How The Most Effective Enterprise Sales Reps Personalize Their Outreach Using Automation

August 10, 2023
 min read

It's 8 AM Monday morning. You're staring at a screen filled with (hopefully) leads upon leads upon leads—and you know each one deserves a unique, personalized approach.

Automation could be the quickest way to speed up your outreach while saving time and energy. But on the other hand, you remember that each lead is a human, not a number. A personal touch can go a long way in building relationships and gaining trust but how do you do it without burning out?

In this article, we'll look at how successful enterprise sales teams are striking the balance between automation and personalization. We'll cover:

-Why Automation Matters In B2B Sales

-The Art of Personalization in Enterprise Sales

-Balancing Automation And Personalization

-Putting It All Together

Why Automation Matters In B2B Sales

Automation is a critical tool in any enterprise sales rep’s toolkit. It’s a hyper efficient, always-on sales assistant who never sleeps and can tirelessly take on hundreds of routine tasks that once took hours out of every sales rep’s day.

Here are just a few ways automation is transforming enterprise sales:

Engagement. For the sales rep at a growing SaaS company, a typical morning used to start with sifting through the CRM, looking for leads to connect with. Today, AI takes care of that for you, automatically surfacing leads to reach out to and follow up with based on their engagement level.

Scheduling. Up until just a few years ago, setting up meetings involved endless back-and-forth over email to find a time. Scheduling tools like Calendly have eliminated the hassle – and made it simple for sales reps to schedule appointments with a simple scheduling link.

Scoring Leads. Veteran sales reps know the pain of manually sorting through leads to determine which ones were most likely to be worth their time to reach out to. Automated lead scoring algorithms have made that a thing of the past, enabling sales teams to spend more of their time on outreach efforts.

Nurturing Leads. Once you know which leads you want to focus on, automated workflows make it way easier to send relevant content, tips, and resources that help you stay top of mind and build trust with them over time.

Automation is having an undeniable impact on enterprise sales. A recent study by McKinsey found up to 30% of sales activities can be automated, improving sales efficiency by up to 15%. And by increasing efficiency, automation allows sales reps to spend more time where they shine: building relationships and closing deals.

The Art of Personalization in Enterprise Sales

Reaching leads at scale can’t be done without automation. Personalization, then, is how you make them feel like you're reaching out specifically to them.

Unfortunately, it’s also incredibly easy to get personalization wrong. It's not just about slapping a first name into an email template, or randomly mentioning their local sports team in your email. You want to make it clear that you've taken the time to do your homework on them – even when you're juggling dozens of leads.

Here are four ways to do personalization that actually resonates:

  • Focus on your prospect: Prospects don't care about you. Focus on their needs and desires. Based on your research, talk about what's most relevant to them, such as challenges they're likely to be facing in their role. By taking a prospect-centric approach, you can show how your solution can meet their specific needs.
  • Focus on their pain: A powerful way to build a relationship with prospects is to address their pain points. Rather than talking about your product, focus on the problems they are facing. For example, if your software reduces the time spent on manual data entry, highlight how it eliminates paperwork and saves time. By framing your solution as a way to alleviate their headaches, you can capture their attention.
  • Focus on the value you offer: Prospects want to know what's in it for them. Be sure to highlight the value your product or service can add to their lives. This could be in terms of cost savings, increased efficiency, or other benefits. For instance, if your product boosts productivity, translate that into potential revenue growth for their company.
  • Focus on their company or industry: If you're having trouble finding details about your prospect, focus on their company or industry instead. Look for recent news, blog posts, or specific language on their website that you can reference. Did they recently receive funding? Launch a new product? Hit a major company milestone? These wins are a great reason to reach out.

Effective personalization requires research. Digging into a prospect's industry, role, and past interactions with your company gives you the background information you need to craft effective messages that resonate with your reader.

And while it seems like a lot of work, the payoff is worth it. Studies show that personalized subject lines can double your email open rates – and personalized email content delivers 32% higher email response rates.

Balancing Automation And Personalization

When personalization is done at scale using effective automation practices, it can totally transform your sales operation.

Finding that balance is all about implementing automated workflows to gain efficiency – while ensuring that you achieve the personal connection prospects need to experience at every touchpoint.

Here's how to strike the balance:

  • Automate routine tasks: Use automation for routine tasks like scheduling and follow-ups, and personalization for unique touches like initial outreach and content sharing. Consider using an AI-powered tool like to write and send follow-up emails, all while personalizing the content based on the prospect's industry, role, or past interactions.
  • Leverage AI and data: AI can deliver invaluable insights you can use to personalize your outreach – like pinpointing patterns in a prospect's behavior to determine the best time to send an email or the type of content they're likely to engage with.
  • Add a human touch: Automation is great for routine tasks, but it's important to inject human touch points throughout the sales cycle – in the form of touches like personalized video messages or handwritten notes after an on-site. Adding a personal touch at the right moment in time will help you stand out from the crowd of sellers who are going all in on AI and automation alone.

Putting It All Together

For enterprise sales pros, mastering AI and automation isn't a nice to have. It's a necessity. Expert salespeople know how to integrate automation into their workflow to reach prospects at scale – while still delivering the personal touch they expect.

Here's what a typical day could look like for Fred, a B2B sales rep at a SaaS company:

8 AM: Fred logs into his CRM. Overnight, the system has sorted through hundreds of leads, categorizing them based on engagement levels. Follow-up emails for warm leads are already written, and scheduled, thanks to AI and automation.

10 AM: Fred's spent the morning crafting cold pitches for several high value prospects. He doesn't rely on generic templates. Instead, he uses to help him craft personalized messages. By weaving in details about the prospect's specific industry challenges and sharing relevant content, he can create a conversation starter that resonates with each prospect.

12 PM: Around lunchtime, Fred schedules meetings with several potential customers. He uses an automated scheduling tool – but adds a human touch by sending a customized video message with the scheduling link to enhance the prospect's experience.

2 PM: Fred analyzes recent outreach campaigns, using AI-powered analytics to gather insights into what content is working with different segments of his audience. AI platforms like make it easy for Fred to gather actionable intelligence he can use to personalize future outreach.

4 PM: At the end of the day, Fred sends handwritten notes to prospects he has recently met with at an event. A few years ago, Fred never had time for personalized touches like this – but these days, he finds technology has given him more time back in his day so he can really take the time to stand out from other sales reps who focus all their efforts on digital channels.

Automation and personalization aren't mutually exclusive. When they work together, they make for a powerful sales strategy that can help you build relationships and close more deals.

Closing Thoughts

In this article we've seen one theme over and over again: balancing automation and personalization is absolutely essential for success in the world of modern enterprise sales.

Automation, with its efficiency and scalability, is a powerful ally, but without the human touch of personalization, it can feel cold and impersonal.

And while personalization is how you truly connect with your prospects, without automation it'll quickly become unsustainable.

Let automation do the heavy lifting. And make sure that all your outreach has a genuine, personal touch. It's a path that leads to more meaningful connections, higher engagement, and ultimately, more successful sales.

If you're ready to start selling more effectively with a Generative AI platform built specifically for sales teams, it's time to try Check out Regie today – and start delivering ready to use sales messaging in seconds.
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