Why repetitive email reminders fail with customers

I had one of those tiny but telling email moments this weekend. One of my favourite beauty brands emailed me with a lovely loyalty offer: Buy between Friday and Monday and get 200 loyalty points. Value: £10. Lovely. Relevant. Clear. Enough of a nudge to get me to purchase. So I did. I bought on Saturday morning. Then on Sunday, I received another email reminding me to buy so I didn’t miss out on the free £10. Then again on Monday. And do you know what happened? It made me second guess myself. I actually went back and checked that I had placed the order properly. That’s not the feeling you want to create after someone has done exactly what you asked them to do. At a minimum, I should have been suppressed from the remaining reminder campaigns once I purchased. Preferably, I should have received a different email entirely: You’ve qualified for your 200 loyalty points. They’ll be added to your account soon. That would have reassured me. It would have closed the loop. It would have made me feel good about buying. Instead, the campaign left me with doubt. And this is where email marketing gets interesting. Because the issue wasn’t the offer. The issue wasn’t the copy. The issue wasn’t the timing. The issue was the customer logic. Too often, we think of campaigns as individual sends. Email 1. Reminder 1. Reminder 2. Last chance. But customers don’t experience them as separate sends. They experience them as one continuous conversation with the brand. And if that conversation doesn’t recognise what they’ve already done, it can feel clumsy, confusing, or even a little careless. This is why post-purchase suppression isn’t just a technical hygiene task. It’s part of the customer experience. And confirmation messaging isn’t just transactional admin. It’s reassurance. Sometimes the most persuasive email is not the one that gets someone to buy. It’s the one that makes them feel confident after they have. Where are the gaps in your campaign logic that might be creating doubt instead of confidence?

₦47 million in unpaid invoices. Reminders were sent every week like clockwork. Yet there was no response. Then we went deeper to find out what was happening: Operations would finish a project and tell finance: "It's done." Finance would immediately fire off the full invoice. But the real problem was that the clients never signed off that the work was complete. So when invoices landed in their inbox, they ignored them. As far as they were concerned, the job wasn't finished. No amount of reminder emails would fix that. I've seen this exact scenario play out dozens of times across different industries. While it affects cash, it's not really a cash flow problem. It's a process problem disguised as a cash flow problem. Here's what we did to rectify the situation: We reviewed every single disputed project. Resolved the issues clients had flagged. Within 3 weeks, we recovered 90% of that ₦47 million. Crucially, we then made one simple change to the process: No invoice goes out without a signed Completion Certificate from the client first. Operations initially pushed back hard and called it an extra hassle. But we reframed it as ..." a quality check to ensure clients are happy before we bill them." That shifted everything. Invoices started getting paid on time. Cash flow improved dramatically. It's simple psychology. Customers who are satisfied with the work pay on time. Customers who feel blindsided by an invoice for unfinished work? They don't. So if unpaid invoices are piling up in your business, pause and first ask: • Is the work truly finished? • Has the client actually accepted it? Because in business, "done" doesn't mean when 𝘺𝘰𝘶 say it's done. It means when the customer says it's done. #myCFOng

Everyone sends: “You left items in your cart. Come back.” Stop. That’s lazy. Here’s why it fails: - It reminds people what they’re losing, but doesn’t reduce friction. - It ignores the reason they abandoned. Better approach: solve the friction before asking to buy again. 1. Identify top abandonment reasons (shipping cost, size uncertainty, confusion). 2. Address them directly: - “Your cart qualifies for free shipping if it reaches $X” - “Our size chart has been updated based on thousands of customers” 3. Show micro options to complete the purchase: - “Complete in 1 click” - “Choose delivery window” Lesson: Abandoned cart emails are problem solving nudges

Stop spamming your best customers with the same offer. I nearly unsubscribed from one of my favourite spas last month. And this is a place I actually love, I go twice a year, without fail. But every single week my inbox was hit with the exact same thing: ➡️ “FLASH SALE 50% OFF MIDWEEK” ➡️ “FLASH SALE 50% OFF MIDWEEK” ➡️ “FLASH SALE 50% OFF MIDWEEK” Same design. Same offer. Same email. Here’s the problem: If I’m already a loyal customer, I don’t need endless reminders.  I don’t need to be treated like I’ve never been before. I need to feel valued. That’s where so many hospitality brands go wrong with their email marketing. They send the same blanket message to everyone instead of recognising the difference between: → A new customer they’re trying to win. → A loyal customer who already comes back. → A VIP guest who spends the most with them. Each of those people needs a different message, a different experience. Email isn’t just a sales blast, it’s a system for loyalty, retention, and advocacy. If you reduce it to the same generic offer every week,  You don’t just lose sales.  You lose trust. Your best customers deserve more than a discount code. They deserve loyalty.

I’m increasingly convinced that what separates good Customer Success from great Customer Success is this: The ability to predict customer behaviour… and act on it correctly. I read a brilliant post from Covenant Obioma (CCSS, CCSE) yesterday. She shared how Duolingo sent her a funny email begging her to come back after months of inactivity. It caught her attention. It made her smile. But it didn’t make her return. Why? Because the message didn’t meet her where she was. Technically, Duolingo wasn’t wrong. She could start a lesson. But her relationship with the product had changed. If the message had aligned with her current context maybe learning a new skill, exploring something new, or a lighter re-entry she said she would have clicked. This is the part most teams miss. Duolingo didn’t fail because the copy was bad. They failed because the signal was shallow. They treated inactivity as one thing. Instead of asking: what type of inactivity is this? And that’s where segmentation comes in. Good Customer Success isn’t about reacting to behaviour. It’s about understanding what that behaviour means. Two customers can look identical in your data inactive for 90 days but be in completely different places: • One is overwhelmed • One has outgrown the use case • One is waiting for a new reason to care • One is simply done Sending the same message to all of them is lazy. And expensive. This is why CS motions can’t be based on gut feel or generic rules. They have to be empirical. Consistently tracked. Continuously refined. Backed by both qualitative insight and quantitative data. Proper segmentation helps you answer better questions: Not just “What did they do?” But “Why did they do it?” And “What’s the most sensible next action now?” So when a customer exhibits a behaviour don’t rush to trigger a playbook. Pause. Ask what it signals. Ask what changed. Ask who this customer is now. That’s how you stop pushing the “right” message at the wrong time and start guiding customers forward instead.

This eCom lie needs to be addressed: “Replenishment emails are effective at driving repeat purchases”. They’re not if you don’t pair them with other strategies. Your repeat purchase rate also depends on other factors:  - Timing and need for the product  - Resonant pricing  - Product quality, results, social proof Most importantly? Product usage. If your customers aren’t regularly using the product? No amount of reminders will convince them to buy again. I even see this gap in the 7-8 figure brands that I audit. Their strategies are overly focused on reminding customers to repurchase without ensuring:  - Product activation (the customer actually uses the product)  - Consistent consumption (regular and ongoing use)  - Value maximization (customers get the most benefit possible) One way to ensure all of the above? A rock-solid onboarding flow that:  - Helps customers use the product  - Educates customers on all possible use-cases  - Informs customers on the best way to use the product This is more likely to boost repurchase rate than email reminders. Positive product experiences are what *actually* increases repurchase rate. Much better than trying to incentivise repurchases with discounts.

When did you last read the email your company sends to ask a customer to pay? I don't mean the invoice. I mean the reminder, the one that goes out when payment is late, written once by someone who has since left, automated, and never read again. For a lot of companies it lands like a threat with a due date. If you bill monthly or on usage, that reminder may be the most repeated deliberate ask you ever make of a customer. You onboard them once. You renew them maybe once a year. But you ask them to pay again and again, and every ask carries a tone. The person who feels that tone is usually someone in accounts payable, not the champion who chose you. But friction travels. A billing experience that feels careless becomes an internal complaint, and it reaches the people who decide whether to renew and whether to refer you. We spend real money on the first impression and the product experience, then hand the most repeated moment in the relationship to a system nobody designed: a dunning sequence on a timer, a portal that rejects the invoice without a bounce-back, a reminder sent to a contact who left months ago. The payment experience is the last first impression. The best finance teams I know have started treating that moment the way they treat onboarding. Same money owed. A completely different message about who they are. You can't always control when a customer pays. You can control what it feels like to be asked.

One cold email isn't enough. But most follow-ups are just reminders, that's why they fail. And the worst part? You already know this. You've felt it on the receiving end. Someone pings you. You mean to reply. Life happens. They send "Just wanted to circle back on this" and suddenly you have zero desire to ever respond. That's not a follow-up. That's friction dressed up as persistence. Real sequences don't remind people you exist. They give people a reason to care. So here's what a real sequence looks like: ► Email 1: Don't open with your product, open with their world. A shift in their industry. A problem they're probably losing sleep over. End with one question so low-effort it feels weird not to answer. ► Follow-up 1: Same person, different door. Not the same pitch with a smiley face. A new angle. A benefit they haven't considered. Make them think: "huh, I hadn't thought of it that way." ► Follow-up 2: Stop talking. Show A company that looked exactly like theirs, had the same headache, and fixed it. Let the proof do the selling. ► Follow-up 3: Give them the exit with grace. "Worth a quick chat, or should I close your file?" That sentence works because it's honest. It respects their time. And somehow, that respect is what finally makes people reply. The best cold email sequences don't feel like sequences at all. They feel like the right person showing up at exactly the right moment. Build momentum. Not a paper trail. What do you send in follow-ups? #leadgeneration #coldemail #emailmarketing #intentbasedcoldemail #demandgeneration

If your control is "Please ensure...", think again.... How many emails have you sent or received that begin with: "Please ensure..." Please ensure the customer is informed. Please ensure the approval is taken. Please ensure the document is uploaded. Please ensure the quality check is completed. Let's be clear. There's absolutely nothing wrong with saying "Please ensure..." In fact, it's often appropriate. A leader may use it to emphasize a critical priority. A manager may send it as a one-time reminder. A team may use it during a transition or while implementing a new process. But here's the question. What if every other email in the organization starts with "Please ensure..."? Then it's worth pausing and asking why. Why does this activity depend on someone remembering? Why does it require repeated follow-ups? Why does it need constant intervention? At that point, "Please ensure..." is no longer just a reminder. It may be compensating for something deeper. Perhaps the process needs to be redesigned. Perhaps the system can trigger the next step automatically. Perhaps accountability isn't clearly defined. Or perhaps the team simply needs better capability and training. The answer isn't always process redesign. The answer isn't always capability building either. The real question is: What is making this reminder necessary in the first place? High-performing organizations don't try to eliminate reminders. They strive to eliminate the need for repeated reminders by strengthening their systems, processes, governance, and people. So the next time you type "Please ensure...", pause for a moment and ask yourself: Is this a one-time reminder... or is it quietly exposing a weakness in the way our organization operates? Sometimes, the problem isn't the people. It's the design of the organization!!