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