Cold Email Outreach Tips

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.

Here are 3 phrases I avoid using in cold outbound to Enterprise CXOs. 1. "CXOs like you often struggle with..." Using a generic "like you" with someone we've never met unintentionally reads a bit like: "I couldn't be bothered to look up your unique situation, so I'll just throw out these 3 broad statements and hope one sticks." Ex: "driving revenue growth" or "increasing efficiency". There's too much publicly available info about ENT accounts and what they're trying to achieve. Instead, I prompt ChatGPT with "What are ACME CEO's most recent interviews about the company's growth strategy?". Helps me find a specific observation about the account + tie it back to a specific problem hypothesis (with unsure tonality). Ex: "Mark spoke about X (objective). Seems like you might be doing Y (current state). Not sure if you're seeing Z (related problem), but Acme tested a few different options to fix it. Open to hearing what they learned?" Also - I prefer to kill "struggling". Not sure many people like to be told it seems like we're struggling to do their job by a stranger. 2. "Do you have a quick 15 mins?" Suggesting that 15 mins of an Enterprise exec's time is "quick" makes us sound naive. It unintentionally diminishes the value of their time. Instead, remove 'quick' + A/B test a call to learn instead. (Ex: "Open to seeing how?") 3. "I just wanted to" / "I'd love to" / "I'd like to" Prospects don't care what we want. I used to think this language showed execs how much I cared about booking a meeting. Until I saw how much it's used in cold emails. It's white noise to buyers & unintentionally selfish. Instead, kill as many "I", "we", "our", "Company Name" statements as possible. *As always, nothing never works and nothing always works. You could write a cold email with all 3 of these and probably still book a meeting. But, once I stopped using these phrases, my cold emails felt less sales-y and I was more confident hitting send.

Last quarter I received a perfect cold email. It followed the same simple prospecting framework I teach. Here's a line-by-line breakdown of why it works so well: SUBJECT LINE: Make it all about them and reference your research Why it works: Shows that it's not spam or automated, and creates curiosity to open the e-mail and here what they have to say PARAGRAPH #1: Warm, personal, with a sincere compliment Why it works: Shows the prospect you took the time to learn about them, and humanizes you. PARAGRAPH #2: Share relevant observations based on research and a potential problem which their research uncovered Why it works: Shows that you are reaching out to identify a potential way to help them which they may not be thinking about PARAGRAPH #3: Shares specific, clear value proposition which includes the problem you solve and the outcomes you deliver Why it works: people need to clearly understand what you do so they can decide for themselves if it makes sense to meet with you. Sharing generic outcomes without being direct or specific confuses and annoys prospects because they still don't know what you do after reading the e-mail. PARAGRAPH #4: Soft Call to Interest (CTI): Ask if they have ever given thought to what you wrote, and if they're open to discussing further. Why it works: Never assume that a prospect needs what you are selling. Instead, confirm whether they've thought about the problem you solve and are open to discussing further. A call to interest (CTI) is much softer than a call to action (CTA), such as asking them to meet before you've confirmed they even have a need or interest. Don't assume anything, just ask and validate first. Kudos to the seller for sending a well-written, thoughtful e-mail.

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

Sure, cold email is hard right now. But dude, we gotta stop playing the blame game. It's not because of poor deliverability rates. It's not because of spam filters. And it's not because people don't use email anymore. It's because your email probably sucks. You use copy/paste templates. Sending the same emails to multiple people with different jobs. And not personalizing. What do you expect to happen? Alright, rant over. Let's talk about what to do about it. Lesson today: Make sure your emails are "mobile ready." Lavender 💜 has some great data on cold emails: - Prospects are 8x more likely to open emails on their phone - Short and mobile-optimized emails see 83% more replies - Emails under 50 words get 60% more replies than emails with 150+ words If your emails aren’t short and mobile-optimized, you will not likely get a response. - Word count: Keep emails under 75 words - Mobile ready: Use short, 1-2 sentence paragraphs The basic formula looks like this: ✅ Reason: Why you’re reaching out to the prospect ✅ Problem: Speaks to the prospect’s potential problem(s) ✅ Social proof: References relevant work with similar companies ✅ Call-To-Action (CTA): Speaks to prospect’s priorities and problems === Example #1: A company that sells electronic document capture software to clinical operations leaders Subject line variations:  - FAPI - Startup timelines - FDA approval Hi Frank, Reason 👉 Saw that you just got FDA approval to proceed with the Fibroblast Activation Protein Inhibitor (FAPI) clinical trial. Problem 👉 As you launch this trial, we usually hear that manual paper systems and Excel databases create extra work that could delay startup dates. Social Proof 👉 We’re helping operations leaders capture trial data more easily to shorten startup timelines to under 4 weeks. CTA 👉 Worth a quick chat? Jason === Example #2: A company that sells software to help contact centers reduce incoming calls Subject: Interconnection cost reduction Reason 👉 Saw the announcement of the interconnection cost reduction initiative, Anne. Problem 👉 Usually, that means there’s a focus on reducing incoming support calls and pushing customers to self-serve. Support leaders oftentimes run into challenges knowing which digital investments are actually deflecting calls. Social Proof 👉 We helped Constellation dramatically reduce cost to serve by finding the sources of increased call volumes. CTA 👉 Can I share those insights with you? === You can't get away with mediocre cold emails anymore. Tighten up your message. Optimize for mobile. And invest more time to improve your copywriting skills. Tomorrow, I'm partnering up with ZoomInfo to teach the Cold Email playbook we've taught to AE/SDR teams at Shopify, Gong, Rippling, Zoom, and many more. Register here to join us: https://hubs.ly/Q02_Y0fW0

Raise your hand if cold emailing someone actually makes you sweat 😓 I get it — cold emailing can feel incredibly daunting, but it doesn't have to be. As someone who has "shot her shot" many times over InMail, DMs, emails, etc. there's a few tips I have on how you can (as my amazing co-host Gianna Prudente says) make the cold email a little warm: 1. First, remember there's still another person on the other end. Behind every inbox is a human being with their own goals, challenges, and experiences. Approach your email with that in mind. Instead of diving straight into a request, take a moment to acknowledge their work, share why you admire it, or highlight something you have in common. BE PERSONABLE, Y'ALL. 2. Balance professionalism with personality. Yes, you want to sound polished, but don’t be afraid to let your personality shine! Authenticity goes a long way. Share why you’re reaching out, what you hope to learn, and how you see this connection being valuable for both of you—not just you. I also do believe in courtesy: When you reach out, say "good morning" or "hello". Don't just jump into the ask. 3. Focus on building community. Networking isn’t a one-way street. The strongest relationships are built on mutual value and not feeling like you're being taken advantage of. Instead of making it feel transactional (“Can you do this for me?”), think about how you can contribute to the conversation or be helpful in return. You’ll go farther by fostering relationships over time rather than expecting quick wins. Remember: the goal isn’t just to make a connection—it’s to build a relationship. Let me know in the comments below what some of your favorite networking tips are, and be sure to check out the latest episode of "Let's Talk Offline" (and be sure to follow the show!) where Gianna and I hang out with our work bestie, Morgan Young all on building your network and getting more comfortable with building your community.

Most cold emails don’t fail because of bad writing. They fail because they talk too much about the product… …and not enough about the problem. Here’s the cold email formula I’ve used in over 100,000 sends - including while helping scale Gong from $200K to $200M in ARR. It’s simple. It works. And it doesn’t require a single bullet point about features. The 4-part cold email formula: 1. Relevant intro Personalized and specific - not robotic. “Looks like you're hiring across your revenue org — congrats.” 2. Agitate the pain Make your prospect feel like you’ve read their internal Slack threads. “You either hit your headcount targets and sacrifice quality… Or you hire strong reps but miss your number.” 3. Paint the future state Share what you help others accomplish - not how your product works. “We’ve helped 100+ VPs reduce their miss-hire rate to single digits.” 4. The ‘Solve’ CTA End with a yes/no question - not a time request. “Is reducing sales mis-hires this quarter worth a quick chat?” You don’t need long emails. You need relevance, resonance, and a reason to reply. That’s how you build pipeline. P.S. Want to have actionable techniques, strategies, cheat sheets, & case studies to help you master your SaaS sales skills? Join 100,000+ other sellers who receive our newsletter every Tuesday: https://lnkd.in/egVNiFce

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! 👇

I used to send >250 custom outbound emails every week. Yesterday, I was introduced to someone who remembered one of those emails from literally 10 years ago. Here's my outbound strategy for anyone that wants to master cold outreach: 1️⃣ do not sell yourself at the open >> seriously, stop talking about yourself. no one cares about you << Instead: just say who you are, and move on to talk about them. 2️⃣ tell people why they are great - I liked to make a list of at least 5 points - I would write custom points for each recipient - I wrote simply and directly - Inspired by Dale Carnegie - people like to be liked 3️⃣ sell the CONVERSATION, not the opportunity - I never pushed people into existential consideration - I only asked them for 15 minutes, they could spare it - I NEVER sold the role or company, I'd only give them 1 sentence about it 4️⃣ be very direct - I always told people "I think you could be a fit for a job here" - But... I never said the specific job, or qualified it further - People need to know what you want, but they don't need all the details 5️⃣ use humor - I've meme'd since the dawn of my professional time - It seemed to work, lots of people just wanted to respond - Them responding = opening to get them on a call 6️⃣ be fast + use tools - you need to move fast to get 50 good messages out per day - I used a template to populate my open + add bullet points (but not content) - I used TextExpander to insert saved "custom" points. If I'd already written to a musician and explained why I thought their background in music made them an interesting prospect for an engineering role, I'd save that exact verbiage and re-insert it with TextExpander in future messages. - I use all the gmail hotkeys, it helps give you little bits of advantage on a process you will repeat tens or hundreds of thousands of times - it's worth getting gud -------------------------------------- That's it. Remember that people like being liked. Remember that no one cares about you. Remember not to force people to think too far ahead. Oh... and remember that 90% of the time, it won't be the right time, and that's just the process of finding the 10% who are ready to talk.

This cold email hits all the right notes. Yes, you can steal the template, but it's the underlying psychology that will help you apply it to your prospects. ___ "Hi Lisa – Looks like your team has 12 SDRs cold emailing Benefits Directors at companies with 3,000+ employees. With ACME, your reps can see which Benefits Directors searched for ALEX-related keywords in the last 24 hours—along with their names and emails—so they can reach out while interest is high. Want me to send over a few examples?" ____ Why This Works: The Psychology Behind It 1. Personalization & Relevance – By mentioning Lisa’s SDR team and their current outreach strategy, the email signals that this isn’t a generic blast. People are more likely to engage when they feel like the message is tailored to them. 2. Curiosity & Information Gap – The line “your reps can see which Benefits Directors searched for ALEX-related keywords in the last 24 hours” creates intrigue. Lisa now wonders, “Who’s searching? How can we use this?” This open loop makes her more likely to respond. 3. Timing & Urgency – The phrase “while interest is high” suggests that taking action sooner leads to better results. It plays on loss aversion—the fear of missing out on a warm lead. 4. Low-Friction Call to Action – Instead of asking for a meeting (which requires effort), the email simply offers to send examples: “Want me to send over a few?” This feels easy to say yes to, reducing resistance. 5. Conversational Tone – The email avoids formal, sales-y language. It reads like a natural, quick note, making it feel less intrusive and more approachable.