor, an advisory board member at ShopTalk, and an Adjunct Professor at FIT.  In this episode… During the pandemic, brick-and-mortar brands began shifting to digital, with pandemic-born brands launching DTC exclusively. In the pandemic’s aftermath, DTC has become less profitable, so brands must integrate online and in-store efforts to survive. How can you build a robust omnichannel strategy? As omnichannel brand builder Andrea Moore says, it doesn’t matter where your consumers shop as long as they purchase from you and not your competitors. You can establish storefronts on Walmart, Amazon, and Target’s online marketplaces as well as your personal website and brick-and-mortar shop. By targeting your customers where they shop, you can dominate the market. Omnichannel strategies often require a significant amount of tech tools to execute effectively, and it can be challenging to determine the precise fit for your tech stack. Andrea advises assessing your business goals, go-to-market strategy, and margin structures to capitalize on profitable growth opportunities. Join Aaron Conant in today’s episode of The Digital Deep Dive as he sits down with Andrea Moore, the Chief Digital Officer at NEST New York, to discuss omnichannel brand strategies. Andrea shares how brands should consider data when utilizing AI, the digital landscape’s most urgent issues, and how AI will impact leadership roles. 
39:52 5/2/24
Seller’s Crossroads: Exploring the Decision to Enter the Amazon Marketplace With Matthew Rosenfeld
Matthew Rosenfeld is the Founder and CEO of Crush, which provides boutique Amazon management services for retail and DTC brands. He is also the Founder of Retail Racer, which leverages proprietary software to automate retail outreach for DTC brands. As a former Amazon seller, Matthew has launched, acquired, and sold multiple brands. In this episode… As Amazon gains a greater presence in the market, launching your brand on the platform is crucial for driving awareness. Yet some brands are hesitant to take this leap, fearing that Amazon will drop product prices and allow others to resell products on their sites. How can you generate sales and profitability on Amazon without exhausting resources? Selling on Amazon provides an opportunity to drive traffic to your DTC storefront, but Amazon veteran Matthew Rosenfeld warns that the platform’s landscape is constantly shifting, so you must develop calculated strategies to avoid major losses. The two main components retail-first brands should focus on are demand capture and net new customer acquisition. Without capturing sufficient demand on social media platforms like Meta and TikTok, brands that exceed $3-5 million in annual revenue experienced profit losses. Consumer purchase intentions are substantially higher on Amazon, so brands must acquire new customers on the platform to boost conversion rates. In today’s episode of The Digital Deep Dive, Aaron Conant sits down with Matthew Rosenfeld, the Founder and CEO of Crush, to make the case for why your brand should have an Amazon presence. Matthew shares his perspective on brand aggregations in the Amazon space, the future of Vendor Central, and how to analyze profitability on the platform.
40:47 4/25/24
Digital Deep Dive With Amitai Sasson From
Amitai Sasson is the VP of eCommerce at, the largest online retailer of handmade oil paintings in the US. In his role, he has designed and developed the company’s online store, with annual sales of over $2 million. Amitai is also responsible for enterprise resource planning, customer relationship management, and supply chain systems. As an eCommerce authority and web marketer, he specializes in developing innovative technology solutions to improve sales and performance. In this episode… Online shopping has become the norm, and some brands operate entirely from an eCommerce model. Despite this, eCommerce is still in its infancy, so brands are struggling with the basics, like sales, shipping, and traffic. What strategies can brands employ to stay ahead of the eCommerce game? According to eCommerce specialist Amitai Sasson, shipping costs are rising, but packaging products in smaller boxes can reduce fees. He also recommends that brands with essential products utilize Shopify for third-party shipping to provide consumers with a seamless shopping and checkout experience. You must also understand your website traffic drivers by analyzing first-party data, available inventory, best-selling products, and ad spend. Additionally, integrating new technology into your website may increase your traffic and conversion rates. Welcome back to The Digital Deep Dive as Aaron Conant welcomes Amitai Sasson, the VP of eCommerce at, to discuss the latest eCommerce trends. Amitai talks about’s early online presence, how the demise of third-party cookies impacts data collection, and how to drive free traffic to your website.
46:01 4/18/24
eCommerce Strategies With Economic Headwinds With Todd Hassenfelt
Todd Hassenfelt is the Global Digital Commerce Senior Director of Strategy and Execution at Colgate-Palmolive, an innovative growth company that reimagines a healthier future for people, pets, and the planet. He has extensive leadership experience in brick-and-mortar and eCommerce channels, serving as a leader on both sales and marketing teams.  Todd has also sold some of the top brands in the US to multiple channels, including C-stores, mass merchandisers, wholesale clubs, supermarkets, and eCommerce. As an eCommerce and content contributor, his articles appear in publications such as BRAVE Commerce, Ecommerce Braintrust, and The Digital Shelf Cast. In this episode… Following post-pandemic spending sprees, credit card interest debt in the US has reached a staggering $578 billion. With consumers cutting back on spending to pay off their debts, how can eCommerce brands adjust their strategies to retarget them? The proliferation of retail media has simplified online shopping significantly, with consumers making purchases through buy now, pay later options after using a QR code through a connected TV ad. To address consumer spending cuts and increased budgeting, eCommerce and digital strategy engineer Todd Hassenfelt advises offering discounts and perks like subscribe and save initiatives to encourage quick purchases. You can also bundle products to provide consumers with greater value for their money and promote routines and regiments. When retargeting customers through retail media, advertise your lowest-priced products first and reevaluate your messaging to capture budget-conscious consumers. The Global Digital Commerce Director of Strategy and Execution at Colgate-Palmolive, Todd Hassenfelt, returns to The Digital Deep Dive to talk with Aaron Conant about pivoting eCommerce strategies during economic turmoil. Todd shares frontrunning financial trends in the DTC space, how to manage and diversify ad spend to align with consumer spending habits, and how to make informed business decisions.
41:17 3/14/24
Amazon Ads and Entrepreneurship With Destaney Wishon
Destaney Wishon is the Co-founder and CEO of BTR Media, a retail media company empowering growth for brands. The company rebranded from BetterAMS, where Destaney started as an Account Executive, providing perspective on new industry standards for brands’ eCommerce strategies. She is passionate about providing in-depth, strategic recommendations on sponsored products, brands, displays, and DSP. As an Amazon advertising thought leader, Destaney has spoken in over 9,000 podcasts and events. In this episode… As the digital landscape evolves seemingly by the day, Amazon is no longer the only advertising platform to invest in, and entrepreneurs are inundated with business growth strategies. How have advertising and media evolved, and how can entrepreneurs adapt to the constantly shifting space? As a digital advertising strategist regularly pivoting to address challenges in the digital landscape, Destaney Wishon notes that Amazon has transitioned into a media company to compete with retail media networks like Walmart. Rather than investing solely in niche Amazon ads like PPC, brands must diversify their spending to include sponsored product, brand, and display ads and social media platforms like TikTok. As entrepreneurs transition out of their companies’ daily operations, they must create effortless, consistent, and engaging content to scale. Destaney recommends hosting networking events or podcasts to develop partnerships and create outreach strategies on LinkedIn to navigate the digital space effectively. Tune in to this episode of The Digital Deep Dive as Aaron Conant talks with Destaney Wishon, The Co-founder and CEO of BTR Media, about the current state of Amazon advertising and entrepreneurship in the space. Destaney explains how paid media has skyrocketed, how to scale an agency strategically, and content creation strategies.
47:25 3/7/24
Trends To Win in 2024 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 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 eCommerce landscape is advancing rapidly, and first-mover organizations are capitalizing on digital trends for 2024. What eCommerce projections should you observe, and how can you implement them to drive explosive growth in 2024? First mover and change leader Chris Perry notes that shoppers expect omnichannel integrations at every touchpoint, so everything from online and in-store shopping experiences to retail media should include omnichannel strategies. With the rapid adoption of retail media, first movers must dismantle advertising and media silos to develop a full-funnel approach that engages audiences. As Gen Z consumers shop on social media platforms like TikTok, social commerce has become the leading driver of digital, making it crucial for first movers to leverage. Additionally, increasing acquisitions and partnerships have led to competition, so by partnering with agencies of record (AOR), you can enable long-term leadership and growth. Category management strategies are imperative in generating incremental omnichannel growth. To ensure effective omnichannel capabilities, you must update your processes, details, and workflows. In this episode of The Digital Deep Dive, Aaron Conant welcomes Chris Perry, the Co-founder and Chief Learning Officer at firstmovr, to discuss the leading digital commerce trends for 2024. Chris shares how to develop winning online and in-store shopping strategies, how to promote first-mover leadership training and education, and how to execute omnichannel strategies.
54:23 2/22/24
Accurate Amazon Market Share and Content With Spencer Millerberg and Justin Maner
Spencer Millerberg is the Founding Partner of DetailPage, which helps brands optimize traffic and gain Amazon market share. He founded OneClickRetail, the first Amazon market share measurement tool that was sold to Asscential. As an eCommerce and data analytics expert, Spencer has helped over 650 brands improve sales, margins, and search positions on eCommerce sites. Justin Maner is the Founding Partner of DetailPage. He was also the CEO of Data Spark, a startup that offered actionable insights to brands and sellers on Walmart Marketplace. Having spent 10 years as an Amazon director, Justin led the baby registry to become the #1 US registry, reinvented the vendor negotiation process, and created a new communication system for vendors and sellers. In this episode… As brands compete for shelf space on digital retailers like Amazon, Walmart, and Target, market share has become top of mind for many. With fragmented data sources, outdated PDPs, and competition at an all-time high, how can you drive retail sales and market share on Amazon? Data insights masters Spencer Millerberg and Justin Maner stress the importance of acquiring accurate first- and third-party data sources to measure performance and market share. These can be collected and analyzed using disruptive, AI-driven technology that’s affordable and 95% accurate. Driving retail sales requires increasing traffic and conversions, so Justin and Spencer advise optimizing your PDPs for competitor keywords. Yet rather than gauging competition based on specific categories, you must analyze keywords customers use when searching for similar products. This allows you to segment competition effectively.  Tune in to this episode of The Digital Deep Dive as Aaron Conant invites Spencer Millerberg and Justin Maner, Founding Partners of DetailPage, to speak about gaining market share in the competitive Amazon landscape. Together, they talk about disruptive technologies in eCommerce, how to update PDPs using relevant competitor keywords, and how to allocate first- and third-party data.
55:30 2/15/24
Winning With Site Speed, Conversion, and Security With Ajay Kapur
Ajay Kapur is the GM and CTO of Security and Applications at Edgio, a platform helping companies deliver online experiences and content. In his role, he handles product management and marketing, engineering, infrastructure, and technology operations. Ajay was the Co-founder and CEO of Layer0, a developer-focused platform-as-a-service that was acquired by Edgio. Before founding Layer0, he published mobile apps and invested in technology companies for Goldman Sachs’ private equity arm. In this episode… Website speed and performance are at the forefront as many eCommerce brands try to secure conversions. Yet instantaneous and seamless site experiences can be compromised by unwanted traffic, data theft, and other security concerns. How can you integrate site speed, performance, and security to improve online shopping experiences and generate quality conversions? According to web developer Ajay Kapur, unauthorized traffic and compromised data diminish site speed, resulting in a cumbersome user experience. CDN security removes unwarranted traffic and safeguards workflow data to free up your infrastructure. However, achieving instant website speed and above-average performance requires recreating retail shopping experiences and increasing available products by eliminating page load times. This optimized performance accelerates conversion rates and revenue per user.  On today’s episode of The Digital Deep Dive, Aaron Conant hosts Ajay Kapur, the GM and CTO of Security and Applications at Edgio, for a conversation about site speed, performance, and security. Ajay shares strategies for analyzing website speed and performance, how to surpass competition through high-performing websites, and online shopping trends and experiences.
45:59 2/8/24
Finding the Voice of the Shopper via UGC With Kim Rayburn
Kim Rayburn is a Client Engagement Advisor at Cohley, a content generation and testing platform that helps brands create content for social ads, email marketing, websites, and more. She is also a Principal and Consultant at Topnotch Consultancy, where she helps companies transform their sales growth strategies. With 25 years of consumer-focused experience in various global executive roles, Kim has worked in research, finance, product development, retail, and analytics. In this episode… With brands competing for consumer attention, observing shoppers’ behaviors, preferences, and demands has become crucial for engagement and sales. How can you capture the shopper’s voice to foster lifetime brand loyalty? As a consumer insights analyst, Kim Rayburn emphasizes creating a content strategy to recognize and adapt to customer feedback throughout each stage of their journey. This involves generating authentic content like video testimonials highlighting a brand’s compelling features to drive purchasing decisions. Consumers rely heavily on reviews to make decisions, so Kim recommends integrating text and video reviews demonstrating daily use cases and overall value. Brands can harness and summarize insights from shopper responses to refine and optimize their strategies. In today’s episode of The Digital Deep Dive, Aaron Conant welcomes Kim Rayburn, a Client Engagement Advisor at Cohley, for a discussion about leveraging the shopper’s voice through UGC content. Kim describes how to optimize UGC content, how AI is fundamentally altering paid media, and the top retail trends and priorities for 2024.
45:07 2/1/24
2024’s Most Impactful Digital Marketing Trends 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… As brands gear up for 2024, there are three major shifts they must navigate: the widespread use of AI chatbots, the end of third-party cookies, and the metaverse revival. How can you capitalize on these trends to gain a competitive advantage in 2024 and beyond? With AI fundamentally altering the digital marketing agency structure, online marketer Udayan Bose has observed leading companies leveraging chatbots to generate consumer data insights, personalize the online shopping experience, and enhance search results. Udayan emphasizes these chatbots’ roles as personal search assistants, facilitating personalized and accurate answers to complex questions. By the end of the year, Google will disable third-party cookies completely. Yet only 15-20% of marketers are prepared for this change. Alternatively, you can leverage retail media to combine in-store and online advertising, circumventing new privacy regulations. Although the metaverse has primarily targeted gamers in the past, Udayan predicts that Apple’s release of a mixed-reality headset in February will restore interest by revolutionizing social commerce. Tune in to this segment of The Digital Deep Dive as Aaron Conant welcomes Udayan Bose, the Founder and CEO of NetElixir, back to the show to discuss the pressing digital marketing trends of the near future. Udayan explains his company’s AI-first efforts, how to manage rapidly changing digital marketing trends, and the growing potential of retail media.
44:45 1/25/24
Multichannel Retail Media Success With Nate Pinkston and Paul Brenner
Nate Pinkston is the Head of Growth for Retail Media at Microsoft, where he manages end-to-end ownership of sales, customer success, and account management for the world’s largest retail media networks. As a digital marketing and engagement leader, he uses analytics to develop innovative solutions in the AdTech, MarTech, and retail industries. Nate has led teams to design and launch new products, reach new customer segments and markets, and work with C-suite executives to drive growth. Paul Brenner is the SVP of Retail Media and Partnerships at Vibenomics, an in-store advertising audio and display media publisher for retailers. With 30 years of experience in retail media technology, he has worked across areas, including media and entertainment, advertising, manufacturing, pharma, retail, and automotive. Paul specializes in helping brick-and-mortar businesses enhance their in-store shopping experiences by leveraging retail media. In this episode… Retail media is gaining traction in the digital advertising ecosystem, and retailers are leveraging it to drive in-store conversions. Yet with multichannel advertising a growing necessity and ad dollars spread thin, how can you incorporate retail media seamlessly into your strategy? Digital impressions drive many point-of-sale conversions online, but with 80-85% of these conversions occurring in-store, retailers must engage shoppers through visual and auditory mediums. However, retail media mavens Nate Pinkston and Paul Brenner say you must combine in-store and digital advertising and retail media to generate conversions across multiple channels. This requires attributing impressions to specific campaigns and retail media networks through transparent data analytics and distributing ad spend across corresponding channels. A strong relationship with retail media networks is the foundation for an effective strategy. Join Aaron Conant in this episode of The Digital Deep Dive as he chats with Nate Pinkston of Microsoft’s retail media department and Paul Brenner of Vibenomics about developing a retail media advertising strategy. Together, they share best practices for adopting retail media, how AI enhances retail media effectiveness, and how to leverage retail media for creative ad campaigns.
47:37 1/18/24
Increasing Conversion Through Optimized Delivery With Corey Apirian
Corey Apirian is the CEO of Davinci Micro Fulfillment, a full-service logistics company that uses technology and partners with brands and retailers to help market, sell, fulfill, and ship their products. As an accomplished supply chain and operations leader, Corey has over 15 years of senior management experience. With more than 20 years of experience in the eCommerce fulfillment industry, Corey has been drop shipping for every major retailer since 2004 and has launched over 50 different subcategories through individual online and brick-and-mortar channels. In this episode… Many brands consider expanding into DTC channels, but with only one fulfillment center, they struggle to achieve optimal delivery times in various areas. With profitability a top concern in fulfillment and delivery, how can you meet consumer demands to drive additional conversions? Instituting multiple hyper-local fulfillment centers throughout the country reduces shipping costs while ensuring inventory reaches the end consumer in 1-2 days. However, direct fulfillment alone is not enough to secure conversions. As fulfillment leader Corey Apirian notes, DTC delivery is a holistic process involving integrating multiple delivery methods and partners to maximize accuracy. Larger items may require you to leverage 3PL companies, whereas compact items can be shipped using Seller Fulfilled Prime to deliver directly to domestic Prime customers. In today’s edition of The Digital Deep Dive, Corey Apirian, the CEO of Davinci Micro Fulfillment, returns to chat with Aaron Conant about DTC fulfillment considerations for 2024. Corey explains the importance of transparency in communicating delivery times, why CPG brands should have a DTC presence, and inventory management strategies for profitability.
44:09 1/11/24
Delivery - Increasing Profitability and Expectations With Avi Moskowitz
Avi Moskowitz is the Co-founder and CEO of PrettyDamnQuick, a fast-growing eCommerce delivery app facilitating delivery experiences for top DTC and CPG brands. As an eight-figure veteran entrepreneur, he specializes in improving brands’ checkout conversions and shipping revenues. Avi also hosts the Delivering Delight podcast and co-founded BeerBazaar, a top-rated craft brewery with an online shop that became one of the top 10 Shopify stores in Israel. In this episode… As customer acquisition costs rise, brands try to generate conversions to secure loyalty and lifetime value. Checkout and delivery are often overlooked during the customer journey, with brands missing out on profitable opportunities. How can you optimize the fulfillment process to enhance the consumer experience? In traditional retail shopping, customers receive the item upon purchase. However, seasoned business owner Avi Moskowitz notes that when shopping online, customers leave the shop without the product and must wait for delivery. To cultivate trust during this variable period, you must communicate reasonable and thorough expectations of shipping and delivery, ensuring you fulfill this commitment accurately. This may entail establishing omnichannel fulfillment methods through multiple hyperlocal warehouses to meet demands efficiently.  In today’s episode of The Digital Deep Dive, Aaron Conant hosts Avi Moskowitz, the Co-founder and CEO of PrettyDamnQuick, for a conversation about increasing profitability through effective delivery. Avi shares how he conducts A/B testing at checkout, how to convert customers from checkout to delivery, and how to navigate shipping costs and delivery times.
45:54 1/4/24
Convergence of the Digital Shelf and Media With Mike Black
Mike Black is the CMO of Profitero, a leading eCommerce acceleration company offering intelligence-driven solutions for profitable growth. With a background in marketing, he held leadership positions in product marketing and demand generation at various global analytics companies. Before Profitero, Mike was the Vice President of Product Marketing at Nielson, where he launched new analytics products for the company’s retail measurement business. In this episode… Digital marketing has shifted from an occasional perk to a new business standard as brands optimize content to drive conversions on the digital shelf. Yet with so much demand for innovative content and record-high consumption rates, how can you test and measure your content to ensure your efforts generate maximum ROI? According to eCommerce-focused marketer Mike Black, the first step in content optimization is to assemble your briefs to target retail algorithms and advertise in the appropriate categories. However, keywords and competitors change dynamically and frequently, so you must leverage automation and other analytics tools to track incremental performance. Mike cites the digital shelf as a key performance driver but warns that data sets can become siloed, so by applying the data to various marketing channels like retail media, you can develop an integrated strategy for informed decision-making. In the latest episode of The Digital Deep Dive, Aaron Conant hosts Mike Black, the CMO of Profitero, who talks about the convergence of media, commerce, and the digital shelf. Mike addresses the democratization of eCommerce and technology, how to leverage software tools for paid media, and how data-driven insights boost content performance.
32:26 12/28/23
Breaking Down Amazon Data With Sreenath Reddy
Sreenath Reddy is the Founder of Intentwise, a technology platform that provides professional advertisers, large-scale aggregators, and high-volume agencies with automation, competitive intelligence, and data infrastructure for Amazon and other eCommerce sites. With more than 20 years of experience in the digital advertising and data analytics space, he utilizes AI to solve marketplace eCommerce challenges. Before founding Intentwise, Sreenath was the Senior Director of Marketing Strategy at Orbitz Worldwide. In this episode… With the rapid adoption of eCommerce, online marketplaces like Amazon and Walmart share more data than ever. Yet, as brands collect this data, it becomes fragmented within advertising, retail, and operations departments. How can you integrate data signals to make informed decisions? Data analytics problem solver Sreenath Reddy classifies data into three distinct categories: strategic, operational, and diagnostic. Strategic data comprises customer lifetime value, competition, and incrementality, in which brands must take a predictive approach to develop actionable insights. Analyzing operational data requires automating performance metrics from inventory levels, ad spend, and profitability. With diagnostic data, Sreenath recommends developing a system to identify potential disruptions, causes, and solutions.  In today’s edition of The Digital Deep Dive, Aaron Conant welcomes Sreenath Reddy, the Founder of Intentwise, back to the show to discuss analyzing and grouping Amazon data. Sreenath shares how to align ad spend with product profitability, how to analyze incrementality, and his mission to unify data signals.
29:36 12/21/23
Walmart Advertising Deep Dive
Michael Lebhar is the Co-founder and CEO of SellCord, which helps brands scale and maximize sales on He is also the Co-founder and CMO of Engaging, where he develops marketing campaign strategies. 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… When attempting to advertise on, many brands miss the mark and fail to spend effectively. What should you know about’s advertising landscape, and how can you structure your investments on the platform? According to specialist Michael Lebhar, advertising on the platform occurs through Walmart Connect, an integrated, self-service ad network for 1P and 3P brands. With significantly less competition than other leading ad platforms, profitability on Walmart Connect depends on your strategy and objectives and the placements you leverage. For instance, you can advertise on sponsored displays, the buy box, videos, or targeted items. Michael informs that emphasizes ad relevance, so optimizing your listing for search terms allows you to secure additional placements. In this part two episode of The Digital Deep Dive, Michael Lebhar, the Co-founder and CEO of SellCord, returns to talk with Aaron Conant about advertising on Michael discusses the rise of third-party sellers on the platform, how to reinvest in, and how to navigate the transition from Amazon to advertising.
41:45 12/14/23
Understanding the Ecosystem
Michael Lebhar is the Co-founder and CEO of SellCord, which helps brands scale and maximize sales on He is also the Co-founder and CMO of Engaging, where he develops marketing campaign strategies. 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… As the largest retailer in the world and the fastest-growing online marketplace in the US, Walmart has gained significant traction among brands. Yet many apply the same sales and growth strategies when selling on Amazon and struggle to achieve results, attributing the lack of sales to scarce demand and opportunity. What should you consider before selling on, and how can you scale on its marketplace? With fewer third-party sellers than Amazon, offers ample opportunity to drive sales growth in multiple categories. Additionally, Walmart merchants encourage growth by facilitating first-party vendor relationships, where the retailer lists your products and ensures high-ranking search results. With expertise in the early stages of, Michael Lebhar recommends evaluating profitable categories, opportunities, and competition before launching products on When transitioning from other marketplaces like Amazon, it’s crucial to alter your content, shipping, and growth strategy to align with Walmart’s ecosystem. In today’s episode of The Digital Deep Dive, Aaron Conant returns to welcome Michael Lebhar, the Co-founder and CEO of SellCord, for a conversation about Walmart’s online marketplace. Michael shares Walmart’s most profitable categories, how to facilitate long-term growth and partnerships on the retail site, and how to transition to the platform. 
40:50 12/7/23
Understand Growth With Retail Media and CTV
Chris Bruderle is the Vice President of Industry Insights and Content Strategy at the Internal Advertising Bureau (IAB), which empowers the media and marketing industries to thrive in the digital economy. As a web analytics, market research, advertising, and content expert, he has over 10 years of experience mining data and collecting insights for various web publishers.  In this episode… Retail media and CTV are the key drivers of growth in the digital advertising ecosystem. However, with consumer privacy regulations hindering targeting efforts, brands must maintain compliance while gathering insights. What should you know about the evolving digital media space, and how can you profit from it? Digital media researcher Chris Bruderle recommends partnering with retail media networks to obtain consumer insights in a privacy-compliant manner. Once you’ve gathered data from your target demographic, upload the information to a data clean room to remove sensitive material. Retailers can also integrate their first-party data and offer feedback and results-driven metrics. Leveraging CTV advertising is essential for profitability in the digital landscape, so Chris advises developing and adapting shoppable videos, QSR codes, and sponsored ads on streaming networks to encourage action from consumers.  In today’s episode of The Digital Deep Dive, Aaron Conant welcomes Chris Bruderle, IAB’s Vice President of Industry Insights and Content Strategy, for a discussion about the exponential growth of retail media and CTV. Chris addresses the integration of CTV and retail and social media, his predictions for live digital shopping, and how to maximize retail media spend.
43:43 11/16/23
China Market Entry Deep Dive
Jacob Cooke is the Co-founder and CEO of WPIC Marketing + Technologies, a leading eCommerce and technology consultancy driving growth for global brands in China, Japan, and Southeast Asia. Under his leadership, the firm has built an expansive solution set in data analytics, eCommerce activations and store management, brand strategy, creative campaigns, merchandising, and more. Having lived in Beijing since 2003, Jacob frequently contributes to Bloomberg on eCommerce, retail, and technology trends in China. In this episode… As sales growth in the US declines, brands are launching in the China and APAC markets to drive additional sales. eCommerce is a profitable market in China, with 50% of retail sales occurring online and 80% influenced by social platforms. What should you know about China’s eCommerce market, and how can you launch products there? As consumers focus more on health and wellness, categories like supplements, outdoor wear, and appliances have expanded significantly in Asian markets. With deep expertise in China market trends, Jacob Cooke emphasizes launching with an exclusive online strategy and innovating in these categories to demonstrate value to consumers. Partner with experienced agencies, leverage influencers, and live stream videos on Chinese platforms like Douyin to develop a widespread presence in these markets. Join Aaron Conant for another episode of The Digital Deep Dive as he interviews Jacob Cooke, the Co-founder and CEO of WPIC Marketing + Technologies, about breaking into the China eCommerce market. Jacob explains how to drive sales and target consumer demographics, the costs of launching in the market, and the difference between China, Japan, and South Korean markets.
41:25 11/9/23
Gen Alpha and Immersive Commerce
Michael Zakkour is the Founder and Chief Strategist at 5 New Digital, a consultancy that advises clients on strategy, structure, implementation, and transformation in the digital realm. Michael has over 20 years of experience in eCommerce, specializing in digital transformation, data science, the China/APAC market, digital commerce, and new retail strategy. He is also the Founder and Managing Director of China BrightStar, LLC. As an author and speaker, Michael has been interviewed by The Wall Street Journal, Forbes, NPR, the BBC, and many other media outlets. In this episode… Younger generations like Gen Alpha interact with commerce brands by balancing physical and digital interactions, playing video games like Fortnite and Roblox while socializing with friends. This online and offline integration has initiated a new retail class, where brands must amplify the shopping experience to reach younger audiences. How can you leverage immersive and experiential commerce to excel in the new digital age? With consumers becoming disinterested in two-dimensional shopping experiences, traditional eCommerce is underperforming. According to digital thought leader Michael Zakkour, eCommerce’s pervasive presence has led consumers to desire more meaningful interactions. Immersive commerce integrates live streams, shoppable videos, virtual environments, and avatars to create engaging and pragmatic experiences. Capitalizing on modern retail requires identifying top-performing digital tools and channels and developing a video commerce strategy involving streaming and live shopping videos with real-time purchasing options.  Tune in to the latest Digital Deep Dive episode as Aaron Conant welcomes Michael Zakkour, the Founder and Chief Strategist at Five New Digital, back to the show to discuss leveraging immersive commerce to engage younger generations. Michael shares actionable steps for success in the new digital realm, the importance of interactive video content, and how to optimize your budget for experiential commerce.
35:36 11/2/23
Marketing and the Attention Generation
Steven Moy is the CEO of Barbarian, a leading creative digital advertising agency. Throughout his career, Steven has worked on large-scale digital transformation initiatives for global brands, including American Express, McDonald’s, CVS Health, and AT&T. Since joining Barbarian in 2019, he has significantly reshaped the agency by launching its first global office, adding new clients, and initiating new business practices. In this episode… According to a recent study conducted by Insider Intelligence, social media is the first touch point for over 40% of consumers under 30. These younger generations consume hours of high-velocity, compelling content, prompting brands to compete for attention. How can you produce large volumes of creative content to target digital-first generations? As an early adopter of digital during the dot-com bubble, Steven Moy endorses attention economics, which forces brands to capture consumers’ limited attention spans on fast-paced, content-rich platforms like TikTok. Highly targeted content captures consumers within the first second and communicates value propositions in the following three to four seconds. To reach younger generations effectively, Steven recommends hiring college students to create engaging short-form videos that resonate with audiences. In today’s episode of The Digital Deep Dive, Aaron Conant welcomes Steven Moy, the CEO of Barbarian, to discuss creating content for digital-first generations. Steven explains how to adapt to the digital paradigm shift, AI and the metaverse’s roles in the creative process, and how to budget for rapid content creation.
46:10 10/26/23
Winning on Shopify in Q4
Brad Dey is the President of Dey’s End Consulting LLC, a full-service certified Shopify Plus partner focused on solving eCommerce and operational challenges. He has experience working on enterprise-level projects in financial services at Fortune 100 and 200 companies. As an eCommerce solutions architect, Brad has had CIO-level involvement at some of the world’s largest eCommerce companies. In this episode… At the height of Q4, profitability remains top of mind for many Shopify brands. As you evaluate new integrations and tools, how can you drive sales while managing demand challenges? Rather than exhausting resources by upgrading your front-end tech stack, eCommerce solutions consultant Brad Dey encourages brands to focus on optimizing their back-end operations to ensure sufficient demand. As you prepare for the holidays, manage your inventory by identifying your highest and lowest-selling products to determine discounted items. This allows you to develop an ideal cost structure for your 3PLs. With consumers purchasing and returning multiple sizes and variations of one product, you must develop systems to mitigate the resulting profit loss. Consider leveraging a sizing tool to provide customers with accurate sizes, boost loyalty, and improve experiences. Tune in to this episode of The Digital Deep Dive as Aaron Conant hosts Brad Dey, the President of Dey’s End Consulting LLC, who shares strategies for a profitable Q4 on Shopify. Brad explains how he conducts tech stack audits, Shopify’s new releases and functions, and how to integrate Buy with Prime and Shopify.
47:12 10/19/23
Measuring Incremental Retail Media ROI
Meghan Corroon is the 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 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… Incrementality has become imperative in distributing retail media spend and measuring sales growth from marketing efforts. With so many trending advertising channels and retailers, brands often invest in each one simultaneously, creating data silos and inhibiting visibility into top-performing platforms. How can you measure incremental ROI holistically? In today’s volatile economy, consumers are spending less money, so brands must invest in their shoppers’ most frequented platforms. According to data enthusiast Meghan Corroon, this requires evaluating your channel budgets and resulting performance to make real-time, data-driven decisions. After performing a comprehensive analysis, brands often find they’ve invested too much money in underperforming channels. By reducing your budget for low-engagement platforms, you can measure impacted sales growth to identify your most profitable networks and boost ROI. Tune in to this episode of The Digital Deep Dive as Aaron Conant invites Meghan Corroon, the Co-founder and CEO of Clerdata, to speak about measuring incremental sales growth on retail media networks. Meghan explains the importance of incrementality, real-time marketing analytics, and how the evolution of retail media has impacted brand growth.
45:37 10/12/23
Where the Digital Org Is Heading
Lauren Livak Gilbert is the 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 experience driving impactful multi-channel 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… Digital and eCommerce are necessary capabilities for brands, but integrating them at scale has become increasingly complicated. Some organizations position these functions in their IT departments, whereas others incorporate them in marketing or sales. How should you consider digital’s role in organizational structures? Digital shelf expert Lauren Livak says that while you may integrate eCommerce into your IT department initially, it must expand throughout the business. Evaluating your organizational structure helps you determine its primary focus and consolidate digital capabilities within the specified area and the remaining departments. This should include cross-functional collaboration and involve every member of the company. With retail media extending throughout all major merchandisers, connecting your advertising efforts to digital is crucial. When considering eCommerce’s position in your business objectives, prioritize your investments to target consumers in their most frequented channels rather than distributing your ad spend based on industry trends. In today’s episode of The Digital Deep Dive, Aaron Conant chats with Lauren Livak Gilbert, the Director of the Digital Shelf Institute, about digital’s place in organizational structures. Lauren talks about the barriers to rapid eCommerce acceleration, key shifts in organizational structures, and how to implement digital into business departments.
46:04 10/5/23