How to Use Content in Prospecting Emails to Avoid the Cold Shoulder

As a Sales Development Representative, you know that cold emails are a necessary part of your job. You've sent thousands of "let's get on a call" messages to prospects — and lost count of how many times you've been ignored. Ouch. 

We feel you, sales reps.

"Let's get on a call" messages are spammy and impersonal. That's where email personalization comes in — specifically, using content to personalize your sales outreach. When you share valuable content that addresses your prospect's specific challenges, you transform cold outreach into warm conversations.

What is real email personalization in sales prospecting?

Meaningful email personalization goes beyond the basic [First Name] tag. It's strategically tailoring your message to address a prospect's specific challenges and goals. You're not blasting identical templates. You're crafting relevant messages that offer genuine value. When you demonstrate you've done your homework, you instantly cut through inbox noise and build credibility to actually start conversations.

Why people don't respond to outbound emails

Ask any decision-maker about their email inbox, and they'll tell you it's flooded. Even as the CEO of a seed-stage business, I get over 30 emails a day selling me lead gen services or outsourced developers. You can only imagine what the inbox of a VP of Engineering at a 1,000-person company looks like.

When you send impersonal emails about your product and ask for a meeting, you're making a request without providing any value.

Now why should they give their time to a total stranger?

I generally only respond to emails if:

1. There's a personal connection. This is out of your control; you can't have gone to the same school as all your prospects.
2. They give me something valuable at the right time. This is completely under your control and what we're going to focus on.

That's what Meera Kanani from the Bento team did for me recently when she shared content on fighting spammy in-app notifications. Our own self-serve onboarding notifications were top of mind, and she sent me a very helpful guide on how to think about them.

‎We practice what we preach at Letterdrop and use content in our cold emails too. I got a demo booked within minutes of sending this email where I sent them an article from our blog:

TLDR? You need to provide value before you make an ask. Otherwise, your cold emails will be moved to the trash (or even worse — the dreaded spam folder... shudders).

Create cold email sequences around targeted customer problems

Be honest — do you tend to spam everyone with the same email?

It may be the easy way out, but it also makes it look like you don't care about individual customers. No one wants to respond to a mass email.

You want to personalize emails, but you also need to send hundreds every week to hit your targets. Segmenting your prospects is a good way to personalize while still operating at scale. Think about a problem you're trying to solve and look for public sig nals that a person might face those problems. Segment your list by the problem and personalize those emails to address that specific pain point.

Use data from AI research, social media posts on LinkedIn, company blogs and websites, platforms like BuiltWith, new funding rounds, employee growth numbers, positions they're hiring for, etc, to identify problems.

Example 1: Using BuiltWith To Create Sequences

Letterdrop is a CMS for Webflow that brings it to parity with WordPress. We use BuiltWith to find companies that have sites on Webflow and email their Head of Marketing or Content.

Example 2: Sequence for People Who Started a New Job

We also have a sequence for when a Head of Content starts a new job.

We know they probably need to orient themselves at the new company and be successful. So we send them an email offering to help them think through a strategy for their first three months.

Generic outreach makes your customer feel like they're just another number you're trying to hit. A personal approach makes them feel that you've specifically thought of them and reached out because you want a two-way conversation.

Tailor your content to your sequences

You've got your sequence. Now it's time for content that educates your buyer and increases your response rate.

Talk to your marketing team and create thoughtful sales enablement content for every sequence to share with and help your prospect.

Example 1: Sharing Webflow Tutorials in an Email Sequence Targeting Companies that Use Webflow

For our Webflow sequence, our second sequenced email has a guide on adding dynamic tables to Webflow if we notice that they don't have one.

Example 2: Sharing a 90-Day Guide in an Email Sequence Target for Newly Hired Content Leads

We also created a 90-day guide for new Heads of Content. It's an actionable plan to get them that first win in their new role.

The response we received was overwhelmingly positive.

Since we started including content in outbound emails last month, our cold email response rate has increased by 4%. We're creating even more sequences with tailored sales enablement content to help our prospects do their jobs better and using that to start sales conversations.