How to Write Emails That Convert

A note on strategy

Archetypes

There’s a strategy for optimizing your cold email open and response rates:

• Create 2-3 high-level archetypes of emails ahead of time.
• Then A/B test them on a portion of the target emails you’ve collected (~100 emails for each archetype is enough).
• Analyze data to see which email had the best reply rate and call booking rate.
• Then send the winning email to the rest of your list.

Here are two email archetypes. These sell a video tool that helps with meetings and team collaboration:

For each option, you want to create:

1. A thesis: The style and tone of the email you want to test. Make sure each thesis considers what sort of behaviour you’re trying to drive:
   1. “Humble and inquisitive” tone should drive a booked call from the prospect.
   2. “Educational and value-driven” tone should drive a click through to a helpful resource.
   3. “Straightforward and honest” tone could prompt a quick reply.
2. Subject options: At least 3 different subject lines. Then choose your favorite by surveying people on your team.
3. Body copy: The contents of the email.

Consider sending emails from your founder

You should also consider the “who” behind your email. Are your emails coming from sales reps? Or your founder?

We’ve found that emails from founders drive action more than those coming from sales reps. Consider setting up a derivative user account like founder@e.domain.com so that anyone on your team can send cold emails that look like they’re coming from your founder.

Now on to creating great body emails.

Personas

To write great emails, you need to understand who you’re writing to. Luckily, you’ve done a lot of the hard work earlier in finding the right people to talk to.

Now it’s time to dig in and create customer personas. Here’s what you’ll want to know about your prospect:

• Job title.
• Company size.
• Company location.
• What unique challenge they’re facing.
• What stage of the buyer’s journey they’re at.
• What objections they’ll have that will keep them from buying.
• Who the ultimate decision maker is, if it’s not them.
• What technology they use

If you haven’t already interviewed your best 10-50 customers, do that before you craft your emails.

Use this information to craft compelling subject lines and body copy.

Say your prospect is the owner of a small business with 10 employees and they need more clients. You could write the subject, “I’ll help you land five more clients this month” and create body copy that proves that you did your homework.

Subject line

Subject lines (paired with your domain name) dictate your open rate.

Important: Emails should be measured not just by open rate, but by completion rate on the desired behavior. Vague or baity subject lines often perform well in terms of open rate yet fail in terms of conversion. Lower open rates with strong conversion are more optimal.

Optimize for designed completion rate, not just open rate.

Subject line needs to be:

• Informal: This shouldn’t feel like a typical cold email. You want to distinguish yourself from the mass of spam that your prospects get in their inboxes each day.
• Concise: Stick with 50 characters or less so that you also optimize for mobile. Long subject lines are cut off in most ISPs (like Gmail) on mobile.
• Self-evident: We’ve found that self-evident subjects convert best because prospects generally don’t like guessing what your email is about. But it’s worth testing slightly opaque subjects if they include sharp hooks and get people to open and convert.

Subjects need to be relevant to a problem that the reader is currently facing. We suggest following the guidelines above to start. Then iterate on the versions that resonate with your audience. Break the rules and see if your open rates and completion rates are rising.

Good subject lines:

• “Love your work—want to feature you in one of our guides”
• “A creative way to engage students and employers”
• “Seeking advice on [relevant subject]”
• “[Mutual connection] thought we should connect”
• “Advice on making SAAS spending more visible”
• “Controlling SaaS Spend”
• “A Free Facility Management Platform”
• “Trending WFH Benefits”

Bad subject lines:

• “Request to connect”
• “A better way to improve your ROI”
• “Let’s hop on the phone”
• “Check this out”
• “Are you prepared to overcome X?”
• “URGENT”
• “Quick question”

Body copy

Subject lines get people to open, but it’s the body content of the email that will get you replies and booked meetings.

Body copy should do a few things:

1. Hook the reader
2. Explain why you’re reaching out
3. Predict target customers’ hesitations and objections
4. Include a personal touch
5. Include one clear next step

Most importantly, be concise. Try to avoid writing more than 2 sentences per paragraph, and we’ve found that emails with less than 5 sentences perform best.

Long emails get skimmed. Keep it short and there’s a better chance prospects will read it.

Hook the reader

The first sentence means everything—it determines whether or not the target will read the rest of your email.

Here are three ways you can hook readers with your first line:

1. Ask a question to pique interest: Hey {{first.name}}—curious if you have to log into a bunch of different places to manage {{company}}’s health insurance, 401K, FSA / HSA, and other benefits?
2. Address a pain point: Hey {{first.name}}—I noticed you work with 6 different vendors to manage {{company}}’s adtech. We can help you manage them all in a single system, if you’re interested.
3. Demonstrate clear value: Hey {{first.name}}—want to run something by you that can help you complete {{insert SaaS thing}} in 2-3 days, instead of 2-3 weeks.

Once you’ve hooked them, win them over within a sentence or two.

Indicate why you’re reaching out

When you send an email to someone who’s never heard of you before, it’s important to explain why you’re reaching out.

One way to accomplish this is to show the reader that you value what they value:

• I was on your personal site and loved what you wrote about X.
• Just saw your tweet about Y and it made me realize that you’re interested in [the thing you offer].
• I listened to your podcast interview about Z and I had a follow up question.
• I was on a call with [person they know] and we thought you’d be interested in this.
• Saw you're working on X problem. I’m also working to improve X.
• I saw you were in the last YC batch and figured I’d reach out. We were in S19.
• Love the idea behind building a more sustainable and eco-friendly business to improve the world's wastage.
• XYZ stood out while I was browsing through Instagram and I was so impressed I wanted to reach out.

Brainstorm 2-3 excuses to cold email individuals. Why would someone in your position, representing your company, reach out to a specific person?

But avoid coming off as salesy. Avoid things like:

• I see you’re a sales professional. Me too.
• Given that we both work at agencies, I thought we should connect.
• I just messaged you on LinkedIn, so I figured I should also email you.

This is where you research the person you’re emailing. Look at their LinkedIn profile, Facebook profile, personal site, Medium posts, etc. The more you know about them, the better you can tailor your message.

If you’re strapped for time, there are virtual assistants that research and write intro sentences for emails for around $1 USD/per intro—and they’re high quality.

Objection handling

Each of your prospects will come armed with objections depending on their stage of the buyer’s journey. You should be aware of all possible objections, and have calculated ways in which you handle them proactively:

Objection: Say your prospects continually fail to convert because they think your product will cost them too much.

Handling: Subtly indicate that your product either doesn’t cost more than competitors or that your product solves their problem in a better way.

Objection: Or say your prospects drop out of the funnel because they think that it would take too much time to learn about and integrate your product.

Handling: Concisely explain that your product has a short learning curve, and that integration is seamless.

This is why you surveyed customers earlier: You learned about their key objections and now you can repurpose them in cold emails.

Your prospect’s default is to assume that your product is not right for them. You have to proactively prove that it is.

Make sure you only preemptively handle your biggest objections in cold outreach:

• List your objections in order of severity—which came up most in your surveys?
• Handle the top one or two objections in your emails—only the most obvious ones.
• Leave out anything trivial—you don’t want to raise awareness to objections that customers didn’t even know they had.

Lastly, consider using social proof as your objection handling. Most companies won’t know who you are, so their first and biggest subconscious objection will be that they don’t trust you. Social proof can help targets trust you, quickly. A few social proof ideas to test:

• Indicate which competitors you’re already working with.
• Include a one-line testimonial.
• Highlight any relevant names or companies that speak highly of your brand.
• If you’re seeking an investment with your email, consider including your other investors.

Personal touch

At some point in your body copy, add a personal touch to indicate to your prospect that you’re not spraying and praying—that you took the time to learn about them.

You can take one of two approaches:

1. Keep it relevant to work: Signal to the prospect that they’re uniquely fit for your solution.
   1. Since I saw that you invest in startups in addition to your role at Demand Curve, I thought you’d like this.
   2. P.S. we’re in the X Slack group together. Loved your post on referral programs.
   3. We met back at SXSW in 2018. Really enjoyed our chat about XYZ. Glad you’re doing well!
2. Get personal: Connect through a personal note that’s unrelated to work. You might build trust with your prospect. Then they’ll be more likely to buy from you.
   1. BTW, saw you played soccer in college. I played at URI. You still playing these days?
   2. One more thing. I saw on your personal site that you make music. I love music, myself. Actually listened to (name of their song) on spotify. Loved it!
   3. [Mutual friend] mentioned you live in SOMA. Even if this isn’t a fit, let’s grab a coffee one of these days!
   4. On a personal note, I see you’re working with Big Brothers Big Sisters. I volunteer with them myself—one of my favorite projects.
   5. P.S. really liked your blog post on climbing Kilimanjaro. Any adventures on the horizon for this year?

An addition to signaling that you did your homework before reaching out, consider asking a question to show genuine interest:

E.g. I read your blog post on X. How did you think of that topic?

Do things that demonstrate that your email isn’t automated, and you’re more likely to get responses.

Tip: You’ll likely have a few critical prospects that require extra personalization. Check to see if your prospects have social media accounts (Twitter and LinkedIn). Spend a few minutes on their timeline and get a rough idea about what they’re interested in. Then add a subtle note leaning into an interest of theirs. There’s a high ROI when you take 10-15 minutes to add a meaningful note for your key prospects.

Pick one CTA

Only include one call to action—the next step your prospect should take after they read your email. It should feel natural.

You want a next step that is low enough investment so they don’t feel like they’re rushing into a decision, but compelling enough that they understand how it will help them solve their problems.

Some examples:

Legal disclaimer‌

When you send cold emails, make sure you comply with CAN-SPAM rules, which govern cold emailing in the United States.

(Complying with CAN-SPAM tends to hurt conversion, since it makes cold emails follow a similar format and people will instinctively screen them out. In particular, having an “opt-out” link immediately makes your email look like spam and can drastically hurt conversion.)

Consult a lawyer if you want definite legal advice (we can’t offer it), but they may recommend following these guidelines at a minimum:

• Don’t use false or misleading header information
• Don’t use deceptive subject lines
• Tell recipients where you’re located with a physical address (this information can go in your email signature)
• Tell recipients how to opt-out of receiving future email from you.
  • This doesn’t have to be a link. It can be a line in the email asking them to reply to you directly if they don’t want any more emails from you.
• Honor opt-out requests promptly.