Sales emails fail for a reason. It’s not because email is dead. It’s not because people don’t respond anymore. It’s because most sales outreach is lazy, generic, and disconnected from what the customer actually needs.
The biggest mistake sales reps make?
They assume the customer has a problem. They assume the customer understands their value. They assume the customer even cares about what they’re offering. And that’s where everything falls apart.
So, let’s break this down. We’ll look at real-life sales emails, show where they went wrong, and—most importantly—show how understanding customer pains and gains can make all the difference.
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Why Most Sales Emails Miss the Mark
Sales reps often send emails based on what they want to sell, instead of what the customer actually needs.
The problem? Not every customer is in "pain."
A company may be struggling with inefficiencies (pain), or they may be thriving and looking to scale (gain). Your email has to reflect where they are. If you get that wrong, your outreach is DOA.
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Let’s see this in action with two real-world examples:
Example 1: Selling a CRM to a Customer Who Already Has One
Let’s take the Salesforce email outreach example we reviewed in our live session.
A rep sent an email to a HubSpot partner (bad move). But even if the recipient was just a HubSpot customer, the email still wouldn’t have worked. Here’s why:
What went wrong:
- Assumed the customer had problems with their CRM.
- No research on how they were actually using HubSpot.
- Jumped straight into a discount pitch.
How to fix it:
If you’re reaching out to a company already using a competing product, you need to change the angle based on research.
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Scenario 1: Pain-Based Messaging (Customer is Struggling with Their CRM)
Context: The company has HubSpot but is struggling with adoption—sales teams aren’t fully using the CRM, reporting is messy, and they’re not seeing ROI.
✅ Better Email Approach:
Subject: Struggling to Get the Most from Your CRM?
Hi [First Name],
I came across [Company Name] and noticed you’re using HubSpot. Many companies we speak with love HubSpot but face challenges with CRM adoption—whether it’s sales teams not using the system properly, reporting gaps, or missing integrations.
We’ve helped teams:
- Improve CRM adoption by 35% with hands-on training.
- Simplify reporting for real-time pipeline visibility.
- Integrate marketing tools for smoother lead conversion.
Would it make sense to chat for 15 minutes to see if any of these challenges sound familiar?
Best,
[Your Name]
🔥 Why This Works:
- Acknowledges their existing CRM instead of pushing a replacement.
- Focuses on common pain points without assuming they apply.
- Adds credibility with specific data (35% adoption improvement).
Scenario 2: Gain-Based Messaging (Customer is Happy with HubSpot but Wants to Stay Ahead)
Context: The company is already successful with HubSpot but wants to scale and increase efficiency.
✅ Better Email Approach:
Subject: How High-Growth Companies Scale Beyond CRM Basics
Hi [First Name],
I came across [Company Name] and saw that you’re leveraging HubSpot—it’s a great platform, and we’ve helped many companies take their CRM strategy even further.
We work with high-growth companies to:
- Automate complex sales workflows, cutting admin time by 40%.
- Integrate predictive analytics to help sales teams forecast revenue with greater accuracy.
- Improve multi-channel marketing alignment for higher customer retention.
If you’re exploring ways to scale and optimise your HubSpot setup, I’d love to share some insights from companies that have done it successfully. Would a quick chat next week be helpful?
Best,
[Your Name]
🔥 Why This Works:
- Acknowledges HubSpot as a good choice instead of pushing a switch.
- Focuses on gains (automation, forecasting, marketing alignment) instead of problems.
- Positions the sender as an expert, not just a salesperson.
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Example 2: Selling Network Security – Pain vs. Gain Messaging
Cybersecurity is another excellent example of how context changes messaging.
A company may have recently suffered a security breach (pain-based outreach) or maybe proactively investing to stay ahead (gain-based outreach).
Scenario 1: Pain-Based Messaging (Customer Recently Suffered a Security Breach)
Subject: After [Recent Attack], Is Your Network Fully Protected?
Hi [First Name],
Recently, a company in your industry faced a cybersecurity issue—unfortunately, they were not alone. In the Caribbean, ransomware attacks have surged by 300% over the past year, costing businesses hundreds of thousands, or in some cases millions, in downtime, lost data, and the expense of regaining access to their information.
Have you considered the value of your network's strength, including your staff's training and awareness?
Would it be worthwhile to have a quick chat about how others in [industry] are bolstering their security following this incident?
Best,
[Your Name]
🔥 Why This Works:
- References a known pain point (security breach).
- Offers clear solutions with measurable results.
Scenario 2: Gain-Based Messaging (Customer Has Good Security But Wants to Stay Ahead)
Context: The company already has security measures in place but wants to stay ahead of evolving threats.
✅ Better Email Approach:
Subject: How [Industry Leaders] Are Staying Ahead of Cyber Threats in 2025
Hi [First Name],
Security threats evolve fast, and staying ahead means continuous improvement. We have been helping [Company Name] stay ahead of the curve and clever cyber threats by showing them how to invest in.
- AI-driven threat detection to predict & stop attacks before they happen.
- Zero Trust frameworks to prevent internal security breaches.
- Automated compliance tracking to simplify audits & reduce risk exposure.
- Training
If you’re exploring ways to stay ahead of cybersecurity trends in 2025, I’d love to share what we’re seeing in the industry.
Would you be open to a brief call next week?
Best,
[Your Name]
🔥 Why This Works:
- Frames security as a competitive advantage.
- Focuses on proactive investment, not just fixing problems.
- Positions the sender as an industry expert.
If we examine the emails above, you’ll see that they can be adapted in numerous ways, beginning with a customer-first perspective. It's essential to understand where the customer is, what they're aiming to accomplish, and how you can assist them in solving a problem or maintaining their competitive edge.
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Final Takeaways: Fixing Sales Outreach with Better Research & Content Strategy
Prospecting is cool once done right, but there are some fundamental things you need to do when trying to connect with your audience.
- Understand where your customer is today—pain or gain? Are they looking to fix a problem or scale their success? Your messaging should reflect their reality, not just your pitch.
- Align messaging with their actual needs. A one-size-fits-all approach to sales outreach leads to wasted efforts. Research, segmentation, and real-time insights help tailor conversations to be more relevant and impactful.
- Use research, not assumptions, to guide your outreach. The best sales emails feel like they were written for one person, not a mass audience. Research should drive personalization, helping you craft messages that actually resonate.
- Don’t just sell—position yourself as a trusted expert. The best salespeople aren’t just sellers—they’re problem solvers, advisors, and educators. Whether through email, LinkedIn content, or sales calls, the goal should always be to build credibility first.
The Bigger Picture
If sales outreach isn’t working, the problem isn’t just in the sales department—it’s a content problem, a strategy problem, and a messaging problem. A weak email isn’t just a failed sales attempt; it’s a symptom of a broken sales and marketing alignment.
When marketing and sales work together, outreach becomes insightful, valuable, and timely. Instead of pushing the same generic message to everyone, reps are equipped with data-driven insights, competitive positioning, and messaging that speaks directly to a prospect’s reality.
So, before blaming sales performance, take a step back and look at the content. The way your team researches, writes, and communicates determines whether they open doors—or get ignored.
