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.

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.

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.

• (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