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Checkin to Checkout

Checkin to Checkout

By: Justin Aronstein
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About this listen

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© 2025 Career Success Economics Management Management & Leadership Marketing Marketing & Sales
Episodes
  • How to Strategically Scale Your E-commerce Business | Garrett Peters
    Jan 13 2026

    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 Dunkin' 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. 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. -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.

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    30 mins
  • Building a Golf Community through E-commerce - Jonah Redel-Traub
    Jan 7 2026

    summaryIn 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.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
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    43 mins
  • How to Say No To Stakeholders (Without Getting Fired) | Grace Edinger
    Dec 10 2025

    "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?
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    47 mins
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