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

______

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

______

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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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

In this episode of Send It!, Jimmy and Chase sit down with Sarah Levinger, founder of Tether, to unpack how psychology drives performance in email and SMS marketing.

Sarah is known for helping brands decode why people buy—and today she’s sharing practical frameworks, emotional triggers, and real-world tactics to make your campaigns hit harder (without crossing the ethical line). Whether you’re crafting a subject line or building a full retention strategy, this one’s packed with gems.

EP 26: Emotional Marketing in Email & SMS: Tapping Into Psychological Triggers with Sarah Levinger

Here's what we're diving into:

- What emotional marketing really is—and why it beats pure logic

- Using NLP and Core Identity Mapping to shape messaging

- Real examples of emotional hooks in subject lines, body copy, and CTAs

- The most common emotional triggers in ecom (and how to find yours)

- Balancing persuasion with trust: how to stay ethical and authentic

- Long-term strategy tips for integrating psychology across the customer journey

- Lightning round: Sarah’s top tools, biggest misconceptions, and favorite triggers

Thank you our friends at Omnisend, Nacelle 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

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://eemtrk.com/sendit-nacelle

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

______

00:00 Understanding Audience Segmentation

02:45 Meet Sarah Levenger: The Emotional Marketing Expert

08:33 The Power of Emotional Marketing

14:06 Psychological Frameworks in Marketing

21:36 Testing and Validating Emotional Triggers

23:44 Crafting Effective Subject Lines

26:30 Marketing Trends and Their Evolution

26:54 Ethical Considerations in Marketing

29:22 Leveraging AI for Personalization

31:51 Building a Brand's Emotional DNA

36:57 Actionable Tips for Emotional Marketing

39:04 Long-Term Strategies for Emotional Marketing

41:41 Lightning Round: Insights and Tools

______

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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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Email deliverability isn’t just a buzzword—it’s the backbone of every successful retention strategy. In this episode of Send It, Jimmy Kim and Chase Dimond take you behind the scenes of their recent “Retention Reimagined” webinar, giving you an unfiltered, tactical breakdown of what deliverability actually means in 2025. If you’ve ever wondered why your emails land in spam, how Gmail decides your fate, or what “reputation resets” are—this is the episode to bookmark.

From real-time scoring mechanics to seed testing strategies and the impact of content structure on inbox placement, this masterclass is packed with actionable advice. Stay till the end for 10 tips that will reshape how you send in 2025—and some candid Q&A you won’t want to miss.

EP 25: 2025 Email Deliverability Masterclass - How Email is ACTUALLY delivered

Here's what we're diving into:

- How inbox placement actually works (hint: it’s not your ESP’s fault)

- Real-time scoring: how Gmail evaluates your emails- How to run a seed test like a pro

- What Google Postmaster and Yahoo Sender Hub tell you

- 10 tactical deliverability tips for 2025

- How to handle dark mode, spam words, and content engagement

Thank you our friends at Omnisend, Nacelle, 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/email-sendit-nacelle

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://eemtrk.com/sendit-nacelle

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://www.ecomemailcertified.com/

Join our community of 320+ Retention marketers! https://ecomemailcertified.com/join-community

______

00:42 Welcome to the Show

05:29 The Importance of Deliverability

12:09 How Deliverability Actually Works

18:38 Promotional vs. Spam Folders

23:37 Improving Your Deliverability

29:30 Importance of Good Content in Emails

29:39 10 Quick Tips for Better Email Delivery

31:36 Fast Fire Tips for Email Success

35:55 Best Practices for 2025

44:50 Q&A Session

______

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 Kim at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Apple's latest privacy updates—Mail Privacy Protection (MPP), Link Tracking Protection, and ongoing iOS 18 changes—are making it harder than ever for eCommerce marketers to track email and SMS performance. Open rates are unreliable, link parameters are being stripped, and App Tracking Transparency (ATT) is limiting data visibility. So, what now?

In this episode, we break down what these changes actually mean, share real-world brand insights, and lay out a step-by-step strategy for navigating this new era of retention marketing. If you've noticed inflated open rates, misattributed clicks, or challenges in SMS tracking, this one's for you.

EP 24: Navigating iOS and Privacy Changes: Email & SMS Marketing in a New Era

Here's what we're diving into:

- How Mail Privacy Protection (MPP) inflates open rates & skews data

- The impact of Link Tracking Protection on email & SMS attribution

- Why ATT is still a major hurdle for retargeting & cross-channel marketing

- The rise of first-party & zero-party data (and how to collect it)

- What KPIs actually matter now (hint: clicks & revenue over opens)

- Tech solutions & workarounds to maintain accurate tracking

- Expert insights on the future of email & SMS in a privacy-first world

Thank you our friends at Omnisend, Nacelle, 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/

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://go.nacelle.com/get-started?utm_source=ecomemailmarketer&utm_medium=linkedin&utm_campaign=product_launch&utm_id=npr_li_202504

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://www.ecomemailcertified.com/

Join our community of 320+ Retention marketers! https://ecomemailcertified.com/join-community

______

02:34 Deep Dive into iOS Privacy Changes

08:18 Impact on Email Marketing Metrics

14:06 Impact on SMS Marketing

16:35 Technical Deep Dive: MPP and Link Tracking

19:20 Adapting to Privacy Changes

25:51 Future Outlook and Predictions

27:49 Conclusion and Final Thoughts

______

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 Kim at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Tired of guessing what your subscribers want? The key to better engagement isn’t more emails—it’s better data. In this episode, we’re breaking down how to collect and use first-party data through interactive content like polls, quizzes, and surveys to create hyper-personalized campaigns that actually convert.

You’ll learn how to leverage first-party data to personalize campaigns, improve deliverability, and build stronger relationships with your audience—without creeping them out. We’ll cover the best ways to implement polls, quizzes, and surveys to gather subscriber insights, how to segment your audience based on their responses, and share real-life examples of brands using these strategies to boost retention and revenue.

EP 23: First Party Data in Email & SMS: How Polls, Quizzes & Surveys Boost Engagement

Here's what we're diving into:

Why first-party data matters in 2025 (and beyond)

The impact of polls, quizzes, and surveys on engagement and deliverability

How to use first-party data for segmentation and automation

Real-world examples of brands successfully leveraging subscriber data

Best tools for collecting and integrating first-party data

Common pitfalls to avoid when gathering subscriber insights

Thank you our friends at Omnisend, Nacelle, 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/

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://bit.ly/nacelle-eem

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://www.ecomemailcertified.com/

______

03:23 Understanding First Party Data

06:18 Collecting First Party Data: Polls, Quizzes, and Surveys

11:57 Tactical Application of First Party Data

17:58 Leveraging SMS for First Party Data Collection

22:05 Utilizing First Party Data: Segmentation, Dynamic Content and More

26:00 Tactical Examples for Different Industries

31:10 Tools and Technology for Data Collection

33:09 Common Pitfalls in Data Collection

35:53 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:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

A bloated, unengaged email or SMS list isn’t just hurting your deliverability—it’s costing you money. If your messages are landing in spam, your engagement is dropping, and your platform costs are rising, poor data hygiene is the culprit.

In this episode of Send It!, Jimmy Kim and Chase Dimond break down everything you need to know about keeping your email and SMS lists clean, engaged, and high-converting. From avoiding spam traps to segmenting by engagement, they’re sharing the strategies top eCommerce brands use to maintain a healthy list (and a strong sender reputation).

EP 22: Data Hygiene for Email & SMS Marketing: Maintaining a Clean, High Converting List

Here's what we're diving into:

- Why data hygiene is crucial for email & SMS success

- The biggest risks of an unclean list (and how to avoid them)

- Step-by-step tactics for list cleaning & maintenance

- How to segment engaged vs. unengaged subscribers

- The role of double opt-in & email verification tools

- Preventing bots, spam traps, and fake signups

- The direct cost savings of a well-maintained list

Thank you our friends at Omnisend, Nacelle, 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

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://bit.ly/nacelle-eem

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

______

02:55 Deep Dive: Why Data Hygiene Matters

06:15 Strategies for Cleaning Your Email List

13:26 SMS List Cleaning Best Practices

17:11 3 Core Audience Segments

22:10 Bots, Spam Traps, and Bad Addresses

25:12 Cost Savings and Better Deliverability

27:31 Recap and Key Takeaways

______

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 Kim at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Product recommendations can make or break your revenue—so why do so many brands get them wrong?

This episode of Send It! dives into AI-powered product recommendations with Brian Anderson, CEO and Founder of Nacelle. Brian joins Jimmy Kim and Chase Dimond to explore how AI is reshaping eCommerce personalization, allowing brands to craft more engaging shopping experiences that drive higher conversions.

In this episode, Jimmy, Chase and Brian uncover what most brands get wrong about personalization, the biggest challenges in building a recommendation engine, and explore the importance of human oversight in leveraging AI for marketing, to ensure it serves as a tool to enhance human creativity rather than replace it. They also discuss the future of eCommerce personalization and what’s next for Nacelle.

EP 21: AI-Powered Product Recommendations: Driving Revenue Without Compromising Privacy

Here's what we're diving into:

- Why retention marketing is more valuable than ever—and AI’s role in it

- The biggest challenges in building meaningful product recommendations

- How Nacelle balances personalization with privacy concerns

- The importance of metadata and product context in AI recommendations

- Why giving merchants manual control over AI suggestions is critical

- Common mistakes brands make with eCommerce personalization

Thank you our friends at Omnisend, Nacelle, 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/

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://go.nacelle.com/early-access/product-recommendations?utm_source=ecomemailmarketer&utm_medium=linkedin&utm_campaign=personalization_50off_rebuy_nosto&utm_id=npr_li_202502

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://www.ecomemailcertified.com/

______

02:15 Introducing Brian Anderson

06:24 The Importance of Retention Marketing

13:35 Product Recommendation Engines

16:34 Navigating Personalization and Privacy

25:39 Busting the Myth of Personalization

28:29 The Importance of Metadata in Recommendations

30:21 AI and Human Collaboration in Marketing

34:57 The Role of AI in Engineering and Marketing

45:12 The Future of E-commerce Personalization

48:04 Wrapping Up and What's Next for Nacelle

______

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 Kim at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Customer acquisition costs have risen 60% in the last five years—which means squeezing more revenue out of each purchase is more important than ever. One of the best ways to do that? Boosting your Average Order Value (AOV).

Higher AOV means more revenue per customer—without injecting more into your marketing budget. And one of the best ways to boost AOV? Cross-selling and upselling through email and SMS.

In this episode, hosts Jimmy Kim and Chase Dimond are giving you a masterclass in using cross-sells and upsells to increase AOV. They’ll walk through the exact strategies, timing, and automations you need to seamlessly integrate these tactics into your retention marketing.

EP 20: The Secret to Higher AOV: Cross-Selling and Upselling with Email & SMS in eCommerce

Here's what we're diving into:

- Why AOV is crucial for profitable growth

- The difference between cross-selling & upselling—and when to use each

- The two key trigger points for automating these strategies (post-purchase & lifecycle)

- How to structure email and SMS flows for maximum conversions

- Building a cross-sell/upsell content calendar to stay consistent

- Balancing evergreen vs. time-sensitive offers

Thank you our friends at Omnisend, Nacelle, 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/

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://go.nacelle.com/early-access/product-recommendations?utm_source=ecomemailmarketer&utm_medium=linkedin&utm_campaign=personalization_50off_rebuy_nosto&utm_id=npr_li_202502

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://www.ecomemailcertified.com/

______

00:00 Introduction to Cross-Selling and Upselling

00:57 Celebrating Podcast Milestone

02:39 Strategies for Cross-Selling and Upselling

10:08 Email Structure and Flow for Cross-Selling

16:25 SMS Flow Structure for Cross-Selling

17:43 Developing a Cross-Sell and Upsell Content Calendar

35:16 Practical Examples of Seasonal Bundles

39:22 Measuring Success Beyond AOV

43:43 Conclusion and Next Steps

______

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 Kim at:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

The future of customer engagement is here—are you ready to keep up? As the modern commerce experience evolves, brands that master omnichannel marketing will dominate. In this episode of Send It, Jimmy Kim and Chase Dimond sit down with Rytis Lauris, Co-founder and CEO of Omnisend, to explore the next frontier of customer connections. From maximizing automation effectiveness to seamlessly integrating email and SMS, Rytis shares what it takes to stay ahead in retention marketing.

You’ll learn the biggest pitfalls in automated campaigns and how to avoid them, the latest trends in marketing automation, and how to leverage AI for smarter, more personalized communication.

EP 19: Email, SMS, and Beyond: Rytis Lauris on the Future of Customer Engagement

Here's what we're diving into:

Why visual appeal is crucial for high-ticket online sales.

The real story behind Omnisend's “customer-funded”/bootstrapped success.

How to combine email, SMS, and automation to boost conversions by 47%.

The secret to avoiding common automation pitfalls.

What’s next for Omnisend—including new features and AI integrations.

Thank you our friends at Omnisend, Nacelle, 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/

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://bit.ly/nacelle-eem

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://www.ecomemailcertified.com/

______

02:24 Podcast Introduction and Guest Welcome

05:12 The Founding Story of Omnisend

11:04 The Evolution of Marketing Automation

19:16 The Role of SMS in Marketing

22:16 Omnichannel Marketing Strategies

30:07 Common Pitfalls in Automated Campaigns

31:34 Maximizing Automation Effectiveness

33:37 Testing Strategies for Email and SMS Campaigns

37:53 Navigating Privacy Regulations

44:00 Omnisend Customer Success Stories

47:25 Overcoming the Learning Curve with New ESPs

51:16 Upcoming Features and Solutions at Omnisend

54:16 Advice for Founders and Final Thoughts

______

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:

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Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!

Want to make your email and SMS marketing work while you sleep?

In this episode of Send It, Jimmy Kim and Chase Dimond break down the power of behavioral triggers—automated messages that reach customers at the perfect moment. Whether it’s abandoned cart reminders, price drop alerts, or personalized re-engagement flows, these automations can drive revenue on autopilot and the two hosts will walk you through the exact strategy for each one.

Tune in to learn how to set up, optimize, and refine your email & SMS automations for better conversions, higher engagement, and a seamless customer experience.

EP 18: Automate Perfectly Timed Emails & SMS with Behavioral Triggers

Here's what we're diving into:

• Why behavioral triggers are essential for retention marketing
• Key automation flows every brand should have
• How to optimize automations for better engagement & revenue
• The importance of reviewing and tweaking flows every 30 days
• Real-world examples of high-performing automation strategies

Thank you our friends at Omnisend, Nacelle, 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/

Nacelle’s AI-powered personalization suite helps merchants create tailored marketing campaigns, smart product recommendations and dynamic landing pages that speak directly to its customers. https://bit.ly/nacelle-eem

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://www.ecomemailcertified.com/

______

02:58 Defining Behavioral Triggers

05:27 Welcome Series for Non-Buyers

07:28 Abandoned Cart Strategies

09:02 Abandoned Checkout Strategies

12:24 Browse Abandonment Tactics

13:46 Welcome Series for New Customers

16:08 Price Drop Notifications

18:27 Out of Stock Notifications

22:16 Date-Based Triggers

24:14 Order Confirmation and Shipping Follow-Up

25:50 Re-Engagement and Sunset Flows

27:14 Reviewing and Optimizing Automations

28:52 Certification Program Announcement

30:05 Final Tips and Advice

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