EP 82: The 160-character masterclass: Writing SMS that actually converts
Send It! · with Chase Dimond · May 26, 2026 · 35 min
Summary
SMS marketing, when done correctly, is a high-converting channel. This episode provides a masterclass in crafting SMS messages that convert by focusing on conciseness, context, and customer intimacy. Learn copywriting formulas for various campaigns and how to leverage AI to optimize your SMS strategy and avoid common pitfalls like high opt-out rates.
Key takeaways
Don't shrink emails for SMS; SMS copywriting is a distinct skill demanding extreme brevity and directness. Every word, including brand name and link, must earn its 160-character spot.
Implement the "hook, value, action" framework for every SMS. The hook (first 5-10 words) must immediately convey urgency, curiosity, or value, as this is what recipients see in notifications.
Tailor SMS content dynamically based on user behavior and intent. Use specific formulas for abandoned carts, replenishment reminders, VIP drops, and flash sales to ensure relevance and drive conversions.
Leverage AI tools to generate, compress, and A/B test SMS copy. AI can help tighten messages to fit character limits while maintaining urgency and value, and generate variations for optimization.
Prioritize segmentation and frequency control. Unlike email, SMS is highly intrusive; excessive or irrelevant messages lead to high opt-out rates. Send only valuable, timely messages to highly segmented audiences.
A bad email gets ignored. A bad SMS gets you blocked.In this episode of Send It, Jimmy Kim and Chase Dimond unpack why SMS keeps falling flat for so many brands and walk through the copywriting formulas that actually convert. The problem isn't the channel, it's that nobody learned how to write for it. With only 160 characters up for grabs, every word has to earn its place, every hook has to land in the first three seconds, and every send has to feel worth interrupting someone's day for. Jimmy and Chase break down the three part structure every high-performing SMS follows, the specific formulas for abandoned cart, replenishment, VIP drops, and flash sales, and the AI prompts they use to write and tighten copy fast.EP 82: The 160-character masterclass: Writing SMS that actually convertsHere's what we're diving into:- Why SMS copywriting is a different skill than email and the four constraints that make it harder- The hook → value → action formula every high-performing SMS follows- Specific formulas for abandoned cart, replenishment, VIP drops, and flash sales- The AI prompts they use to generate, compress, and A/B test SMS copy- The frequency, segmentation, and testing rules that protect opt-out ratesThank you our friends at Omnisend, Superscale, Retention Roadshow 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/Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Crea
Frequently asked about this episode
What does this episode say about email & sms?
Don't shrink emails for SMS; SMS copywriting is a distinct skill demanding extreme brevity and directness. Every word, including brand name and link, must earn its 160-character spot.
What does this episode say about conversion & cro?
Implement the "hook, value, action" framework for every SMS. The hook (first 5-10 words) must immediately convey urgency, curiosity, or value, as this is what recipients see in notifications.
What does this episode say about ai & automation?
Tailor SMS content dynamically based on user behavior and intent. Use specific formulas for abandoned carts, replenishment reminders, VIP drops, and flash sales to ensure relevance and drive conversions.
What does this episode say about email & sms?
Leverage AI tools to generate, compress, and A/B test SMS copy. AI can help tighten messages to fit character limits while maintaining urgency and value, and generate variations for optimization.
What does this episode say about email & sms?
Prioritize segmentation and frequency control. Unlike email, SMS is highly intrusive; excessive or irrelevant messages lead to high opt-out rates. Send only valuable, timely messages to highly segmented audiences.
