Best practices for C-level email engagement

Cold outreach to executives: a game most sellers lose and shouldn’t play with their current skill set. The way most play is poisoning the buyer landscape with run rate high velocity prospecting motions. There is SO MUCH OPPORTUNITY for sellers who learn to do it right. But here’s what you need to overcome first: Facts: Only 6.4% of cold emails to C-level execs get a reply - sellers are losing 93 out of 100 times. Why? 1. Copywriters fuel centralized demand gen teams with email sequences made for broad markets. Then mass distribute them across wide definitions of their ICP (corporate speak for spam). This “non-hyper-relevant” outreach does nothing but piss off customer executives, many of whom receive 400+ unsolicited emails per DAY. 2. Tens of thousands of sellers copy “top-performing templates” from LinkedIn gurus. They work… until they don’t. Executives sniff out when they've been sent email templates faster than savvy investors flee a crypto scam. Strike two. 3. Sellers will actually attempt a well thought-out email but then every follow-up is “did you get my email?”, “I’m still waiting for your reply…”, or some other needy, begging request to drive activity for the rep, not value for the executive. These motions are making you worse, not better. Each email template you borrow from anyone else delays when you actually learn how to think and how to write. If you want to start executive conversations consistently, master these 4 non-sexy skills: 1. Contextual Intelligence Deep account research isn’t about getting informed. You are investigating how to make business transformation in a room full of people who have been burned by noobies before. That means reading annual reports, earnings calls, exec interviews, and investor presentations. You’re not just looking for facts. You’re hunting for patterns—proof that your solution matters to them. That’s how you earn executive trust. 2. Multi-layered Personalization Mention their job title or recent funding…and you’ll get ghosted like everyone else. It’s not about flattering their ego. It’s about relevance. Real personalization means: - Tying your message to a specific initiative they own - Speaking their language - Aligning with their budget cycle - Giving them a clear POV on why this matters now That’s when a CFO, CIO or VP will pause and think, “This seller actually gets it.” 3. Point of View Development In enterprise, you’re not just up against other vendors. You’re competing with status quo, internal priorities, and budget battles. That’s why you did the research, to form a sharp, strategic point of view on how you can help: “What transformation could this company achieve with our solution—and why now?”. Make your POV concise (2–3 sentences), tied to business outcomes. Don’t lead with product features or vague ‘we help companies do X’ lines. If you’re an experienced seller looking to level up outbound in 2025, comment “Skills” and I’ll send the Forum Workshop invite for this Friday

When I was at Salesforce, I used this exact cold email framework to book meetings with CEOs, COOs, and CFOs at the biggest companies in the world. Now I coach 100s of reps to use it—and they’re landing meetings that most sellers only dream about. Most reps never get to sell to the C-suite. Not because they don’t work hard. But because they reach out with transactional garbage that looks like every other email in the inbox. Executives don’t want another seller. They want a partner who understands their business. Here’s the cold email formula that works: 1. Warm and personal Lead with a sincere compliment. “I saw your podcast on ___…” “I read your Forbes interview and was moved by…” Show them you did your homework. Not some AI-generated flattery—real human admiration. 2. Shared values or struggle Make it human. “I related deeply when you talked about overcoming ___. I’ve faced something similar.” Vulnerability isn’t weakness—it’s how you earn trust. 3. Research-backed insight Cite a 10-K, public statement, or article. “Based on your Q1 earnings call, I noticed you're focused on X.” Link to the source. Build credibility. 4. A sharp POV + direct linkage Don’t say, “We help companies like yours.” Say, “You’re trying to achieve X. Companies on that journey often hit Y. Here’s how we solve it.” Make the connection crystal clear. 5. Soft CTA, strong conviction No desperate energy. Just: “If this is a priority, would it make sense to connect?” You’re not begging. You’re offering value. If you want my exact cold email template (and to see 13 real email examples me and my clients used to book C-suite meetings) grab them here: https://lnkd.in/g84w_utx

If you're cold emailing or calling me – or any C-level executive – here’s what NOT to do. Don’t ask for a meeting with me. Executives are more overwhelmed and more ruthless with our time than ever. So if you’re trying to break in at the top, here’s the play that works today: ✅ Keep the ask simple. ✅ Show me you understand my business by personalizing your message.
 ✅ Ask me to connect you to the right person on my team. You don’t want me in that first meeting. You want me curious enough to forward your message with context to my CRO, CMO, or CIO and say, “Hey, this looks interesting. Can you take it?” When that happens - you’ll get a meeting with one of our top leaders. But if you ask me to take the meeting? 99% of the time, I won’t. Maybe I forward it - usually I hit delete. But if you’ve done a good job of personalizing your message - I’ll always be open to connecting you to the right person on my team. Your CTA to the CEO shouldn’t be a 30-minute demo. It should show me that you can solve a problem that I care a LOT about. So ask for that intro - and give me a reason to make it.

Here's how to book meetings with C-Level executives: 1. Identify the exec's key priorities (hint: check their LinkedIn posts) 2. Create a valuable resource addressing those priorities (report, case study, etc.) 3. Offer exclusive early access in your cold email Example: "[Name], saw your post about scaling customer success. We just compiled a report on how the top 1% of SaaS companies are reducing churn by 40%+. Want early access before we publish?" When the value is OBVIOUS... the prospect would be stupid not to reply. That reply gets your foot in the door. It gets the prospect interested in information that leads DIRECTLY to your offer. If you want high-value clients, you need to lead with value (not your pitch). What valuable resource could you create for your ideal clients? Note: This is a "sniper-rifle" approach that focuses on quality over quantity. But if you aren't willing to sweat a bit... the C-suite is not for you.