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 BuyingHere'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 performanceThank 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-senditRaleon 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-raleoneCom 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-senditJoin our community of 320+ Retention marketers! https://eemtrk.com/eecc-sendit______02:47 Google's New Email Feature04:33 Seasonal Campaign Tactics15:21 Maintaining Engagement Post-Peak Season28:47 Implementing Strategies on Email and SMS Platforms39:16 Summary and Key Takeaways42:53 Conclusion and Next Episode Preview______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/______Follow Jimmy & Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at [email protected] for sponsorships, appearance requests, interviews, or general information!