Personalizing Sales Outreach

I just deleted 147 cold emails without reading them. Here’s what they all got wrong: Every morning, my inbox looks the same. A flood of pitches from people trying to sell me something. Most days, I just mass delete them. But this morning, I decided to actually read through them first. Within 5 minutes, I spotted a pattern. Everyone was making the exact same mistake. They were all trying to close the deal. ALL IN THE FIRST MESSAGE 🥵 Let me show you what I mean (with two small examples): APPROACH A: "The Wall of Text" Send 100 cold emails with full pitch, calendar link, and case studies. • 3 people open • 0 responses • 0 intros This looks exactly like the 147 emails I just deleted "Hi [Name], I noticed your company is scaling fast! We help companies like yours optimize their marketing stack through our proprietary AI technology. Our clients see 300% ROI within 90 days. Here's my Calendly link to book a 15-min chat: [LINK]. Looking forward to connecting! Best, [Name]" BORING!!! APPROACH B: "Micro Conversations" Same 100 prospects, broken down into micro-convo's. Email 1: "Do you know [mutual connection]?" • Send 100 • ~40 open • ~20 respond Email 2: "They mentioned you're scaling your marketing team. I'd love to connect about [specific thing]." • Send to 20 who responded • ~15 continue engaging Email 3: "Would you mind if they made an intro?" • Ask 15 engaged prospects • ~10 intros Final score: • Approach A: No intros • Approach B: 10 intros How to Apply These Lessons (Tactical Summary): 1. Focus on Micro-Conversations: Break your cold outreach into smaller, manageable steps. Build rapport before making any asks. 2. Personalize Everything: Reference mutual connections, specific company milestones, or shared interests in every message. 3. Play the Long Game: Aim for replies in the first message.. not conversions. If you’ve been struggling with cold outreach, you might just need a new approach. Give this one a try and lmk how it goes.

Want your words to actually sell? Here’s a simple roadmap I've found incredibly helpful: Think of crafting your message like taking someone on a mini-journey: 1. Hook them with curiosity: Your headline is the first "hello."  Make it intriguing enough to stop the scroll.  Instead of just saying "Email Marketing Tips," try something like "Want a 20% revenue jump in the next 60 days? (Here's the email secret)."  See the difference? Promise + Specificity = Attention. 2. Tell a story with a villain: This might sound dramatic, but hear me out.  What's the problem your audience is facing?  What's the frustration, the obstacle, the "enemy" they're battling?  For the email example, maybe it's "wasting hours on emails that no one opens."  Giving that problem a name creates an instant connection and a sense of purpose for your solution. 3. Handle the "yeah, but..." in their head: We all have those internal objections.  "I don't have time," "It costs too much," "Will it even work for me?"  Great copy anticipates these doubts and addresses them head-on within the message. 4. Show, don't just tell (Proof!): People are naturally skeptical.  Instead of just saying "it works," show them.  Even a simple "Join thousands of others who've seen real results" adds weight. Testimonials, even short ones, are gold. 5. Make it crystal clear what you want them to do (CTA):   Don't leave them guessing!  "Learn the exact steps in my latest guide" or "Grab your free checklist now" are direct and tell them exactly what to do and what they'll get.  Notice the benefit in the CTA example: "Get sculpted abs in just 4 weeks without dieting." And when you're thinking about where you're sharing this (LinkedIn post, email, etc.), there are different ways to structure your message. The P-A-S (Problem-Agitate-Solution) or A-I-D-A (Attention-Interest-Desire-Action) frameworks are classics for a reason. The core difference I've learned? Good copywriting isn't about shouting about your amazing product. It's about understanding them – their challenges, their desires – and positioning your solution as the answer in a way that feels like a conversation, not a sales pitch.

How many times have you logged on to Linkedin and found yet another email that starts with: "Hey [First Name]," followed by a generic pitch that does not concern your interests or needs. Sound familiar? We've all been there. And it's frustrating. As a fractional CMO/Consultant, I've seen this happen repeatedly. Businesses think they're doing personalization right but need to do better. It's not enough to use someone's name or company. 👉🏾 True personalization is about understanding their challenges, goals, and needs. For example, on LinkedIn, scroll through their feed and see what they post, talk about, like, and comment on. This helps as a starting ground on how to approach them and what to discuss. So, instead of sending a LinkedIn message that says: "I'd love to connect and learn more about your business," try something like: "I noticed you're working on [specific project]. I have some ideas on how you could [achieve a specific goal]. Would you be open to a quick chat?" See the difference? It's not just about being personal; it's about being relevant. And when you're relevant, you're not annoying — you're helpful. 👉🏾 So, think about this the next time you craft a personalized outreach campaign. →"Would I find this message valuable? →Does it address my specific needs and interests?" If the answer is no, it's time to return to the drawing board. 👉🏾 Also, tools like Crystal Knows help you fine-tune your message and tone when reaching out to maximize the impact of every conversation. Let's aim for genuinely helpful messages, not just another annoyance in their inbox. What do you think about personalized outreach? #b2bmarketing #demandgeneration #leadgeneration #ABM

76.6% open rate. 21% reply rate. 7.3% interest rate. These are the current benchmarks for recruiting outreach emails sent through Gem‎. But here's what's really fascinating: the teams consistently beating these benchmarks aren't using fancy automation or gimmicky subject lines. They're simply speaking to what candidates actually care about. At Gem, we've analyzed millions of recruiting emails, and the pattern is unmistakable. The highest-performing outreach directly addresses the core motivations driving today's job seekers: 1. Career advancement opportunities 2. Meaningful work flexibility 3. Strong, visionary leadership 4. Clear paths for skill development (especially for Gen Z, who prioritize this 36% more than other generations) One customer I was talking to challenged conventional wisdom by A/B testing short vs. detailed messages. The surprising result? While the shorter message got more opens, the longer, more detailed message that explained team impact and challenges generated more interested replies. Why? Because it spoke directly to what high-value candidates actually wanted to know. The market has shifted. By 2030, Gen Z and millennials will represent nearly 60% of the global workforce. These candidates don't just want jobs—they want growth trajectories. They don't just evaluate offers—they evaluate leadership. Here's my challenge to every recruiting team: Review your last 5 outreach templates. Count how many sentences focus on what you need vs. what the candidate gets. If it's weighted toward your requirements, you're leaving responses on the table. The best recruiting teams at companies like Anthropic, Yext, and Doordash are already making this transition, shifting from requirement-focused to candidate-centric messaging. And it's working… "We're not trying to sell anything in our outreach," explains Michael Franco at Yext‎. "We're trying to start a genuine conversation... When we understand their pain points, we know exactly what value prop to use." This isn't just feel-good advice—it's data-backed strategy. In 2025, understanding what candidates truly care about isn't just nice to have. It's the difference between hitting your hiring goals and falling short of them.

What makes a decision-maker actually reply to your LinkedIn message? I wanted to find out. So we ran an experiment. At my recent Get Paid To Speak Bootcamp, I invited Brian Tee, Head of Sales at SingPost, as one of our corporate guests. Why? Because I wanted my aspiring speakers to hear directly from someone who hires speakers: what gets their attention, what turns them off, and what actually gets you booked. So here’s what we did: Everyone in the room had to reach out to Brian on LinkedIn. No scripts. No templates. Just thoughtful outreach. Brian received 95 connection requests and he took the time to go through every single one. Then he shortlisted the messages that stood out to him and shared WHY they worked. That’s what this post is about (you might want to bookmark this post!) Here are five things the best outreach messages had in common: 1. They anchored to a real, shared moment. “I really appreciated your insight at GPTS, especially when you said ‘leadership today requires empathy and adaptability.’ That stayed with me.” 2. They focused on Brian first not their pitch. “May I ask what business challenges you're currently facing? How do you envision inspiring your sales team in 2025 and beyond?” 3. They asked meaningful, open-ended questions. “What’s your take on vulnerability in the workplace? Does it have a place in leadership today?” 4. They aligned their offer with Brian’s values and goals. “Given your focus on transformation, I believe my talk on resilience could complement your vision at SingPost.” 5. They offered to add value without sounding transactional. “If there’s any way I could contribute to your work at SingPost, I’d be happy to explore how.” One big lesson from this? The best outreach doesn’t try to impress, it tries to connect. Respect. Curiosity. Relevance. That’s what opens doors. A huge thank you to Brian Tee for being so generous with his feedback, this was GOLD for every speaker in the room. And now, for you reading this: If you’re trying to reach high-value contacts, use the above five insights as your blueprint. Your turn: if you were a potential client, how should we reach out to you that will elicit a positive response? #LinkedInTips #GetPaidToSpeak

If you ask (and answer) this 1 question before starting cold outreach, you'll be on track to see 2x results from your outbound in 2025. 📌 The question is simple: Does this matter to THEM? Too often, outbound efforts are built around what we want: to book a meeting, to hit quota, to close the deal. But here’s the reality: no one cares about your goals unless they align with theirs. This is where my #EarnTheRight approach comes in. Before you send an email, pick up the phone, or craft a LinkedIn message, stop and ask yourself: “Am I talking about what matters most to my prospect?” Taking the time to create email copy and phone talk tracks that align with their priorities is critical. This is not about prospect-specific personalization. This is about RELEVANCE. ➡️ Here’s why: Relevance drives response. When you speak to the challenges and goals that matter the most to your prospect, you’re no longer interrupting them—you’re engaging them. Want to stand out in 2025? Believe me when I say the bar is low and stealing this strategy will help you 2x your results this year. Most outreach is about the seller: “We offer X,” “Our platform does Y.” Flip the script by focusing on the prospect’s world instead, and you instantly differentiate yourself. Trust builds faster when your messaging reflects that you’ve done the homework. In 2025, relevance isn’t just important—it’s essential. Buyers are busier than ever, and generic outreach is the quickest way to get ignored. When your outreach centers on what truly matters to your prospects, you earn the right to their time, their attention, and eventually, their business. 📌 How are you ensuring your team’s messaging speaks to what matters most to your prospects?

I recorded a 2-minute video last week that transformed my client pipeline. No fancy equipment. No production team. Just me speaking authentically to my phone. The results? 5 quality leads within 48 hours. 3 discovery calls. 2 new clients. This wasn't luck. It was a deliberate strategy that anyone can implement. Before I built my community of professionals on LinkedIn... Before I coached thousands on personal branding... I was just posting occasionally, hoping something would strike. The turning point? I stopped hiding behind text and showed my face. That single decision ignited real conversations and transformed my profile from a digital resume into a lead-generating asset. Here's the exact formula I used: 1️⃣ Start with vulnerability, not perfection My opening line: "From student to speaker in 21 months, here's what changed my life." No scripts. No rehearsing. Just the real me. 2️⃣ Deliver tangible value, not self-promotion Instead of listing achievements, I shared actionable insights: • How to optimize your LinkedIn profile • The post structure that consistently gets visibility • Converting followers into actual clients 3️⃣ Speak to ONE person, not an audience I imagined helping a friend over coffee. That conversational energy makes people stop scrolling. 4️⃣ Close with crystal clarity Instead of the vague "let me know your thoughts," I said: "DM me if you want help building your LinkedIn brand." And they did. The power of video for personal branding is undeniable: 🔸 Your voice builds trust faster than text 🔸 Eye contact creates immediate connection 🔸 Body language enhances credibility 🔸 Authenticity makes you memorable A static profile shows what you've done. Video shows who you are. That's what transforms browsers into buyers. Even if you're camera shy, you can start simple: • Define your core message first • Use natural lighting • Choose a clean background • Speak clearly and smile Remember: it's not about perfection. It's about connection. My challenge to you this week: Record a 2-minute video sharing one challenge you overcame, one tip for your audience, and one way to connect with you. The first attempt might feel awkward. That's normal. But that first step opens the first door. #personalbrand #branding #leadgeneration Ready to build a brand that attracts dream clients and generates consistent leads? DM me "linkedinbrent" and I'll show you how to create your first branded video, even if you've never hit record before. I'm Brent. I'm opening 10 spots this month for professionals serious about becoming authorities in their field.

Most outreach tools help you send more messages. But if you look under the hood, volume is rarely the problem. The harder part is giving someone a reason to reply when they have absolutely 𝐧𝐨 𝐢𝐝𝐞𝐚 𝐰𝐡𝐨 𝐲𝐨𝐮 𝐚𝐫𝐞. The workflow we use is simple: → 𝐅𝐢𝐧𝐝 𝐭𝐡𝐞 𝐫𝐢𝐠𝐡𝐭 𝐩𝐞𝐨𝐩𝐥𝐞: Start with people already connected to your market through relevant audiences and LinkedIn conversations, not another cold list of job titles. → 𝐋𝐞𝐚𝐫𝐧 𝐛𝐞𝐟𝐨𝐫𝐞 𝐲𝐨𝐮 𝐰𝐫𝐢𝐭𝐞: Look at the person, their company, and what they have been discussing recently. A title tells you who they are. Their activity tells you what may matter now. → 𝐁𝐮𝐢𝐥𝐝 𝐟𝐚𝐦𝐢𝐥𝐢𝐚𝐫𝐢𝐭𝐲 𝐰𝐢𝐭𝐡 𝐭𝐡𝐨𝐮𝐠𝐡𝐭 𝐥𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩 𝐚𝐧𝐝 𝐞𝐱𝐩𝐞𝐫𝐭𝐢𝐬𝐞: Follow the conversations that matter i. Add something useful when you genuinely have a point to contribute. → 𝐌𝐞𝐬𝐬𝐚𝐠𝐞 𝐰𝐢𝐭𝐡 𝐚 𝐫𝐞𝐚𝐬𝐨𝐧: Use what you have learned to explain why this conversation makes sense now. If the opening line could be sent to 50 people, it is not ready. → 𝐊𝐞𝐞𝐩 𝐭𝐡𝐞 𝐜𝐨𝐧𝐭𝐞𝐱𝐭: Save the outreach and reply together so the next interaction does not restart from zero. That is the lesson behind Fuzzy AI 🚀: better outreach begins before the message. Which step takes your team the most time?

A year ago, I was that guy—writing copy that sounded like a university thesis. Buzzwords, jargon, and enough fluff to fill a pillow factory. My readers? Confused. My conversions? Nonexistent. Then I stumbled upon brands like Moosejaw and BarkBox. Their copy felt like a friend texting me, not a robot pitching me. That’s when I realized: conversational copy isn’t just “casual.” It’s strategic. It builds trust, makes you memorable, and (most importantly) gets results. Here’s how brands like these taught me to write copy that clicks with people: Conversational copywriting is all about writing like you're talking—no jargon, no sales-y pitch. But how do you nail it? Here’s a guide based on brands that get it right. Thread 🧵 1/ Moosejaw Fun and quirky copy that hooks you instantly. Examples: ✔️ “We love NFTs (Nacho Fun Times).” ✔️ “Remember to season your concrete after shoveling snow.” ✔️ “No, our website isn’t powered by hamsters in wheels… yet.” Takeaway: Don't be afraid to let your personality shine—it’s what makes people remember you. 2/ BarkBox What do they sell? Adorable joy for dogs. ✔️ They use relatable humor + 100% satisfaction guarantees. ✔️ They speak their audience's language—dog parents, not just dog owners. Takeaway: Know your audience. Write for them, not at them. 3/ Innocent Drinks Natural products, natural tone. ✔️ They use ultra-specific details like “botanical” to emphasize quality. ✔️ They lean on transparency to eliminate buyer anxiety. Takeaway: Be real, and get specific—your audience will trust you more. 4/ OkCupid DTF? They redefine it. ✔️ Their copy flips expectations. ✔️ They invite users to define their version of dating. Takeaway: Play with cultural norms to create an emotional connection. 5/ Gymit Copy that feels like a casual gym chat. ✔️ They make gyms approachable—not intimidating. ✔️ The honesty in their tone makes them relatable to everyone, not just fitness buffs. Takeaway: Use language that removes barriers for your audience. 6/ Lego Timeless yet relevant. ✔️ Nostalgia meets values. ✔️ One ad paired a retro toy with a modern message about equality. Takeaway: Tie your brand’s history with current values to create powerful storytelling. Conversational copy isn’t magic—it’s empathy. Think: What would your audience actually want to hear? Then say that.

I’ve trained hundreds of sales reps over my career. Here’s the exact framework I use to write good cold emails from start to finish: 1. Lead with the pain not the pitch The goal of a cold email is to start a conversation, not close the deal. It’s to reflect back a real pain your buyer is already feeling often before they’ve articulated it themselves. No one cares about your product. Especially not in the first touch. They care about themselves and their problems. The biggest mistake I see reps make is trying to close too early. They shove value props, case studies, feature sets, and “we help companies like…” I always come back to this: “No pain, no gain, no demo train.” You’re not here to educate. You’re here to trigger recognition. To make them nod and go: “Yeah, we’re feeling that.” 1. Write like a human The best cold emails don’t have long intros. No “hope this finds you well.” Just a clear, honest attempt to connect over something they care about. Let’s say we’re targeting agencies running 10+ client accounts. Here’s how I’d start: “Hey — I saw you’re managing multiple clients. Curious if you’ve had to deal with deliverability issues lately, especially with the new Google/Microsoft changes. Is this on your radar?” That’s it. No pitch. No product. Just a relevant question that hits a live pain. You don’t need clever. You need to be clear. 1. Structure matters (but keep it stupid simple) I’m not into formulas. You don’t need a 7-step framework to write a good email. You need to understand the buyer and speak to them like a peer. Think about it like this: Line 1: Show you’ve done your homework. Line 2: Bring up a real, relevant pain. Line 3: Ask a question that invites a reply — not “yes.” If your email looks like a blog post, you’re doing it wrong. The goal isn’t to explain. The goal is to start a conversation. 1. Use follow-ups to build narrative (not nag) Most follow-ups sound like this: “Just bumping this to the top of your inbox.” “Not sure if you saw my last message.” Useless. Instead, think of your cold email sequence as a way to diagnose pain over time. Email 1 brings up the initial problem. Email 2 digs into what happens if it doesn’t get solved. Email 3 introduces that you might have a solution, if they’re open to it. Each message earns attention and adds value. Follow-ups shouldn’t be annoying. TAKEAWAY Conversations > conversions. Relevancy always wins.