How sales emails get lost in executive inboxes

I've reviewed thousands of cold emails written by AEs & SDRs for my Sales training workshops this year. Here's one of the most common (yet, easily fixable) culprits that causes buyer to delete our cold emails, before they ever open them. The culprit: we're pitching a value prop in the subject line. Examples: "Elevate your procurement strategy" "Stay ahead of compliance risk with ACME" "Optimize your tax software" Buyers don't have to open the email to know it's a pitch. See the first word of every one of those subjects? We're selling. The buyer smells it from a mile away. Because they don't write subject lines like that. Marketers and sellers do. If you were late updating your forecast, which email would your Sales VP send you? Option A: "Improve your forecast accuracy with HubSpot! 🚀" Option B: "Q2 forecast" If we sound like sellers and marketers in the subject - we're just making the job harder for ourselves. Tip: search your inbox for any 1:1 emails that execs at your own company have sent you (or ask to see emails those execs have sent each other). Look at the subject lines they used (and the email itself). We can learn a lot about executive writing style patterns by doing so.

Enterprise buyers don’t hate cold email. They just ignore 99% of it because most of it’s lazy. You probably heard: “Cold email doesn’t work for enterprise.” What people really mean is: “We blasted 1,000 generic emails and didn’t book a single meeting.” We booked meetings with companies like: - Deel - Tesla - Netflix - Typeform - Mercedes - PandaDoc All through cold outbound. Here’s what we did differently: Myth 1: You can send the same message to everyone. Reality: Enterprise cold email starts with segmentation. Most teams build one list, write one email, and hope it resonates. It never does. Instead, start with deep research on your ICP (beyond job title and company size). We use tools like Clay, Common Room, Relevance AI and others to enrich for: - Company news or GTM shifts. - Role seniority and time in role. - Tech stack and integration fit. - Recent funding or layoffs. - Website activity. - Buyer history. From that, we create multiple angles per persona. So, a sales leader at a $300M company who just switched roles gets a different message than a CMO at a bootstrapped startup using HubSpot. This is how you write emails that feel 1:1. Without doing everything manually. Myth 2: Hitting send is enough. Reality: If you don’t land in the primary inbox, nothing else matters. Enterprise domains are notoriously strict. The filters are tighter. The send limits are lower. So we take deliverability seriously: - Proper DNS + DMARC. - Single-tenant workspaces. - Domain warm-up using high-quality pools. - Controlled sending volume and ramp-up. - Focused testing in smaller segments before going wide. Think of it like this: Before you run your “hero” campaign to enterprise accounts, test your messaging on Tier 2 audiences. Build up positive replies. Age your domains. Then scale. It’s slow. But it’s the difference between “no replies” and “thread with Mercedes.” Myth 3: Your offer doesn’t need to change. Reality: A good offer is contextual, not static. Enterprise buyers aren’t swayed by clever lines. They say yes when the offer solves a real problem. A few offers we’ve used successfully: - Free workshops or audits (for high-ticket services). - Custom business cases (when selling into economic buyers). - Webinar invites and ungated playbooks (for earlier-funnel plays). - Product trials framed as risk-reducers, not demos. The offer is part of the message. Get that wrong, and even a perfectly timed, personalized email falls flat. When you do all this well, here’s what happens: - You land in the inbox, not spam. - Your message sounds like it was written for that person. - Your offer matches where they are in the buying cycle. - You feel familiar, even if it’s the first touch. This is how you book meetings with logos most teams can’t crack. Because cold email does work for enterprises. Just not the way most people are doing it. What’s the most effective cold offer you’ve seen or used lately? Let me know 👇

You can't pitch a CFO like you pitch a sales rep. But that's exactly what I see most cold emails do. After analyzing 100+ executive outreach sequences, here's the pattern that kills response rates. 👇🏻 What doesn't work with executives: - Feature lists ("our AI-powered dashboard...") - Workflow improvements ("save 2 hours per day...") - User-level benefits ("cleaner reports, fewer clicks...") Executives don't implement tools. They approve budgets. What actually works: the 3-layer translation framework: Layer 1️⃣ Product outcome starts with what your tool does. example: "Reduces rep ramp time from 6 months to 3 months" Layer 2️⃣ Business Impact Translate to departmental results. example: "Sales team hits quota 2 quarters faster" Layer 3️⃣ Executive Metric Connect to numbers they report to the board. example: "$1.2M additional ARR in year one" Bad exec email: "Our CRM integration automates lead scoring and creates cleaner dashboards for your sales team." Good exec email: "Companies using our platform see 23% faster deal velocity, which typically translates to $500K-$2M additional ARR in the first year. Happy to share the ROI calculator we built for <similar company size>." The 4 languages executives speak: CFO: ROI, burn rate, cost per acquisition, payback period CEO: Growth rate, market share, competitive advantage, scalability Head of Sales: quota attainment, pipeline velocity, win rate, team productivity Head of Marketing: CAC, LTV, attribution, conversion rates Quick audit for your outreach: - Do you lead with outcome, not features? - Does your email mention a specific metric? - Can you quantify the impact in dollars or percentages? - Is that metric something they'd discuss in a board meeting? Pro tip: Before writing to any executive, spend 5 minutes on their LinkedIn. Find their latest post about challenges or wins. Reference that context in your first line. Here’s a 30-second executive email template you can use: "Saw your post about <specific challenge>. <Similar company> faced the same issue and saw <specific metric improvement> after implementing <solution category>. Worth a 15-minute conversation to see if there's a fit? I can share the exact playbook they used." Same product. Same features. Just reframed in their language. What's the biggest mistake you see in executive outreach?

𝗔𝗜 𝗦𝗗𝗥 𝘁𝗼𝗼𝗹𝘀 𝗽𝗿𝗼𝗺𝗶𝘀𝗲 𝘂𝘀 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗼𝗻 𝗮𝘂𝘁𝗼𝗽𝗶𝗹𝗼𝘁. What many delivered instead? 𝘈𝘶𝘵𝘰-𝘣𝘭𝘢𝘴𝘵𝘪𝘯𝘨 or "𝘴𝘱𝘳𝘈𝘐 𝘢𝘯𝘥 𝘱𝘳𝘈𝘐" as I like to call it. For teams selling into a small universe of high-value accounts (think anything <10,000 named accounts per year) this approach is a non-starter. Every touchpoint matters. Especially when that email is landing in the inbox of a Fortune 1000 CRO. This was a key takeaway from my recent conversation with Ian Kistner, Sales Development Leader at HG Insights, on MadKudu's 𝘚𝘢𝘭𝘦𝘴 𝘊𝘰𝘯𝘧𝘦𝘴𝘴𝘪𝘰𝘯𝘴 episode. Ian shared how his team tested some of the well-known AI email tools. One particularly interesting insight was around the “grades” they would assign to outbound messages. The red flag: SDRs were showing him emails that 𝘨𝘰𝘵 𝘢𝘤𝘵𝘶𝘢𝘭 𝘮𝘦𝘦𝘵𝘪𝘯𝘨𝘴, but were graded as a “C.” Meanwhile, the AI recommended a 12-word “A+” email… to a CRO. No context. No insight. Just vibes. While that might fly in a high-velocity SMB motion, in enterprise that email’s not getting opened. Worse—it damages your credibility and brand. My take on the issue is that these tools are often trained to optimize for open rates and structure—not trust, insight, or real engagement. The vast majority of training data is listicle posts on "emails that get opened" not actual emails that landed enterprise-account meetings. So what’s the better play? Don’t use AI to 𝘸𝘳𝘪𝘵𝘦 the email end-to-end. Use it to: • Gather context and account-level insights • Summarize relevant news, product launches, or leadership shifts • Suggest hooks based on mutual connections or tech stack signals • Draft angles to use for the outreach and possibly the email based on 𝗲𝗺𝗮𝗶𝗹𝘀 𝘁𝗵𝗮𝘁 𝗵𝗮𝘃𝗲 𝘄𝗼𝗿𝗸𝗲𝗱 𝗳𝗼𝗿 𝗬𝗢𝗨 Then let your reps put it together—with intent and care. It’s not 𝘴𝘦𝘵-𝘪𝘵-𝘢𝘯𝘥-𝘧𝘰𝘳𝘨𝘦𝘵-𝘪𝘵. It’s 𝘤𝘰-𝘱𝘪𝘭𝘰𝘵, 𝘯𝘰𝘵 𝘢𝘶𝘵𝘰𝘱𝘪𝘭𝘰𝘵. This story might sound familiar. I've spoken to many sales leaders disappointed with the output of these AI SDRs. There's no doubt they will get there but it's also clear they aren't yet. #salesdevelopment  #b2bsales  #salesconfessions  #personalization  #AI

Your sales emails suck. And guess what? I know because I get 30 of them a day. I see the same mistakes over and over...the boring intros, the endless rambling, and the generic pitches that make my inbox feel like a nightmare. Want to know why? Because your email has 3 seconds to make an impression. THREE. Seconds. That's how long you have before I hit "delete" So if you’re not cutting through the noise, you’re just part of the problem. Here’s why your outreach isn’t working: 🚫 Cut the fluff, now – “Hope you’re doing well” or “Just checking in” is a one-way ticket to the trash. No one has time for that. If you don’t get to the point within the first 5 words, you’re done. ✂️ Get to the point fast – Lengthy emails are a killer. Research shows emails under 50 words see 83% more replies. That means if you're writing a novel, you’re already losing. 📚 Personalize (like actually personalize) – "I see you're in [insert job title here]”—that's not personalization, it’s lazy. Do your homework and show that you understand my specific challenges and goals. If you don’t, I’m clicking delete before you even finish your sentence. 🎯 Relevance matters more than anything – If your email isn’t directly tied to what I’m trying to accomplish, it’s not going to get a reply. I don’t need a generic pitch; I need to know how you can help me solve my problems today. 🔥 Stop the lazy copy-paste – If I can tell you’re sending the same message to 100 people, I’m out. Your outreach should feel like you’re speaking to me, not to the entire world. Personalization isn’t just a buzzword. You’ve got 3 seconds to grab attention and show value. If you’re still using the same tired tactics, you’re wasting your time...and mine. 🎤 🫳 ALSO MASSIVE SHOUTOUT to the folks using video to prospect, can say that personalized video messages get a response from me every time. I LOVE them.

Most AEs can’t get a meeting with a CFO. My clients are getting them with CEOs, COOs, and CFOs—consistently. The secret? Not magic. Not spamming. Hyper-personalized, multi-channel outreach powered by ChatGPT. Here’s the exact framework we use (that gets replies when “short and sweet” emails fail): When I ask sales teams how many times they follow up with an executive before moving on, the most common answer is: “Two emails, maybe a call.” That’s why you’re losing. Executives don’t respond because: Your outreach is generic You stop before you break through the noise You rely on ONE channel (usually email) Here’s how we fix it. 1. Go narrow before you go deep Stop prospecting to everyone in your patch. Pick your A accounts—the top 10-20 that would change your year if you closed them. 2. Use 3-4 channels every time If you send an email and don’t follow it with a call, a video, and a LinkedIn touch, you’re invisible. I’ll use ZoomInfo or Seamless to get the cell number, call right after sending the email, leave a voicemail, then send a voice note or video if no pickup. 3. Reach out 10+ times (not 2) My largest deals took 10-15 touches before the first meeting. If you believe you can help them, they need to know you’re serious. 4. Hyper-personalize using AI Forget “Hope you’re doing well.” Here’s the structure: Line 1: Personal, sincere compliment tied to research Line 2: Observation about their stated goals/priorities Line 3: The gap between where they want to go and where they are today Line 4: How you can close that gap Close: Soft call to action 5. Steal my favorite ChatGPT-4o prompt “I’m a sales rep at [Company] targeting [Name, Title]. Write a personalized, executive-ready email that speaks to their role, their publicly stated goals or quotes, and how we can help them. Be concise, use bullet points, and end with a soft CTA.” (more in the video below) Combine this with deep account research before you ever reach out, and you’ll have emails that sound like you wrote them just for that exec—because you did. I’ve seen this method work when: - You’re selling to an account that already uses your product (reference it in the first line) - You can’t find public info on a prospect—personalize at the account level instead - You need to enable champions to sell internally You don’t get meetings with executives by sending “short and sweet” emails. You get them by showing you’ve done the work— And proving, in detail, that you understand their business better than 99% of reps hitting their inbox. Get my top 4 ChatGPT prompts for tech sellers here: https://lnkd.in/gbznEjgq

I receive over 100 sales in-mails and emails every day . I don’t respond to 99% of them. I was wondering why is this . So I opened the inmails and emails to check. Most of the emails / inmails get down to selling at the first step . They are outright salesy. Salesy cold emails often fail, with response rates as low as 1%–2%, according to HubSpot, because they focus on hard selling rather than building connections. And then I reflected on the 1% that I respond to. They are conversational. The mails that I respond to are those who are about me , those who have been following what I share on LinkedIn. They begin with “ME”. They are crisp and they build a conversation over time. They have been commenting on my content on LinkedIn and sharing their thoughts . They understand me , what I do and what are the challenges I face. A conversation is buit at multiple touch points with no rush . These are micro conversations at the level of one. There is no strong push to sell but rather the approach is to build relationship. This cannot happen at the scale of mass marketing or cut paste similar messages. In B2B marketing there are no impulse purchases , decisions take time , where you target only a few companies and you have to talk to only a few people . Conversational emails, supported by marketing’s thought leadership, can achieve response rates of 15%–20%, as per Woodpecker’s research, by being personalized, empathetic, and value-driven. Marketing establishes trust and credibility through content and thought leadership, while sales micro-personalizes communication to address specific pain points, creating a seamless bridge between brand awareness and engagement. Both are needed. LinkedIn reports that personalized InMails see a 40% higher response rate than generic messages. By aligning marketing’s broad impact with sales’ tailored approach, businesses can craft cold emails and LinkedIn InMails that foster genuine connections and drive results . To cut the long story short I have not only responded to but met those 1% and I know them. Their thinking is not salesy but genuinely partnership driven. What are your thoughts on micro conversations in the world of cold calls , cold emails and inmails where the pressure of targets is high. To check out my full video on this subject on YouTube link shared in comments. #EmailMarketing #B2Bmarketing

"Cold email doesn't work for enterprise." Our meetings booked with Netflix, PandaDoc, Sony, Tesla, Mercedes, Deel, Typeform, and Roche say otherwise. There are 3 things in common across these campaigns: 1️⃣: Deep research to segment lists. People often misunderstand exactly how to do this. Let's take an example. e.g. You're selling a solution that helps with attribution. You might sell to leaders in sales, marketing, ops, or directly to the exec team. If you send the same message to all these personas, the message will fall flat. So you'll want to use data providers + AI agents, to dig deeper and answer questions like: ↳ How big is the company? ↳ Is this person new in role? ↳ Do you integrate with their tech stack? ↳ Did they just receive funding to expand? ↳ Or are they cutting down on headcount? ↳ What sub-segment of the market are they in? ↳ Are there any recent company announcements? ↳ Did the prospect previously work for a customer? ... and many more. With all this data, You may now have 5+ unique angles per persona. This is how you create emails that feel 1:1, at scale. And it is why I always echo Jordan Crawford's quote: "Your list is your message." 2️⃣: Deliverability optimization. Landing in the primary inbox for enterprise is a science. At the very least, you need a solid tech setup: ↳ Double-verified lists. ↳ Proper DNS settings. ↳ Single-tenant workspaces. ↳ Throttling on emails sent/day. ↳ Usage of a high-quality warm-up pool. Next step is to build up that sender reputation over time. That's why it's best practice to find winning campaigns. In your smaller segments. And only start sending to enterprise once you've: ↳ Racked up replies. ↳ Have proven angles. ↳ And you've aged those domains a bit. 3️⃣: A compelling offer. A great offer will change depending on your market: - Selling a service that's highly commoditzed? You may want to offer some sort of upfront, free work. - You solve a complex, widespread problem? Your best offer might be free information (e.g. webinar). - You're PLG and have a better product than competitors? Framing your trial the right way could be your best bet. - You'll do anything to secure that meeting? We've seen success with dinner invites, free merch, etc. If you do all this, here is what it's like for your prospect: - You landed in the primary. - Your message feels 1:1 (even if isn't per say). - It feels like you've done your research. - Because of the above, you may provide upfront value. - And your offer is actually something they care about. It's no surprise that you'll book meetings like this. Anything I missed? 👇 Follow Dan Rosenthal for more GTM tips.

After thousands of campaigns, I’ve noticed the same mistakes come up again and again. Here are the 6 biggest ones (plus, how to fix them): 1. Subject lines don’t grab attention - Keep it short (1–3 words). - Make it look like a colleague sent it. - Vague enough to spark curiosity. 2. Emails don’t feel personal - First line = about them, not you. - Go beyond surface-level triggers (like “congrats on the new role”). 3. The problem doesn’t resonate - Use transcripts from real discovery calls to mine actual pain points. - A/B test until you find the one that hits. 4. They don’t believe your solution - Call out how they’re currently solving the problem. - Show the inefficiencies. Then position your approach as the fix. 5. No credibility - Bridge the gap with specifics. - Bad example: “We help teams book 10+ meetings.” - Good example: “We helped [Company] grow meetings 43% by automating follow-ups. Here’s how...” 6. Weak CTA - Not every CTA has to be “book a meeting.” - Test smaller asks: resources, teardowns, benchmarks, quick breakdowns. Which of these mistakes do you see most often in your inbox? #sales