Sales Email Strategies for Mid-Level Managers

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.

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.

You find a path in to a cross-functional exec leader, they give you a meeting + intel, and tell you to email the leaders responsible for what you sell while they put in a good word. But...those leaders never reply to you. What's the play? Status Quo: An email to the OG leader "Hey, we haven't heard from X, can you nudge them for us? ^^Do this and you're now a pest + they'll regret offering the help. You now become a seller vs. a partner The Edit: First, your play should have been a clear subject line email "Referred by Name Of OG + MQL Conversion Discussion (<--or whatever you do), and a few emails that are value-driven (challenge you solve, getting around their hidden/forthcoming objection, why time with you would be well spent). Bonus: be smart about timing - email one on Thu/Fri, email two on Sat/Sun Bonus: connect with each person on LI with a message that makes it clear who you are and that you've sent them a few emails Second, if all else fails, your email back to the OG leader is this: "Hi XYZ, Wanted to quickly close the loop on our conversation. We reached out to X and X a few times, and connected on LI as well, but haven't heard back. Timing might be off, but wanted to simply say thank you for the time and intel - I'm hopeful we can get their attention down the road." This simple change in language not only shows you as someone who closes the loop on referrals, etc. but might prompt the OG to Slack that team and say, "Hey, did you guys get these notes, think it's worth a chat..." without you even having to ask. #samsales

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

Your prospects don’t need another “Hope you’re doing well” in their inbox. And they definitely don’t need another “Just following up…” If your outreach sounds like everyone else’s, it gets ignored. Every salesperson is saying the same thing. Every inbox is flooded with weak, low-effort messages. If you want a response, you need to stand out. Here’s what you should STOP saying: "I’d love to connect!" → No one connects for the sake of connecting. "Are you the right person for this?" → Lazy research kills deals. "Let me know if you’re interested." → Your job is to create interest, not wait for it. Instead, say something worth replying to. Open with relevance: “I saw your post on [topic], and…” Make it about them: “Curious—how are you handling [pain point]?” Challenge their thinking: “Why are you doing [X] this way, when you could do [Y] instead?” Provide value upfront: “We found [insight] works best for [pain point]. Thought you’d find it useful.” The best messages feel natural. They read like something you’d send to a colleague. No fluff.  No filler.  No corporate nonsense. Fix your outreach, and you’ll fix your response rates. Share this with your team if they’re still sending bad messages.

STOP following up with your deals like this: 🚫 Any thoughts? 🚫 Just checking in 🚫 Did you see my text? 🚫 Did you see my email? 🚫 Did you see my proposal? 🚫 Did you chat to your boss? 🚫 Following up on my last email 🚫 Bumping this to the top of your inbox They're lazy and add 0 value for the recipient. Here are 10 alternatives: 1. You mentioned X is a challenge so thought this article would be helpful 2. As Y metric is a priority, this calculator may be useful for you 3. You said your colleague is struggling with Z, so this video may help them 4. As you're a fan of (music/sport/hobby), thought you'd like this 5. You mentioned your legal team wants D, so this may be useful for them 6. You said your CFO is interested in X metric, so they may like this case study 7. As you're hiring Z role, here's the LinkedIn profile of a friend of mine I'd be happy to intro you to 8. Here's a post I wrote related to X challenge you said you "hate"! 9. You mentioned your colleague will have Z objection, so this may be useful to share with them 10. As you're looking to solve Z, this cool software that may help with that What else would you add as number 11? #b2bsales #salestraining #salesmanagement

The inbox is a battlefield. Your email’s enemy? The ‘Delete’ button. Between promotions, spam, and auto-blasted sales pitches, your email has seconds—seconds—to stand out and survive. So how do you write an email that doesn’t get sent to the trash right away? You make it personal and valuable. Here are 5 battle-tested tips to craft personalized, high-converting outreach emails: 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲𝗶𝗿 𝘀𝘁𝗼𝗿𝘆, 𝗻𝗼𝘁 𝘆𝗼𝘂𝗿𝘀. Ditch the “Hi, my name is…” opener. Show them you’ve done your homework. → “I saw your recent post about [specific topic]—your perspective on [insight] really stood out.” Lead with them, and they’ll be more inclined to care about you. 𝗕𝗲 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝗮𝗯𝗼𝘂𝘁 𝘁𝗵𝗲 𝘃𝗮𝗹𝘂𝗲. Generic promises like “We’ll save you time and money” won’t cut it. 𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝘁𝗵𝗲𝗶𝗿 𝘂𝗻𝗶𝗾𝘂𝗲 𝗻𝗲𝗲𝗱𝘀: → “I noticed [pain point]. We helped [similar company] achieve [specific result]. Here’s how we can help you too.” 𝗞𝗲𝗲𝗽 𝗶𝘁 𝘀𝗵𝗼𝗿𝘁 𝗮𝗻𝗱 𝘀𝗸𝗶𝗺𝗺𝗮𝗯𝗹𝗲. Your email isn’t a novel. Busy people don’t have time to read paragraphs. → Use short sentences. → Break up text. → End with a clear ask (no more than one action). 𝗦𝗼𝘂𝗻𝗱 𝗵𝘂𝗺𝗮𝗻—𝗱𝗶𝘁𝗰𝗵 𝘁𝗵𝗲 𝗿𝗼𝗯𝗼𝘁 𝘁𝗼𝗻𝗲. If it reads like a template, it is a template. Write how you speak. 𝗕𝗲 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝗮𝗹 𝗮𝗻𝗱 𝗮𝗽𝗽𝗿𝗼𝗮𝗰𝗵𝗮𝗯𝗹𝗲: → “Hope this finds you well—saw your team’s new project, and I’m seriously impressed.” Make the ask easy to say “yes” to. Don’t overwhelm them with a big ask. 𝗦𝘁𝗮𝗿𝘁 𝘀𝗶𝗺𝗽𝗹𝗲: → “Do you have 15 minutes next week to explore this? I’ll make it worth your time.” Remember this: A great email isn’t about selling—it’s about starting a conversation. Show you understand their world, add value, and respect their time. --- Follow Michael Cleary 🏳️🌈 for more tips like this. ♻️ Share with someone who needs help with their emails #sales #emails #marketing