Personalizing Outreach at Scale: Customize Connections without Sacrificing Relevance

June 9, 2023
 min read

The days of mass emailing lead lists and cold calling the phonebook are over —that is, if they ever existed in the first place. The best sales teams know that hitting revenue targets today means actually building a rapport with prospects. 

Personalization at scale is not just about reaching more people. It’s about communicating with  your audience using custom, relevant messaging that’s right for them even when you are reaching out to a large number of people.

In the world of enterprise sales, personalization at scale isn’t a nice-to-have anymore. It’s an imperative. Personalization drives engagement, builds trust, and fosters connections – enabling you to scale your client base without diluting the quality of your outreach.

In this article, we're going to break down the fundamentals of personalizing emails at scale, then dive into five actionable sales plays you can implement right away.

Here’s what we’ll cover:

- Understanding Personalization At Scale

- Best Practices for Personalizing at Scale

- Four Approaches to Personalization

- Sales Play 1: Trigger-Based Sales Sequences

- Sales Play 2: Outbound Sales Sequences

- Sales Play 3: Inbound Sales Sequences

- Sales Play 4: Follow-Up Sales Sequences

- Sales Play 5: Event-Based Sales Sequences

- Closing Thoughts

Let’s get personal(ized), {{first_name}}

Understanding Personalization At Scale

Personalization at scale might sound like one of those unsolvable puzzles or an oxymoron, but we assure you it’s not. Done right, personalization at scale helps you tailor outreach to each individual prospect so that you hit the right notes, address their specific pain points, and offer a solution that seems custom-made for them, all while maintaining a level of volume that supports your growth goals.

The challenge lies in maintaining a high level of customization and relevance in your outreach, while also scaling the number of people you’re reaching. But by leveraging the right tools and processes, you can ensure that your outreach is both personalized and scalable.

Best Practices for Personalizing at Scale

Let's dig into best practices you can implement to master personalization at scale in your sales outreach. It's time to move beyond "Greetings, [First Name]" in your emails. Let's go deeper.

Use Generative AI solutions to create content. Advanced personalization solutions like are indispensable. They help you automate the research aspect of personalizing emails, which tends to be the most time intensive part of the process, and use those data points to craft a relevant and relatable piece of outreach. That way, you can send tailored emails to a large audience without sacrificing relevance. And the hours saved can be put back into prospecting, scaling your impact.

Always be relevant. Make sure the personalized content relates to what your buyer actually does day-to-day. Don’t settle for just mentioning their name, company, or role. Focus on their unique pain points, and highlight how your offer can help solve them. Persona based messaging can greatly help scale this.

Create custom fields. Building custom fields into your outreach messages makes it easy to inject personalized details into your sales details. For example, you might create fields that automatically insert details from their LinkedIn profile or highlights from articles they've written.

Include social proof. Customer stories are a compelling way to get prospects thinking about what you could do for them, if they see themselves in that success story. To build trust and credibility, share examples of similar companies you've worked with.

Take advantage of data. Psychographics, firmographics, and demographics are the holy trinity of personalization. Use all available data at your disposal to tailor your outreach. That could include:

  • Psychographics: interests, attitudes, behaviors, motivations
  • Firmographics: industry, company size, location, revenue
  • Demographics: contact details, job level, work history, certifications

Record video messages. Personalization doesn’t always mean text. Custom video messages add a human touch to your outreach abd help put a face to the name in their inbox. Plus they're an engaging way to quickly deliver value to prospects. Tools like Vidyard and Loom make it easy to record and send personalized videos as part of your outreach.

The key to personalization at scale is to keep your messages relevant, meaningful, and authentic – while reaching as many prospects as possible. It's all about striking the right balance.

Four Approaches to Personalization

There's more than one way to personalize a message. Each approach offers a unique way to tailor your message to an individual prospect, without sacrificing scalability. Let's take a look at these approaches for achieving personalization at scale.

Prospect-Centric Approach 

So you're at a party and someone goes on and on and on about themselves until you find some excuse, any, to extricate yourself. That's how it feels when you show up in someone's inbox with a long email about your services. 

Instead, make every word about the person you're talking to. Identify what will be most relevant to them. What's their role? What challenges are they going through? Focus on their needs and desires, and show how you can offer a solution.

Did you know the email analyzer will automatically highlight your I:You ratio in your email message to make sure you stay focused on your reader? 

Pain-Centric Approach 

Pain points are a powerful way to start building a relationship with your prospects. Rather than talking about your product, dial in on the pains they are dealing with. Say your software helps reduce the time spent on manual data entry. Don’t talk about how great your product is. Empathize with the reader about the tedious busy work that must introduce and how there are ways to eliminate that administrative burden. Frame it as a solution to your prospect's headaches, and you'll get their attention.

Value-Centric Approach 

With this approach, you answer the eternal question, WIIFM (what's in it for me)? Your prospects want to know how your product or service adds value to their lives. Whether it's in terms of cost savings, increased efficiency, or other benefits, be sure to highlight the value proposition relevant to their unique pains and gains. For instance, if your product boosts productivity, translate that into potential revenue growth for their company.

Company-Centric Approach 

Having a hard time digging up personal 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 launch a new product? Hit a major company growth milestone? These wins, as long as they relate to your problem space, are a great reason to reach out.

Choosing the right approach depends on your prospect's profile, their company, and the reason you want to reach out. Sales outreach isn't about blasting emails mechanically – it's about demonstrating genuine understanding and offering real value to what is relevant and top of mind to them. With that in mind, let's take a look at some of the most powerful sales plays you can use to implement these strategies.

Sales Play 1: Trigger-Based Sales Sequences

What's a trigger-based sales sequence? Every now and then, you get the perfect opportunity to introduce your product to a buyer – and that's what a trigger-based sequence is designed for. It's all about timing your outreach to coincide with significant events or 'triggers' in your prospect's life or their company's lifecycle.

Trigger-Based Newsworthy Event Sales Sequence

When something newsworthy happens in your prospect's company, this is your go-to. Maybe they've just launched a new product, or been written up in a major publication. This is your chance to show that you're paying attention.

Acknowledge their success and express your congratulations. Craft your message around how your solution can help them take their company to even greater heights. Your goal is to show that you're not just trying to sell something – you're genuinely invested in amplifying their success.

Trigger-Based New Job Status Sales Sequence

When you notice a prospect just landed a new job, this is the one to use. A new role means new challenges and perhaps new budget authority. Personalize your outreach to congratulate them on their new position and gently show how your solution can make their transition smoother.

The beauty of trigger-based sales sequences lies in their relevance. You're not just another salesperson pushing a product; you're offering a solution that fits their current needs perfectly.

Sales Play 2: Outbound Sales Sequences

With an outbound campaign, you’re playing proactive offense instead of reacting off of a trigger like the above examples. These sales sequences are all about proactively reaching out to potential customers instead of waiting for them to find you. The key here is personalization and timing. You want to reach the right person at the right time with the right message.

General Outbound (Automated) Sales Sequence / Cadence

In this sequence, automation is your best friend. You want to maintain that personal touch but also reach a larger audience, and automation helps you strike that balance. The trick is to personalize key elements of your messaging – like addressing pain points specific to the prospect's role or industry.

Promotion: Pilot or Trial Sales Sequence / Cadence

This sequence is ideal when you have a tempting time based promotion, like a pilot or trial offer. The goal here is to pique the prospect's interest enough and drive urgency to give your product or service a shot. A good approach is to highlight the value they'll get from this trial and how it's a risk-free way to see how your solution fits their needs.

Sales Play 3: Inbound Sales Sequences

With inbound sales sequences, your prospects have shown interest in your product or service and have come to you. These sequences are all about keeping them engaged, delivering value, and going above and beyond their expectations – so they’ll be eager to stay engaged in your funnel.

Respond to Content Downloads (Sped Up, Automated)

Creating exceptional content is a great way to drive interest in your brand and product by directly addressing your prospects’ needs. It is what has made Inbound marketing an especially popular methodology. That said, following up on content downloads can be a huge time sink for sales teams — especially if the prospects aren’t in market but just self educating on a problem space. Use this sequence to maintain a touchpoint with prospects, offering to help without being too forward and squandering the relationship at an early stage.

Responding to Demo Requests: Sales Sequence / Cadence

When a prospect requests a demo, that’s great news – they're a hand raiser and interested! That’s where you can shine by delivering a personalized demo that hits their pain points. Make sure to research their business, understand their challenges, and tailor your demo to show how your solution can solve their specific issues.

Sales Play 4: Follow-Up Sales Sequences

Every successful salesperson needs to master the art of the follow-up. Effective follow-ups re-engage the prospects who seemed to have slipped through the cracks or leveraging the potential of referrals to create net new opportunities. One well-placed follow-up can make the difference between a closed-lost opportunity and a contract signed.

Closed Lost Re-Engage: Sales Sequence

So your prospect was all set to move forward, but then – who knows what? Maybe they lost budget. Maybe they went with a competitor. Maybe their priorities shifted. It’s a tough blow, but it doesn’t have to be the end of the story. With this sequence, you can reignite the conversation and potentially win back those lost deals. It's great for reconnecting, reestablishing the value of your product or service, and showing the prospect that you're there to support them. Remember, a 'no' now doesn't mean a 'no' forever!

Use a Referral: Sales Sequence

Referrals can be an incredible source for new business. There's nothing quite like a warm introduction to a new potential prospect from a trusted mutual connection. By reaching out to those referred prospects with credibility and context right off the bat, you can get an automatic advantage on the competition that makes it far easier to close deals. It's a powerful approach to expand your network and create new opportunities.

Sales Play 5: Event-Based Sales Sequences

If you’re looking to take advantage of event-based sales, it’s not enough to just show up with your business card and then send a follow-up email afterward. With event-based sales sequences, you can ensure that your events, be it virtual webinars, meetups, or trade shows, become a prime ground for nurturing leads and closing deals.

Pre-Event Reminder Sales Sequence

Before the big day arrives, this sequence is an ideal tool to build buzz and ensure a high turnout. It’s a great way to hype up your event, outline what attendees can expect, and make it clear that their presence is highly valued – so they'll feel like the VIPs they are.

Post-Event Sales Sequence for Attendees

The event may be over, but your sales play is just getting started. And that’s where your post-event email sequence comes into play. You'll want to thank attendees for their presence, share key takeaways or resources, and propose next steps. It's your chance to continue the conversation and turn attendee interest into concrete sales pipeline.

Closing Thoughts

In this article, we’ve covered best practices for personalization, looked at different ways to approach it, and dove deep into the five critical sales plays that can accelerate your B2B sales performance. With these sales plays at the ready, you’re now equipped with a powerful playbook to maintaining a high level of personalization at scale.

The key is to truly understand your prospect's needs, their pain points, how your value prop fits in, and tailor your communication accordingly. Use the personalization strategies we covered above to make these sequences personal and relevant to your ideal prospects. Success in sales is all about creating connections that resonate and adding real value, not just playing the number game.

In the high-stakes world of B2B and SaaS sales, every interaction counts. That’s where can help you streamline the personalized prospecting process by crafting relevant, personalized messages. It’s a great way to stand out in the crowded inbox – and start closing more deals.
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