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EP 59: The real lessons from Black Friday + Cyber Monday 2025

Send It! · December 9, 2025 · 39 min

Summary

This episode dissects the key lessons from Black Friday and Cyber Monday 2025, offering ecommerce operators a strategic playbook to optimize their retention efforts for 2026. It emphasizes moving beyond conventional sales tactics to build a robust retention engine focused on long-term revenue and customer lifetime value.

Key takeaways

Themes

customer retentionemail & smsdtc strategy

Topics covered

black friday cyber monday insightsretention strategycustomer journey mappingemail automationssms marketingecommerce sales eventslong-term revenue generation

Episode description

BFCM 2025 didn’t play out the way anyone expected. In this special report, Jimmy Kim and Chase Dimond break down what actually happened, why it happened, and what it means for ecommerce brands heading into 2026.Pulling fresh data from Omnisend, Shopify, Adobe Analytics, and hundreds of brand conversations, they unpack the consumer behavior, sales trends, offer performance, inbox shifts, SMS usage, and emerging AI-driven shopping habits that defined this year’s results.Jimmy and Chase also share real examples of what worked, what flopped, and how brands can approach 2026 with smarter pre-launch planning, tighter segmentation, stronger waitlists, better bundling, and more intentional offer design.EP 59: The real lessons from Black Friday + Cyber Monday 2025Here's what we're diving into:- Why Black Friday still dominated, even with earlier offers- Why Cyber Monday surged for many brands- How offer fatigue and creativity collapse hurt performance- What Omnisend data showed about AOV, flow revenue, and list behavior- How AI-driven shopping and inbox filtering changed resultsThank you our friends at Omnisend, Kintsugi 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://eemtrk.com/omnisend-senditKintsugi is an AI platform that monitors, files, and optimizes sales tax for you with a 98.3% reduction in errors. Mention Chase and Jimmy to receive your first three months free! https://eemtrk.com/sendit-kintsugieCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified ema

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Frequently asked about this episode

What does this episode say about customer retention?
Prioritize customer retention by building out a strategic 'retention engine' rather than just focusing on acquisition during sales events.
What does this episode say about email & sms?
Implement comprehensive audit worksheets and customer journey mapping to identify gaps in your current retention setup and convert high-level ideas into actionable plans.
What does this episode say about dtc strategy?
Utilize campaign and flow planning templates to create core campaigns and high-impact automations that drive repeatable revenue.
What does this episode say about customer retention?
Focus on revenue-driven retention initiatives over mere email send volumes.
What does this episode say about customer retention?
Learn from the successes and pitfalls of major sales events like BFCM to refine future strategies for sustained growth.

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