Respectful Re-engagement in Email Marketing

I see this mistake constantly. 👇 Someone has a list of 10K, 20K contacts. Nothing sent in a year. And they come to me ready to monetize. Cool. But the first email cannot be a promotion. Think about it from their side. They forgot you exist. They signed up for something months ago, moved on, and now a random email shows up trying to sell them something. That's a spam complaint. That's your domain's reputation tanking before you even get started. Here's what to send instead: One plain text email. No design. No template. "Hey, I haven't emailed in a while. Mind if I start again? If yes, just reply or click here. If not, unsubscribe link is below." That's it. No raffle. No win-back offer. No limited-time deal. Just ask permission. The people who click yes are now a warm, engaged segment you can actually sell to. The people who don't? Let them go. They were dead weight dragging your deliverability down. My actual rules: - 30 days of no engagement gets someone moved to a re-engagement segment.  - 180 days means they've forgotten who you are and need a full re-permission sequence before anything promotional. Clean list beats big list. Every single time. How long has it been since you emailed your full list?

Your “cold” email list isn’t dead, it’s just waiting for you to listen. Let’s get this out of the way - a “cold” list doesn’t mean it’s a dead one. It means you’ve stopped showing up consistently, and your audience has stopped expecting you to. That’s exactly where one of my clients was when we started working together. A 25,000-strong list that hadn’t been emailed properly in months. Engagement had dropped. The team was stretched. They assumed the audience had lost interest. They hadn’t. We didn’t start with a hard sell. We started with a reintroduction. A simple re-engagement sequence that did three key things:   • Set expectations (“You’ll see us in your inbox more often”) • Invited feedback and self-segmentation (“What’s your biggest challenge with topic X?”) • Gave an easy out (“If it’s not for you, unsubscribe - no hard feelings”) Then we used smart sending to protect deliverability -  starting small, measuring engagement, and scaling. The results: • 97.5% deliverability • 0.3% unsubscribes • 20 new leads before a single sales email Once we’d reestablished trust, we launched a targeted, data-led campaign, and less than two months later, that “cold” list had generated $203k in revenue. With zero ads. No social media postings whatsoever. And no fake urgency. Just clean data, consistency, and genuine communication. If your list feels cold, it’s not because your subscribers have stopped caring. It’s because they’ve stopped hearing from you in a way that feels meaningful to them. Stop ghosting your audience or sending emails that are irrelevant to your folks. Start listening to what your data is telling you. If your list feels stuck and you want to bring it back to life (ethically and effectively), book in a disco call: https://lnkd.in/gUTyunWE

Last week, I received a weird email from someone I've followed on Substack for over a year. Her newsletters are fun and quirky, and I always look forward to seeing them in my inbox. So, imagine my surprise when I received an email declaring that I haven't opened one of her newsletters in a while. My punishment? I was being automatically unsubscribed from her email list. Uh, OK. But I do read the emails. Every time one lands in my inbox. Sometimes I stop what I'm doing to read them because they're that entertaining. I was confused. I reached out to the person and told her so. Crickets. And now I no longer receive her newsletter because she automatically purged a regular reader based on heaven knows what criteria. Did whatever tool she's using to track engagement give her incorrect data? I'll never know. And she apparently didn't value me enough as a loyal follower to respond to my question about why she thought I was no longer opening and reading her stuff. I'm kinda salty about being purged from a list I was actively using. If you're a creator managing an email list, here's how to handle list hygiene without losing loyal readers: - Send a re-engagement email first. Before removing anyone, give them a chance to opt back in. If they don't respond to that, then removal is fair game. - Don't trust open rates blindly. Apple's Mail Privacy Protection and certain email clients can prevent opens from being recorded even when someone reads every word. Low open rates don't always mean disengagement. - Respond when someone reaches out. A confused subscriber contacting you directly is a sign of investment. Ignoring them doesn't just lose you a reader. It loses you someone who genuinely cared about your work. List hygiene is a legitimate practice, but a little humanity goes a long way.

Retention Isn’t Sexy - Until You’re Broke Brands chase growth. But when the faucet turns off and the market tightens, email becomes your backbone. So why do we treat it as a short-term fix rather than a long-term asset? I hear this conversation replayed to me all the time from CRM and Brand Managers: Their Manager: Targets are down. Budget’s gone. Just send more emails. CRM: We already sent one this week with a promo. Manager: Send another. Bigger discount. CRM: Unsubscribes were high last time… Manager: Send to everyone — even non-engagers. Add urgency. And so it begins. 📉 Deliverability drops. 📉 Clicks tank. 📉 Unsubscribes rise. 📉 The database - your only owned audience - starts eroding. But the revenue target stays the same. This is what happens when you treat email like a faucet you can turn on and off — instead of a system you build and respect. 💡 Want to break the cycle? Here’s how smart brands avoid the spiral: 1. Build an acquisition engine, even when times are good. Don’t just chase sales. Chase subscribers, on all channels, not just site pop-ups. If 2% of traffic buys, aim for 20% to subscribe. That’s your future revenue. 2. Agree on discounting guardrails. Not every campaign needs a percentage off, even if times are tough. Consider other conversion tools like: - loyalty perks - free gifts - tiered basket incentives - competitions - outlet-style categories 3. Treat non-converters as humans, not dead weight. Reduce frequency, but stay visible. Try to understand why they’re lapsing e.g gift buyers? Promo-only? Seasonal? 4. Use peak trading to re-acquire, not just sell. Black Friday can re-engage lapsed customers. But the follow-up can’t be more noise. Build a new journey. Reset the relationship. 5. Track long-term metrics. Not just revenue-per-send. Show your management week on week how these are growing: -LTV - Repeat purchase rate - AOV - Site visit frequency from consumers on your database 6. Invest in content, not just campaigns. Nurture a community. Give them reasons to stay subscribed. Boost engagement before you ask for a sale. Remember nobkdy going to buy daily and weekly, you need more to keep them engage. Think weekly style tips, news Roundup, podcast drops, games, polls etc Email can be your safety net — but only if you protect the list, grow it intentionally, and stop burning it out with knee-jerk sends. Want to find out our playbook for growing your subscriber base rapidly. (like how we grew out base to 17m). DM me. Build it right. Because when things get tough, it’s your email list that keeps the lights on.

Is your email marketing actually building relationships — or just filling inboxes? If your open rates are dropping and conversions are flat, it’s time to rethink your strategy. Here are 6 smart rules that can transform your email campaigns into valuable conversations: 1. Divide and Conquer Don’t treat your audience as one giant group. Segment them by age, interests, location, or buying behavior to make your emails more relevant and targeted. 2. Make It Personal Use details like names, preferences, or birthdays to customize your emails. A personalized touch can dramatically improve engagement and click-through rates. 3. Build Trust First, Sell Later Avoid jumping straight into sales mode. Share helpful content, insights, or updates before making any offers. Relationships come before revenue. 4. Give Before You Ask People are more likely to share their email if there’s value in it for them. Think exclusive deals, useful downloads, or insider access. 5. Let People Unsubscribe Easily An easy-to-find unsubscribe button isn’t a threat—it’s a sign of respect. If they want to leave, let them go without friction. 6. Start Real Conversations Encourage replies, ask for feedback, and respond to your audience. Email shouldn’t be a one-way broadcast—it’s a dialogue. Email marketing is more than sending messages—it’s about delivering meaning. Refine your strategy. Respect your audience. Reap the rewards.

I grew my client’s best email month by 148% from €525K to €1,3M. Here’s how I did it: When I first took on this client, I loved his vibe and product. But it was tricky… • They only sell 1 product • My client hates being salesy • They sell in multiple countries using native languages Step 1: Audit Every client I take on goes through a thorough list audit. I audited his list with my 66-point Klaviyo checklist to: • Identify what’s leaking revenue • Pinpoint what’s working to double down • Develop a strategy plan to increase his sales Once done and discussed, we got to work on: Step 2: Building and optimizing flows He had multiple flows set up but only his welcome flow was good. The rest was non-existent or only had 1-2 basic emails. So we redid his flows. When I was done, we instantly saw an increase in email revenue. The secret? I used founder-led content. The emails feel like a 1:1 convo, and most of my time went into the copy because… Design attracts but copy sells. The next step was… Step 3: Proper segmentation For a brand that sells one product, it’s easy to neglect the ones who’ve bought. (especially since it’s not a replenishable product) But my client is working on new products. Neglecting anyone would be a HUGE mistake - it always is. Here’s how I segmented: • Language • Engaged vs non-engaged • Customer vs non-customer All emails are properly targeted and personalized with the right intention. It makes people feel like we’re talking directly to them. But this wasn’t enough as… Step 4: Ramp up campaign volume They weren’t sending campaigns which meant a lot of revenue was left on the table. I started with re-engagement campaigns to identify the engaged segment. (if you don’t know this your deliverability will go down the drain) Then I split the engaged segment into: • Non-customers • Everyone That’s how I ensure we don’t send emails that aren’t relevant to the reader. The more campaigns you send, the more touch points and familiarity you create. Which leads to closer relationships and more sales. Many eCom founders are scared of being annoying if they send too many campaigns. If you only send: 1/ Sales and discounts 2/ Things that people don’t care about Then yeah you’re being annoying. But if you do email marketing the quiet way, people want to hear from you. It wasn’t all sunshine and rainbows. This job was brutal. But our hard work paid off because we… ↳ Topped his best sales day in Oct ↳ Grew total revenue by 69% to 4.51M ↳ Beat his best email month by 148% to 1.30M ↳ Grew campaign revenue from 0 to 414k (in Oct) ↳ Involved his customers in his new product development process And the best part? I’ve only been working with them for 3 months. We’re just getting started. -- If you’re an eCom owner who wants to scale your revenue: I’m looking to work with 2 eCom brands to help them increase their email revenue in the next 60 days. DM me “email” and I’ll get you the details.

Stop sending re-engagement emails to people who never bought.... Here’s what most brands do: • Add to cart with no purchase? • No opens in 60 days? → “We miss you 😢 Here’s 10% off” That’s not a winback. That’s a discount to someone who doesn’t care. Here’s the fix: Split your unengaged users into 2 buckets: Bucket 1 → Past purchasers (already trusted you once) Bucket 2 → Never purchased (still cold) For bucket 1: → Send benefit based reminder of the product they bought → Offer support, not a sale (“Need help using it?”) For Bucket 2: → Use a 3 email re-introduction series: • Email 1: “Still struggling with [pain point]?” • Email 2: “Here’s how others solved it using [product]” • Email 3: “Want in before we close the door?” Stop treating everyone like they’re one email away from a sale. Relevance > desperation.

Brands LOVE telling me they have 50,000 subscribers. Then I ask how many opened an email in the last 90 days... Because THAT number is your real list, and everyone else is dead weight that's actively costing you thousands of dollars on Klaviyo. Gmail and Apple Mail both watch what happens when you send. • Keep hitting 9,000 people who never open • And the algorithm decides you're a sender nobody wants.  • Your emails get pushed to promotions and then to spam.  • Now even your buyers stop seeing you. Segmenting by behaviour fixes this. Instead of blasting one email at everybody, you split the list by how people actually act. We pulled a real account and broke it into four groups: → Engaged: opened or clicked in the last 30 to 90 days. These people hear from you the most. → One-time buyers: bought once, never came back. They get a sequence built to pull them into a second purchase. → VIPs: early access and exclusive offers that make them feel like an insider. → Lapsed: nothing in 90 days or more. Re-engagement campaign, or suppress them to protect your reputation. One of our engaged segment campaigns to a 90-day engaged group of 22,000 people, bounced emails excluded, pulled a 60% open rate, a 1.94% click rate, and $6,000 in revenue. The same brand ran a campaign that included unengaged, all-time non-buyers, and it managed a 29% open rate, a 0.99% click rate, and $2,900. There's STILL money in the unengaged... you just need to save them for the moments that matter (like a final-hours sale or a product drop) The engaged audience gets the regular sends, and the unengaged gets the big moments only. That protects deliverability for the other 28 days of the month, and you still squeeze the full list when it actually counts.

When this client reached out, they had given up.  Their email list was dead. No opens.   No clicks.   No sales.  They were convinced email marketing didn’t work.  But the problem wasn’t email.  It was their strategy.  So, I asked one question:  "When was the last time your audience heard from you?" Their answer? Two months ago. No wonder it wasn’t working.  Here’s what we did:  1. Re-engagement first. We sent a simple email:   "Still interested in hearing from us?"   People who replied yes got moved to an engaged segment.  2. Value before selling. For the next three weeks, we sent pure value.   No hard sells.   Just helpful content that builds trust.  3. The right offer at the right time.  Once engagement increased, we made a low-risk offer.   A small $30 product.   Nothing fancy.  And guess what?  People bought it.  It wasn’t a huge number.   But it proved something critical. Their list wasn’t dead. It just needed the right approach.  Now they’re scaling up to bigger offers.  Revenue is growing.  And email is their highest ROI channel.  If you have a "dead" email list, it’s not over.  You just need the right plan.  Are you leaving money on the table?

Duolingo sent 6 emails in 4 days to win back a lapsed user. The user unsubscribed. It all went wrong before the first email was ever sent. First, to be clear, Duolingo has one of the best brand voices in the market. The subject lines are fine. The creative is not the problem. The problem sits upstream of the inbox entirely. Because before you send a single re-engagement email, you need to answer 3 questions 👇 🖐 Why did this user lapse? Disengagement, a life change, a bad experience, and a change of habits all look the same in a suppression list. They don't require the same response, so never send the same sequence to all of them. ❗ Is this user worth re-engaging? Not every lapsed user has the same value. Some will come back, but some have already decided they're done. Sending 6 emails in 4 days to someone who has mentally moved on won't change their mind. 🔄 What does coming back actually look like for this person? If you don't know why they left, you cannot know what would bring them back. Their reason for leaving has to inform the message, or they'll never listen to you. This is a common problem that doesn't just apply to Duolingo. Most re-engagement programs are built around send volume and subject line testing. Very few are built around understanding why users lapsed in the first place. The brands that handle retention well start with the data on why users lapse. They segment before they send. The ones that don't send 6 emails in 4 days make the problem worse. With Henry Rose, we took the opposite approach to volume. We started with a careful warming send for their kickoff sale. Prioritizing the right audience over the widest reach. Sales increased by 122%. But the result wasn't about the email. It was about the decision made before the email was sent. More emails don't fix a retention problem. Spamming ex-customers with emails won't solve the problem. You need to know why they stopped opening in the first place. Have you ever received a re-engagement sequence that brought you back?  What made it work? Let me know in the comments. ♻️ Repost if you've ever watched a win-back campaign accelerate the churn it was supposed to reverse. Follow me, Jacob Rokeach, for more on lifecycle strategy and signals-first thinking.