Do you do cold emailing right?


You write a “perfect” cold email, hit send… and get silence. So you push harder: longer copy, bigger claims, a calendar link. Still nothing.

The problem isn’t that email “doesn’t work”, it’s that you aimed at the wrong target. The goal of a cold email is not to pitch, demo, or close. The goal is a reply that starts a buying conversation.

Your subject lines, body, and CTAs should all be focussed on just getting a response.

The mindset: replies over meetings

Don’t aim for: ❌ value dump ❌ demo request ❌ “15–30 mins on your calendar?”

Do aim for: ✅ A short, relevant note that earns a quick “yes,” “no,” or “tell me more.”

Personalization + relevance (by lead quality)

Not every prospect deserves the same effort. Tier your list and match your personalization.

Tier Who Effort Personalization focus
1 High-value lead, decision-makers 1:1 research Mutual context, interests, timely initiatives, buying intent
2 Good-fit lead Semi-automated Industry pain, recent triggers (funding, hiring, tech, location)
3 Everyone else Mostly automated First name, company, role-based pains

lead pyramid
Figure: Prioritize effort. More 1:1 at the top, more segmentation at the bottom.

Source: Apollo.io

Anatomy of a cold email

  1. Subject: Craft a subject line that interrupts their inbox autopilot. For top-tier prospects, use hyper-personalization with details so specific only they would understand, creating a powerful curiosity gap. For broader outreach, you can use personalization tokens like company name to increase open rates
  2. Opener: The first line must prove you've done your homework. Start with a specific observation about them or their company to show this isn't a generic "spray and pray" email, but a message with a genuine human element behind it. “Show Me You Know Me®”.
  3. Value: Immediately connect their problem to your specific benefit (no feature dump) Avoid a generic list of your product's features and instead focus on the tangible, personalized value you can provide them.
  4. CTA: One soft, easy question (no calendar yet). The goal is to make replying feel effortless. Focus on starting a conversation.
  5. Length: Keep emails concise, ideally between 50 and 125 words, as this range sees the highest response rates. T1 (first email) can be longer if it’s truly personal. Allocate your effort accordingly: spend the most time on hyper-personalized emails for your most valuable prospects and use smart automation with some personalization for lower-tier leads.

SUBJECT: Exploring Synergies with Coupons2Go

Hi [Contact Name],

OPENER: My name is Josh and I am with Coupons2Go, an industry-leading, award-winning digital couponing platform that has been providing innovative solutions since 2015.

We are reaching out to key players in the travel center space to introduce our comprehensive suite of services.

VALUE: Our proprietary platform leverages cutting-edge technology, including AI-driven analytics and machine learning algorithms, to optimize customer engagement and maximize ROI. Our key features include a customizable user interface, robust back-end reporting, seamless POS integration, and a nationwide network of participating brands. We offer multiple service tiers, from our basic package to our enterprise-level solution, all designed to enhance brand loyalty and drive incremental revenue.

CTA: I would like to schedule a 30-minute demonstration of our platform's capabilities with you and your team. Please let me know what time works best for you next week.

Best regards, Josh

Bad Example - Long, generic, self-focused “brochure email” gets skimmed and ignored

SUBJECT: question about your loyalty program

Hi Jim,

OPENER: Just saw on LinkedIn that your team at Pilot/Flying J is hiring for a new loyalty marketing manager — congrats on the growth.

VALUE: Usually when companies expand that team, it means they're struggling to keep their massive customer base engaged beyond the point of sale. It's a huge challenge to make each of your 1.5 million daily visitors feel like an individual.

We recently helped a similar multi-location brand, [Lesser Competitor Name], boost their repeat customer visits by 15% in one quarter by implementing a targeted digital coupon strategy.

CTA: Do you have 15 minutes next week to chat about how you're approaching this? Might be able to share a few ideas that have worked for others.

Cheers,

Josh

Good Example - Short, segmented template: pain → proof → small ask

More examples

Tier 1 (hyper-personalized 1:1)

Subject: Le Dip cheeseburger + {{Your Company}}

Hi Sam, Your post on LinkedIn about the new Le Dip burger made me smile. I noticed you’re hiring 3 CSMs while launching in EU. Teams I help cut onboarding time ~30% by unifying playbooks and usage data.

Worth a quick reply if “faster ramp before Q4” is on your list? If not, I’ll leave you in peace.

Figure: Personal detail + timely company priority + soft, single-question CTA

Tier 2/3 (short, segmented)

Subject: For {{Company}}’s printing leads

Hi {{FirstName}}, Printing services often lose local search traffic to aggregators. We’ve helped peers lift inbound quotes 10–20% by fixing GMB + service pages.

Open to a quick reply if local visibility is a 2025 focus for you?

Figure: Industry-specific pain + outcome + 1 easy question

The 3-email sequence that works

1) The personalized introduction

Use one of the templates above. End with a single question.

2) The follow-up (reply in-thread)

Keep it to one line. No “just checking in.”

Hi {{FirstName}} — curious if “faster ramp before Q4” is on the list?

Figure: Short, direct restatement of the original question

3) The breakup (pattern interruption + give an out)

Re-state value → playful P.S. → permission to say “no.”

If speeding up onboarding isn’t a priority this quarter, happy to close the loop. P.S. If you’re already buried in onboarding fires, just reply with “no” and I’ll vanish faster than free snacks. No hard feelings. 🙂

Figure: ✅ Pattern interruption in the P.S. earns smiles and replies

Keep it human (AI is co-pilot, not autopilot)

AI can help you brainstorm variants, but raw AI copy reads… like AI. Use it to draft, then humanize: Add one real detail, cut flab, end with a question, the crucial step is to infuse them with genuine, human details.


Do’s and Don’ts

A practical framework for putting this philosophy into action:

✅ Do ❌ Don't
Research First: Always lead with insight, especially for high-value (Tier 1) prospects. Paste Your Pitch: An email is not the place for your full sales deck.
Focus on Them: Frame your message around their problem and the specific outcome you can help them achieve. Ask for Too Much: A 30-minute meeting is a big ask from a stranger. Start smaller.
Use a Soft CTA: Ask one simple question that is easy to answer. Create Walls of Text: Avoid long paragraphs and multiple, confusing calls-to-action.
Test and Learn: Continuously A/B test your subject lines, opening hooks, and questions to see what resonates. Over-Automate: Don't send the same generic message to everyone. Segment your lists properly.
Go Multi-Channel: Combine your email efforts with calls, LinkedIn messages, or video for a significant lift in engagement. Forget the Final Check: Always ask yourself, "Would I genuinely reply to this email?"

Quick Pre-Send Checklist

Before you hit send, run through these final checks:

  • Subject Line: Is it specific enough that it would likely only make sense to the recipient?
  • Conciseness: Is the email under 100 words (especially for Tier 2/3) and focused on a single problem and outcome?
  • ROI Hook: Is there a tangible cost saving, benefit, or other measurable ‘hook’ e.g. We’ve reduced bug fix times on average by 30%
  • Call-to-Action: Is there only one soft question without a calendar link?
  • The Gut Check: Would you be comfortable receiving this email in your own inbox?

Louis Roa
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