Checkin to Checkout

Checkin to Checkout

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Checkin to Checkout episodes

  • The 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.
    • 35 min
    • Driving 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/

        29 min
      • Navigating Team Dynamics in E-commerce | Kasey Wiese

        In this conversation, Kasey Wiese, the Director of E-commerce at Liberty Safe, shares insights into her role and the challenges of leading an e-commerce team. She discusses the importance of prioritization, delegation, and emotional resilience in leadership. Kasey emphasizes the need for a culture of experimentation and the complexities of personalization in e-commerce. She also reflects on the stress of Black Friday and Cyber Monday, the significance of trust and communication in leadership, and the value of implementing best practices from the Baymard Institute. Kasey's experiences highlight the evolving landscape of e-commerce and the continuous learning required to succeed in this field.

        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

        • Kasey Wiese is focused on growing e-commerce at Liberty Safe.
        • Prioritization is key in leadership roles, focusing on controllable factors.
        • Delegation depends on the touch required for each role.
        • In-house development can be more efficient during critical times.
        • Emotional resilience is crucial in handling failures and mistakes.
        • Creating a culture of experimentation is essential for growth.
        • Personalization in e-commerce can be tricky and often misapplied.
        • Black Friday and Cyber Monday present unique challenges for e-commerce leaders.
        • Trust and communication are vital for effective leadership.
        • Implementing best practices from Baymard can significantly improve user experience.
        • 37 min
        • 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.
          • 31 min
          • 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.
            • 43 min
            • 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
                47 min
              • 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.

                  47 min
                • 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.

                    41 min
                  • 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
                    35 min
                  • 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.
                    •  

                      47 min

                    About Checkin to Checkout

                    From the publisher's feed

                    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…