July 8, 2024

Personalization at Scale: How AI is Revolutionizing B2B Outbound Sales

In the competitive landscape of B2B sales, sending generic, one-size-fits-all messages is no longer effective.  Decision-makers are inundated with generic cold emails daily by the tens or hundreds. This results in sellers competing for less and less of their prospects' time.   The key to unlocking higher engagement and conversions lies in personalization. Research from McKinsey & Company has shown that personalized messages can dramatically boost revenue, sometimes up to 10-15%, compared to generic ones, emphasizing the importance of understanding and connecting with your prospects. Today, advancements in AI sales assistant software are taking personalization to the next level, making it achievable at scale and driving unprecedented results.

How to Execute Personalization in Outbound Sales:

Before diving into the impact of AI, let's revisit the foundation of effective personalization:

  1. Know Your Audience:

You must effectively know your audience to grab their attention with cold email outreach.  Otherwise, your message will be promptly deleted, and your target prospect will move on with their day.  The more you can make your copy read to them like you know them better than they know themselves, the better.  Now, that is certainly easier said than done.  However, here are some tips for analyzing your target prospects:  

  • Conduct thorough market research to understand your industry, competitors, and target audience.
  • Develop Ideal Customer Profiles (ICPs) to outline the characteristics of your perfect customers.
  • Create detailed buyer personas, delving into their roles, challenges, goals, and communication preferences.
  • Understand what their competition is doing; this will help you create FUD (fear, uncertainty, and doubt) in your email messages.
  • Analyze sales call recordings to identify your prospects' language and pain points.

  1. Segment Strategically:

Once you complete your market research and have established your ideal customer profile (ICP), it is time to segment your audience.  By segmenting, you can bucket your prospects into specific groups and tailor your messaging more effectively to those smaller groupings. 

  • Group your prospects based on demographics, behaviors, or specific needs.
  • Demographic segmentation: If you choose to segment based on demographics, consider splitting your audience by job title, industry, or location. 
  • Behavioral segmentation: If you choose to segment based on behavior, consider segmenting based on purchase history or website engagement you’ve been able to monitor.
  • Needs-based segmentation: Consider segmenting based on specific needs or problems you’ve heard expressed. 
  • Any of these approaches ensures your messages are tailored to resonate with each segment.

  1. Craft Compelling Messages:

The way you structure your message, the writing style you choose, and the overall tone play a significant role in effective personalization. Consider these tips:

  • Hook Them from the Start:some text
    • Begin your message with a compelling opening line that immediately grabs your prospect's attention. Address a specific pain point they're likely experiencing or mention a relevant interest to spark their curiosity.
    • Example: "I noticed your company recently expanded into new markets. We've helped similar companies streamline their onboarding processes to support rapid growth. Would you be interested in learning more?"
  • Tailor the Content:some text
    • Don't just use their name – truly personalize the content to align with their individual needs, challenges, and goals.
    • Leverage information from your CRM to reference past conversations, purchases, or content they've engaged with.
    • Clearly explain how your product or service directly addresses their specific pain points and provides tangible benefits.
  • Strike the Right Tone:some text
    • Adopt a professional yet approachable tone that resonates with your target audience.
    • Avoid jargon or overly formal language. Instead, opt for clear, concise communication that feels like a genuine conversation.

By mastering these message crafting techniques, you can create personalized outreach that feels authentic, relevant, and valuable to your prospects. Remember, it's about demonstrating a deep understanding of their world and offering tailored solutions that address their specific needs.

  1. Leverage Technology, Especially AI Sales Assistants:
  • AI-Powered Personalization:
  • Dynamic Content Generation: AI can analyze vast amounts of data to automatically generate personalized email subject lines, body copy, and calls-to-action tailored to each prospect's unique attributes and interests.
  • Smart Segmentation: AI algorithms can segment your audience with greater precision, uncovering hidden patterns and nuances that humans might miss. This leads to even more targeted messaging.
  • Predictive Analytics: AI can predict which prospects are most likely to convert, allowing you to prioritize your outreach efforts for maximum impact.
  • Real-Time Optimization: AI can continuously analyze and refine your messaging in real-time, ensuring your campaigns always perform at their best.
  • Automation Tools (Supercharged by AI):
  • Automated Email Sequences: AI-powered tools can create and send personalized email sequences triggered by specific actions or behaviors, nurturing leads throughout the sales funnel.
  • Chatbots and Virtual Assistants: AI-driven chatbots can engage with prospects on your website, answer questions, qualify leads, and even schedule meetings, all while providing a personalized experience.

personalization at scale example
an example of a personalization strategy

Best Practices for Personalized Outbound Sales:

Here's how to maximize the effectiveness of your personalized outreach:

  1. Test and Refine with A/B testing:
  • Utilize A/B testing to quickly identify the most effective messaging variations, significantly accelerating your optimization process.
  • Send variants of messages and compare them on how they perform.  Look at open rates, click-through rates, and conversions to understand which variant performs better. 
  1. Respect Privacy and Regulations:
  • Understand and ensure your outbound sales and marketing efforts comply with data protection laws and respect customer privacy.  Here are the big three:some text
    • CAN-SPAM Act: Mandates a precise mechanism for opting out of emails in the U.S. 
    • GDPR (General Data Protection Regulation): Requires consent before gathering data from individuals in the EU. 
    • CCPA (California Consumer Privacy Act): Gives California residents the right to know what personal data is being collected and to refuse the sale of their personal information. 
  • Be transparent about how you collect and use data.
  1. Strategically Time Your Outreach:

Determining the optimal timing and frequency of your outbound messages is crucial to ensure they're seen, acted upon, and don't irritate your prospects. Research and industry best practices suggest the following:

  • Cold Email: Tuesdays often see the highest open rates, with mid-morning (9 AM) and lunchtime (12 PM) being effective times to send emails. Avoid weekends and evenings when work emails are less likely to be checked.
  • Cold Calling: Consider Tuesdays, Wednesdays, and Thursdays as your primary calling days, as Mondays and Fridays tend to be filled with meetings. Lunch breaks or late mornings can be opportune moments for a short conversation.
  • LinkedIn Outreach: LinkedIn engagement is often highest on Tuesdays, Wednesdays, and Thursdays, although weekdays in general may be more effective than weekends. Like emails, mornings are often a good time to catch people checking their notifications.


Finding the right balance between persistence and respect is key. For email and LinkedIn, a follow-up after 3-5 business days without a response is generally acceptable. Depending on your sales cycle and industry norms, cold calls can be spaced out weekly, with a maximum of 2-3 attempts.

Considering these timing and frequency guidelines, you can increase the chances of your personalized messages reaching your prospects at the right time and context, leading to more meaningful interactions and higher response rates.

  1. Track the Right Metrics:
  • Use AI-powered analytics platforms to monitor your campaign performance in real-time and gain deeper insights into customer behavior.


In the age of AI, your competition is leveling up their outbound strategy, and so should you.  It is no longer effective to send the same generic message to 1,000 recipients, expecting enough of them to convert to paying customers.  It simply is no longer realistic.  These methods are the equivalent of sales and marketing malpractice that have worn out and burned out that channel.  Personalization at scale is no longer a luxury but a necessity for successful B2B outbound sales. By combining the power of human expertise with AI-driven insights and automation, you can forge stronger connections with your prospects, deliver hyper-personalized experiences, and ultimately achieve greater sales success.

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Who does Leadmatic partner with?

Companies with the following characteristics are best suited for working with Leadmatic:

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    Average contract value of over $10,000
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    A clear understanding of their prospects and their problems
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    A clear value proposition for their products and services

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