The Art of Email Courtship in the Era of Anti-Spam

In the fast-paced world of sales outreach, one thing is clear: generic, one-size-fits-all messages just won't make the cut. There are instances where these messages work, particularly as many sales professionals rely on tools to create sequences with monitored cadences, automating certain steps in the outreach process.

However, with Google and Yahoo introducing new requirements to enhance email security and improve user experience, it's crucial for sales professionals to adapt their strategies and understand that standing out is now more important than ever.

The Sales Outreach Volume Challenge

The pressure to meet targets seems even greater than last year. The ultimate goal is to convert your prospects, or rather your next best customers, into successful sales. You want them to experience the joy and benefits that your product/service offers, to the extent that they enthusiastically recommend it to ten of their professional friends, giving you the most coveted lead - a referral.

Let's take a moment to put ourselves in your prospects' shoes. Imagine waking up to an avalanche of emails in your inbox, each one blending into the next. You don't have to imagine it, because you probably experience it too, especially if you've ever signed up for any kind of e-commerce. Just like you, your prospects start their day with over 30 emails. It's overwhelming even before they've had their first sip of coffee. Being bombarded like this can be frustrating, but we all understand that this is the reality. However, it can be different for you and your prospects.

Capturing and holding your target audience's attention is a difficult task. Nothing prompts recipients to hit the dreaded unsubscribe or delete button faster than receiving irrelevant, impersonal, or, worst of all, boring messages.

Google and Yahoo’s recent announcement underscores the importance of email authentication, easy unsubscribes, and maintaining a low spam rate. While these requirements primarily focus on email security and reducing spam, they also highlight the significance of personalization and the need to stand out from the crowd.

The importance of the message and recipient in today’s world

  • Prioritize Alignment with the Recipient: When you align yourself with the recipient, you demonstrate that you value their time. Instead of simply seeking a sale, take the time to understand the 8 seconds that they may have to read your message(s). Conduct research, make it engaging, and adopt the mindset of a sleuth or journalist. When drafting your outreach consider using the questions of "Who, What, Where, When, and Why” as your guide.

  • Building Relationships: Personalization is key to establishing trust and credibility, which serve as the foundation for all types of relationships, whether professional, personal, or even romantic.

  • Boosting Open Rates: Tailored outreach has a higher chance of being opened. Pay attention to subject lines, experiment with concise phrases or even adding an emoji. Be creative, but be cautious with using all caps. Although it might work for some, it's worth a try, right?


    Minimizing Unsubscribes: When prospects perceive your communication as creative and valuable, they are less likely to ignore, delete or at worst unsubscribe. Break through the noise and provide meaningful content that reduces the urge to opt out or delete your emails.

Valuable Tips to Enhance Your Outreach Effectiveness

  1. Segment your list- Divide and conquer by grouping your audience based on demographics and behavior. This allows you to tailor your message to specific groups.

  2. Personalize your identity- Stand out by using your name in a way that reflects your unique style. If you have a nickname that you want your prospects to remember, go for it. For example, if your name is Adam Johnson but everyone calls you AJ, experiment with using Adam 'AJ' Johnson. (Insert example)

    • Quick hint - Address prospects by their first name, avoiding any shortened versions until you've established a more friendly rapport. 

  3. Help with pronunciation- If your name might be challenging to pronounce, consider closing your email with the phonetics of your name. This not only provides a memorable touch but also adds a touch of comedy and reduces any anxiety when they connect with you.

  4. Reference past interactions- If you have had previous engagements with a prospect, mention them. It could be a recent webinar, event attendance, or something their CEO or marketing leader shared on LinkedIn. Utilize these references to grab their attention and stand out.

  5. Solve the Problem - Craft your outreach with a personal touch while addressing the recipient's pain points. If you struggle to identify their specific pain points, consider leveraging tools like ChatGPT to assist you. According to LinkedIn State of Sales Report 2022,  82% of top performers say they ‘always’ perform research before reaching out to a prospect. Remember, the specific prompt you provide to ChatGPT will determine the output, so be precise. For example, ask questions like, "What does a CTO at [insert company] do? How can my product [insert company] help them?"

  6. Use your colleagues or other contacts- Following on from the previous point, if you’re connected with someone within a similar profession or role to your prospect, ask them for quick advice. Ask them what a good email (outreach) looks like to get their attention. What made them respond to a sales email that they received. If you’re trying to reach marketers - ask someone from your marketing team what would get their attention.

  7. Optimize for mobile - This one is easy to forget as it's common to over share information in your initial outreach. But short and sweet is the most effective. Nothing more than what can be read without scrolling on a mobile phone, particularly as 81% of all emails are opened and read on mobile devices.

Consider Using These Tools To Help With the Quality of Your Outreach

Crystal Knows - is a website that provides insights and advice on understanding and communicating with different personality types. It uses artificial intelligence to help individuals improve their interpersonal relationships, whether it be in the workplace or in personal settings. 

Owler AI - is a prospecting assistant that helps you effortlessly craft outreach (emails, voicemail, LinkedIn messages) using real-time data and news relevant to your prospects.

Grammarly - is an online writing assistant that helps users improve their writing by checking for grammar, spelling, punctuation, and style mistakes. It provides suggestions and explanations to enhance clarity, coherence, and overall writing quality. 

These tools can help you minimize being ignored and ensure that your messages are polished and professional.

To Wrap Up

Email changes are on the horizon, but it's not the end of the world for outbound communication. The truth is, personalization has become a must. With Google's new requirements emphasizing relevance and reducing unsubscribe rates, it's clearer than ever that personalized and tailored outbound emails are the way forward.

Don't forget that your prospect is a person. Take the time to truly understand the individual you're reaching out to and deliver something that will genuinely resonate, delight, entertain, and form a genuine connection. By doing so, you'll witness your engagement rates soar and sales increase.

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