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He ranked 3,000 quizzes

Send It! · with Chase Dimond & Jimmy Kim · July 21, 2026 · 44 min

Summary

This episode reveals how a rigorous analysis of 3,000 quizzes provides a playbook for optimizing email and SMS retention strategies. Ecommerce operators will learn advanced tactics for crafting high-converting welcome flows, abandoned cart sequences, and SMS campaigns, directly impacting their bottom line. The host emphasizes moving beyond generic advice to implement proven, data-backed retention programs.

Key takeaways

Themes

email & smscustomer retentionconversion & croanalytics & attribution

Topics covered

email welcome seriessms marketing strategyabandoned cart sequenceswinback campaignscustomer segmentation with quizzesretention marketing analytics

Episode description

Access Jonathan’s FREE eCommerce Quiz Audit Button: https://optimizeyourquiz.com/research/best-and-worstEvery question your quiz asks costs the buyer something. And the best ones make it worth paying.In this episode of Send It, Jimmy Kim and Chase Dimond sit down with Jonathan Drake, who audited and ranked more than 3,000 ecommerce quizzes across 27 benchmark points to find out what separates the best quiz funnels from the worst.They dig into why the first question matters so much, how brands lose shoppers at the email and SMS capture step, when 6-9 questions can actually work, and why quizzes should feel more like guided product discovery than a default template built to collect zero-party data.Jonathan also shares what he learned from ranking the top and bottom ecommerce quizzes, including how visitor experience, business leverage, readability, product discovery, and lead capture all play into whether a quiz helps shoppers buy or just creates more data your team never uses.Follow Jonathan on social: https://x.com/JonathanDrakehttps://www.linkedin.com/in/jonathanrdrake/Here's what we're diving into:- The survey vs quiz difference most brands get wrong- Where quizzes lose people, and how to earn the email- Why more questions can actually mean a better customer- Using a quiz as a product discovery and selling tool- Where AI and the "conversation" model fit inThank you our friends at Omnisend and eCom Email Certified for sponsoring the podcast!Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscrib

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Frequently asked about this episode

What does this episode say about email & sms?
Implement a 'quizzes' strategy for deeper customer segmentation and personalized communication, moving beyond basic demographic data to understand purchase intent and preferences.
What does this episode say about customer retention?
Optimize welcome and winback flows using insights gleaned from high-performing quizzes, focusing on personalized content delivery post-quiz completion.
What does this episode say about conversion & cro?
Integrate SMS marketing seamlessly with email strategies, using quiz data to tailor SMS campaigns for compliance and increased engagement.
What does this episode say about analytics & attribution?
Regularly conduct teardowns of your own email and SMS campaigns against industry top performers, identifying what to adapt and what to discard based on quantifiable results.
What does this episode say about email & sms?
Leverage "signal, not news" by focusing on immediately actionable tactics from successful case studies rather than broad industry trends, ensuring rapid implementation and ROI.

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