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.

I increased my open rates by 17% with these 5 subject line tests: Your subject line is the first impression your email makes. It determines whether your audience opens the email or skips it entirely. Here are 5 subject line tests I ran that actually moved the needle (and why they work): 1. Add Personalization: Instead of: “Improve Your Email Marketing Results” I tested: “Chase, These Email Tips Could Boost Your Revenue” Why this works: Seeing their name feels personal and grabs attention in a crowded inbox. Personalization also shows you’ve tailored the content specifically for them. --- 2. Tap Into Curiosity: Instead of: “Email Marketing Strategies for Your Business” I tested: “You’re Leaving Money on the Table with Email” Why this works: Curiosity compels people to open. But the key is delivering on the promise—your content has to match the intrigue, or you’ll lose trust. --- 3. Create Urgency: Instead of: “How to Improve Your Email Campaigns” I tested: “Last Chance to Fix This Email Mistake” Why this works: FOMO (fear of missing out) gets people to take immediate action, especially when there’s a sense of a ticking clock. --- 4. Go Shorter: Instead of: “Here’s Everything You Need to Know About Email Marketing” I tested: “Better Emails, Today” Why this works: Short, punchy subject lines cut through the noise, especially on mobile where 50%+ of emails are opened. --- 5. Use Numbers or Specificity: Instead of: “Email Tips for Business Owners” I tested: “3 Subject Lines That Boosted Open Rates by 17%” Why this works: Numbers and specificity make your email feel actionable and credible. People know exactly what they’re getting. --- The Big Lesson: Your subject line is your email’s best salesperson. Start testing small variations today—personalization, curiosity, urgency, or brevity. Even a 1% improvement across a large list can make a massive impact. What’s the best subject line you’ve tested?

Sales reps email "just checking in" an average of 5 times per day. Does this work?  Rarely. The habit of saying "just checking in" negatively impacts your sales efforts: ⇒ It doesn't add any value to the conversation. ⇒ It can come across as lazy or insincere. ⇒ By using this phrase, you miss opportunities to engage meaningfully. Here are 10 tips to stop saying "just checking in" and do something else instead: 1. Provide Value:  Instead of "just checking in," offer a useful piece of advice or a relevant resource. For example, "I came across this article that might help with your current project." 2. Ask Specific Questions:  Directly ask for the information you need. For example, "Can you update me on the status of the proposal we discussed?" 3. Share a Success Story:  Highlight a recent success that relates to the prospect's industry. For example, "We recently helped a company similar to yours achieve X. Would you like to hear more about it?" 4. Offer a New Insight:  Share a new piece of information or a market trend. For example, "I wanted to share some recent data on how companies in your sector are handling Y." 5. Suggest a Next Step:  Propose a clear next action. For example, "How about we schedule a call next week to discuss this further?" 6. Follow Up on a Previous Conversation:  Reference a specific point from your last interaction. For example, "Last time we spoke, you mentioned interest in Z. I have some additional information that might be useful." 7. Invite to an Event:  Offer an invitation to a webinar or industry event. For example, "We’re hosting a webinar on [topic] next week. Would you be interested in joining?" 8. Highlight a New Feature:  Inform them about a new feature or update. For example, "We’ve just launched a new feature that could benefit your team. Would you like a demo?" 9. Ask for Feedback:  Request their opinion on something specific. For example, "I’d love to get your feedback on our latest product update." 10. Express Genuine Interest:  Show that you care about their progress. For example, "How are things going with your current project? Is there anything I can assist with?" By replacing "just checking in" with these strategies,  you can make your follow-ups more engaging and valuable. This ultimately leads to better responses and stronger relationships. ♻️ Share this cheat sheet to help more sales reps improve their follow-up game. ______ 📌 p.s. FREE GIFT: If you’re looking to streamline sales plays across your sales team, you can click here: https://www.distribute.so/

The worst cold email I received this month started with: "I'd love 15 minutes to introduce myself and show you what we do." Nobody cares about your introduction. Nobody has time for a generic pitch. After analyzing thousands of outreach sequences, I've discovered a psychological shift that's doubling meeting rates for innovative sellers. The best performers aren't focusing on their product. They're focusing on buyer psychology. Here's what's actually working in 2025: 1. The Curiosity Gap When you write "Other VPs in your space are seeing X trend" instead of "We help companies do Y," you create an information gap buyers want to fill. Our brains hate incomplete information. Use this. 2. Relevance Triggers Generic outreach gets generic results. When you mention a buyer's LinkedIn post or recent initiative, you're bypassing their "sales defense system." Relevance is required. 3. Specificity Signals "This could help you grow revenue" gets ignored. "Companies like yours are seeing 22% reduction in CAC" gets attention. Specific numbers signal you actually know what you're talking about. 4. Miniature Commitments Don't ask for 30 minutes. Ask for feedback on one specific insight. Small asks lead to bigger conversations. 5. Value-First Mindset Position yourself as a resource, not a vendor. Share insights without expecting anything in return. Reciprocity is powerful. The old playbook of "smile and dial" is dead. Meeting quotas in 2025 requires understanding human psychology. What psychological principle has worked best in your outreach?

I’ve coached thousands of sellers on how to create the perfect sales pitch using a framework called the 5 P’s. Until today, I have never shared this with anybody except my coaching clients. Here’s why it’s so effective: when most companies create a first call deck or sales pitch, they make it all about their own company and how great they are.   𝐓𝐡𝐢𝐬 𝐍𝐄𝐕𝐄𝐑 𝐰𝐨𝐫𝐤𝐬! The reason why is simple: customers don’t care about your products and services. They care about themselves, achieving their goals, and solving their own problems. Yet most pitch decks fail to speak to the problems which customers face and the pains they are causing. That’s why I created a framework which focuses solely on the customer’s challenges and how your solution can solve them. 𝐈 𝐜𝐚𝐥𝐥 𝐭𝐡𝐢𝐬 𝐭𝐡𝐞 𝟓 𝐏’𝐬 𝐨𝐟 𝐏𝐢𝐭𝐜𝐡𝐢𝐧𝐠. 𝐇𝐞𝐫𝐞’𝐬 𝐰𝐡𝐚𝐭 𝐞𝐚𝐜𝐡 𝐏 𝐬𝐭𝐚𝐧𝐝𝐬 𝐟𝐨𝐫: 𝟏. 𝐏𝐫𝐨𝐛𝐥𝐞𝐦: What problem do most prospects you work with face that your company can solve? The problem should be very high level, and important to Senior Executives at the company. It should be a business problem, not a technical problem. For example, if I sell CRM, the problem I solve would be rep underperformance, low rep productivity, or missed forecasts. All of which are important to a CRO or CEO. 𝟐. 𝐏𝐫𝐢𝐦𝐚𝐫𝐲 𝐑𝐞𝐚𝐬𝐨𝐧: Why does the problem exist? What is the root cause of the problem? By understanding the source of the problem, you demonstrate credibility and establish immediate trust with prospects because you are speaking their language. In the above example, I could say that reps often miss their forecasts because leadership has poor visibility to their sales pipeline and no way to accurately predict which deals are most likely to close, all of which a CRM solves for. 𝟑. 𝐏𝐚𝐢𝐧: What pain is the problem causing? The pain is always focused on the metrics that are impacted by the problem. For example, missed forecasts could mean a reduction in stock prices, missed revenue targets, and sales layoffs. 𝟒. 𝐏𝐫𝐨𝐦𝐢𝐬𝐞: How does your company solve the problem? The promise should always solve the primary reasons you just outlined. So for example, AI driven forecasting would prevent inaccurate manual forecasting and low visibility to deals. 𝟓. 𝐏𝐚𝐲𝐨𝐟𝐟: What metrics do you positively impact by solving the problem? Key payoff metrics for a CRM would be improved rep quota attainment, productivity, and accurate forecasting, all of which drive top line revenue & profitability. In this week's training video, I walk you through how to create the perfect sales pitch using the 5 P framework. You can find the training here: https://lnkd.in/gmu_Bdu3 PS - If you want to access a copy of the Problem Mapping Template so you can fill out the 5 P’s for your own solutions, get it here: https://lnkd.in/gASNe_em

If 2024 taught us anything about Cold Email, it’s this: 👇 General ICP Outreach isn’t enough to drive results anymore. With deliverability getting tougher every day, there’s only one way to make outbound work: → Intent-Based Targeting Here’s how we do it at SalesCaptain to book 3x more demos ⬇️ Step 1️⃣ Identify High-Intent Triggers The goal? Find prospects showing buying signals. ✅ Website visits – Someone browsing pricing or case studies? (We use tools like RB2B, Leadfeeder, and Maximise.ai). ✅ Competitor research – Tools like Trigify.io reveal when prospects engage with competitor content. ✅ Event attendance – Webinar attendees or industry event participants often explore new solutions. (DM me for a Clay template on this) ✅ Job changes – Platforms like UserGems 💎 notify us when decision-makers start new roles (a prime buying window). ⚡️ Pro Tip: Categorize triggers: → High intent: Pricing page visits → Medium intent: Engaging with case studies This helps prioritize outreach for faster conversions. Step 2️⃣ Layer Intent Data with an ICP Filter Intent data alone isn't enough, you need to ensure the right audience fit. Tools like Clay and Clearbit help us: ✅ Confirm ICP fit using firmographics ✅ Identify the right decision-makers ✅ Validate work emails ✅ Enrich data for personalized messaging ⚡️ Key Insight: Not everyone showing intent fits your ICP. Filter carefully to avoid wasted resources. Step 3️⃣ Hyper-Personalized Outreach Golden Rule: Intent without context is meaningless. Here’s our outreach formula: 👀 Observation: Reference the trigger (e.g., webinar attended, pricing page visit) 📈 Insight: Address a potential pain point tied to that trigger 💡 Solution: Share how you’ve helped similar companies solve this pain 📞 CTA: Suggest an exploratory call or share a free resource ⚡️ Pro Tip: Use tools like Twain to personalize at scale without landing in spam folders. 📊 The Results? Since focusing on intent-based outreach, we’ve seen: ✅ 3x Higher Demo Booking Rates 📈 ✅ 40% Reduction in CPL (focusing on quality over quantity) ✅ Larger Deals in the Pipeline with higher-quality prospects It’s 2025. Let’s build smarter, more profitable campaigns. 💡 Do you use intent signals in your outreach? Drop me a comment below! 👇

There's a lot of pressure riding on your subject lines. They create a first impression and determine whether a candidate decides to engage with you or not. And the pressure makes sense— After analyzing over 4 million email sequences, our data shows that while 22.6% of sequences see replies, only 12.1% see interested replies. In other words, around 50% of replies are of the "thanks, but no thanks" type. It’s already hard out there to get the response you want, but sending an email that isn’t opened reduces your chances to zero. Here's what our data reveals about effective subject lines: 1. Balance detail and brevity Subject lines with 90%+ open rates… - Appeal to the candidate’s values (e.g., “Flexible Technical Work”) - Ask questions (e.g., “{company} - Your application: When are you available to chat?”) - Clearly outline the next steps of the hiring process (e.g., “{company} - screening interview”) - Send event invitations and follow-ups (e.g., “Nextplay San Francisco spotlight - tonight! [event details inside]”) - Highlight specific aspects of the opportunity (e.g., “{first_name} + {company} = Leadership Opportunity”) 2. Choose words that drive engagement When deciding what words to use in your subject line, consider these key trends: - Personalization is powerful - Be clear right away - Keep it conversational - Tap into ambition To personalize, for example, you might use the first name token and the word “you.” This makes messages feel like they’re speaking directly to the prospect. If you’re a Gem user, you can take this further by using a short personalization token in the subject line and a longer one in the body of your email. 3. Don’t overlook tokens Teams should generally include at least one token in their subject lines. It can make a nearly 5% difference in open rates… and which tokens work best will be well worth testing. Larger companies typically include the company name in the subject line. This makes sense since bigger brand names are more likely to capture candidates’ attention. On the other hand, smaller companies are more likely to use the job title to attract them. 4. Keep it short and sweet When it comes to subject line length, shorter is generally better. The sweet spot for achieving the best open rates is between 3 and 9 words… …though some subject lines as lengthy as 11 words still see good open rates (if they’re catchy!). 💡 One final tip: Keep proven engagement tactics in mind— Appeal to curiosity. Mention mutual connections. Indulge in a little flattery. These go a long way to craft winning subject lines that inspire your candidates to respond and move forward. To see more data-backed recruiting insights like these… Download our eBook detailing email outreach benchmarks and best practices: https://bit.ly/4ffcn5B

Here is how I got an 80% Success Rate in Cold Reach-Outs (even as a student) 1. Quality over Quantity Don’t mass message. Focus on high-potential connections and personalize each message. 💡 Example: “Hi [Name], I saw your talk on [topic] and it really aligns with my work on [project].” 2. Get to the Point Fast Introduce yourself and state why you’re reaching out in the first two sentences. 💡 Example: “I’m [Your Name], working on [specific project]. I’d love to chat about [shared interest].” 3. Choose the Right Platform Some respond best to LinkedIn, others to email, X, or their website’s contact form. Find the right way to reach them. 4. Be Specific About Your Ask Clearly state what you’re asking for- advice, a call, collaboration, etc. 💡 Example: “I’d love a quick 15-minute call to discuss [topic].” 5. Showcase Credibility Include a link to your GitHub, blog, or research to build trust. 💡 Example: “Here’s my recent work on [topic]: [link].” 6. Follow Up (Respectfully) If they don’t respond, send polite follow-ups 2-3 times with a week between messages. Persistence works, but don’t spam. 7. Respect Their Time Keep your message short and to the point. Show you respect their busy schedule. 💡 Example: “I know you’re busy—just a quick 15-minute call would be great!” Try these tips to level up your cold outreach! 🚀 #NetworkingTips #AICommunity #GrowthHacks

The WRONG way to teach discovery is to tell sellers which questions to ask. The questions don't matter until the team knows what they are trying to get the prospect to SAY in the first place. Once they know what they need to get the prospect to say, then they just need to work backwards to reverse engineer what question(s) will get them to say that! Just handing everyone a list of questions robs sellers of their authenticity - memorized questions often come across stiff and salesy. --- Once you've decided what you're trying to "discover", here's a couple question types I really like to use: Remember, focus less on the wording and more on what I'm trying to get the prospect to say. 𝟭. 𝗪𝗵𝘆'𝗱 𝘆𝗼𝘂 𝘁𝗮𝗸𝗲 𝘁𝗵𝗲 𝗰𝗮𝗹𝗹? We need to know what's motivating them to show up on a sales call with us in the first place. Use this as your opening question right after setting an agenda: "𝘌𝘮𝘮𝘢, 𝘸𝘩𝘢𝘵 𝘮𝘢𝘥𝘦 𝘺𝘰𝘶 𝘥𝘦𝘤𝘪𝘥𝘦 𝘵𝘰 𝘳𝘦𝘢𝘤𝘩 𝘰𝘶𝘵 𝘵𝘰 𝘶𝘴?" [inbound] "𝘌𝘮𝘮𝘢, 𝘐 𝘤𝘢𝘯'𝘵 𝘪𝘮𝘢𝘨𝘪𝘯𝘦 𝘺𝘰𝘶 𝘵𝘢𝘬𝘦 𝘮𝘦𝘦𝘵𝘪𝘯𝘨𝘴 𝘸𝘪𝘵𝘩 𝘦𝘷𝘦𝘳𝘺𝘰𝘯𝘦 𝘵𝘩𝘢𝘵 𝘢𝘴𝘬𝘴. 𝘞𝘩𝘢𝘵 𝘮𝘢𝘥𝘦 𝘺𝘰𝘶 𝘥𝘦𝘤𝘪𝘥𝘦 𝘵𝘰 𝘵𝘢𝘬𝘦 𝘵𝘩𝘪𝘴 𝘤𝘢𝘭𝘭? [outbound] --- 𝟮. 𝗠𝘂𝗹𝘁𝗶𝗽𝗹𝗲 𝗖𝗵𝗼𝗶𝗰𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 Use these to "offer" problems you know you solve and steer the conversation in that direction. [what I heard] 𝘠𝘰𝘶 𝘮𝘦𝘯𝘵𝘪𝘰𝘯𝘦𝘥 𝘺𝘰𝘶𝘳 𝘯𝘦𝘸 𝘤𝘭𝘪𝘦𝘯𝘵 𝘪𝘯𝘵𝘢𝘬𝘦 𝘱𝘳𝘰𝘤𝘦𝘴𝘴 𝘪𝘴 𝘵𝘰𝘰 𝘴𝘭𝘰𝘸. [multiple choice] 𝘜𝘴𝘶𝘢𝘭𝘭𝘺 𝘐 𝘧𝘪𝘯𝘥 𝘵𝘩𝘢𝘵'𝘴 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘦𝘪𝘵𝘩𝘦𝘳 𝘤𝘰𝘯𝘧𝘭𝘪𝘤𝘵𝘴 𝘤𝘩𝘦𝘤𝘬𝘴 𝘢𝘳𝘦 𝘵𝘢𝘬𝘪𝘯𝘨 𝘵𝘰𝘰 𝘭𝘰𝘯𝘨 𝘖𝘙 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘵𝘩𝘦 𝘵𝘦𝘢𝘮 𝘥𝘰𝘦𝘴𝘯'𝘵 𝘩𝘢𝘷𝘦 𝘨𝘳𝘦𝘢𝘵 𝘷𝘪𝘴𝘪𝘣𝘪𝘭𝘪𝘵𝘺 𝘪𝘯𝘵𝘰 𝘸𝘩𝘦𝘳𝘦 𝘢 𝘤𝘢𝘴𝘦 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘪𝘴 𝘪𝘯 𝘵𝘩𝘦 𝘪𝘯𝘵𝘢𝘬𝘦 𝘱𝘳𝘰𝘤𝘦𝘴𝘴. [simple ask] 𝘈𝘳𝘦 𝘦𝘪𝘵𝘩𝘦𝘳 𝘰𝘧 𝘵𝘩𝘰𝘴𝘦 𝘵𝘩𝘪𝘯𝘨𝘴 𝘧𝘰𝘤𝘶𝘴 𝘢𝘳𝘦𝘢𝘴? --- 𝟯. 𝗣𝗿𝗮𝗶𝘀𝗲 + 𝗣𝗮𝗶𝗻 Sometimes you need to just directly ask about pain points you suspect they have. But to avoid coming off too leading, try pairing compliments with your direct question to soften the blow: "𝘠𝘰𝘶 𝘢𝘭𝘭 𝘤𝘭𝘦𝘢𝘳𝘭𝘺 𝘩𝘢𝘷𝘦 𝘢 𝘬𝘪𝘭𝘭𝘦𝘳 𝘱𝘳𝘰𝘥𝘶𝘤𝘵 𝘵𝘩𝘢𝘵 𝘮𝘰𝘳𝘦 𝘱𝘦𝘰𝘱𝘭𝘦 𝘴𝘩𝘰𝘶𝘭𝘥 𝘬𝘯𝘰𝘸 𝘢𝘣𝘰𝘶𝘵. 𝘛𝘰 𝘸𝘩𝘢𝘵 𝘦𝘹𝘵𝘦𝘯𝘵 𝘥𝘰 𝘺𝘰𝘶 𝘧𝘦𝘦𝘭 𝘭𝘪𝘬𝘦 𝘺𝘰𝘶'𝘳𝘦 𝘮𝘪𝘴𝘴𝘪𝘯𝘨 𝘰𝘶𝘵 𝘰𝘯 𝘱𝘰𝘵𝘦𝘯𝘵𝘪𝘢𝘭 𝘯𝘦𝘸 𝘥𝘦𝘢𝘭𝘴 𝘫𝘶𝘴𝘵 𝘣𝘦𝘤𝘢𝘶𝘴𝘦 𝘧𝘰𝘭𝘬𝘴 𝘩𝘢𝘷𝘦𝘯'𝘵 𝘩𝘦𝘢𝘳𝘥 𝘰𝘧 𝘺𝘰𝘶?"

Most reps start cold outreach with: "I saw your company..." Then wonder why they get ignored. I’ve reviewed 1000+ cold outreach messages. The ones that worked all followed the same pattern: INSIGHT → PAIN → QUESTION Most cold outreach fails because you lead with YOUR agenda: "I'd love to show you our solution..." "I think we could help you with..." Prospects immediately think: "Another sales pitch." Delete. The framework that gets 15-20% response rates: Step 1: INSIGHT Lead with something they don't know about their situation. Share an industry trend or benchmark. "Most VPs we work with don't realize that 60% of their pipeline stalls because..." Why insights work: They position you as an expert, not a salesperson. They create curiosity instead of resistance. Step 2: PAIN Connect that insight to a potential problem they might be experiencing. "...which means you're probably dealing with longer sales cycles and more 'no decisions'..." The key word is "probably." This feels consultative, not presumptuous. Step 3: QUESTION Ask if they're seeing something similar. Not if they want a demo. "Are you seeing similar patterns in your pipeline?" Why questions work better: Questions start conversations. Asks trigger resistance. Full example: "Hi [Name], Most sales VPs don't realize that 73% of deals stall because reps are selling to champions instead of decision makers. This usually shows up as lots of 'positive feedback' but deals dying in committee. Are you seeing similar patterns where reps have great conversations but struggle to get deals across the finish line? Best, [Your name]" What this accomplishes: ✅You sound different from every other rep ✅You lead with value instead of ask ✅You focus on their problem, not your solution The psychological shift: Instead of "This rep wants something from me," they think "This person might understand my situation." Common mistakes to avoid: ✅Don't make the insight too generic ✅Don't make the pain too assumptive ✅Don't end with a meeting ask The result: 15-20% response rates because you sound like a consultant, not a vendor. Stop pitching. Start consulting. — AEs! Check out the 3 questions that break through price objections here: https://lnkd.in/gbBjgxxS Sales Leaders: Want to install a revenue system that your reps can follow? DM me.