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Dan Brownsher is the Founder, Executive Chairman, and CSO at Channel Key, a full-service channel management marketplace agency. A recognized national thought leader in marketplace retail strategy and emerging eCommerce trends, Dan is a trusted commentator on Amazon and marketplace technologies and is frequently quoted by outlets such as Bloomberg, Forbes, Reuters, MSN.com, and the LA Times. He also co-founded Trend Nation, a top-200 global Amazon private label developer and seller that surpassed $1 billion in merchandise sales and achieved a private equity exit.

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

[1:41] Dan Brownsher shares his background and the evolution of Channel Key
[3:12] The role of consumer trust and eCommerce adoption in omnichannel growth
[7:01] How brands should approach omnichannel strategically
[12:08] How Channel Key helps brands identify and prioritize commerce channels
[17:10] What the Consumer Electronics Show revealed about agentic commerce and the future of digital transactions
[19:18] How brand websites, trust, and AI agents fuel future buyer journeys
[28:22] Dan’s top priorities for 2026: channel expansion, LLM indexing, and agentic commerce

In this episode…

As digital commerce scales across marketplaces and AI-driven experiences, brands aren’t deciding if they should sell online — they’re deciding which channels to prioritize, which products belong on each, and how to operate at scale. From Amazon and Walmart to TikTok Shop and emerging agent-led buying journeys, the number of viable paths to purchase is expanding fast. How can brands pursue growth without wasting margin, media spend, or internal resources?

According to national eCommerce thought leader Dan Brownsher, this shift is driven by consumer trust in digital commerce and expanding shopping habits across marketplaces. He advises brands to evaluate channels based on SKU-level profitability, fulfillment constraints, and measurable incrementality rather than solely omnichannel expansion. Dan also recommends narrowing assortment by channel, actively shifting media spend to where returns are provable, and using AI to accelerate analysis and execution — not replace judgment.

In this episode of The Digital Deep Dive, Aaron Conant chats with Dan Brownsher, Founder, Executive Chairman, and CSO at Channel Key, about the future of omnichannel commerce. Dan discusses why consumers are driving marketplace expansion, how brands should manage assortment and media across channels, and what agentic commerce and AI-powered discovery mean for search, trust, and buying behavior.

Resources mentioned in this episode:

Quotable Moments:

“Ultimately, what that boils down to my brand is trust. People trust that they consume products on the internet.”
“You don’t need to be on every channel. There’s still specific channels that work for brands.”
“It’s not just a syndicate and push everything. That ain’t the way. That is not the way.”
“Brands are built off of trust with the consumer, and is the trust layer going to be with the agents?”
“It takes a long time to earn credibility and trust, but you can lose it really quickly.”

Action Steps:

Audit channel profitability at the SKU level: Understanding margin, fulfillment costs, and media efficiency by product prevents unprofitable omnichannel expansion. This ensures growth decisions are driven by economics, not assumptions or pressure to be everywhere.
Limit channel expansion to where customers already shop: Prioritizing marketplaces based on real customer behavior reduces wasted operational effort. This keeps teams focused on channels that can efficiently scale revenue.
Actively reallocate media spend across marketplaces: Shifting budgets based on incrementality and performance maximizes return on ad spend. It also prevents overspending on channels that no longer deliver profitable growth.
Use AI to increase speed, not replace strategy: Leveraging AI for analysis, forecasting, and content production improves efficiency while preserving human judgment. This allows teams to manage complexity without sacrificing strategic control.
Prepare for agent-driven product discovery now: Optimizing data, content, and indexing for LLMs positions brands for emerging buying behaviors. Early preparation reduces risk as search, trust, and transactions evolve beyond traditional marketplaces.

About BWG Connect...

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

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

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

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

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.

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

[1:22] Max Sinclair introduces Azoma’s mission in AI-driven brand recommendations
[3:19] What is agentic commerce?
[5:00] How AI health agents are changing consumer trust, personalization, and buying behavior
[9:27] Steps brands should take to prepare for AI recommendations and agent-driven shopping
[18:01] The importance of hands-on experimentation for AI learning
[24:41] A future-looking view on world AI models and their potential impact on commerce and media

In this episode…

AI is no longer just influencing how people search; it’s starting to decide what they buy. As intelligent agents take on more decision-making, brands are facing a future where visibility depends less on ads and more on recommendations. How should businesses prepare for an environment where AI chooses on behalf of the consumer?

Max Sinclair notes that agentic commerce is already emerging, driven by AI systems that can analyze multiple data points and make personalized decisions for users. As an expert in AI-driven commerce and digital optimization, he emphasizes that brands must optimize for how AI understands, evaluates, and recommends products, not just how humans search. Max advises moving fast, aligning content across channels, and empowering teams to experiment rather than wait for certainty. The brands that act decisively now can leverage AI-driven recommendations effectively.

In this episode of The Digital Deep Dive, Aaron Conant chats with Max Sinclair, Founder and CEO of Azoma, about the rise of agentic commerce and its implications for brands. Max shares how AI agents influence purchasing decisions, what companies must do to stay visible in AI search, and why fast organizational adoption will define the winners in 2026.

Resources mentioned in this episode:

Quotable Moments:

“It's not truly agentic because it's not taking multiple independent steps.”
“This adoption moves quicker than anyone thinks is even possible.”
“What better way to learn than just to jump into it?”
“Either you…want to be part of it, or you don't.”
“I think we will move in 2026 beyond LM and the large language model.”

Action Steps:

Establish an AI readiness task force: Creating a cross-functional team with executive backing enables faster decision-making and experimentation as AI-driven commerce evolves. This prevents bottlenecks and ensures your brand adapts at the speed of AI adoption.
Optimize content for AI recommendations, not just search engines: AI agents evaluate context, credibility, and narrative consistency across channels. Aligning messaging across product listings, websites, and PR increases the likelihood of being recommended by AI systems.
Empower teams to experiment and learn by doing: Hands-on testing with AI tools builds real understanding faster than training alone. This approach helps teams stay current as AI capabilities and consumer behaviors shift rapidly.
Secure senior leadership buy-in early: Agentic commerce impacts revenue, marketing, and operations, making it a C-level priority. Leadership support ensures resources, authority, and urgency are aligned with the scale of the change.
Act before certainty arrives: Waiting for perfect clarity risks falling behind competitors already adapting. Early action allows brands to learn, iterate, and defend visibility before AI-driven buying behaviors become the default.

About BWG Connect...

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.

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

[2:11] Chris Perry breaks down the hype versus reality of AI
[6:00] How AI will eliminate, reshape, or hybridize roles rather than boost productivity
[10:43] Step zero for AI adoption: experimenting with tools to build comfort and intuition
[20:03] Navigating organizational restrictions, security concerns, and uncertainty around AI usage
[26:10] The emerging workforce categories created by AI, including displaced, reskilled, fractional, and AI-native roles
[33:49] How continuous learning, community conversations, and humility sustain relevance in AI-driven environments

In this episode…

AI has sparked excitement, fear, and confusion across the digital and commerce landscape. Leaders are pushing adoption, teams are unsure of how to respond, and individuals are left wondering what it implies for their careers. How can professionals prepare for an AI-driven future without being left behind?

Commerce and digital transformation leader Chris Perry notes that professionals can manage AI’s impact by taking ownership of their learning. He urges professionals to start by experimenting with AI tools, then applying them to eliminate tedious tasks and elevate strategic thinking. By asking intentional questions, understanding the tools required for the work, and reshaping your role, AI can enhance, rather than replace, your value.

In this episode of The Digital Deep Dive, Aaron Conant talks with Chris Perry, Co-founder and Chief Learning Officer at firstmovr, about how AI is reshaping work and careers. Chris discusses the hype of AI, practical first steps for adoption, and how professionals can reskill to stay indispensable.

Resources mentioned in this episode:

Aaron Conant on LinkedIn
BWG Connect
Chris Perry: LinkedIn | Email
firstmovr: Website | Email
Oskar Kaszubski: LinkedIn | Email
What Color Is Your Parachute?: Your Guide to a Lifetime of Meaningful Work and Career Success by Richard N. Bolles
Good to Great: Why Some Companies Make the Leap...And Others Don't by Jim Collins

Quotable Moments:

“There is a lot of hype around AI, but also less positive forecasting for what that means for work.”
“AI plus human equals Super Mario. Mario plus mushroom equals fire Mario.”
“One plus one can equal three. It’s not to totally remove all jobs.”
“Don’t then go, ‘oh, the tool stinks.’ No, you stink because you don’t know how to use it.”
“Be so good they can’t ignore you. Be indispensable because you’ve figured out how to add immense value.”

Action Steps:

Start using AI tools in low-risk, personal ways: Experimenting with AI outside of work builds comfort and confidence without fear of making mistakes. This hands-on familiarity makes it easier to apply AI effectively in professional settings later.
Learn how to ask better questions with AI: Strong prompts lead to better outputs, making AI far more useful for real work. Developing this skill helps you move beyond surface-level results and unlock meaningful productivity gains.
Identify and automate your most tedious tasks: Removing repetitive, low-value work frees up time for strategic thinking and higher-impact contributions. This shift makes your role more valuable and harder to replace.
Clarify which AI tools are approved at your organization. Understanding which tools you’re allowed to use reduces hesitation and inaction. Clear boundaries empower experimentation while minimizing risk.
Proactively evolve your role with AI in mind: Adapt your responsibilities before change is imposed, putting you in control of your career path. This approach helps ensure AI enhances your impact rather than diminishing it.

About BWG Connect...

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.

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

[1:43] Davinci Micro Fulfillment’s approach to placing inventory closer to customers through a distributed network
[5:11] Fulfillment as a growth lever amid TikTok commerce, tariffs, and Amazon capacity limits
[9:35] How fulfillment strategy impacts profitability, customer experience, data visibility, and marketing performance
[13:10] Corey Apirian debunks the myth that faster delivery costs more and explains how proximity improves margins
[18:59] How Amazon’s evolving fulfillment model favors precision, smaller facilities, and faster delivery windows
[22:59] The importance of multi-marketplace visibility, real-time inventory control, and fast delivery

In this episode…

Fulfillment has become a competitive advantage in eCommerce. With TikTok accelerating demand, Amazon tightening constraints, and customer expectations shifting toward faster delivery, brands are being forced to rethink how products reach buyers. How can you build a fulfillment strategy that keeps pace without destroying margins?

According to omnichannel fulfillment authority Corey Apirian, brands should start leveraging fulfillment as a growth lever rather than a back-end cost center. This involves placing inventory closer to customers, matching delivery speed to buying behavior, and using data to align marketing and operations. Corey maintains that faster delivery doesn’t always mean higher costs and that intentional assortments, bundling, and carrier selection can improve conversion and profitability. Fulfillment works best when it’s designed as a coordinated system rather than a standalone function.

In this episode of The Digital Deep Dive, Aaron Conant talks with Corey Apirian, CEO of Davinci Micro Fulfillment, about how fulfillment strategy is reshaping eCommerce growth. Corey shares why inventory proximity drives conversion, how Amazon and TikTok are changing delivery expectations, and what brands must prioritize in 2026 to stay competitive across channels.

Resources mentioned in this episode:

Quotable Moments:

“You don’t have to, like, pick one of three. You can have speed and precision and cost and quality.”
“The whole key is to move inventory closer to the end customer, which is what everyone's trying to do right now.”
“You have to fish where the fish are, right? So you can’t just sell the same item everywhere.”
“It’s an orchestration of good planning and good technology and good systems and process and people.”
“If you don’t have your inventory closer to that final destination, it’s hard to take advantage of that.”

Action Steps:

Place inventory closer to your customers: Shortening the distance between products and buyers improves delivery speed and reduces shipping costs. This directly boosts conversion rates while protecting margins as delivery expectations rise.
Design fulfillment strategies by channel, not by convenience: Different marketplaces demand different assortments, service levels, and delivery speeds. Aligning fulfillment with how customers actually buy on each platform increases relevance and profitability.
Use fulfillment data to inform marketing decisions: Delivery speed, availability, and inventory placement influence ad performance and conversion more than many brands realize. When operations and marketing work together, spend becomes more efficient and scalable.
Build density through intentional assortment and bundling: Higher order values and repeatable product mixes create the volume needed for better carrier rates. This density lowers per-unit fulfillment costs and unlocks faster delivery options.
Treat fulfillment as a strategic capability, not a back-end function: Planning, technology, people, and carriers must operate as a coordinated system. Brands that orchestrate fulfillment well gain flexibility, resilience, and a long-term competitive advantage.

About BWG Connect...

Danny Silverman is the Executive Vice President of Digital Commerce at Market Performance Group, a leading end-to-end strategy and services omnichannel commerce agency. He is also the Founder and Digital Strategy and Growth Consultant at Silverstream Strategic Consulting. As a digital commerce executive, Danny 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.

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

[1:13] Danny Silverman explains his role at Market Performance Group and the fundamentals of eCommerce
[3:55] Using traffic-and-conversion principles to explain AI, automation, and digital priorities to executive teams
[7:55] The shift from keyword-based optimization to contextual content across PDPs and digital assets
[10:35] Limitations of current AI tools and the importance of human oversight
[12:47] How AI-driven search behaviors on ChatGPT, Google, and Amazon Rufus are reshaping shopper discovery
[18:45] The impact of tariffs and guaranteed margin demands on 1P relationships and the shift to 3P
[23:46] Inventory challenges during peak season and the rise of micro-fulfillment and SFP alternatives
[28:47] Danny’s optimism for omnichannel integration and the influence of TikTok on eCommerce performance

In this episode…

Brands are overwhelmed by rapid shifts in AI, search behavior, and digital commerce expectations. With executives demanding clarity while teams face mounting complexity, how can companies cut through the noise and refocus on what drives growth?

Seasoned digital commerce expert Danny Silverman says that brands should return to eCommerce fundamentals: traffic and conversions. He urges them to streamline assortments, double down on high-quality contextual content, and use AI tools as enhancers — rather than replacements — for human judgment. This helps leaders translate emerging trends into practical actions that strengthen performance instead of complicating it.

In this episode of The Digital Deep Dive, Aaron Conant sits down with Danny Silverman, Executive Vice President of Digital Commerce at Market Performance Group, to discuss navigating AI-driven commerce. Danny explores contextual content’s rise, the need to focus on profitable hero items, and how shifting 1P and 3P dynamics impact brand strategy.

Resources mentioned in this episode:

Quotable Moments:

“The tools are awesome, the productivity tools are fantastic, but you have to have that human in the loop.”
“If your content was in the keyword stuffing game, I think you were already behind the times.”
“It comes back to the depth of content, I think, in categories where there's a lot of ASINS.”
“There's a really increased importance on looking carefully at your assortment.”
“That human in the loop is so critical to making sure that it's staying on task.”

Action Steps:

Refocus on your hero products: Concentrating spend and effort on top-performing SKUs strengthens profitability and improves algorithmic visibility. This focus ensures your resources have the greatest impact rather than being diluted across underperforming items.
Upgrade PDPs with contextual content: Shoppers now search in natural language, so pages must answer real questions rather than stuff keywords. This shift improves discovery across AI-driven search tools and strengthens conversion.
Use AI tools with human oversight: Automation accelerates workflows, but models drift and misunderstand brand nuances without guidance. Keeping a human in the loop maintains accuracy, protects brand voice, and prevents costly errors.
Align pricing strategy across sales channels: Amazon’s algorithms can suppress or match prices, affecting both 1P and 3P sellers. Managing omnichannel pricing prevents margin erosion and protects the buy box.
Plan inventory and fulfillment proactively: FBA constraints tighten during peak seasons, risking stockouts or blocked shipments. Strengthening backup fulfillment options ensures continuity, maintains Prime eligibility, and protects holiday revenue.

About BWG Connect...

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.

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

[1:15] How Todd VanderStelt and Sam Hager met and founded MixShift
[3:45] Todd shares his forecasting background at Amazon and the origins of MixShift’s top-down model
[7:43] How MixShift connects ad spend and revenue to guide forecasting decisions
[10:30] The three key drivers of MixShift’s forecasting model: ad spend, seasonality, and organic trends
[14:25] How historical data shapes forecasts and reveals insights from unexpected sales spikes
[19:05] Integrating MixShift’s forecasting tools into inventory planning
[22:30] Future developments for unit-level forecasting and customer acquisition modeling at MixShift

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.

Resources mentioned in this episode:

Aaron Conant on LinkedIn
BWG Connect
Todd VanderStelt on LinkedIn
Sam Hager on LinkedIn
MixShift: Website | Forecasting Tool | Email | LinkedIn

Quotable Moments:

“One of those things that hasn't changed is forecasting — is still a really hard thing to do.”
“We were trying to solve our own problems, frankly, and got pulled into a lot of those data problems.”
“If you can identify the key inputs that drive your forecast, you can basically aggregate all those errors.”
“There's this trade-off of profitability and revenue that we're always kind of faced with as operators.”
“You can't actually isolate the impact of advertising on your revenue without separating out these pieces.”

Action Steps:

Build forecasting models from the top down: Starting with total revenue and spend data reduces complexity and improves accuracy across large catalogs. This approach helps teams make confident, data-driven decisions even with incomplete SKU-level data.
Connect ad spend directly to revenue outcomes: Understanding the relationship between marketing investments and sales allows for smarter budgeting and realistic growth goals. It ensures spending aligns with actual performance rather than assumptions.
Incorporate qualitative insights into quantitative models: Adding context like promotions or media exposure helps refine forecasts and explain unexpected sales spikes. This balance of data and human insight strengthens decision-making across teams.
Use historical data for trend recognition: Analyzing at least two years of sales and spend history reveals reliable seasonality and organic growth trends. These patterns guide strategic planning and help brands anticipate market shifts.
Continuously validate and adjust models: Monitoring forecast accuracy over time ensures the model evolves with changing business conditions. Regular refinement keeps predictions relevant and actionable for leadership and operations.

About BWG Connect...

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.

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

[1:54] Spencer Millerberg shares his background at Amazon and Walmart and how he founded OneClick Retail before DetailPage
[4:11] The rise of AI-driven shopping and ChatGPT’s influence on product discoverability
[8:48] How brands can improve visibility through detailed website content and ChatGPT product feeds
[14:30] Why most brands fail at SEO by prioritizing internal product language over customer terms
[18:22] How adding context to product content improves discoverability
[25:19] Using ROI dashboards to identify and optimize overlooked B SKUs
[31:13] How DetailPage helps brands sustain organic growth and outperform competitors

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.

Resources mentioned in this episode:

Quotable Moments:

“About 61% of customers are using AI to shop now.”
“Retailer content actually has become the highest weighted source for these AI recommendations that you have.”
“You got to have the why in order to match up.”
“If you're going to remodel your kitchen, don't just take care of the sink.”
“We're seeing about a 17% average lift on organic search when customers optimize for GEO and SEO.”

Action Steps:

Audit and update your SEO content quarterly: Regular updates keep your listings aligned with changing search algorithms and customer behavior. Fresh content also earns a temporary bump in visibility from major retailer platforms.
Optimize for both SEO and GEO (Generative Engine Optimization): Balancing search engine keywords with generative AI context ensures your products are discoverable across Google, Amazon, and ChatGPT. This dual strategy strengthens visibility in traditional and AI-driven recommendations.
Focus on your B SKUs: Mid-performing products often have untapped potential and can drive major growth when optimized. Prioritizing these SKUs boosts sales without relying solely on top sellers.
Use customer language, not internal product terms: Writing listings the way customers actually search bridges the knowledge gap. This shift improves discoverability and aligns your brand with search intent.
Leverage retailer and brand site content strategically: Ensure both your retailer listings and brand pages contain rich, structured product data. These are the highest-weighted sources AI tools and LLMs use for product recommendations.

About BWG Connect...

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.

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

[1:23] Aaron Schwartz shares his career trajectory from founding Modify Watches to co-founding Orita.ai
[4:22] Why brands overuse email during downturns and how it hinders engagement and deliverability
[9:20] How machine learning reveals insights missed by rules-based customer segmentation
[15:17] Why inbox placement and timing matter more than click or spam metrics
[19:51] Common mistakes brands make in retention marketing
[23:18] How retention marketing leadership varies across organizations
[31:34] The founding story of Orita.ai
[35:42] Aaron’s views on AI and personal shopping agents

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.

Resources mentioned in this episode:

Quotable Moments:

“Let's not think about segmentation based on time bound. Let's go build a very, very big model.”
“Take off your marketer hat and put on your consumer hat; don't be the brand that emails somebody.”
“Stop thinking about metrics and start thinking about your customer and when they want to hear.”
“If you're not questioning your priors all the time, those are the places it becomes hard.”
“Focus on what is the job to be done first before you go try solutions.”

Action Steps:

Use data-driven segmentation instead of rules of thumb: Relying on clicks or opens over fixed timeframes misses valuable customers. Machine learning models uncover deeper engagement patterns and help send the right message at the right time.
Balance communication frequency with customer preference: Over-sending emails can lead to unsubscribes and deliverability issues, even if it boosts short-term revenue. Respecting audience tolerance builds long-term trust and stronger retention.
Expand beyond email to multiple retention channels: SMS and direct mail can be profitable when targeted to the right segments. Diversifying outreach increases touchpoints without overwhelming customers.
Adopt a consumer-first mindset in marketing decisions: Thinking like your customer shifts the focus from what the brand wants to when the customer is ready. This improves engagement and reduces wasted effort.
Align leadership expectations with data insights: Mandates to send more campaigns often conflict with what the numbers say will work best. Empowering teams to follow the data prevents burnout and strengthens customer relationships.

About BWG Connect...

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.

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

[1:37] Lauren Livak Gilbert introduces the reinvented omnichannel organization of the future
[3:01] Why companies must evolve their organizational structure to match consumer shopping habits
[6:21] The stages of organizational maturity and the three key principles of reinvention
[11:38] Amazon’s shift toward automated negotiations and Walmart’s expanding partnership opportunities
[16:25] How AI can automate forecasting and content creation
[23:23] Lauren’s future vision of humans as strategic orchestrators supported by AI agents
[32:32] Embracing data-driven decisions and learning through experimentation and failure

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.

Resources mentioned in this episode:

Quotable Moments:

“What I actually found is that we're asking the wrong question about where eCommerce should sit.”
“You have to show up to your customers as one company, not separate disconnected teams.”
“If every team is doing something different, it's just common sense you're not going to reach goals.”
“You can use AI to automate a lot of forecasting and free up more mindshare.”
“Brands waiting to play around with AI will be light years behind when competitors move quickly.”

Action Steps:

Establish shared goals across departments: Aligning marketing, sales, and eCommerce teams ensures everyone works toward the same outcomes and prevents teams from competing against each other. This unified focus drives higher eCommerce sales and builds organizational cohesion.
Present a single face to retailers: Showing up as one company when working with retail partners fosters trust and clarity. This approach avoids miscommunication and helps negotiate stronger opportunities for growth.
Invest in data standardization: Cleaning and organizing your data infrastructure prepares the business for seamless AI integration. Without accurate and consistent data, AI tools cannot deliver reliable insights or value.
Use AI to automate repetitive tasks: Automating forecasting, content creation, and other manual work frees employees to focus on strategy and innovation. This shift enables teams to think more holistically and drive long-term growth.
Redefine HR recruitment and career paths: Updating hiring practices to identify and develop digital-savvy leaders ensures a strong talent pipeline. Preparing future leaders now safeguards the organization against skill gaps as technology and commerce rapidly evolve.

About BWG Connect...

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®.

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

[1:13] How Jana Weinstein joined TikTok Shop’s founding team and her leadership role at Blue Wheel Media
[2:43] Insights on TikTok’s growth and opportunities for brands
[6:42] Three key reasons to leverage TikTok Shop: audience reach, the halo effect on other channels, and revenue potential
[12:43] How affiliates and creators drive TikTok Shop revenue and an overview of the affiliate program
[20:39] The shift from creating viral content to focusing on targeted influencer and affiliate marketing
[23:14] New AI-driven tools and first-party data initiatives on TikTok
[28:08] Navigating TikTok Shop operations by partnering with agencies

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.

Resources mentioned in this episode:

Quotable Moments:

"I was one of the first 50 founding members of the TikTok Shop US team."
"Creators are the lifeblood of the platform, so after you gain followers, lean into affiliates."
"If you are going to be measuring your affiliates within the platform, TikTok Shop is the way."
"There is validity in investing in this channel, but it can’t be with hopes to go viral."
"It's important to build that community…because they essentially are your salespeople selling for you."

Action Steps:

Start posting authentic TikTok content consistently: Regular posting trains the algorithm and builds recognition without requiring polished production. Consistency helps brands reach audiences faster and sets the foundation for future paid growth.
Use paid media to amplify reach: Boosting organic content with paid ads accelerates follower growth and improves placement on For You pages. This early investment ensures content reaches potential customers beyond initial followers.
Build an affiliate creator program: Affiliates drive the majority of TikTok Shop revenue and act as dedicated brand advocates. Developing a strong creator network increases sales and provides authentic promotion to engaged audiences.
Cultivate long-term relationships with key creators: Establishing ongoing partnerships fosters loyalty and enhances brand storytelling over time. Strong relationships encourage creators to consistently promote your products and generate repeat revenue.
Monitor and adapt to TikTok’s evolving features and data tools: The platform changes rapidly, from AI-driven analytics to new seller tools. Staying updated allows brands to leverage new capabilities and maintain a competitive edge.