Segmenting Leads Without Over-Personalizing Emails

If you’re segmenting based on engagement, you’re already behind. Everyone does 30/60/90 day engagement windows. It’s not advanced. It’s basic hygiene. Here’s the real segmentation play most marketers miss: Segment by intent signals, not just opens/clicks. Examples: • Viewed shipping/returns policy? ➝ Hit with reassurance focused CTA • Time on product page > 30 seconds? ➝ Trigger a cart based reminder • Opened 5+ product emails but never clicked? ➝ Try plain text emails with a customer story • AOV based segments - low priced vs high priced ➝ show them the right products • FAQ viewers ➝ Give them more trust • Recent abandon carts/checkouts ➝ Leverage their interests • Time since they opted in for a coupon ➝ Remind them about it • Time since last purchase ➝ Show them complimentary products The list goes on and on... THEN add your engagement for best deliverability Engagement ≠ intent. Intent = actual buying behavior. Stop treating every click the same. Treat the reason behind the click differently.

Stop personalizing your cold emails. "I noticed you were hiring for X." "Saw your recent post about Y." "Congrats on the Series A." It looks thoughtful. But most prospects can smell it instantly because the "personalization" is just a toll you paid to get permission to pitch. Personalization is a tax on poor targeting. If you have to hunt through someone's LinkedIn for something to reference, you probably don't understand their problem well enough to be in their inbox. The real work isn't writing 47 custom first lines. It's finding 47 people who share the exact same pain so specific that a single message hits all of them like it was written just for them. A CFO at a 50-person SaaS company burning $400K/month with 14 months of runway doesn't need you to mention their podcast appearance. They need someone who understands that their board is asking hard questions about burn rate and they're weighing layoffs vs. fundraising in a brutal market. That's personal. Not personalized. The difference: Personalization = I researched you for 3 minutes and found a hook. Personal = I understand your situation so well that this message could only be for people like you. One is a parlor trick. The other is positioning.When your ICP is tight enough, your message does the targeting. Every word filters for fit. The people who don't have the problem ignore it. The people who do feel seen. Stop asking "what can I reference about this person?" Start asking "what problem is so specific that anyone who has it will stop scrolling?" Make your list the message. P.S. I put together a doc with 5 "personal" cold emails that booked meetings without a single line of personalization just tight targeting and problem-aware copy. Comment "PERSONAL" and I'll send it over. Personal = I understand your situation so well that this message could only be for people like you. One is a parlor trick. The other is positioning. When your ICP is tight enough, your message does the targeting. Every word filters for fit. The people who don't have the problem ignore it. The people who do feel seen.Stop asking "what can I reference about this person?" Start asking "what problem is so specific that anyone who has it will stop scrolling?" Make your list the message. P.S. I put together a doc with 5 "personal" cold emails that booked meetings without a single line of personalization just tight targeting and problem-aware copy. Comment "PERSONAL" and I'll send it over.

SDRs, stop over-personalizing your emails. The trend of using AI to dig up every personal detail about a prospect is backfiring. When you lead with details like a prospect’s favorite coffee spot or latest 5K time, it feels more creepy than meaningful... and worse, it blends in with the hundreds of similar "over-personalized" emails they’re getting every day. Instead, use AI to get hyper-relevant. I leverage tools like LinkedIn and Instantly.ai, not to fake a connection but to spot actual triggers, like product launches or key hiring trends, that show a genuine need for our solution. This isn’t about faking intimacy – it’s about real relevance. Focus on pain points, not personalities. You'll get more real conversations and fewer eye-rolls.

AI can recommend the right thing at the right time…  if you don’t freak people out first! When I was running June, we did what most b2b startups do: Outbound. Segments Personalization Lots of data stitched together I assumed the more personalized the email, the better it would perform. I was wrong ❌ Somehow, the more we customized our outbound... the less engagement we got 😅 Replies dropped. Trust dropped. Some people were genuinely uncomfortable. We eventually learned there is a sweet spot Personalize TOO MUCH. Use irrelevant details. Or tell people exactly what you know about them. And engagement falls off a cliff 😒 Personalize TOO LITTLE. Generic copy. No signal that you understand their world. Same outcome 😢 One campaign made this painfully clear. We targeted users using Segment, identified via BuiltWith Solid targeting. But the email said “I noticed you’re using Segment” That single sentence killed performance Some replies were direct “How do you know that?” Others were defensive “That’s creepy!!” And then came the worst part. False positives 😡 “You should check your data, we’re not using Segment” So we managed to do 3 things at once: ❌ Sound invasive ❌ Break trust ❌ And be wrong That experience stuck with me. Personalization should feel helpful, not observant. Relevant, not revealing Implied, not explicit. If users can clearly see how you know something about them…  you are probably over the line ☝️ This question matters even more now with AI. AI makes personalization incredibly powerful. But it also makes it dangerously easy to overdo it 🤡 Below are a few examples from the ebook Amplitude just released “Personalization in the age of AI” It goes deep on how to create value with personalization. Without crossing into creepy territory Especially when AI is involved ✨ (you missed this AI emoji, didn't you?) If you are building or shipping personalization today It is worth reading! Link: https://lnkd.in/ee3DEnCf Hope this helps 💜 --Enzo

If you are writing sales messaging that could apply to anybody in your TAM, you're writing sales copy that nobody gives AF about. OUCH! I know that might be hard to hear, but here's the hack to better segment your TAM in 2025. ➡️ The harsh truth is that Founders who take a "boil the ocean" approach to selling in will fail. Here's how you can get better results in 3 steps: Step 1 - Move your focus from everybody who *could* possibly buy from you to the group of folks who are most likely to buy now, buy at a high price point, and later renew or be a referral source. Step 2 - From that much smaller group of accounts, create segments. These are not the traditional segments that help your organize your territories. These are segments that help you speak the language of a deep sub-set of prospects. I suggest at least 5 layers of segmentation blending firmographic data, signals, and contact-level data. EXAMPLE: You sell production line automation software. You believe your ICP is: US-based supply chain executives in manufacturing organizations with at least 1k employees. Great start, but it's time to add 5+ layers of segmentation before you can create a message that matters. Segment 1: Midwest "Manufacturing Belt" only Segment 2: Chief Supply Chain Officers only Segment 3: Machinery manufacturing only Segment 4: 50,000 to 100,000 employees Segment 5: New CFO hired in the past year Now you are only speaking to the CSCO or a sub-industry working in the region where you have the strongest social proof. By tightening the employee range you know they have a big enough problem to solve (+ can pick the best name drops) and a new CFO signals an openness to (re)explore cost-saving software. Step 3 - Use this process to launch dozens of micro-campaigns that speak to specific sub-sets of your territory because you've created enough segmentation to be 99% sure your copy will be RELEVANT to them. This is THE only way I've found to personalize at scale. I love teaching orgs how to better segment their accounts and create segment-specific value props. I call it #ValueBasedSegmentation ➡️ The result is: - Highly relevant copy - Emails that can be fully automated - High CTRs/replies without tedious personalization 📌 How do you personalize at scale?

You can’t “prompt” your way out of bad targeting. Yes, AI is great, personalizing Cold Emails is awesome 🔥   But there’s a better hack:   Break your list into smaller targets.   Let me tell you a story 👇   A few months ago a client came to us asking to target: “Ecommerce founders.” That was the whole brief.   So, what do you do?   You ask questions. For example:   → Shopify or Amazon? → Fashion or supplements? → Funded or bootstrapped? → Do they grow through paid ads or organically? → Who’s handling growth?   Then you build the list:   → Shopify brands → Selling skincare → Based in the EU → Running Meta ads → Hiring but no Head of Growth → Founder posts 3x/week on LinkedIn   Now your Cold Email doesn’t need a clever opener. It’s already relevant.   This is how we build Outbound at SalesCaptain. We don’t stop at “industry.” We segment by:   📦 Category → Not just HR software → but compensation platforms, 100–300 headcount, scaling in LATAM, using Gusto   📡 Signal → Not just “growing teams” → Teams hiring SDRs, posting on LinkedIn, with no RevOps function in place   We use AI, but not to fake relevance. We use it to find signals that show who’s actually in-market.   Because in 2025: Signals > prompts Context > copy   The broader the list, the harder the message has to work. Shrink the list. Sharpen the context. Let relevance do the work. Have a nice weekend.   #b2bsales #coldemail #leadgen #gtm #personaliztion #aiinsales

I keep hearing founders and revenue leaders say "we want to stop spray and pray." And I had an epiphany on this yesterday after talking with Jen D’Amico. And reflecting on some posts by 🦾Eric Nowoslawski and Nick Abraham. The average SDR is MORE spray and pray. Than intelligent automated demand gen. FROM THE BUYER SIDE. Let me explain. In your shoes, you're looking at your SDR team and thinking. "We researching, we're targeting, we're doing smart cold calls, we're personalizing emails, what gives?" Think about what is happening from the buyer side. If your SDR team is in the normal situation... the buyer is getting hit with 20-30 touches. 9 emails, 6-12 calls, 2-5 Linkedin touches. Maybe 12 emails in some cases! And the average Outreach sequence has about a 2.9% reply rate. So think about how this looks from the buyer's side. 97.1% of your prospects have gotten 9-12 emails from you. They haven't replied. They didn't think your emails were valuable. Constrast this with another model, where you take literally everyone you think is worth emailing in your TAM. Say 20k people. Drop them in Clay, enrich, maybe drop them Google Sheets. Group them by titles, industries, maybe a few other data points relevant to you (number of AEs for example). Get 1-3 pieces of content that create value for those segments of your market (by title or industry) even if they don't buy from you. Create a 2 email sequence offering that content, with merge fields for each segment. Then send just 2 emails a month. Imagine that from the buyer perspective - you get just 2 emails a month offering you something useful Those 2 emails will probably get a 1-2% reply rate Your SDR team can call the opens and replies And your buyers first experience with you is that you offered them something relevant and helpful More volume? Yes More volume from the BUYER'S perspective? No More overall lead flow? Yeah, significantly (DM if you want help with this)

Lead nurturing ≠ 5-email automated sequence + retargeting begging a prospect to book a demo. Here are 5 pillars of successful nurturing. 1. 𝐏𝐫𝐞𝐩𝐚𝐫𝐞 𝐚 𝐥𝐞𝐚𝐝 𝐧𝐮𝐫𝐭𝐮𝐫𝐢𝐧𝐠 𝐩𝐫𝐨𝐠𝐫𝐚𝐦. Interview your best customers and dive into a sales process of recently won deals to understand what triggers the buyer journey and how your best customers actually buy. Ideally, you need to define: - Business and demand triggers - Channels - Buying committee - Questions and concerns they have at different stages Next step is auditing all the available content: blog, youtube, knowledge base and use it to develop lead nurturing cadence. For content gaps, you need to create a plan to fill them in. 2. 𝐔𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝 𝐭𝐡𝐞 𝐛𝐮𝐲𝐞𝐫 𝐣𝐨𝐮𝐫𝐧𝐞𝐲 𝐬𝐭𝐚𝐠𝐞. Not everybody that engages with your ads, content, or sign-ups for your events is a lead. Don't put everybody into a "push cadence" asking to book a demo. Instead, segment every prospect by: - a tier based on the firmographics - job role and the role in the buying committee - engagement intent 3. 𝐃𝐨 𝐩𝐫𝐨𝐠𝐫𝐞𝐬𝐬𝐢𝐯𝐞 𝐩𝐫𝐨𝐟𝐢𝐥𝐢𝐧𝐠 𝐟𝐨𝐫 𝐭𝐢𝐞𝐫 1 𝐚𝐧𝐝 𝐭𝐢𝐞𝐫 2 𝐚𝐜𝐜𝐨𝐮𝐧𝐭𝐬. - Run account research to collect as much information about their needs and goals as possible. - Connect and ask for feedback about the content on LinkedIn or via email. Ask about the context (why they downloaded/engaged/signed up) and if it helped (content quality feedback). - Reach out with a self-segmentation email or survey - Ask if they are interested in learning more about the topic. If yes, suggest signing up for your newsletter, podcast, or other demand-gen assets. 4. 𝐃𝐞𝐯𝐞𝐥𝐨𝐩 𝐦𝐮𝐥𝐭𝐢𝐜𝐡𝐚𝐧𝐧𝐞𝐥 𝐧𝐮𝐫𝐭𝐮𝐫𝐢𝐧𝐠. - Add the prospect to a relevant retargeting sequence with nurturing content - Replicate the retargeting sequence in your email automation - Put the same content into a personalized content hub that also includes buyer enablement content and product information - Engage with their content or updates on LinkedIn - Tag in relevant threads or share relevant content - Invite to the relevant events - Connect and engage with other buying committee members 5. 𝐓𝐫𝐚𝐜𝐤 𝐞𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 𝐬𝐩𝐢𝐤𝐞𝐬. Whenever you see a spike in engagement, reach out and ask if they have any questions or need any help. --- Understand what triggers the buyer journey and what are the typical steps. Understand the questions and information your buyers are looking for. Understand their jobs to be done and the education they need to get to at least become curious about your product. Then, develop your nurturing system aligned with how your buyers actually buy. ---- Next week we'll have a few talks about nurturing at our Full-Funnel Summit. Sign up here: https://lnkd.in/ddZ6Qyk8

“Relevancy is all you need” “Don’t waste your time personalising” Here’s why I disagree with 99% of these takes People say it as a general statement without thinking about the specifics. Your segment (SMB → MM → ENT) plays a huge role. As an SMB rep you could be given 1000+ accounts to go after. At MM that could drop to 200 - 500 accounts. At ENT that could be as low as 20 - 100. So how you prospect and use relevancy / personalization changes a ton depending on how many accounts are in your name. So this is how I’d do balance the two depending on my segment. 1: SMB / MM - Not personalized but relevant The whole goal of this is to have a clear reason to reach out. If you have thousands of accounts you likely won’t have the time to do it 1 by 1. So this is were triggers or intent signals can come in like” Team Growth → “Noticed the sales team has grown by 15% in the last 5 months” Tech Stack → “Saw you are using Salesforce at company” As an SMB rep I would use this the most as it’s more transactional. If I was MM most of my Tier 3 & 2 accounts would also fall into this. 2: MM / ENT - Personalized and relevant This is similar to the first, but you are taking time to research the company. The research allows you to build a stronger POV on the account & potential issues they could be facing. News → “Read Company names 10k report and it seems like there’s a focus on…” Specific Hiring → “Saw on LinkedIn you have 2 SDRs roles open in EMEA” As an MM rep by Tier 1 accounts would get this messaging. As an ENT rep, if I only had a few accounts then I would spend the time to do this for all of them to allow for a more strategic approach. BONUS: Personalized but not relevant This is great as a P.S at the end of your emails Location → “Saw you are also from NYC, the met’s are doing great!” College → “Noticed you went to college at ___. Had some close friends love it there!" This is again only what I’d use for my top accounts Don’t make it creepy, but genuine effort can show you’ve gone the extra mile. Hopefully this was useful, I’ll be breaking this down in more detail on my Sunday newsletter “Sell Smarter.” So if you want to check it out I’ll put the link in the comments.