Reasons Sales Messages Fail

What's wrong with this message? 8 reasons this DM will fail. ➡️ The message is too generic. It looks like it was sent to thousands of people, not just me. ➡️ It lacks research on my company. Showing no knowledge of my business makes the message feel irrelevant. ➡️ It fails to mention a specific problem. People only reply if you address a pain point they are currently feeling. ➡️ The opening sentence is wasted filler. "Hope you're doing well" takes up space without providing any value. ➡️ It focuses only on what the sender sells. The language is "We do this," not "Here's what you gain." ➡️ The bullet points are features, not solutions. Listing tools (like Power BI) is less impactful than listing results. ➡️ It gives me homework. I'm busy; why do I have to match your services to my needs? ➡️ The subject line sounds like spam. Vague terms like "Transform Your Systems" get flagged or ignored immediately. ➡️ The call to action is too passive. "If this aligns" is weak; the sender should state why it aligns. The best type of outreach is → The only goal of outreach is to start a conversation. → You don't sell in the DMs. → You sell on the call. Sometimes your eagerness for leads makes you forget the human part. Keep it conversational Make it about them Keep it short Be specific

Look, cold call pick-up rates and landing in spam are NOT the reasons why outbound isn't working for you in 2025. How do I know? We've worked with thousands of reps in the last few years: - I see all the sh*tty emails - Hardly any reps leave voicemails - People are afraid to call cell phones - Leaders are afraid to set call activity targets - Product pitching like crazy So why isn't outbound working for you? Messaging. I know. Messaging isn't a sexy topic. But poor messaging is likely why outbound doesn't work for you. Common messaging mistakes: ⛔️ Creating outbound messaging in a silo Mistake: A lone BDR leader, sales exec, or marketing exec creates all the cold call talk tracks and email sequences by themselves. Impact: Messaging sounds generic and has too much personal bias. ⛔️ Marketing or product creating outbound messaging Mistake: A PMM or marketing leader writes all the outbound messaging Impact: Since they've had little (or zero) conversations with real customers, the messaging is super generic ⛔️ Product voice: feature heavy messaging Mistake: Messaging focuses on how the solution works, specific features, etc. Impact: This might work on a webpage, but not in a cold email. Messaging feels super salesy and isn't appealing to execs. ⛔️ Not "chunking up" to business outcomes Mistake: Messaging addresses all of the pains of the user, not the decision-makers Impact: Reps get delegated down to product users and struggle to start sales conversations at the exec level ⛔️ Not leveraging customer conversations Mistake: Not using recorded customer conversations to inform messaging Impact: Messaging doesn't use the customer's language and feels generic. What to do instead: ✅ Build a messaging team Get no more than 10 of the best people together to build common messaging. This should include a few of the best AEs, marketing, customer success, sales leaders, product specialists, etc. And make sure to assign a single person to own messaging. ✅ Live workshop messaging by persona/vertical Run live workshops to work out messaging together. At a minimum, messaging should be created for each specific persona. For enterprise, messaging should be created by persona AND industry. A healthcare security leader speaks a different language than a SaaS security leader. ✅ Build a messaging matrix This is what the end product should look like: Personas → Priorities → Current Solutions → Problems/Impact → Desired Outcomes Now you have something that can easily be repurposed into talk tracks and emails. ~~~ If 2025 H1 pipeline looks thin—and outbound isn't producing results—get back to the basics and start with great messaging. Marketing should NOT own sales messaging. Sales needs to own sales messaging. And everyone needs to collaborate together for great messaging. Agree or disagree? 

We must do better. I'm IMPLORING everyone to do better. PLEASE. This is a blind/cold LinkedIn message I received from someone trying to sell me on exploring "business ownership as a career option." Here are a few things that went wrong immediately: Generic Opening: "Still Exploring Career Options?" assumes something about me that may or may not be true. Do your homework and personalize the message. Lack of Specifics: The phrase "very significant leadership experience" is vague and feels (probably is) automated. Mention something specific about my background. Show me you took 2 minutes to scan my profile. Ambiguous Value Prop: "Business ownership as a career option or an investment" is unclear. What exactly are you pitching? Franchise opportunities? Angel investing? Own a Subway? D&D Modeling Business? Clarify the ask. Call Without Context: Asking immediately for a call without clearly stating why I’d benefit or why it's worth my time won't get a response. Make the value clear first. Using a Middleman: Hiring someone else to send LinkedIn messages on your behalf is outdated, especially in the age of AI and automation. Genuine connections matter. If you're going to automate, do it thoughtfully. Unrealistic Timeframe: "10-15 minutes" seems arbitrary and screws the ask. Be mindful of people's time. Clarify why the call would genuinely be valuable, regardless of length. I'll take the time if you sell me appropriately. Sales and business development are hard. I get it. But sending automated, generic messages without taking 60 seconds to personalize or clarify hurts your credibility and the brand you represent. This isn't solely on the person sending it. It's on their leadership and their process (the person who hired them in the first place). Do better. Warm Regards, Kyle

"Our market is too saturated" I hear this excuse constantly from companies with stagnant sales Then I look at their outreach messages And I see the real problem The pattern is clear: 80%+ were completely indistinguishable from their competitors Same opening lines Same value propositions Same calls to action Same generic case studies It's not market saturation that's killing your sales It's message saturation → Your prospects can't differentiate you because you sound exactly like everyone else. Example: A financial services client was struggling with a 0.3% response rate on outreach Their emails started with "I hope this email finds you well" and included phrases like "industry-leading solutions" and "drive efficiency" We rewrote their entire sequence using what I call "Pattern Interrupt Messaging": - Eliminated ALL industry jargon - Removed every claim their competitors could also make - Added specific, unusual metrics their prospects had never seen - Completely changed the visual format of their emails Response rate jumped to 4.1% - a 13x improvement The market wasn't saturated Their messaging was just invisible If your outreach could have your competitor's logo placed on it and still make sense, you've already lost Differentiation isn't just about your product It's about how you communicate What's the one thing only YOU can say about your solution that no competitor could claim? P.S. If you need help with your sales, send me a message

This billboard is controversial. Borderline unethical. But from a sales positioning perspective, it’s sharp. The lawyer isn’t speaking to everyone. He’s speaking directly to people who already feel exposed, anxious, and judged. That’s the core lesson. He’s not selling law. He’s selling psychological relief. Now, what can we learn for sales and outreach? 1. Speak to the internal truth, not the public story Most buyers won’t admit their real situation out loud. Founders won’t say: “I’m scared our pipeline is dying.” They’ll say: “We’re just exploring options.” Effective sales messaging speaks to what they feel, not what they say. 2. Position as defense, not offense This message doesn’t attack. It reassures. In outreach: • Don’t accuse prospects of doing things wrong • Don’t imply incompetence Instead: “You’re not failing. The environment changed.” That lowers resistance instantly. 3. Clarity beats comfort Is this message ethically perfect? Debatable. Is it memorable and relevant to the buyer? Absolutely. Most sales messages fail because they try to be: • Polite • Generic • Safe Strong positioning risks discomfort to gain relevance. 4. Targeting matters more than approval The billboard isn’t meant to be liked by everyone. It’s meant to be noticed by the right few. Great outreach works the same way: If everyone agrees with your message, no one feels compelled to act. The takeaway Sales messaging should: • Reflect the buyer’s real fear or pressure • Remove shame, not add it • Be specific enough to exclude the wrong audience You don’t win deals by sounding ethical to everyone. You win deals by being relevant to someone who already needs help. That’s the uncomfortable truth behind effective sales.

Your campaigns are burning cash but not converting. The problem isn't your ad spend or targeting. Here's what's actually killing your performance... Most Series A founders blame low conversion on budget or channels. But I've seen the real culprit in dozens of active funnels. Your messaging is broken. Here are the 5 errors I find repeatedly: 1. Feature-first headlines that confuse prospects Your landing page leads with what you built, not what customers get. Prospects can't connect your features to their actual problems. 2. Generic pain points that don't hit home You're addressing surface-level frustrations instead of urgent business needs. Real buyers need specific outcomes, not vague improvements. 3. Competitor-copying that makes you invisible Your messaging sounds exactly like everyone else in your space. Prospects can't tell why they should choose you over alternatives. 4. Technical jargon that loses decision-makers You're speaking to engineers when the buyer is a VP or director. The person with budget doesn't understand your value proposition. 5. Weak calls-to-action that don't drive urgency Your CTAs ask for meetings without explaining immediate value. Prospects need a compelling reason to act now, not someday. I just helped a Series A founder fix these exact issues. Before: 2.1% landing page conversion, 45-day sales cycles. After: 8.7% conversion, 22-day average close time. Same traffic. Same product. Different messaging. The fix isn't more ad spend or better targeting. It's messaging that connects your solution to urgent buyer needs. Stop throwing money at broken funnels. Your messaging determines whether prospects convert or click away. If your campaigns are spending but not converting, send me a DM. I'll audit your funnel and show you exactly what's killing performance. ___________________________ 👋 I’m Marina Kogan 🌊 I help founders position tech products as must-have solutions.

It’s 2026. And most sales messages still sound like they were written for 2018: You open LinkedIn.  You see the same pattern again and again. Someone mentions your company. Compliments your role. Drops a line about “helping teams like yours.” You already know what’s coming and you don’t reply. Not because they’re irrelevant. But because nothing they said connects to what you’re actually dealing with today. People don’t respond to ideas. They respond to pressure they’re already under. Before I send any outbound message, I slow down and ask myself one thing: What is this person stressed about right now? If they’ve hired new reps recently, their real headache isn’t tools. It’s how long those reps will take to perform. If their pipeline has gone quiet, the issue isn’t more leads. It’s that deals aren’t converting. If the company is growing fast, the pain isn’t ambition. It’s systems starting to break. That’s where the message starts. Not with my product. Not with a pitch. If your outbound doesn’t speak to a problem they’re already feeling, it’s not ignored because it’s bad, it’s ignored because it’s unnecessary.

98% of sales emails fail. And it’s not because cold outreach is dead. It’s because most of it is lazy. I’ve been on the receiving end of thousands of sales emails. I can read the first sentence and gauge whether or not I should read on. Im not trying to be rude. Im trying to protect my time so I can also do my job. So Ive learned to judge a solicitation in seconds. What am I looking for? Does this person understand my world and want to add value or are they just trying to get something? Here’s what guarantees no response. Sounds basic but unfortunately its not: - Misspelling my name or company (this still happens way too often) - Writing a long, self-indulgent novel - Leading with who you are - The small (and sometimes not so small) tells that its a copy and paste solicitation. Think name in one font color and body of the email in another. The emails that get my attention do a few things differently: - They demonstrate real understanding of my business or network - They reference specific operational realities, not generic “solutions” - They show HOW value is created, not just that it exists - They make it clear the outreach was crafted specifically to me. Cold outreach isn’t dead. The bar has just been set incredibly low and the results have followed.

🚨 HAPPY MONDAY SALES PROS 🚨 This one is bad. Let’s break this down, one cringe-worthy line at a time. 👉 First line (spoiler alert - It's only one line) "I assist businesses in the Milledgeville area secure operating capital with no hassle and no collateral within 24-48 hours - could you use some funding?" Oh, where do I start? 𝗧𝗵𝗲 𝗽𝗲𝗿𝘀𝗼𝗻𝗮𝗹𝗶𝘇𝗮𝘁𝗶𝗼𝗻 𝘁𝗿𝗮𝗽: You mention Milledgeville, a town with fewer than 17,000 people. Sure, that’s technically my corporate address, but my business is mostly remote. I highly doubt you’re hanging out in Milledgeville helping the "local community." Tell me this was a mail merge with one variable, without telling me it was a mail merge. 𝗭𝗲𝗿𝗼 𝗰𝗿𝗲𝗱𝗶𝗯𝗶𝗹𝗶𝘁𝘆: The email gives me nothing to work with about who you are, what company you represent, or why I should trust you. Saying you assist businesses doesn’t make it true...it makes it vague. 𝗣𝗿𝗲𝗱𝗮𝘁𝗼𝗿𝘆 𝘃𝗶𝗯𝗲𝘀: “No hassle, no collateral loans in 24-48 hours” screams high-interest rates, shady terms, and desperation. If your business model depends on people in a financial pinch, it’s probably not something worth bragging about. 𝗧𝗼𝗼 𝘀𝗵𝗼𝗿𝘁 𝘁𝗼 𝗯𝗲 𝗲𝗳𝗳𝗲𝗰𝘁𝗶𝘃𝗲: I love a concise email, but this isn’t short and sweet, it’s short and sketchy. No context, no reason to trust you, no effort to connect beyond a name and city you pulled from a database. 𝗧𝗵𝗲 𝘁𝗮𝗸𝗲𝗮𝘄𝗮𝘆: Desperation might make this email work for some, but that doesn’t make it good. If you’re reaching out to small businesses, build trust first. Tell us who you are, why you’re emailing, and how you’re different from the hundreds of other emails just like this one. Until then, this is getting filed under 🚮. #SalesFail #Sales #DoBetter

This cold email landed straight in the trash, despite being from an "AI SDR platform." Here's exactly why it failed: 1. Terrible intro personalization. "NAME - saw you went to Miami U. How was it?" This is lazy if it's your only layer of personalization. If you're going to personalize, do it right. The prospect knows immediately this is automated - and poorly done at that. Even basic Clay enrichment would have prevented this embarrassing mistake. 2. Too obvious of a pain point. "Do you ever get tired of manually researching prospects...?" This reads like every other cold email in their inbox. Prospects are numb to these generic pain points. You need to be more specific and tie it to their actual business challenges. Example, in this case: "I know how hard it is to find perfect fit accounts based on your existing clientele" 3. Over-reliance on "we" language. Every line is "we started," "we're an," "we're trusted." This is a classic mistake - focusing on yourself instead of the prospect. Your cold emails should be about THEM, not you. 4. Extremely weak social proof. "We're trusted by tons of companies." What companies? What results? This vague claim adds zero credibility. Name specific companies in their industry or share concrete metrics from case studies that matter to them. 5. Hard CTA with no value established. Jumping straight to "free demo next Tuesday" without establishing any real value is why this email failed. Always use a soft CTA that offers value first. Remember: Even AI tools need proper configuration. Poorly executed automation is worse than no automation at all. What's the worst cold email you've received lately?