The $270 Billion Checkout Problem (And How to Recover Your Share)

Most e-commerce brands pour everything into getting customers to checkout — and then hand them a generic, one-size-fits-all experience that quietly kills the sale. Avi Moskowitz, co-founder of PDQ, has processed millions of checkouts across top Shopify brands (including Jones Road Beauty), and his diagnosis is blunt: cart abandonment isn't a technical problem. It's an emotional one. And it's leaving $270 billion on the table every year.

Inside the episode:

• Why your checkout is the one place segmentation goes to die — and how personalizing it by customer type (first-time, returning, high-value) can drive an 18% AOV lift or double-digit conversion jumps
• The "WISMO problem": why more than 50% of order-related support tickets arrive the same day the order was placed — and what it tells you about the trust gap you're creating at checkout
• The free shipping threshold mistake almost every brand is making (hint: they copied a competitor who also just guessed)
• Surprising checkout wins from PDQ's testing: why moving the economy shipping option down one slot meaningfully increased revenue per session — without a single new ad or product
• How to think about every order as its own P&L — factoring in CAC, COGS, fulfillm

—

Sponsored by OMG Commerce - go to https://www.omgcommerce.com/contact and request your FREE strategy session today!

—

Chapters:

[00:00] Intro — The $270B checkout abandonment problem

[00:22] Welcome & Guest Introduction: Avi Moskowitz, Co-Founder of PDQ

[01:52] Avi's Background: From Craft Beer to SaaS Founder

[03:23] COVID Timing & The eCommerce Wake-Up Call

[05:09] The Root Cause of Cart Abandonment: Trust, Not Technology

[07:27] How PDQ Solves the Checkout Confidence Gap

[14:30] Reducing Friction: Shipping, Delivery Dates & Upsells

[23:00] Free Shipping Thresholds & AOV Optimization

[34:00] Building a Checkout That Converts Like Amazon

[43:24] Thinking in Mini P&Ls: Per-Order Profit Optimization

[46:26] Personalized Checkout Logic at the Customer Level

[48:24] Where to Find PDQ & Get Your Free Checkout Audit

—

Connect With Brett:

LinkedIn: https://www.linkedin.com/in/thebrettcurry/

YouTube: https://www.youtube.com/channel/UCQmbMwBW8LYDfFAqNqlgTGw

Website: https://www.omgcommerce.com/

Request a Free Strategy Session: https://www.omgcommerce.com/contact

Relevant Links:

Avi's LinkedIn: /moskowitzavi

Past guests on eCommerce Evolution include Ezra Firestone, Steve Chou, Drew Sanocki, Jacques Spitzer, Jeremy Horowitz, Ryan Moran, Sean Frank, Andrew Youderian, Ryan McKenzie, Joseph Wilkins, Cody Wittick, Miki Agrawal, Justin Brooke, Nish Samantray, Kurt Elster, John Parkes, Chris Mercer, Rabah Rahil, Bear Handlon, JC Hite, Frederick Vallaeys, Preston Rutherford, Anthony Mink, Bill D'Allessandro, Stephane Colleu, Jeff Oxford, Bryan Porter and more