Checkin to Checkout

About Checkin to Checkout

We tell the stories of e-commerce leaders and let them explain how they got where they are, and where they think e-commerce is going in the next 12 months. In every episode, we uncover something that only this e-commerce leader can explain

Publisher

Justin Aronstein

Category

business

Language

en

Explicit

No

First episode

13 Jun 2025

Latest episode

15 Apr 2026

Latest episodes

26 episodes in the feed.

1. 

   15 Apr 2026

   The B2B Revolution Is Here (It Just Doesn't Look Sexy) - Daniele Tedesco

   Daniele Tedesco is responsible for e-commerce at a company most people have never heard of but everyone has touched. Essity makes $15B in annual revenue selling everything from the napkins at Dunkin' Donuts to incontinence products to medical compression devices. A billion people interact with their products every single day. As Global E-Commerce Process Owner, Daniele and his team built a single commerce template on SAP Commerce Cloud that powers both B2B and B2C across 14 markets. On one end, they're shipping a single pair of compression socks directly to a patient. On the other, they're filling entire trucks with janitorial supplies. Same platform. Same instance. Wildly different customers. But the most honest moment in this conversation isn't about architecture. It's about what happened when some of their brands pushed back on the enterprise solution. Not because it was broken. Because it wasn't fast enough for teams that wanted to experiment. Daniele's biggest learning: you can't police adoption. You have to attract people to it. We also get into why B2B e-commerce is approaching a major inflection point, how distributor ownership is aging out and digital-native successors are demanding better ordering experiences, the difference between going headless and headful on the same commerce instance, why Essity started with B2C to learn lessons before tackling the B2B side where revenue is 100X larger, how AI fits into a manufacturer's world where brand trust and hallucination risk create real tension, why machine-readable data and GEO are the unsexy priorities that will matter most in the next 12 months, and how the "wedding cake" template model lets brands customize the top layer while sharing a common foundation underneath. If you're managing e-commerce across multiple brands, multiple markets, or both B2B and B2C on the same platform — and you've ever struggled to get internal teams to adopt the thing you built for them — this one's for you. Want any help Personalizing Every Customer Touchpoint? Check out https://Mobile1st.com Interested in talking to Justin or getting on the show, find him on LinkedIn: https://www.linkedin.com/in/justinaronstein/ Key Topics: Attraction over policing: why forcing platform adoption across brands creates more resistance than buy-in Building a composable commerce template that scales across 14 markets for both B2B and B2C on SAP Commerce Cloud The "wedding cake" architecture: shared base layer, business-type middle layer, and brand-specific customization on top Headless vs. headful on the same commerce instance — and why different business units need different approaches Why Essity's B2B revenue is 100X their B2C — and why they tackled B2C first anyway The B2B e-commerce revolution: aging distributor owners, digital-native successors, and a growing digital maturity gap PunchOut as a channel for small and mid-sized B2B customers who don't have an ERP or EDI capability Why manufacturers approach AI differently — back office enablement first, customer-facing later, because hallucination risk meets decades of brand trust Machine-readable data and GEO as the next SEO — the unsexy cleanup work that will separate winners from everyone else How professional buyers already expect Amazon-level digital experiences at work and the gap is only growing The Project Hail Mary connection: invisible infrastructure layers that executives never appreciate until they break Why capability-focused conversations create neutral ground when internal teams get stuck debating tools

2. 

   8 Apr 2026

   Everything Is Downstream from Your ERP - Wayne Stratbucker

   Wayne Stratbucker has seen both sides of the omnichannel equation. He's helped brands sell on Amazon, Walmart, TikTok Shop, and Instagram. He's watched clients try to modernize their frontend while their ERP runs on a green screen. And he's had it with the LinkedIn vaporware parade of "I built a full e-commerce app in a day." Now, as Senior Ecommerce Strategist at Codel, Wayne works across the full stack of digital commerce — translating business goals into technical requirements, building omnichannel growth strategies, and pushing clients to fix what's broken before chasing what's shiny. But Wayne's hottest take isn't about channels or platforms. It's that the e-commerce industry is lying to itself about what AI can actually do today. Vibe coded checkout flows that can't survive an hour of UAT. Apps that look great in a LinkedIn post and fall apart the moment real money touches them. Wayne's argument: if you work in e-commerce, you know what a shippable product looks like. Start acting like it. We also get into why your ERP is the single most important (and most ignored) piece of your digital transformation, the difference between first party and third party marketplace strategy, how AI is finally breaking down the data literacy barrier so non-technical stakeholders can actually use the insights they've been sitting on for years, and why personalization doesn't require a six-figure platform purchase — just Shopify Flow and some customer tags. If you're a Director of E-Commerce who's been told to "do personalization" but can't answer basic segmentation questions yet, or you're staring at a backend system from the Clinton administration and wondering where to start — this one's for you. Want any help Personalizing Every Customer Touchpoint? Check out https://Mobile1st.com Interested in talking to Justin or getting on the show, find him on Linkedin: https://www.linkedin.com/in/justinaronstein/ Key Topics: The difference between first party and third party marketplace strategy — and how margin pressure changes the calculus Social selling versus social discovery: what it means to complete a purchase entirely on TikTok, Instagram, or Facebook without ever hitting your site Wayne's hot take: vibe coded e-commerce apps are vaporware — and the industry needs to stop pretending otherwise Why your ERP is the foundation everything else sits on, and why a green screen backend means you're already a decade behind The "2025 Civic with a 1972 engine" problem: how legacy backend systems silently kill digital transformation efforts How AI is democratizing data literacy — letting non-technical stakeholders ask questions of GA4 and data warehouses in plain language Why companies have more data than ever but aren't using it, and how AI changes that dynamic Personalization without a platform: using Shopify Flow, customer tags, and native tools to customize experiences by segment The "billboardification" of e-commerce: why there are now 50 options where there used to be 15, and what that means for capturing attention Channel-specific demographic targeting: why your TikTok audience and your Facebook audience might need completely different product experiences Data compliance and accessibility as non-negotiable foundations — and the $15K–$25K claims that catch businesses off guard Extreme Ownership applied to e-commerce leadership: why team failures are leadership failures, and how that mindset reduces churn

3. 

   1 Apr 2026

   E-commerce Replatforms: Setting Expectations, Cutting Scope, and Launching - Josh Johnston

   Josh Johnston has replatformed more than once. He's survived the executive pressure, the scope creep, the SI promises that don't hold, and the promotions engine that no out-of-the-box platform can actually handle. Now, as Senior Director of Online Experience at Trail Appliances — a 50-year-old appliance retailer operating across two branches in Western Canada — he's just completed what he calls the smoothest replatform of his career. Full composable rebuild. Twelve months. Under budget. But the replatform is just the backdrop. What Josh really came to talk about is the evolution of the e-commerce leadership role itself — why directors who stay in their lane are becoming obsolete, how to weaponize customer data in executive forums, and what it actually takes to get a CFO to fund something they don't understand yet. We also get into Trail's AI-powered live chat widget that drove a 4x conversion lift, Josh's vision for how LLMs will reconstruct personalized storefronts in the next 36 months, and why composable architecture isn't just a tech decision — it's how you stay ready for what's coming. If you're a Director of E-Commerce who's been asked to do more with less, report to people who don't understand your world, or justify investment in things that won't pay back for six months — this one's for you. Want any help Personalizing Every Customer Touchpoint? Check out ⁠https://Mobile1st.com⁠ Interested in talking to Justin or getting on the show, find him on Linkedin: ⁠https://www.linkedin.com/in/justinaronstein/⁠ Key Topics: Why the e-commerce director role is becoming a cross-functional leadership role — and what happens to directors who don't make that shift How to "weaponize" customer data and bring insights to executive forums in a way that actually moves decisions Building the CFO relationship before you need it — and why being proactive beats being reactive every time The holy trinity of evidence: GA data + customer chat logs + session recordings, and how to use them together to get buy-in fast Trail's composable rebuild: Commerce Tools, Builder IO, Algolia, NuxtVue — why they made the calls they did and what they'd do differently How to manage a replatform without blowing your timeline, budget, or executive trust (including the "minefield" framework for contingency planning) Trail's AI chat widget: 4x conversion lift, what it does, and why Josh believes humans aren't going anywhere in high-consideration purchases The future of personalized e-commerce: how LLMs will reconstruct storefronts based on user history — and why your architecture today determines your readiness for that world Managing a shared e-commerce function across two distinct business units with different pricing, promotions, and go-to-market strategies Why appliance retail is where furniture was 10 years ago — and the opportunity that creates for brands willing to invest in elevated digital experiences Onsite experimentation: where Trail is today, what Josh is skeptical about in CRO culture, and the hire he's making to do it right

Who has been a guest on Checkin to Checkout

Names identified in recent episode analyses. Showing up to five guests.

• Girish Joshi
• Luis Spencer
• Kyle Cole

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Apple Podcasts (US)

5.0 / 5

1 ratings

Podcast Authority Score: 33 / 100

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Quality

66

Social presence

0

YouTube

0

Engagement

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Books guests

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