Outbound sales email best practices in 2024

Tl;dr: If you wouldn’t say something out loud to them, it doesn’t belong in your email. Relevancy is key. Personalization is great, but don’t force it when you couldn’t do it thoughtfully. Show you did your homework. Keep reading for detailed advice on how to write email that works and balance time investment.

Background: I am Shen, a 2x founder, led sales in both and spent 1000+ hours writing cold emails and LinkedIn DMs. I still book 70-80% of qualified meetings from outbound today. 

Last year, I talked to 128 sales focused founders (50+ YC) and 300+ sales leaders about outbound sales and closely helped 40+ teams improve their processes. I noticed some common misconceptions around how to write emails and balancing relevancy/personalization with time investment. So I’m sharing my advice here in a blog. 

Should I ”relevantize" / personalize my emails?

In short, yes. 

One of the biggest mistakes I see founders and SDRs make is trying to be “efficient” by setting up generic email templates and blasting them off to 1,000 random people. Why this won’t work: 

1. Softwares like Apollo made this super simple and almost no cost to do, for everyone. Naturally, everyone has been doing it and the decision makers you’re after are default ignoring anything looking like automated spam. 

   Arguably, there are tricks with subject lines to make open rate look good, but it’s very easy to recognize automated emails in a skim. Most would archive or mark as spam before even thinking about your offer and make your reply rate miserable.

2. All email providers have implemented more aggressive spam filters in 2023, with Gmail and Yahoo announcing new spam policies. They quickly pick up on spam reports and detect automated emails. (even if you’re sending carefully-drafted emails, you should still buy separate domains to protect your main email reputation and refrain from sending more than 50-80 emails/day/mailbox)

How to write emails?

Key boxes to check (in order of importance): 

1. Sound relevant - why they should care

2. Show you did your homework

3. Conversational language, not salesy or robotic

What does sound relevant mean: It’s not enough to just talk about what your product does in general. Instead, you should make clear why they should care about it more than the other 50 cold emails they get, by ideally pointing out actual problems in their world you help with.

Tip #1: Research the prospect and form a good reason for why you believe you can help them. 

Common places to look:

1. LinkedIn posts and profile

2. Personal interviews/blogs/website

3. Job openings

4. News articles

5. Company website

6. Public filings like 10-k reports (public companies only)

Let’s look at three emails for what each of the three checkboxes mean: 

Email 1: “Mira - Saw you are the CTO of OpenAI. 

Many CTOs mention cloud deployment is frustrating as infrastructure scales.

I have a solution that makes it easy for engineers to: 

• Deploy to the cloud easily

• Implement complex logic with Python

• Effectively test infrastructure deployments

We have helped Snowflake engineers increase efficiency by 30%. Wanna chat?”

→

This email tries to sound relevant, but falls into the trap of “fake relevancy.” Many automated cold emails (including many AI-generated) look similar to this.

Trying to justify why you can help with generic and obvious facts like job titles comes off as ingenuine. It hurts your chances more than it helps. If you can’t find anything to justify why you think you can help them (other than job title), you probably shouldn’t reach out to them in the first place.

Note some exceptions apply here - for some products, it can be nearly impossible to find anything publicly to justify relevance. In which case, it’s often better to remove any “fake relevancy,” simply show you did your homework with thoughtful personalization, and jump into a concise value proposition and ask (see email 2 as an example).

Email 2: “Mira, Saw you also went to Dartmouth - I was Dartmouth 2017 and still miss my times of having beer pongs! 

It’s really exciting to see a fellow Dartmouth alum leading the next gen of AI. 

I have built a solution that makes infrastructure deployment and testing easy, and recently helped Snowflake increase efficiency by 30%. Would you be open to take a look?”

→

This email doesn’t justify the relevance of the offer - why they would need an infrastructure deployment product, but it does show you did your homework with thoughtful personalization. This makes the pitch sound more genuine, and you earn a good chance for them to actually think about if they need it. 

A few caveats to note here: 

1. Personalization is great IF you can find commonalities or things special about them to make it thoughtful. If you can't find anything on a personal level, don’t try to force personalization (e.g. I’ve seen a lot of people praising SF’s weather and it doesn’t help). 

   With AI softwares making bad personalization common, awkward personalization is no longer rare or appreciated. 

   A large YC company (didn’t ask for approval to disclose name) actually A/B tested asking their SDRs to personalize when there is nothing good to say, and saw basically no difference in conversions compared to no personalization. 

2. If your value add isn’t obvious or simple, they likely won’t bother to do much thinking over “does this connect to any of my problems today.” 

   This is also why explaining the relevance directly is often key to response rate (even if your assumptions are a little off).

3. Don’t try to list out 5 different value props in three paragraphs and prey one of them resonates.

   The value proposition should be no more than 1 sentence, at max 2. People skim it in F-shape and won’t read this section word by word, so make sure every word counts and covers only the most important stuff you want to convey.

Email 3: “Mira - Saw OpenAI is hiring 3 infra engineers who know Terraform. 

Terraform code is tricky to write when implementation logic gets complex. As ChatGPT pleases 100M+ humans (myself included), I bet your infra is a complex piece of art. 

We helped Snowflake engineers develop 30% faster by using Python instead - can I share how?

--

PS. Do you ever miss beer pong times at Dartmouth? Cause I certainly do.”

→

This email is modified from a real one I helped a customer put together. This is a little longer than the ideal length, but usually fine when it’s relevant and personalized.

By starting with an observation of their recent hunt of Terraform talents, it shows you did your homework on how their world looks (working with Terraform and trying to improve infra). 

It sounds relevant by pointing out how you help with Terraform issues, saves them the thinking work, and shows your genuine interest in helping them. Even if you’re a little off with initial assumptions, it gives them incentives and ideas to seriously consider your offer.

Sound conversational, not salesy or robotic

A person is reading the email, and no one likes a desperate salesperson or robot (which most cold emails sound like). 

Tip #2: For founders or SDRs just starting outbound, you should manually write the first few emails from scratch, before trying to create templates for sections. 

It’s very common and tempting to do it the other way around - first create a bunch of templates, plug them into the email, and manually fill in only the opening/PS/key sentences. This way, you’d often sound robotic and weird without noticing it. 

Tip #3: If you wouldn’t say something out loud to them face-to-face, it doesn’t belong in your email. 

My secret trick: hold up your phone next to your ear and pretend you’re giving the person a phone call right now, then read out loud the email you wrote for them. Then change anything you feel “ah I wouldn’t say that”

Writing emails takes so much time

It’s completely normal and ok to spend 20-30 mins per email at the beginning. It feels unproductive when you have goals to hit. You will get better quickly and become faster at it. This process helps you figure out the best messaging and gives you better idea on who to go after.

Tip #4: Block off 2 hours daily to focus on outbound, and use a stopwatch to time yourself when writing each email. This keeps you motivated and you will notice the time spent going down as you get better.

You don’t have to always write every email from scratch. After manually writing a few of them, you will notice you repeating yourself in certain cases. You can then summarize and extract overlapping parts for future plug-and-use. Text Blaze is great for this purpose. 

(Shamelessly, Coldreach automates the research part so you can focus on drafting - it also drafts pretty neat emails as well, but I don’t recommend relying on any AI to take full control of your emails, especially when you’re starting out.) 

Some general recommendations: 

1. Shorter is better. <50 words ideally; It’s often ok to go up to 75 words if hyper relevant and personalized. But never go above 100 words (it’s harder than it sounds)  

2. 1-3 word subject line, lowercase

3. 5th grade language, extra points for humor

Email sequences:

1. No more than 4 emails in 2 weeks - The chance of getting marked as spam goes up significantly for 5 or more

2. Keep followup emails short and to the point

My personal email sequence: 

Step 1: Email, relevant and personalized (Day 1) 

Step 2: A relevant case study/success story (20-30 words) (Day 2)

Step 3: Very simple followup (this step looks like “Hey [[first_name]]- any thoughts? –Shen” for me and works like a charm) (Day 5)

Step 4: Simple breakup email, ideally personalized (25-40 words) (Day 8)

Consider mixing in LinkedIn steps or cold calling in-between, depending on where your audience is active. For us, LinkedIn works like a charm since sales leaders and founders love hanging out there.

Final thoughts

I hope this very long read helps you in your sales outreach and revenue growth. Outbound is hard but very rewarding to tackle!