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

  1. How to Strategically Scale Your E-commerce Business | Garrett Peters

    4D AGO · VIDEO

    How to Strategically Scale Your E-commerce Business | Garrett Peters

    This is the first episode of Season 2. Episodes in season 2 will be released weekly and will be 30 minutes long. In this episode, Garrett Peters, CEO and co-founder of Duncan and Stone Paper Company, shares insights into his daily responsibilities, the challenges of running an e-commerce business, and the lessons learned from failures. He discusses the importance of breaking down new tasks into manageable steps, the significance of building a strong team, and the strategies for future growth, including influencer marketing and optimizing Amazon sales. Want help hitting your 2026 goals by increasing revenue per visitor? Checkout Mobile1st.com. Takeaways The role of a CEO involves wearing many hats and handling various tasks. Finding joy in unexpected aspects of the job can lead to personal growth. Breaking down new challenges into smaller steps is crucial for success. Learning from failures is an essential part of the entrepreneurial journey. E-commerce requires more time and energy than initially anticipated. Building a team that works on their passions can enhance productivity. Outsourcing tasks can free up time for more critical responsibilities. I Influencer marketing is becoming increasingly important for brand growth. Intentionality in marketing strategies can lead to better results. - Understanding the business's financial health is vital for future planning. Chapters (00:00:00) - Ecommerce Growth Podcast(00:00:47) - How to Be a CEO of a Startup e-Commerce Company(00:01:53) - Is there any part of your job you feel like you maybe would(00:03:17) - President and CEO: Newness(00:03:37) - How To Start a New Business?(00:07:28) - Duncan and Stone: Becoming an Amazon Company(00:08:33) - How To Start a Business in E-Commerce(00:10:45) - Sen. Rand Paul on Momentum(00:11:44) - Duncan & Stone: On Paid Media, SEO & Influencer(00:14:58) - The Importance of Controlling the Business(00:18:48) - A Few Thoughts On Starting a Business(00:22:44) - TikTok, Amazon: Where Are You Going?(00:23:52) - Marketing Executive on Facebook Paid Media(00:24:56) - TikTok Shop: Best Influencer Marketing Strategy(00:27:35) - How to Manage a Small Business

    31 min
  2. Building a Golf Community through E-commerce - Jonah Redel-Traub

    JAN 7 · VIDEO

    Building a Golf Community through E-commerce - Jonah Redel-Traub

    In this conversation, Jonah, the director of commerce and growth at ProShop, discusses his role in building a golf community through e-commerce and content marketing. He shares insights on team structure, customer acquisition, and the challenges of navigating social media platforms like TikTok. Jonah emphasizes the importance of storytelling in brand building, the complexities of attribution reporting, and the impact of AI on the future of e-commerce. He also reflects on personal experiences with failures, setting boundaries, and the significance of clear communication within an organization. Want help growing RPV, checkout Mobile1st.com. Takeaways Jonah is the director of commerce and growth for ProShop, focusing on e-commerce in the golf industry. ProShop aims to build a large golf audience through content and commerce. The e-commerce team operates like an internal agency to incubate brands. TikTok is a growing channel, but the price point for golf products is high. Attribution reporting can be misleading; focus on customer acquisition instead. Customer insights are gathered through direct feedback from a dedicated community. Storytelling is crucial for building a strong brand connection. Failures in e-commerce are common, but personal growth is more significant. Clear communication of e-commerce metrics is essential for stakeholder buy-in. AI is transforming the e-commerce landscape, allowing for rapid implementation of ideas. Chapters (00:00:00) - ECommerce Growth Podcast(00:02:18) - Golf Brand Ambassador on Content First(00:03:38) - Golf Star on His Love of the Game(00:04:29) - What's Your ECommerce Team Look Like?(00:06:55) - Is TikTok the Right Channel for E-Commerce?(00:11:35) - Finding New Insights About Sugarloaf Social Club(00:15:58) - Have You Had Any Failures While At Shopify?(00:18:28) - How to Deal with Ridiculous Ideas(00:20:20) - Have You Had To Fight A Facebook Ad Fire?(00:25:16) - How do you communicate the intricacies of ECommerce to the Channel(00:28:14) - How to Train an E-Commerce Native Employee(00:31:23) - What Would You Do If You Didn't Work in E-Commerce(00:36:00) - How Shopify Is Advancing AI in E-Commerce(00:38:43) - GEO vs SEO: How Will GEO Differ(00:40:41) - How to Get Smarter on Twitter

    43 min
  3. How to Say No To Stakeholders (Without Getting Fired) | Grace Edinger

    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
  4. How to Create a High Converting Store - Brian Purkiss

    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
  5. The Importance of Data Driven Storytelling - Tom Funk

    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
  6. How to Build and Identify Talent - Paige Chilson

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

    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
  8. Trends that Influence Purchasing Decisions - Justin Rinaldi

    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
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About

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

Information

  • Creator
    Justin Aronstein
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © 2025
  • Show Website
    Checkin to Checkout