EP 27: Year Round Retention: Off-Season Strategies to Keep Customers Engaged and Buying

Most brands go quiet after peak season—and that’s where they lose momentum.

In this episode of Send It!, Jimmy Kim and Chase Dimond unpack real-world strategies to keep your emails converting and your customers engaged no matter what month it is—from post-holiday slumps to summer slowdowns.

From monthly gift guides and upsells to flash sales, goal-oriented campaigns, loyalty perks, and how to personalize it all through segmentation, behavior, and purchase data—this is your playbook for staying relevant 24/7/365.

EP 27: Year Round Retention: Off-Season Strategies to Keep Customers Engaged and Buying

Here's what we're diving into:

- Why most brands fumble the off-season—and how to fix it

- Actionable tips to reignite interest throughout the calendar

- Campaign ideas tied to life moments, niche holidays, and goals

- Key strategies to maintain engagement (upsells, cross sells, loyalty, & more)

- Off-season content ideas: behind-the-scenes, customer stories, contests

- How to implement these ideas with segmentation, automation, and personalization

- Key metrics to track off-season campaign performance

Thank you our friends at Omnisend, Raleon 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-sendit

Raleon is your AI-powered retention team—built to help Shopify brands increase LTV and save hours every week. From segmentation to campaign planning, Raleon automates the grind so you can focus on strategy that scales. https://eemtrk.com/sendit-raleon

eCom 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 email & SMS marketer. https://eemtrk.com/eec-sendit

Join our community of 320+ Retention marketers! https://eemtrk.com/eecc-sendit

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02:47 Google's New Email Feature

04:33 Seasonal Campaign Tactics

15:21 Maintaining Engagement Post-Peak Season

28:47 Implementing Strategies on Email and SMS Platforms

39:16 Summary and Key Takeaways

42:53 Conclusion and Next Episode Preview

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Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

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Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!