Cold Email That Actually Gets Responses

In my last article, Developing Your Prospecting Strategy, I walked through how to build a systematic approach to finding prospects within your ICP. You learned to identify your target personas, map your outreach process, and create repeatable systems that turn prospecting into pipeline generation.

Now it’s time to craft the messages that actually get responses.

This article is Part #4 of my Founder Led Sales Series, where I’ll break down the strategic framework behind effective cold email campaigns. For the complete overview of the series, see: The Startup Founder’s Guide to Early-Stage Revenue Success.

Most Founders struggle with cold email because they approach it backwards. They start writing before they understand their prospect’s world. They throw features at strangers. They send novels when they should send postcards.

Cold email isn’t about your product, it’s about interrupting someone’s busy day with something so relevant they can’t ignore it. Here’s a systematic approach to get there.

Pre-Campaign Planning Process

As you plan a cold outreach campaign, constantly ask yourself: “Why would this person respond to my email?”

They’re busy, they don’t know you, and they get dozens of sales emails daily.

Before you draft a single line, work through these four areas to ensure you can answer that question confidently:

1. Campaign Target

This builds directly on your ICP work from earlier articles. You’re not guessing who to target, you’re executing against your defined ideal customer profile.

Take your ICP and get specific about which segment you’ll focus on for this campaign:

Industry & Segment: Not “healthcare” but “independent urgent care clinics with 2-5 locations.” Not “manufacturing” but “mid-market food processing companies with FDA compliance requirements.”

Company Size: Revenue range, employee count, and other qualifying characteristics from your ICP analysis.

Geography: Where these companies operate, considering regulatory environment and your ability to serve them.

Target Personas: The specific roles you identified in your prospecting strategy who own the problem and have authority to solve it.

This precision enables everything that follows from here. Generic targeting produces generic messaging. Specific targeting enables the emotional resonance that drives responses.

2. Features & Benefits

Don’t list every feature your product has. Instead, identify which features matter to your specific target segment.

Ask yourself:

• What does this specific industry struggle with that we solve?
• Which of our features directly address their biggest pain points?
• What benefits matter most to someone in their role?

3. Pain & Excitement 

Features tell, but emotions sell. Your prospects don’t buy products, they buy outcomes and feelings.

When you lead with features (“Our platform has advanced analytics and automated workflows”), you’re forcing prospects into a thinking state. They start analyzing, comparing, and finding reasons to delay or say no.

But when you tap into pain and excitement, you trigger their feeling state which is when people take action.

People buy with emotion and justify with logic. Your job is to anchor them in the emotional buying state first, then give them enough rational justification to feel good about their decision.

Connect features to emotional outcomes:

• Feature: “Push notifications”
• Emotional outcome: “Re-activate customers who stopped engaging and generate new revenue from your existing user base”
• Feature: “60-day deployment”
• Emotional outcome: “While your competitors spend months in development, you’ll launch first and capture market share”

4. Prospect Blockers

Why would someone ignore your email or say no? Common blockers include:

• Cost assumptions: They assume it’s too expensive without knowing the price
• “Too good to be true” skepticism: Your claims sound unrealistic
• Past failures: They’ve tried something similar before and it didn’t work
• Regulatory concerns: Especially in industries like finance or gaming

Address these preemptively in your messaging.

Cold Email Campaign Planner

Below is a real example of pre-campaign planning that we completed before kicking off a cold outreach campaign targeting casinos. This strategic framework generated meetings in its first week because we understood the prospect’s world before interrupting it.

Download the blank Cold Email Campaign Planner to map out your own campaign strategy before you start writing.

The 5-Step Email Framework

Below is a real example of the first cold outbound email of an email sequence to casinos. This email generated responses because it followed a specific psychological framework rather than generic templates. Here’s the step-by-step breakdown of how this initial outreach actually works  and how you can apply the same structure to any industry for your first contact with prospects.

Core Principles of Cold Outreach

Cold outreach works best when you understand these fundamental principles of human psychology. I’ve shown how each one shaped the casino campaign (🎲) with real examples below.

1. Talk in Their Interests, Not Yours

• Frame everything around their pain and excitement (increased revenue, competitor risk, compliance delays), not your product offering.
  • FOMO: “Your competitors have this, where’s yours?”
  • Excitement: New revenue opportunities or competitive advantages
  • Pain: Current problems that keep them up at night or create daily frustration
  • Status: Being recognized as an innovator in their industry
• Address both business and personal motivations. Personal appeals are often more powerful. Everyone wants to be the hero of their own story. People care about their career, their reputation, and their next promotion.
• Why this works: When you lead with their interests, you bypass their analytical filters and natural sales resistance. Instead of thinking “Is this relevant to me?” they’re immediately engaged because you’re addressing their world. This triggers their emotional state where decisions happen.
• 🎲 Example: “I searched the App Store… your players (and I) couldn’t find you!” centers on their customer experience problem, not our app development services. This frames the issue around player engagement and competitive positioning, not what we want to sell.
  

2. The Response Test

• Before sending any email, put yourself in the prospect’s shoes. Ask yourself, “Would I respond to this email?” Be honest. If the answer is no, rewrite it.
• Why this works: Most Founders write from a seller’s perspective, not a buyer’s. This forces you to shift into their emotional state and evaluate whether your message creates genuine interest or feels like another sales pitch.
• 🎲 Example: It passes the Response Test because every part of it is buyer-focused and hard to dismiss. The subject line highlights a specific gap (no app), the screenshot makes the problem undeniable, and the CTA is low-friction. A casino exec would reply because the email shows a risk and opportunity that they can’t ignore.
  

3. Cultivate Curiosity 

• Your objective at this stage is to get a response and to book a Discovery Call, not to get them to make a buying decision. You want them to say yes to finding out more, not yes to buying your product.
• Most Founders share too much information upfront such as detailed feature lists, comprehensive case studies, pricing breakdowns. This creates three problems:
  • Information overload causes people to ignore the email
  • Unaddressed objections arise instead of booking Discovery Calls where concerns can be handled
  • Incomplete context leads to premature “no” decisions
• Provide just enough information to spark interest while leaving key questions unanswered. Create information gaps that can only be filled through conversation.
• Why this works: Curiosity is an emotional state that demands resolution. When you create information gaps rather than providing complete explanations, you trigger their desire to learn more. Partial information with compelling hints leads to “tell me more.” rather than “no” or unresponsiveness.
• 🎲 Example: Teases the solution (“The casinos we work with use our apps to drive retention, promotions, and VIP engagement”) without explaining how the apps work, implementation, or pricing. This creates curiosity while leaving key questions that require a conversation to answer.
  

4. Be Polarizing

• Safe, generic emails get ignored. You need to be willing to risk a strong “no” to get a strong “yes.”
• Why this works: Polarizing messages force an emotional reaction, either positive or negative. Neutral messages get neutral responses (none). You have to risk “no” to get to “yes”. It’s also better to uncover disinterest quickly and focus your time on qualified prospects rather than chasing unresponsive people who were never going to buy.
• 🎲 Example: The subject line “It’s 2025 – Where’s the Walker’s Bluff Casino App?” and first sentence are provocative. It forces the issue and risks offending. It immediately separates interested prospects from those who aren’t ready for digital transformation, saving time on both sides.
  

5. Use Multiple Touchpoints Strategically

• Each touchpoint highlights a different pain or angle (compliance risk, revenue upside, competitive threat). You’re creating a story with your touchpoints.
• Why this works: People often need multiple exposures to new ideas before acting. Each touchpoint from a different emotional angle increases the chances one will resonate. You’re building familiarity while maintaining relevance.
• 🎲 Example: 
  • Email #1 opens with the gap and risk (no app) to create urgency and curiosity.
  • Email #2 shifts to excitement and opportunity with a limited-time offer to amplify urgency. 
  • Email #3 shows a GIF of a real casino app in action, making the solution tangible and getting them excited about what’s possible.

6. Make Saying “Yes” or “No” Easy

• End with clear, low-friction calls to action like: “Interested in finding out more?” Avoid complex requests or multiple options that require analysis.
• Why this works: Decision fatigue kills responses. Simple binary choices keep prospects in their feeling state rather than forcing them into analytical mode where they’ll find reasons to delay or decline.
• 🎲 Example: It ends with a simple question: “Interested in boosting your revenue?” that can be answered with an easy “yes” or “no”. 

Tactical Email Writing Tips

Structure

• Keep It Short
  • You have 3 seconds to earn attention. Assume your subject and the first line decides everything.
  • Most strong cold emails are 50–75 words.

“I didn’t have time to write a short letter, so I wrote a long one instead.”
— Mark Twain

• Pick One Topic Per Email
  • Don’t try to introduce yourself, pitch your product, share case studies, and ask for a meeting in one email. Choose one focus per email. 
  • Example:
    • Email 1: Point out the gap (“Where’s your app?”)
    • Email 2: Present the solution (pricing and timeline)
    • Email 3: Address objections (social proof, urgency)
    • Email 4: Final attempt (breakup email)
• End with a Succinct Question
  • Make it the last line they read.
  • Example: “Are you available this week for a quick conversation?”

Content

• Start With Them, Not You 
  • Avoid talking about yourself first. Lead with their world, their challenges, their opportunities. Save the company introduction for later in the sequence.
  • Example (don’t): “We’re an innovative platform that helps businesses…” 
  • Example (do): “Most casinos struggle to get apps published due to regulatory requirements…”
• Meaningful Personalization
  • Everyone else is sending generic templates. Personalize meaningfully by referencing something specific about their company, include a relevant screenshot, or something unique like wordplay with their company name.
• One Question per Email
  • If you ask two, neither gets answered.
• Enhance with Visuals 
  • Use screenshots, GIFs, or short video clips to break through the noise.

What to Avoid

• Sending Meeting Links
  • It’s counterintuitive, but in cold outreach prospects are more likely to reply to a question about availability than to click your calendar link.
  • “Do you have availability this week?” gets responses, while calendar links feel too presumptuous and get ignored.
  • Note: it’s fine (and helpful) to use meeting links once you have a relationship with someone.
• Ask and Answer Questions
  • Don’t ask a question then immediately provide the answer or justification.
  • Example: “Are you available on Wednesday? At the very least, you’ll get insight into how other firms use apps to streamline operations….”
• Insincere Asks/Offers
  • Don’t promise educational content when you’re planning a sales call. Be honest about the call’s purpose and create accurate expectations.
  • Example: “Are you available for a quick call to see how others are using apps to improve client retention?” when what you’re really booking is a Discovery Call.

The Bottom Line

Cold email works when you make it about them, not you. Do the research upfront, understand their world, and craft messages that interrupt their day with something genuinely relevant.

Most Founders fail because they’re trying to get people to buy instead of trying to get people to respond. Start smaller. Focus on earning a reply and the sales conversation will follow.