I remember sitting in a studio apartment in South Philly in 2018, staring at a blinking cursor. It was 11:42 PM on a Tuesday. I was trying to email the CEO of Loomis—not the armored car company, but a mid-sized logistics firm I wanted to work for. I spent three hours drafting that email. I used words like “synergy,” “value-add,” and “strategic alignment.” I thought I sounded like a professional. I thought I sounded like a peer.
I sounded like a robot with a head injury. He never replied. Obviously.
The reality of the C-suite is that their inbox is a graveyard of good intentions. Most people think getting a response from a CEO is about being impressive. It isn’t. It’s about being brief, being human, and not smelling like a salesperson. If your email feels like it was generated by a marketing automation tool, it’s going to be deleted before the first sentence is finished. I’ve spent the last five years sending hundreds of these things—some for sales, some for networking, some just to ask a question—and I’ve realized that everything we’re taught about “professionalism” is actually a barrier.
The time I tried to be ‘professional’ and failed
That Loomis email was my low point. I remember the physical sensation of hitting ‘Send’ and then immediately noticing a typo in the second paragraph. I had written “I am confident I can help Loomis leverage…” and I’d spelled it “levreage.” I felt sick. I stayed up until 2 AM waiting for a reply that never came. The mistake wasn’t the typo, though. The mistake was the tone. I was trying to play a character of a “Business Person.”
CEOs don’t talk to “Business People.” They talk to people who can solve a specific problem or provide a specific insight in under thirty seconds. My old boss used to carry an old Blackberry way past its prime—this was 2016, mind you—and he’d delete anything that required him to scroll. If he had to move his thumb more than twice, you were dead. Anyway, that’s where I started learning the hard way. You have to write for the thumb, not the brain.
I eventually got a response from a different CEO—this time at a tech firm called Orizon—by doing the exact opposite. I sent a two-sentence email at 7:00 AM on a Saturday. It said: “Hey [Name], I saw your piece on supply chain fragmentation. I think your point about regional hubs is slightly off because of [Specific Reason]. Would love to send over the data I have on this if you’re interested.” He replied in four minutes. Brevity is the only thing they respect.
The data I collected while being unemployed
I’m a bit of a nerd for tracking things when I’m bored. In 2021, during a six-month gap between jobs, I ran a test. I sent 42 cold emails to executives at companies with over 500 employees. I tracked everything in a messy Google Sheet: time sent, subject line length, and whether I used a “hook.”
- Subject lines with 3 words or fewer: 31.4% response rate.
- Subject lines with 7+ words: 8.2% response rate.
- Emails sent on Saturday mornings: 45% response rate (I know people will disagree with this, but it works because the noise is lower).
- Emails that started with “I hope you’re well”: 0% response rate. Literally zero.
I might be wrong about the Saturday thing for every industry—maybe don’t try it with a high-stress trial lawyer—but for most tech and logistics execs, Saturday morning is when they actually clear their head. They’re sitting there with a coffee, looking for something interesting that isn’t a fire they have to put out. Subject lines are like a brief physical tap on the shoulder in a crowded room. If you tap too hard, they get annoyed. If you whisper, they don’t hear you. A subject line like “Question about [Project]” is a gentle tap. A subject line like “Synergistic opportunities for your Q4 growth” is a punch in the face.
Why I hate Superhuman and most ‘productivity’ advice
I refuse to use Superhuman, even though every “productivity influencer” on Twitter treats it like a religion. I hate it. I hate the “Sent via Superhuman” tag. It feels like a status flex for people who spend $30 a month just to feel like their time is more valuable than yours. It makes every email look like it was processed by a machine. When you’re emailing a CEO, you want the exact opposite. You want it to look like you wrote it on your phone while walking the dog.
The best emails look like they were written by a friend who is in a hurry but cares about you.
Most advice tells you to “personalize” by mentioning where they went to college or a recent LinkedIn post. That is garbage. It’s transparent. It’s like when a car salesman asks how your kids are doing. They don’t care about your kids; they want to sell you a Mazda. Instead of fake personalization, try radical relevance. Don’t tell them you liked their post. Tell them why their post changed how you think about your own work. Or better yet, tell them why you think they’re wrong about something minor. Executives are surrounded by yes-men. A polite, data-backed disagreement is a breath of fresh air. What I mean is—actually, let me put it differently. It’s about being a peer, not a fan.
The ‘No-Pressure’ close (and why it works)
This is the part where most people mess up. They end with: “Can we hop on a 15-minute discovery call next Tuesday at 2 PM?”
No. We cannot. I don’t know you. A 15-minute call is a 30-minute commitment once you factor in the mental overhead. It’s an ask for a favor. When you’re emailing someone significantly more successful than you, you shouldn’t start by asking for a favor. You should start by offering a gift or asking a low-friction question.
I’ve found that the most effective way to end an email to a C-suite exec is what I call the “Exit Ramp.” It looks like this: “No need to reply if this isn’t a priority right now, just wanted to put it on your radar.”
It sounds counter-intuitive. Why tell them not to reply? Because it removes the guilt. When an exec sees a long email with a big ask, they feel a micro-stressor. They think, “I have to deal with this person.” When they see a short note with an exit ramp, they feel in control. Ironically, giving them permission to ignore you makes them much more likely to engage. I also think people who use “Best,” as a sign-off are sociopaths. It’s so cold. Just use “Thanks,” or nothing at all.
I used to think I needed a fancy signature with my headshot and links to my portfolio. I was completely wrong. Now, my signature is just my name and my phone number. It looks human. It looks like I’m not trying to sell anything.
Maybe this is all just luck anyway
I’ll be honest: sometimes you can do everything right and still get nothing. I emailed the CEO of a major shoe brand (I won’t name them, but their logo is a swoosh) three times with what I thought was a brilliant insight into their digital returns process. Crickets. Total silence. Maybe he was on vacation. Maybe he thought I was a kook. Maybe he just didn’t like my name.
You can’t control the response, but you can control the “cringe factor” of your outreach. Stop using those templates from HubSpot or Salesloft. They are poison. They make you sound like every other person in their inbox. If you want to talk to the person at the top, you have to stop acting like you’re at the bottom.
Write it. Shorten it. Then delete the first paragraph. That’s the whole trick.
Do you think the era of the cold email is actually over, or are we just getting worse at talking to each other?