Checkin to Checkout

Justin Aronstein

5.0 (1)
MARKETING
UPDATED BIWEEKLY

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

12/10/2025 · VIDEO

How to Say No To Stakeholders (Without Getting Fired) | Grace Edinger

"But our brand is different." It is the most dangerous phrase in enterprise e-commerce. It leads to tech debt, bloated roadmaps, and a digital ecosystem that represents a graveyard of "nice-to-have" features that never scale. In this episode (our first-ever LIVE recording!), we sit down with Grace Edinger, Director of Ecommerce Product Management at Stanley Black & Decker. Grace is responsible for the digital backbone powering some of the world’s most iconic brands—DeWalt, Craftsman, Black+Decker, and Cub Cadet. She joins the show to break down how she manages hundreds of stakeholders, navigates complex corporate politics, and enforces her strict "No Special Snowflakes" rule to keep the roadmap clean. We cover: The "Special Snowflake" Syndrome: Why saying "yes" to every custom brand request is actually destroying your ability to scale. Project vs. Product Mindset: How to stop operating as an "Order Taker" for Marketing and start operating as a strategic partner who demands data before building. The Invisible Work: Why the unsexy work of consolidating ERPs and building a unified foundation matters more than the latest AI hype. Stakeholder Politics: The exact scripts and strategies Grace uses to say "no" to bad ideas without burning bridges. If you are an E-Commerce Director drowning in feature requests or trying to drive digital transformation in a legacy organization, this episode is your playbook for taking back control. Links: Connect with Grace on LinkedIn: https://www.linkedin.com/in/graceedinger/ Follow Justin on LinkedIn: https://www.linkedin.com/in/justinaronstein/ Subscribe to the Newsletter: https://mobile1st.com/news Chapters (00:00:00) - E-Commerce Growth Podcast(00:00:27) - Stanley Black and Decker's Direct-to-Consumer eCommerce(00:03:41) - What's the biggest struggle in your job?(00:05:51) - What's The Part of Your Job That You Dread Most?(00:07:42) - Stanley Black & Decker CEO on Digital Frontend(00:12:06) - How to Build the Future of E-commerce?(00:18:28) - Walmart CEO on Digital Consumerism(00:21:31) - Have You Got To Fight the Fire?(00:25:00) - Drupal 8.1(00:26:16) - How to Test Your Content in the Future(00:27:40) - Black and Decker's CEO on His Failure(00:28:25) - What have you learned working with directors of E Commerce?(00:29:33) - What do you admire about the Director of E Commerce? Think that(00:30:56) - What is something that you wish like your executive team knew about your(00:33:14) - CupCade on Experimentation(00:35:26) - Black & Decker CEO on the Company's Future(00:37:17) - E-Commerce Directors at Ralph Lauren(00:40:20) - Product Manager: The Future of AI(00:42:57) - How Is Microsoft Building AI Into Its Ecosystem?(00:43:55) - Bill ChatGPT: Could Bots Shop For You?

47 min
10/15/2025 · VIDEO

How to Create a High Converting Store - Brian Purkiss

Brian “Purk” Purkiss leads D2C acquisition and the ecommerce site for Honest Paws at OnePet. In this episode, Brian gets honest about what actually moves conversion and what just burns time. We dig into the puzzle of ecommerce decision making, how to turn tiny wins into big results, and why the bravest thing you can do is sometimes remove the shiny thing you just added. You’ll hear: Why small, measured iterations beat year-long redesigns The counterintuitive truth that removing elements often lifts revenue How to set goals, form a hypothesis, and measure impact without ego A practical workflow for roadmapping, testing, and sharing lessons with your team Preventing burnout with “fallback” tasks and Fun Feature Friday Building a culture of ownership and trust on a fully remote team Brian’s hardest leadership lesson and how he fixed it If you care about conversion rate, new customer acquisition, and making your site 0.1% better week after week, this one’s for you. Hosted by Justin Aronstein with Connor. Chapters (00:00:00) - Check In: E-Commerce Growth Podcast(00:00:24) - Check in(00:01:49) - What's the Part of Your Job that You Enjoy Most?(00:05:10) - What Does Your Day-to-Day Look Like as a Product(00:08:38) - How to Manage a Team Without Burnout(00:12:51) - Pdp vs. Competitors(00:14:42) - Product Manager: Strengths and Weaknesses(00:18:25) - Product Manager vs E-Commerce Manager(00:24:28) - How to Lead in E-Commerce(00:28:45) - In the Elevator With a Complainer(00:30:30) - The Work That Made Me a Better Leader(00:36:35) - The Process for Building High-Converting Websites(00:44:06) - Reveal: Ignoring Failure to Grow(00:45:18) - Brian Purkis

46 min
10/01/2025 · VIDEO

The Importance of Data Driven Storytelling - Tom Funk

Should Amazon really be the enemy of DTC? Most e-commerce leaders will tell you to prioritize your own site, own the customer, and push for loyalty. But Tom Funk — E-Commerce Director at Ann Clark Ltd. and veteran of Vermont Teddy Bear, Keurig Green Mountain, and Gardener’s Supply — has a very different take. In this episode of Check In to Check Out, Tom shares why Amazon actually delivers a better customer experience than most merchant sites ever could, why his Shopify product pages send shoppers directly to Amazon, and what happened when he failed to convince a leadership team that Amazon was essential to their growth. We get into: The real ratio of Amazon vs. DTC revenue (and why most brands get it wrong) The operational realities that make Amazon unbeatable for certain products How to position DTC so it complements, not competes with, marketplaces Tom’s hard-learned lessons about culture, data storytelling, and failed persuasion If you’ve ever debated whether to push harder into Amazon or double down on your own site, this episode will challenge your assumptions. Chapters (00:00:00) - E-Commerce Growth Podcast(00:01:16) - How to become a e-commerce director(00:02:25) - Merchant Website: Between Amazon and Shopify(00:06:24) - What Does Your Day-to-Day Look Like at Amazon?(00:08:39) - How Product Development Is Done at Amazon(00:12:18) - Getting Started in E-Commerce(00:15:00) - Top Executives on Amazon's Impact(00:16:49) - Philip Morris on Amazon and the Company's Future(00:23:31) - Mentors in the Workplace(00:27:18) - Cookbook Cutters: What's Special About Selling Cookies?(00:31:21) - Baking and decorating products in The New York Times Catalog(00:34:39) - Where Entrepreneurs See the Future of ECommerce(00:36:52) - Tom Aronstein on The Righteous Mind

40 min
09/16/2025 · VIDEO

How to Build and Identify Talent - Paige Chilson

Paige Chilson joins Check In to Check Out days after a layoff and refuses to spin it. She talks about stepping back to remember who you are outside the dashboard, why e-commerce feels like you’re “in trouble” 24 hours a day, and the simple superpower most leaders ignore: knowing your limits and hiring around them. We get into funnel-based org design, the line between agency and in-house, the interview red flag nobody mentions, a painful failure story that changed how she escalates risk, and a clear-eyed take on where the next 6 to 12 months are headed with social selling and buying inside AI assistants. If you lead revenue online, this one will feel uncomfortably familiar in the best way. What you’ll learn A practical way to spot team gaps by mapping skills to your funnel When agencies outperform in-house and when they absolutely don’t How to hire in the age of AI-polished resumes The interview red flag that separates learners from passengers How to communicate risk without becoming an alarmist Why social selling is still early and how AI will reward brands with clean data Chapters (00:00:00) - E-Commerce Growth Podcast(00:01:06) - How to Plan Your Next Step After Getting Layoff(00:04:28) - Not Wrapping Your Identity Up in Your Job(00:06:48) - How to Find the Best Talent in E-Commerce(00:08:45) - The Need to Identify Leaks in Your Team(00:12:47) - The Search for the AI-Inspired Talent(00:17:11) - In the Elevator With Michael Dell(00:20:32) - Have E-Commerce Directors Learned to Be More Risk Averse?(00:24:39) - Amazon's Risk-Aware Future(00:26:01) - Looking for the Next Role in AI(00:28:35) - E-commerce: Growth opportunities(00:32:34) - E-Commerce Conference 2018: Taking a Break

34 min
08/27/2025 · VIDEO

How to grow an e-commerce business in uncertain times - John Arquette

In this conversation, John Arquete, an experienced e-commerce director, shares insights on managing an e-commerce business through challenging times. He discusses the importance of team dynamics, effective communication, and understanding customer needs. John reflects on his career journey, the lessons learned from failures, and the impact of economic changes on e-commerce strategies. He emphasizes the need for authenticity in marketing and the potential of AI to transform the e-commerce landscape. Overall, the discussion provides valuable takeaways for e-commerce leaders looking to navigate the complexities of the industry. Takeaways Managing burnout is crucial for e-commerce directors. Centralized command with decentralized control helps in team management. Effective communication with the team reduces burnout. Hiring the right team members is essential for success. Understanding customer needs is key to adapting strategies. Economic downturns require quick pivots in product offerings. Learning from failures can lead to significant growth. Authenticity in messaging resonates with customers. AI will reshape the e-commerce landscape significantly. Continuous learning and adaptation are vital for e-commerce leaders. Chapters (00:00:00) - E-Commerce Growth Podcast(00:00:32) - ECOM Director John Walsh on the Week(00:01:24) - E-Commerce Director: How to Manage the Team's Burn(00:05:41) - What's It Mean to Be an ECommerce Director at Gol's(00:08:38) - How to Be Great at Many Things(00:12:13) - How Did You Get Started in E-Commerce?(00:16:29) - Onboarding the Customer Service Managers(00:17:20) - E-Commerce Director: The Big Points(00:19:18) - In the Elevator With Rich People(00:21:56) - Amazon's 'All-Right' Product(00:23:48) - In uncertain times, how to run e-commerce?(00:26:26) - How Military Customers Get What They Need(00:34:06) - How to Reduce Interstitials on Your Site(00:36:51) - E-commerce: Future of AI & Modernity(00:44:01) - How to Keep Up With the Tech Industry

47 min
08/13/2025 · VIDEO

Trends that Influence Purchasing Decisions - Justin Rinaldi

In this episode of Checkin to Checkout, we sit down with Justin Rinaldi, Director of Marketing and E-Commerce at Safety Speed Manufacturing, to unpack the trends shaping how customers make purchasing decisions today. From the decline of trust in search engines to the rise of "brand shepherds" (not influencers), Justin shares why building great user experiences—both on and off your site—is now mission-critical. We cover: Why media consumption enablement is a competitive advantage How the mobile checkout experience can make or break sales The danger of over-automation and what brands lose when they remove human touch Lessons from rebuilding a crashed e-commerce site into a high-performing platform Experiments that worked, ones that didn’t, and what they taught him Why messaging matters more than friction—and how to get it right If you’re navigating the ever-changing e-commerce landscape, this conversation will give you a fresh perspective on customer behavior, digital strategy, and what’s actually driving conversions in 2025. Listen now to hear how Justin is staying ahead of the curve and keeping his customers at the center of every decision.

31 min
07/30/2025 · VIDEO

Identifying Growth Levers for an E-commerce Business - Adam Riback

In this conversation, Adam Riback, Director of Digital at PS Seasoning, shares insights into the complexities of e-commerce marketing, the importance of understanding consumer behavior, and the challenges of managing digital strategies. He discusses his career journey, the role of agencies, the significance of consumer feedback, and the necessity of adapting to market changes. Adam emphasizes the importance of unit economics and the need for marketers to be proactive in testing and iterating strategies to drive growth. Takeaways: E-commerce marketers experience a range of emotions daily, influenced by consumer behavior and market conditions. Balancing daily tasks with long-term strategy is crucial for success in e-commerce. Box breathing and a structured approach to tasks can help manage stress and burnout. Understanding unit economics is essential for making informed marketing decisions. Testing and iterating on marketing strategies is key to finding successful growth opportunities. Consumer feedback is vital for product development and marketing strategies. Collaboration with agencies can enhance digital marketing efforts, but finding the right partner is essential. E-commerce leaders must be adaptable and ready to pivot strategies based on market feedback. The landscape of e-commerce is constantly evolving, requiring marketers to stay informed and agile. Learning from failures is an integral part of growth and development in the e-commerce space.

47 min
07/16/2025 · VIDEO

How To Replatform an E-commerce Site - Brit Tucker

In this episode of Checkin to Checkout, we sit down with Brit Tucker, VP of Product and Technology at Society6, to unpack the real-world chaos and clarity behind one of e-commerce’s most daunting projects: replatforming. Brit leads a team that spans product, technology, UX, analytics, customer service, and operations—and recently spearheaded Society6’s successful 18-month migration to Shopify. She shares how her team balanced redesign with replatform, why “technical debt” is the number one sign it's time to replatform, and what made this her fastest replatform ever. You'll hear: How to spot when technical debt is stalling your growth Why conversion rate optimization must start with first principles, not competitor copycats What most brands forget to plan for during a replatform (hint: it's not engineering) How Society6 saw major gains in add-to-cart and conversion rates post-migration The leadership mistake Brit would fix if she did it again Plus, Brit gets real about career detours, why failure often stems from solving the wrong problem, and how spiritual grounding (and yoga) helps her stay sane leading a 20+ person team across time zones. Whether you're planning a replatform, in the messy middle, or just want to hear how a seasoned e-commerce leader builds with empathy and rigor—this episode is packed with sharp insights and refreshing honesty. Listen now to learn how to replatform the right way—and why saying no might be your most valuable product strategy. Chapters (00:00:04) - Welcome to Checkin to Checkout(00:00:42) - How to Manage Stress in the Workplace(00:03:33) - Have You Got Enough Teams for Your Job?(00:05:38) - How Can E-Commerce Leaders Build a Digital Product?(00:07:55) - Sustainable Conversion: First Principles(00:09:50) - How Did You Get Started in E-Commerce?(00:11:22) - Mentors in E-Commerce(00:13:03) - Have You Changed Anything In Your Past?(00:14:38) - In the Elevator With Rich People(00:21:24) - How Much Engineering Is Necessary for a Digital Initiative?(00:22:33) - The Signs That Your Company Needs to Re-platform(00:28:59) - Replatforming: The Big Things to Know(00:31:37) - Does a Website Decently Need Navigation?(00:35:37) - Did you see a conversion rate bump when you guys moved to Shop(00:36:22) - E-commerce: The Future of Customer Engagement(00:39:52) - The Untethered Soul by Alan Singer

42 min
06/13/2025 · VIDEO

How to Merge the Brand Experience with Trust - Girish Joshi

What do you do when your therapist can’t handle your conversion rate anxiety? You cancel therapy. At least that’s what Girish Joshi did. In this episode, Girish (Director of E-Commerce at LG) unloads the real emotional cost of running a P&L, why he checks revenue dashboards the way some people check horoscopes, and how irritation might be his secret superpower. We get into: Why most frameworks kill creativity How to chase ideas that feel like “oh f***” The surprisingly emotional side of attach rates and checkbox services When your team doesn’t need consensus—they need your conviction Why every E-Commerce director needs at least one diplomat on speed dial And how he’s trying to turn LG into the Apple of appliances, one trusted fridge at a time This episode is part group therapy, part MBA, and part stand-up set for over-caffeinated Directors of E-Com who are wondering if anyone else thinks like them. (They do. And he’s on this episode.) If you’ve ever canceled a vacation appetizer because your AOV dipped, this one’s for you. Chapters (00:00:00) - Interview(00:01:48) - In the Elevator With ECommerce's Director of Therapy(00:03:58) - Checking the Numbers(00:06:43) - Amazon CEO on Creativity and Purpose(00:08:17) - Don't Need a Frameworks(00:11:17) - Getting Your Welcome Offer to the Right Level(00:15:17) - e-commerce: Value vs. Services(00:18:46) - Will Willpower: The Need for Trust(00:20:57) - What's Your Biggest Strength and Weakest Element?(00:22:49) - LG CEO on Stories in Sales(00:27:10) - Justin on Leading From the Front(00:30:28) - Confidence in the Data vs. Personal Intuition(00:36:06) - Have You Ever Failed In Your Ideas?(00:37:01) - How LG Is Making the Brand Experience Reliable(00:39:22) - Three major areas of innovation at LG(00:40:33) - How to Build a Connected Future for Appliances(00:43:29) - LG CEO on E-Commerce Growth(00:47:46) - E-commerce Insights: What Excites You?

51 min
06/13/2025 · VIDEO

Using the Conversion Funnel to Enhance Brand Equity - Luis Spencer

In this episode of Check In to Checkout, Mobile1st’s CPO Justin Aronstein and Director of Optimization Connor Burke sit down with Luis, the dynamic Senior Director of Digital Route to Consumer at Moët Hennessy. What starts as a laugh over shorts at a formal sales convention turns into one of the most insightful deep dives we've had into modern e-commerce strategy. Luis unpacks how digital is redefining brand-building in a category constrained by the 100-year-old U.S. three-tier system. He challenges the outdated idea that brand and conversion live in separate funnels, making the compelling case that seamless, well-timed ecommerce interactions are branding today. You’ll hear how he’s using platforms like Instacart and Uber Eats not just to sell—but to elevate premium brands like Veuve Clicquot and Hennessy. He also shares: The unexpected lessons from launching direct-to-consumer experiences that didn’t work Why focusing only on your business objectives (and not the consumer's actual needs) leads to flops His vision for how AI agents will change product discovery, recommendation, and even how brands get found online A “digital anthropologist” lens on how consumer behavior has evolved—especially in high-regulation industries His “video game” approach to e-commerce burnout and knowing when to put the controller down Sprinkled throughout are honest reflections on failure, a killer Pokémon metaphor, and some top-tier anime and video game recommendations. Whether you're a director of e-commerce, a digital strategist, or just someone obsessed with where the customer journey is heading, this episode is packed with value. Chapters (00:00:00) - The Biggest Failure Of The Week(00:01:18) - The Future of E-Commerce: Building a Brand(00:03:11) - Clara's Kira on(00:04:19) - Top Executives: Moet Hennessy's ECommerce(00:05:46) - Three-Tier system in the US(00:06:51) - The 3-Tier Alcohol Industry(00:08:19) - What's your day-to-day(00:11:02) - Bar and E-Commerce Director Burnout(00:14:33) - Hennessy CEO on the Digital Revolution(00:18:08) - On Real Conversations With the Customer(00:19:20) - Alcohol Brand Chat Online(00:22:10) - How Did I Get Into E-Commerce?(00:27:21) - Mo Hennessy's Ash Ketchum(00:28:16) - How many languages can you speak fluently(00:29:21) - What Are Some Of Your Failures?(00:34:07) - How E-Commerce is driving brand equity(00:38:56) - Uber Eats: Brand Discovery(00:41:26) - E-commerce: The Next Generation of Agents(00:43:43) - Will AI Transform the Consumer Shopping Journey?(00:45:58) - How Is AI Affecting Consumer Behavior?(00:48:03) - Beyond the Book: What's on your Feed?

51 min
06/13/2025 · VIDEO

Sell Stories Not Product - Kyle Cole

Most e-commerce stories start with product-market fit. This one started with Frodo. On this episode of Check-In to Check-Out, we talk with Kyle Cole, co-founder of The Hero’s Journal—a journaling brand built on the idea that life gets easier when you start seeing yourself as the main character. What started as a nerdy side project turned into a seven-figure DTC brand powered by story, community, and a refusal to send boring emails. Kyle opens up about: Accidentally going viral during quarantine with a “Quarantine Quest” Scaling fulfillment from garage to 3PL—and the painful (but hilarious) budget mistake he made What every e-commerce leader gets wrong about community building How to forecast without deluding yourself Why the best marketing emails sometimes have no CTA If you’ve ever tried to justify a warehouse lease based on “the traffic you're manifesting” or had your team melt down over a 3PL gone rogue, this one’s for you. It’s funny, vulnerable, and weirdly practical. And yes, we talk about iOS 14. Perfect for: Directors of E-Commerce, DTC operators, brand builders who think “community” isn’t just a Slack channel Listen in and remember: you are the hero. Just maybe... also the operations oracle. Chapters (00:00:00) - E-Commerce: The Hero's Journey(00:01:40) - Kyle on the Podcast(00:02:11) - What's Your Day to Day at Hero's Journey?(00:02:42) - Have You Had A Good Week?(00:03:32) - What's Your Best Strengths and Weaknesses?(00:08:17) - The Story of The Book(00:09:09) - Startups as a Way to Get Out of Debt(00:12:41) - Do You Wish You Had Done This Lesson?(00:17:13) - How To Grow an E-Commerce Business(00:21:45) - Being Flexible in an E-commerce Business(00:22:56) - Community as a Force multiplier for E-Commerce(00:29:06) - Building a Community for Your Product(00:31:32) - Send inspirational emails to your fans(00:35:58) - E-Commerce Leadership: The Hero's Journal

39 min

11 Episodes

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

Creator

Justin Aronstein
Years Active

2K
Episodes

11
Rating

Clean
Copyright

© 2025
Show Website

Checkin to Checkout