Checkin to Checkout

By Justin Aronstein

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 ... more

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FAQs about Checkin to Checkout:

How many episodes does Checkin to Checkout have?

The podcast currently has 24 episodes available.

Checkin to Checkout episodes:

April 01, 2026E-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
...more
38min
March 25, 2026Why You? Why Now? The Question Every E-Commerce Brand Needs to Answer - Lauren Goodwin
Most brands overinvest in tactics without understanding what truly sets them apart — and they pay the price. Lauren Goodwin, a seasoned e-commerce strategist, uncovers the hidden keys to differentiation that actually drive sales, especially in the saturated beauty and wellness markets. If your brand is struggling to stand out where it matters most, this episode is your blueprint for real impact.
We break down how brands can shift from chasing fleeting growth hacks to developing authentic, compelling stories that resonate with consumers. Lauren shares concrete frameworks for identifying hero products, leading with purpose-driven messaging, and leveraging customer insights — all without throwing money at ads and hoping for results. She reveals how brands often waste resources on vanity metrics and how to use targeted surveys and simple AI tools to unlock real customer needs.
You'll discover why friction isn’t always the enemy — and when it truly is. Lauren explains why many brands overlook core branding issues that sabotage their growth, and how a holistic marketing approach can change the game. From positioning through storytelling to optimizing data and analytics—her insights cut through industry noise to give you clarity. Whether you're launching a startup or steering a mature brand, her advice on balancing strategy, team structure, and leveraging fractional resources is indispensable.
The stakes are high: If your brand remains invisible in the crowded marketplace, you risk falling behind or becoming irrelevant. Conversely, grasping these differentiation tactics opens doors to scalable growth, loyalty, and trust. This episode is perfect if you're tired of chasing the latest growth trend with little to show for it — and eager to build a brand that truly connects.
Lauren Goodwin is an e-commerce director with experience managing brands worth over $50 million annually, known for her strategic agility and data-driven insights that turn brands into category leaders. Her expertise in turning small brands into differentiated leaders makes her insights invaluable for ambitious marketers.
Tune in to transform your approach—and finally shift from tactics to meaningful growth. Don't miss out on the chance to reshape your brand’s story and stand out in a sea of sameness.
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/⁠
Topics:
Differentiation is now the primary driver of brand success, transcending barriers like ad spend or product quality.
The real challenge in conversion isn’t friction but understanding consumer needs and aligning your brand message accordingly.
Data analytics and customer insights are often underinvested, yet they hold the key to genuine differentiation.
A-B testing reluctance stems from a fear of losing control and damaging brand consistency.
As development cycles accelerate, e-commerce leaders must become more proactive in impact measurement or risk flying blind.
The rise of fractional expertise reflects a shift toward lean, flexible teams and decision-making trust. In practice: Smaller brands can benefit from a fractional CMO or e-commerce strategist who challenges assumptions and guides growth without the overhead of full-time roles.
...more
27min
March 18, 2026Distrobution is Solved. Now What? - Dan Pearce
Dan Pearce, CEO of Sovereign Naturals, has spent 30 years watching e-commerce evolve — and he's got a clear-eyed take on where most brands are getting left behind. In this episode, Dan breaks down why the distribution problem is solved, why demand capture is no longer enough, and what it actually takes to build a brand that creates demand from scratch. From TikTok affiliates to doctor interview series to rethinking what your DTC site is actually for, Dan lays out how he's rebuilding Sovereign Naturals' entire go-to-market approach — one snowball push at a time.
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 Insights:
Distribution is solved. Amazon did it. The new game is demand creation — and the brands that understand that are the ones growing.
Demand capture was a straightforward business. Remove friction, capture intent. That era is over.
Channel agnosticism is the right mindset. Consumers buy where they want. Your job is to make them want it, not steer them.
Trust over transactions. If your CRM is 80% promotional, you're training customers to wait for a discount — not build a relationship.
Discounting has diminishing returns. Run a sale twice, then four times, and you've trained your customer not to buy at full price.
Storytelling at scale is the new performance marketing. Blogs, employee stories, doctor interviews, trade show video — all of it builds demand before someone ever searches for you.
Hire experts and then actually let them expert. Bringing in talent and then telling them exactly what to do defeats the purpose.
Minimum viable momentum beats swinging for 10x. Ask if you're better today than yesterday. That's the metric that compounds.
...more
44min
March 11, 2026How to get actionable feedback from customers and your team - Doug Villella
In this episode, Doug Filella, Director of Digital Commerce and Growth Enablement at APG, shares insights on building and scaling e-commerce operations within a smaller organization. Topics include operationalizing marketing, leveraging customer feedback, and future trends in e-commerce technology.
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/⁠⁠
Insights:
Building scalable marketing operations
Operationalizing customer data and feedback
Future of AI and technology in e-commerce
...more
45min
March 04, 2026Building High Growth Architecture Without Breaking Trust - Chad Greiter
In this insightful interview, Chad Greiter, Director of Digital Product at Simon, shares his expertise on e-commerce, AI, build vs. buy decisions, and leadership in digital product management. Discover practical strategies, industry trends, and future outlooks to elevate your e-commerce game.
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/⁠
Insights:
E-commerce team structure and hiring strategies
Impact of AI on build vs. buy decisions
Future of Web3 and blockchain in e-commerce
Balancing legal and privacy concerns in digital marketing
Leadership and technical expertise in digital product management
...more
30min
February 25, 2026Why Every Brand Should Be Working With Amazon in Some Way - Giovanni Papini
The Future of Amazon E-commerce and Digital Strategy with Giovanni Papini
In this episode, we explore the evolving landscape of Amazon e-commerce, innovative strategies for brands, and the impact of AI on marketing. Giovanni Papini, an expert in Amazon marketplace dynamics from Milan, provides a sharp insights into how brands can strategically leverage Amazon and adapt to technological shifts.
Want any help Personalizing Every Customer Touchpoin? 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/⁠
Main insights include:
The importance of balancing operational know-how with strategic vision on Amazon, especially regarding choosing between 1P, 3P, or hybrid models.
How data-driven ecosystems and long-term vision are crucial for brands to succeed in Amazon’s complex environment.
The cultural and regulatory differences between European and American markets, especially concerning health and consumer brands.
The critical role of content and reviews in shaping brand reputation and consumer trust on Amazon.
The potential of AI and LLMs to transform customer engagement, advertising, and product discovery, with an emphasis on bringing meaning and differentiation to digital marketing strategies.
Practical steps for brands entering Amazon, from leveraging infrastructure without immediate sales to phased experimentation and brand extension.
Final takeaway: Success in Amazon today demands strategic clarity, mastery of data ecosystems, and agility in adopting AI-powered marketing tools. Brands that bring authentic meaning and differentiate effectively will thrive in this evolving digital landscape.
...more
38min
February 18, 2026Why Differentiation is all that Matters Right Now - Andrew Horwat
In this conversation, Andrew Horwat shares valuable insights into the world of e-commerce, emphasizing the importance of collaboration, testing, and understanding consumer needs. He discusses the structure of his team, the significance of resonance over reach in marketing, and the challenges of navigating brand guidelines. Andrew also reflects on learning from failures, the critical role of differentiation in a competitive market, and the future opportunities in e-commerce. He concludes with personal reading recommendations that inspire his work.
Want any help improving Revenue Per Visitor? 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/
Takeaways
Andrew oversees a lean team managing digital content for retail partners.
Collaboration across divisions is crucial for generating new ideas.
Testing and experimentation help validate gut feelings in marketing.
Resonance over reach is a key marketing principle.
Understanding consumer insights is essential for effective marketing.
Learning from failures is a vital part of growth.
Differentiation is more important than ever in e-commerce.
The unfiltered voice of the consumer is invaluable for insights.
Brand guidelines can be tested but should not be broken.
Reading and continuous learning are important for personal and professional development.
...more
42min
February 11, 2026How to Use Segmentation to Grow Revenue - Anna Christensen
In this conversation, Anna, the Director of E-commerce for Buff City Soap, shares her insights on leading a small e-commerce team, the importance of storytelling in digital marketing, and the challenges of integrating online and offline retail experiences. She discusses the role of AI in enhancing customer engagement and retention strategies, emphasizing the need for personalization in e-commerce. Anna reflects on her journey, the lessons learned from failures, and the evolving landscape of e-commerce.
Want any help improving Revenue Per Visitor? 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/
Takeaways
E-commerce leaders often wear multiple hats.
Building a small team can lead to agility and innovation.
Storytelling is crucial for engaging customers online.
Creating a unique digital experience requires understanding customer needs.
Testing and learning are essential for e-commerce success.
Navigating challenges between e-commerce and retail requires collaboration.
AI can enhance personalization and efficiency in e-commerce.
Retention strategies should focus on hyper-segmentation and triggers.
Personalization is key to winning back customers.
Continuous learning and adaptation are vital in the e-commerce landscape.
...more
33min
February 04, 2026The Future of E-commerce | Andrew Mosko
In this conversation, Andrew Mosko, Director of D2C and Digital at Throne Sport Coffee, shares insights into his role overseeing digital commerce and marketing strategies. He discusses the evolution of e-commerce, the importance of agency support, and the lessons learned from failures in the industry. The conversation also delves into the impact of AI on consumer behavior, the significance of effective communication within teams, and innovative marketing strategies that leverage consumer psychology. Andrew emphasizes the need for storytelling in e-commerce and shares his current focus on understanding human decision-making processes.
Want any help improving Revenue Per Visitor? 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/
Takeaways:
Agency support is crucial for managing digital marketing efforts.
Failures in e-commerce are common and provide valuable learning experiences.
Effective communication is essential for team dynamics and project success.
AI is changing the landscape of consumer behavior and marketing strategies.
E-commerce strategies must adapt to shifts in consumer engagement.
Understanding human psychology can enhance marketing effectiveness.
Storytelling is vital for connecting with consumers on product pages.
Testing emerging channels can lead to innovative marketing opportunities.
Continuous learning and adaptation are key to success in e-commerce.
...more
35min
January 28, 2026Driving E-Commerce Growth Through Technology | Dmitriy Anderson
In this conversation, Dimitri Anderson, CIO and Head of E-Commerce and Marketplace Strategy at Leroy Merlin, shares insights into his hybrid role that combines technology and business to drive growth. He emphasizes the importance of user feedback, innovative features, and A/B testing in e-commerce. Dimitri discusses the challenges of advertising overspending and the role of AI in enhancing customer experience. He also highlights the efficiency of small teams and the future trends in e-commerce, particularly in the South African market.
Takeaways
Dimitri's role involves weaving technology and business priorities for growth. User feedback is critical for improving customer experience.
Innovative features can significantly impact market response.
A/B testing is a key strategy for optimizing e-commerce performance.
Overspending on advertising can lead to significant challenges.
AI can enhance customer interaction and drive sales. Small teams can be highly productive in e-commerce.
The South African market is receptive to new e-commerce features.
Learning from failures is essential for growth. Future trends in e-commerce will focus on interactive experiences.
Want any help improving Revenue Per Visitor? 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/
...more
29min

FAQs about Checkin to Checkout:

How many episodes does Checkin to Checkout have?

The podcast currently has 24 episodes available.