Cold Email Personalization Strategy for Outbound Sales

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Darren Carter

Co-Founder & CRO at RevenueZen

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Darren has experience leading teams to generate millions in revenue, ranging from bootstrapped startups to public companies. As the co-founder of RevenueZen, he’s helped 70+ bootstrapped B2B startups and agencies build lead generation engines with inbound, outbound, and social.

Since launching in 2017, RevenueZen has become a profitable 7-figure ARR organization that generates a 5.6x average return on investment for clients.

The volume of cold emails you can produce every day is limited by the time you spend targeting, researching, and personalizing your email outreach for each prospect.

It can be a struggle to balance the time you spend on personalization and the volume you need to generate the right results.

Before you start cold emailing, you should get an understanding of the volume needed to achieve the results you want for the conversions you’re realistically able to generate with outbound sales.

Email Personalization: Before You Start

There is no fixed answer to personalization for email. The best approach is unique to your situation and will change as new competitors, strategies, and buyer behaviors emerge.

Not all of the variables in your situation are controllable, so it’s important to build your cold email personalization strategy conjunction with market research.

Otherwise, you pose the risk of diving into a strategy that doesn’t make sense for you.

For example, a hyper-personalized approach would likely be unprofitable for a $3,000 sale and prevent you from touching most of the market. On the other end of the spectrum, mass outreach would likely be ineffective for larger, more competitive deals.

Instead of building out a strategy as you go, you should reflect on the different elements making up your unique environment to get a better understanding of the type of outreach you need to build pipeline.

Factors Impacting Your Personalization Strategy

Market Size

It’s important to size up your target markets so you know the total number of accounts and leads that are available for your cold email outreach.

As you develop an Ideal Customer Profile (ICP), you’ll get a sense of whether your market is larger or smaller in size.

If you have less than 1,000 people to contact, then you’ll likely have to be more targeted and invest more time personalizing each message you send.

However, you don’t have to go as targeted if your target markets have thousands of contactable leads so its easier to generate positive results at a large volume.

With a known number of companies and sales leads to target, you’ll have a much better idea of how to approach your lead generation strategy.

Deal Size

Personalizing cold messaging costs time and money, so you want to make sure the resources you invest to win these outbound sales will be worth the revenue you generate.

You need to evaluate the average deal size or annual contract value (ACV) for your solution in the markets you’re targeting.

There’s a point where a deal size is so low that the conversion rates you generate with personalization don’t make sense at the expense of a lower volume.

Smaller deals can force you to do a higher volume to generate the results you need with cold email, even if you’d convert more by spending time on personalized outreach.

In contrast, a few opportunities every month or quarter can fill your sales pipeline if you have large enough deal sizes, so an account-based, personalized approach would make much better sense.

The right balance between personalization and volume is about spending enough time to convert the right number of deals at the email volume you can realistically achieve.

Deal Complexity

One misstep can tarnish a potential outbound sale, so the deal-making process you go through to win deals has a huge impact on the amount of time you should spend personalizing.

If you’re selling a solution that can be purchased with a few clicks, you can be less targeted and still generate great results at volume.

However, complex deal-making involves more decision-makers, more steps in the buying process, and more evaluation time, so companies selling complicated solutions have to focus more on conversation quality with the right people.

Without the right outbound messaging to the right people at the right time, you’ll often struggle to gain traction with high-volume cold email when trying to win more complex deals.

How Differentiated Are You?

Your position in the market and your differentiation from other competitors has a significant impact on how to approach your cold email outreach.

Even if you sell into larger markets with smaller deal sizes, you’ll struggle to convert if you can’t differentiate yourself.

This scenario is especially true for highly-competitive markets that have 5-10 companies with similar solutions or messaging.

Whereas, you can do more scale, spend less time on personalization, and still generate good results if you have something unique to share about your brand.

To stay competitive, you should regularly reflect on how competitors or alternative solutions present to potential buyers and where you fit into the marketplace.

Time Limitations for Personalizing Emails

Regardless of your situation, one of the biggest variables behind your personalization strategy is the amount of time your team has available to research and personalize cold emails.

Even with the right process, these constraints with team resources will limit your ability to personalize and partly dictate the time you can spend on each prospect.

For example, let’s say you’re going to send to 1,000 new prospects per month. Your team needs a process that can personalize at least 50 prospects per day to reach that volume.

If you have a good sales operations team or sales enablement solution, you can save time on acquiring data and focus on customizing, personalizing, and handling responses.

With no support, you have to do all of the research manually to get the data you need.

Once you’ve cracked the puzzle to personalization for your target buyers, you can shift to a higher volume as you become more efficient.

Set Goals for Cold Email Personalization

After reviewing research on your market, your positioning, and the time you have available, you need to decide on some goals that are realistic for your conversion rates.

The goals you set will guide your entire outreach strategy for cold email.

If you need 20 meetings every month, that will dictate the volume you need to reach based on the conversion rates you expect. How many sales leads do you need to reach in order to convert 20 meetings?

However, your goals also need to be realistic for the number of contactable leads you have available.

With a market size of 5,000, reaching out to 1,000 leads every month only gives you 5 months of runway until your company has to target new markets or re-engage existing accounts.

Ideally, you’ll bring your volume down over time by getting more efficient. The lower you can get your sales prospecting volume while maintaining conversion rates, the longer runway you’ll have to generate opportunities from your lead pool.

Just Getting Started with a Personalization Strategy for Cold Email? Here’s Darren’s Advice:

Follow the Data, Not Your Ego

It’s easy to take too much pride in your messaging. However, it’s a mistake to assume that your approach is going to be the best move for every situation.

If you haven’t emailed anyone, then it’s only an assumption.

The ultimate goal is to generate better results with your emails and ego can disrupt this mission. Instead, continuously test new approaches and don’t be afraid to test the ideas of others.

Consume as Many Sales Emails as You Can

Wherever you are in your journey, it’s invaluable to find access to sales emails so you can absorb and learn how cold email personalization is done successfully.

The best way to do this through a mentor who can show you what makes a good sales email. However, online research or reviewing emails with colleagues can offer similar insights.

Get Good at Writing

While it’s necessary, creative writing is often not taught enough in sales-type courses.

However, creative writing skills are essential for sales or marketing professionals today as conversations move from the phone to more writer-centric channels.

Writing is a skill you need to practice, especially for cold email. Consistently write on new topics and read the writing of other leaders to use as inspiration for your own content.