Crafting Compelling Re-Engagement Emails

Most follow-ups fail because…. They ask for attention without earning it. “Just bumping this up” “Wanted to see if you had a chance to review” “Circling back one last time” That’s not follow-up. That’s spam in disguise. Here’s a value-first follow-up sequence that actually revives cold threads and turns them into booked meetings: Context reset: 2-3 days after no response, send a short message that acknowledges the silence without pressure. “Hey [Name], totally understand if now’s not the right time. Sharing this because it ties into what you’re working on.” Then include a resource that’s directly relevant to them: -A teardown -A market insight -A short case snippet No ask. Just value. Step 2: Targeted insight 4-5 days later, follow up again with a brief, relevant takeaway. “Saw [company] is hiring more AEs. Teams in that phase usually hit a bottleneck around lead-to-demo conversion. This deck breaks down how one RevOps team solved it.” Again, no pitch. Just drop the resource. Step 3: Soft re-engagement Final touchpoint a week later. “Hey [Name], happy to close the loop here. If this becomes a focus later this quarter, happy to re-connect then. Leaving you with this last piece on [topic].” You’re closing the thread politely, while still delivering something useful. Why this works: You shift the dynamic from salesperson to expert. You build trust by showing, not telling. You earn the reply by giving them a reason to engage. Follow-up is not about staying top of inbox. It’s about staying top of mind. Rooting for you, Tom

An ecommerce company recently approached my team to do an email audit as they were facing challenges with low open and click-through rates. After analyzing their email account, here are our main recommendations to revive their email marketing channel: 1. Strategic Email Segmentation: Currently, your emails lack personal relevance due to a one-size-fits-all approach. This is a crucial area to address. Action Plan: Implement segmentation based on purchase history, engagement levels, browsing behavior, and demographic information. 2. Personalized Content Creation: Generic content won't cut it. Your audience needs to feel that each email is crafted for them. Action Plan: Develop emails specifically tailored to the different segments. This includes curated product recommendations, personalized offers, and content that aligns with their interests. 3. Subject Line A/B Testing: Your current subject lines aren't doing their job. You need to be implementing ongoing A/B subject line tests, as this is low-hanging fruit to improve your open rates. Action Plan: Regularly test different subject line styles and formats to identify what resonates best with each segment. Keep track of the metrics to inform future campaigns. 4. Mobile Optimization: A significant portion of your audience reads emails on mobile devices. Neglecting this is causing a decrease in your email engagement rates. Action Plan: Ensure all emails are responsive and visually appealing on various screen sizes. Test your emails on multiple devices before sending them out. Additional Campaign Strategies We Recommend: - Launch a Monthly Newsletter: This should include new arrivals, style guides, and user-generated content. It’s an excellent way to keep your brand in the minds of your customers. - Seasonal Campaign Integration: Tailor your campaigns to align with holidays and seasons. This approach can significantly boost engagement and sales during key periods. - Re-Engagement Campaigns: Specifically target subscribers who haven't interacted with your brand recently. Offer them unique incentives to rekindle their interest. Next steps: 1. If you found this helpful, please leave a comment and let me know. 2. If you own/run/work at an Ecommerce company doing at least $1 million in annual revenue, message me so my team can audit your email channel to see if there's a good fit for working together.

Getting ghosted regularly when you try to book time with your customers? Bad news - it's probably not them. It's very likely you...or at least your emails. Too few CSM emails are receiving training on how to build emails that are compelling. If you need to get that call booked, try to make sure that your email is a VIBE. And by that I mean: V - Value. Make sure you've spelled out the value your customer will get from attending (not just listed your discussion points). Instead of "We're going to dive into roadmap, align on goals, etc) pivot to "We're going to discuss X feature. We'll create an action plan on how this can help your team to achieve Z result." When in doubt, include the sentence "Coming out of this meeting, you should.." I - Individualize. Once you've built a bank of these compelling emails to templatize, don't forget to individualize them. Customize each email to your contact's goals, desired business outcomes, and with key details you know about them or their team. B - Better. Just the act of reading your email should provide insights so impactful they can make your contact better at their role or the project at hand. Provide a key tip or insight up front that's custom just for them. For example, instead of "We'll dive into the metrics" you can share "We'll dive deeper into the 8% lift I've seen recently on team adoption of feature X, and how to capitalize on this momentum." E - Edit. You're providing key insights and value, but you need to do it concisely. So write, write, write away. And then edit judiciously to trim anything unnecessary from your content. Become aware of your filler words (look out for every very, really, and just), remove full sentences that don't say anything new, and make sure you're being crystal-clear in your ask (did you forget to actually ASK them to confirm a time for the call??

Lapsed donors aren’t lost causes. They’re just waiting for a better invitation. Let’s stop pretending your “We miss you!” email blast is doing the trick. It’s not. It’s background noise. And donors? They’ve got inboxes full of it. Here’s how you actually bring lapsed supporters back—without sounding desperate, and without starting from scratch. 1. Ditch the generic. Go personal. If your message could go to anyone, it will resonate with no one. Go beyond “Dear Supporter” and reconnect with their impact. Try this: “Hi Jordan — your gift last year helped provide safe housing for 20 families. We’re building on that work right now, and we’d love for you to be part of it again.” Better still? Send a personalized video or handwrite a note. People remember when you remember them. 2. Add a reason to come back—besides guilt. Sometimes people need a nudge. Not a push. Offer meaningful incentives: – A matching gift opportunity – An exclusive update or behind-the-scenes invite – Public recognition on your donor wall Make it feel special, not transactional. The goal is to make re-engaging feel like a win—for them and your mission. 3. Show your progress, not your panic. Donors want to be part of momentum, not rescue missions. Instead of saying, “We need your help more than ever,” say: “Since your last gift, we’ve provided 10,000 meals. And we’re just getting started.” Show what their past support made possible—and what’s next. 4. Use social proof like a pro. People want to belong. Show them that others are stepping up again. Spotlight returning donors in your newsletter. Share short quotes or videos from beneficiaries. Send a message like:“You’re not the only one we’ve missed—supporters like Maria just renewed their gifts this month. We’d love to welcome you back too.” Validation + community = powerful combo. 5. Make coming back ridiculously easy. This is where most nonprofits drop the ball. Don’t make someone dig through your website or hunt for the donate button. Use: – Direct donation links – Pre-filled forms – One-click options – QR codes in print materials And yes—make sure your mobile experience isn’t stuck in 2012. Lapsed donors aren’t a lost file in your CRM. They’re people who already said yes once. Your job? Remind them why.

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?

If your emails aren't getting responses, it might not be your offer. It could be how you're delivering it. Decision-makers aren’t ignoring you out of spite. They’re busy, selective, and flooded with messages that often sound the same. The good news? A few thoughtful tweaks can make your emails more engaging, easier to read, and more likely to earn a response. Here are 9 practical tips to improve engagement with B2B decision-makers: → Write like a person, not a script → Lead with something helpful → Craft a subject line with purpose → Make your preview text count → Focus on outcomes → Share proof when it makes sense → Keep it easy to skim → Personalize with context → Keep the CTA simple Better emails don’t mean longer emails. They mean smarter, more respectful communication that puts the recipient first. When your email helps someone do their job better, make a clearer decision, or solve a problem they actually care about—that’s when it gets opened, read, and replied to. --- Follow Michael Cleary 🏳️🌈 for more tips like this. ♻️ Share with someone whose emails keep getting ignored.

Your newsletter isn’t just a newsletter. It’s a customer reactivation machine. Most companies treat churned customers like they’re gone forever. We turned Post Planner's newsletter into a reactivation engine — bringing back past customers without sending cringey "reactivation" sequences. Here’s how you can do the same: 1️⃣ Pull Your Churned Customer List Export past customers from your CRM (if they didn’t opt out of emails). Bonus: Include inactive free-tier users or trial users who never converted. 2️⃣ Segment and Clean Your List Before launching, verify your entire list with a tool like Clearout. Slowly drip these emails into your newsletter sends (increasing your sending volume too quickly will cause your deliverability to tank). 3️⃣ Create a Newsletter That’s Actually Worth Reading Most B2B newsletters are dry product updates. Nobody wants that. Instead, send: ✅ Industry insights your audience actually cares about ✅ Playbooks & tactics they can implement right away ✅ Case studies showing how others are getting results with your product ✅ (Subtle) product mentions—but only when relevant 4️⃣ Make It Fun & Engaging Your newsletter should be: 🔥 Scannable (short paragraphs, bullets, bold key points) 🔥 Entertaining (add personality, memes, and humor) 🔥 Consistent (weekly or bi-weekly, never sporadic) 5️⃣ Track Engagement Beyond UTM Clicks Most companies only track “newsletter-driven sales” through UTM links. That’s a mistake. Look for these signs of reactivation: ✅ Increased logins from old accounts ✅ More Intercom/chat support inquiries from churned users ✅ Leads that “randomly” re-enter your pipeline 6️⃣ Stay Consistent & Play the Long Game When done right, newsletters: 💰 Keep your brand top-of-mind with leads (until they're ready to buy) 💰 Nurture past customers until they’re ready to return 💰 Drive revenue without pushy re-engagement tactics that burn through your contacts list #B2BSaaS #contentmarketing #B2Bmarketing

A bloated email list is sabotaging your bottom line. Email providers see unengaged subscribers, put you into spam… …and suddenly, your emails stop reaching inboxes. Even worse, you're paying for contacts who'll never buy from you. Here’s how to turn that around ↓ 1. Segment ruthlessly In 2024, personalized segmentation is an absolute necessity. Break your list into targeted groups: → Active subscribers (clicked in the last 90 days) → Casual browsers (opened but didn’t click) → Lapsed customers (no purchase in 6 months) → Ghost subscribers (no engagement in 180 days) 2. Create engagement ladders Don't blast everyone with the same content. The goal is to move people up the ladder, not off the list. Build paths that nurture relationships: → Welcome series: 3-4 emails over a quick 4-6 day period for new subscribers → Win-back campaign: 3-part series for lapsed customers → VIP track: Early access and exclusives for top spenders 3. Prune dead weight Set clear rules to maintain list hygiene: → No clicks in 180 days? Send a re-engagement campaign → Still no response? Remove them after 2 attempts → Implement soft bounce exclusions to reduce delivery issues A smaller, engaged list beats a massive, unresponsive one every time. 4. Focus on clicks, not opens iOS updates made open rates unreliable. Clicks tell the real story. To boost them… → Put key info and CTAs above the fold → Use action-oriented language (e.g. “shop now”) → A/B test email layouts and content hierarchy 5. Personalize thoughtfully Use the data you have wisely and present… → Product recommendations based on browse behavior → Dynamic content tailored to purchase history → Location-based offers (for omnichannel brands) Show you understand your customers without overdoing it. Because your email list isn't just a database — it's a community of real people who've invited you into their inbox. Treat it with care, and it'll become your most valuable marketing asset.

New email subscriber hasn’t purchased and 30 days have gone by? Here's what to do. The majority of users that sign up for an email list *won't* purchase. But just because a user has cycled through a welcome flow and a month has gone by, it's doesn't mean they're dead. They’re undecided. Here’s a 3-step framework we use to convert this segment: 🔍 1. Re-Engage with a Zero-Pressure Check-In Don’t send another promo. Send a plain-text email from the founder (or just the brand): “Saw you joined but haven’t purchased yet. Mind sharing what’s holding you back?” This soft nudge gets replies, surfaces objections, and re-opens the door. 🎯 2. Personalize Based on Engagement History Look at what they clicked in the Welcome Flow or which product pages they’ve viewed. Build a 2–3 email branch based on product category interest, not just blanket discounts. 📈 3. Time-Limited Offer with a Twist If they’re still cold, go for a curated “First-Time Buyer Bundle” or “Editor’s Picks” offer. → Not just 10% off again. Show them what to buy and why — and make it easy. Don't forget about these subscribers after the Welcome series. That’s a mistake. This segment is warm, just unconvinced. When nurtured right, they convert better than cold traffic.

Re-engaging a closed/lost deal? ⛔️ What lazy reps do: lead with new features, products, or use cases ✅ What sales professionals do: show they did their homework You need to make it easy to pick up where the last conversation left off. Most of the time, you're not even reaching out to the same person involved in the previous deal. The buyer needs easy to understand context from the previous meetings: - Notes in the CRM (good luck) - Call recordings & transcripts - Business cases or presentation decks Here’s an example email: 👇 Subject: 12% cost-cutting initiative Hi Scott, Our teams previously connected last year regarding the priority to cut costs in the contact center by 12%. 60,000 email tickets were coming in every quarter at an estimated $1.3M to handle these tickets and respond accordingly. ABC COMPANY was in a similar situation and used our help to reduce email volume and cost to serve by 25%+ Is this still a priority in 2023? Or did you find a solve for this? Jason ========================== 💬 Here’s the framework Subject: [name of project or priority] Hi [first name], [context of previous meetings] [quantified problem] [social proof] ["this or that" CTA] ========================== Pack your emails with context from previous conversations, and you’ll have a much higher success rate. Agree or disagree with this approach? #sales #outbound #pickupthephone