Think Cold Email Doesn’t Work? Smart Companies Know Better

Let’s be honest: the term cold email makes a lot of people flinch. It sounds pushy, impersonal, and a little 2008. Some execs shy away from it completely… and yet those same leaders will often forward along the occasional cold email that hits just right. (We see the irony too.)

The truth? Cold email works when it’s done with thought and timing.

The Case for Cold Email

It’s about timing and targeting. Yes, cold email is “cold,” but so are job applications, sales calls, and investor pitches. The key is relevance. If the right message lands in someone’s inbox at the exact time they’re evaluating a solution, it works. That’s why leaders sometimes forward along good ones—they hit a nerve. And we’ve seen it firsthand: two of our own vendor relationships at Wheels Up started this way. They caught us at the exact right time.

The risk for reputation damage is very low. Nobody’s waiting breathlessly for your brand to hit their inbox. If it’s not relevant, it’s gone in two clicks. Most people delete, forget, and move on. Open rates average 20–40%, response rates hover at 1–5%. A Woodpecker study of 20M cold emails confirmed what we all know: the bad ones vanish into the ether. The upside of hitting the right person at the right time outweighs the microscopic risk that someone rolls their eyes before hitting delete.

It scales better than waiting. Warm intros and inbound leads are valuable, but they happen on their own timeline. Cold outreach gives you control back. With the right segmented list, the right message, and real personalization, you can reach the right people before a referral ever materializes. Without those ingredients, it’s noise. With them, it’s opportunity.

Done well, it’s not “spam.”

Spam is sloppy, irrelevant, and mass-blasted. Cold outreach done right looks like thoughtful networking. It’s built on a targeted list, written with care, and specific enough that the person on the other end feels like it was meant for them. Think of it like sending your resume to a company you actually want to work for: unsolicited, sure, but intentional. And when the fit is right, it doesn’t feel cold at all.

What the Data Shows

The Woodpecker analysis of 20M cold emails surfaced a few patterns worth noting:

• Personalization matters. Response rates were 17% with advanced personalization versus just 7% without it.

• List quality beats list size. Smaller, more targeted campaigns generated far higher reply rates than blasting 1,000+ contacts.

• Follow-ups triple your chances. Sequences with 4–7 emails saw a 27% reply rate, compared to 9% with only 1–3 emails.
  

It’s not about how many emails you send. It’s about sending the right message, to the right person, at the right time—and following through.

The Thought of Cold Email Still Making You Cringe?

Probably because when you think of cold email, you're picturing those emails. The snarky, sarcastic, trying-too-hard-to-be-funny ones. You know the type: “What if I could get you 50 leads in 50 minutes?” Or the forced-casual ones that scream mass blast. They’re not clever—they’re desperate. And they don’t work.

But cold email doesn’t have to be gimmicky to get attention.

When it’s built on smart targeting, clear messaging, and real intent, it feels like a conversation worth having. The kind of message that earns a second look. The kind that gets forwarded with, “Might be worth chatting with them.”

Because the best cold emails don’t feel cold at all. They’re relevant. Specific. Thoughtful. They meet people where they are and offer something useful and without the buzzwords, fake familiarity, or all-caps subject lines.

And yes, that type of cold email still works.

How Wheels Up Builds Cold Email Programs That Work

At Wheels Up, we’ve built cold email programs that actually deliver results, because they start with the right foundation:

• Message and positioning (optional add-on, but essential if you don’t have it locked). Cold email outreach only works if your story is clear. Many clients start with our messaging framework before we ever write a single subject line.

• Great content that earns attention and drives replies.

• Smart segmenting. This is where most cold email campaigns fail. A narrow, well-defined, human-checked list beats a giant, scraped database every time. We combine human judgment with AI precision so outreach feels targeted, not templated.

• Inbox warmup and deliverability to keep campaigns landing where they should, not in spam.

• Follow-up sequencing that’s persistent without being pushy, designed to lift reply rates and keep conversations alive.
  

The program is built to scale, but if your story isn’t sharp, we’ll tell you. Messaging and positioning is a separate service, but in our experience, it’s the difference between sending cold emails and starting real conversations. Paired with surgical audience targeting, it’s the difference between relevant information and noise.

Ready to scale your outbound program? Wheels Up Collective makes cold email work. 

FAQs About Cold Email Outreach

1. What’s the average response rate for cold email outreach? Industry benchmarks show 1–5%. With advanced personalization and a targeted list, campaigns can climb as high as 15–20%.

2. How many follow-ups should a cold email strategy include? Sequences with 4–7 thoughtful emails get nearly triple the replies of shorter sequences. The key is spacing them out and adding value each time.

3. Does cold email outreach hurt brand reputation? Not when it’s done right. Most people delete what’s irrelevant and move on. Relevance is what separates a quick delete from a reply.

4. How important is personalization in cold email campaigns? Critical. Woodpecker’s data shows reply rates more than double (17% vs. 7%) when emails use advanced personalization beyond a name field.

5. What makes a cold email strategy effective? The right message, sent to the right person, at the right time—and followed up with persistence. That’s what turns “cold” into a real conversation.