Definitive Outbound Email Guide: Part III

Who is this for?

1. This guide is best suited for B2B companies looking to send 1-10K monthly emails (50-500 / day).
2. This guide covers outbound cold emails. I'll be publishing separate guides covering transactional emails, marketing emails, product update emails, etc.
3. You can refer to each part atomically to debug wherever you have issues. I've helped 6 YC companies set up/fix their email stacks in the past 6 months. Want to open-source this information for the benefit of all founders.
4. This is the culmination of 120+ hours of research on this subject. I’ve tried to cover as many tools and questions posted on other forums.

Recap: If you've gone through Part I and Part II, you should have your cold emailing stack ready — dedicated cold emailing domains with Google Workspace setup, fully authenticated, and warmed up to start reaching new customers. You also have a system generating 100+ high-quality leads every day, segmenting and reaching out only to people who actually need your solution.

Now in this part, we'll investigate how to craft the perfect cold email. Let's dive right in.

Part III: Email Copywriting

What is a good cold email?

We're not in English Lit 101, and our goal isn't to sound like Shakespeare. No extra credits for grandiloquent prose. The only metric we'll be judged on is how many people are opening, clicking, and replying to our emails. This part of the outbound email guide will teach you how to transmute email addresses into revenue for your company.

A big part of this process is experimentation. The faster we cycle through different subject lines, openers, and hard/soft CTAs, the faster we converge on what works best with our target persona. 

I'll also share real-life examples of what worked well with our clients (and some that didn't).

Anatomy of an email

1. Subject
2. Greeting
3. Opener
4. Body
5. CTA
6. Sign off
7. Signature

We're using a star rating system to rank the relative importance of each lever. We'll start optimizing for the '⭐⭐⭐' levers first.

1. Subject Line (⭐⭐⭐)

The subject line of your B2B cold email is arguably the most critical component in determining whether your email gets opened or ignored.

A strong subject line piques the recipient's curiosity, creates a sense of urgency, and showcases the value they'll gain by opening the email.

Subject line best practices

1. Keep it short: 50 characters or fewer to ensure your subject line is fully visible on mobile devices.
2. Be clear and direct: Clearly state the purpose of your email to avoid confusion.
3. Ignore point 2: Sometimes, keeping things intentionally vague or quirky in the subject line can drive higher click-throughs. Follow up with a solid body to convert their attention into something tangible.
4. Use personalization: Include their name, company, or industry to establish a quick rapport.
5. Avoid spam triggers: Refrain from using all caps, excessive punctuation, or spammy phrases like "Free" or "Limited time offer."
6. Test and iterate: Continuously test different subject lines to find the most effective ones for your audience.

Subject line formulas and templates

1. Simple: [Your company] x [Prospect's company]
2. Simple: [First name] - quick question
3. Curiosity-driven: "[Prospect's name], have you heard about this new [industry trend]?"
4. Benefit-focused: "Boost your [business goal] by X% with this strategy."
5. Social proof: "[Competitor's name] is already using this solution - are you?"
6. Question-based: "Struggling with [pain point]? We can help."
7. Personal connection: "[Mutual connection] recommended I reach out to you"

I shared 13 best-performing subject lines in 2023 for B2B companies here. Make sure to check it out if you need more inspiration.

2. Greeting (⭐)

This is a low ROI variable to experiment with. We'll only work with this once other low-hanging fruits are all picked. Option 1 is good enough for 95% of cases. We can experiment with the more casual greeting if we're selling to early-stage businesses or a niche where excessive formality is frowned upon (think gen-z eCommerce brands). 

1. Hey John,
2. Hi John,
3. John,
4. John -- 
5. Dear Mr. John,
6. J,

3. Opener (⭐⭐)

The power of personalization

To ensure your email stands out in a crowded inbox, personalize your opening line by using the recipient's name and addressing their specific needs or pain points. Recall from part 2 of the cold email guide:

Personalization is the proof-of-work for outbound emails, making the reader feel there's a human on the other end. A mental model we've used with great success is to score each element we can personalize. Aim for a personalization score of 3+ for your opening paragraph. 

Let's consider the following:

2 points - I'm reaching out to software companies (+1 pt) in your niche who are looking to get a handle on their corporate spending (+1 pt).

vs

4 points - I'm reaching out to environmentally-conscious (+1) logistics companies (+1) in Long Beach (+1). We have launched a corporate spending card designed for early-stage businesses with less than 50 employees (+1).

In general, higher is better, but a score of 2 should be enough to start getting replies. At the bare minimum, we must add their first and company names somewhere in the email.

Cringe

Try experimenting with writing in a tone of voice you consider cringe-worthy. Being over-the-top, using too many exclamations, emojis, or borderline over-enthusiasm are all things we usually steer clear from, but sometimes work insanely well for specific niches. YMMV.

Proven opening line strategies

1. Justifier: "Reaching out because I [plausible reason]."
2. Common pain point: "I noticed that many [industry] companies struggle with [pain point], and I believe our solution can help."
3. Compliment: "I recently read your article on [topic] and was impressed by your insights."
4. Mutual connection: "[Mutual connection] mentioned that you're working on [project], and I thought our expertise could be of value."
5. News or event reference: "Congratulations on your recent funding round! I can only imagine the growth opportunities ahead."
6. Personalized observation: "Your company's focus on sustainability is inspiring, and we share a similar mission in helping businesses reduce their carbon footprint."
7. Responding: "Saw you're [hiring/posted a request/project]."

4. Body (⭐⭐)

Structuring your email content

The body of our B2B cold email needs to be clear, concise, and easy to digest. Do not hit your prospect with a wall of text that they will ignore. Do the work for them, and make your message as easy to consume as possible. Divide your content into short paragraphs or bullet points to improve readability. Focus on the following key elements:

1. Establish credibility: Briefly introduce your company, its expertise, and relevant achievements. Depending on your niche, experiment with name-dropping logos, marquee investors, etc.
2. Benefits, not features: Start with the pain point, amplify it, then describe how your product or service can remove your prospect's pain in one swoop.
3. Social proof, social proof, social proof: Pair every benefit with a demonstration of that benefit for a past client. Share testimonials, case studies, or success stories to build trust. Personalizing the case study to match your prospect closely has a very ROI here.

Formatting tips for better readability

1. Short > Long: Aim for 100-200 words to ensure your message is easily digestible.
2. Add white space: Include line breaks between paragraphs and bullet points to make your email visually appealing and easy to read.
3. Stick to 3 paragraphs: The body of the email shouldn't be longer than three paragraphs, with the middle paragraph doing the heavy lifting.
4. Utilize bullet points: If you find your benefits section denser than you'd like, use a bulleted list for better readability.
5. Emphasize important information: Use bold or italics to highlight critical points, but use them sparingly.
6. One exclamation point rule: Avoid exclamations in a sequence's first cold email. If you really must (trust me, you don't), use just one.

Value Prop + Social Proof

Trigger warning: horribly-written, spammy, cold emails

Consider this poorly written cold email that landed in my inbox yesterday. Nevermind the fact that Suggestr (YC W22) winded down over a year ago. It's addressed not to the CEO/founder, but to an 'info@' email. There's no personalization, and I strongly suspect this person gets close to zero actual leads from this.

You'll notice immediately how the email talks endlessly about what their product does and what services they provide without conveying that they understand the prospect at all. There's also a conspicuous lack of social proof, making me think they've never had a client worth talking about. 

Now instead, use this 1-2 punch comb everything you talk about a benefit of your product or service. Consider this cold email below from Bracket , also for Suggestr. It's hands-down one of the top cold emails I've seen. Vinesh also uses the cool tactic of putting a "Sent from my iPhone". I knew for a fact he didn't, but it made me smile. 😉

Which one builds more trust in your mind? You be the judge.

Images/GIFs

Lemlist is perhaps best known for its coffee cup with your name trick. These tricks are anti-inductive and stop working fast if your prospects have seen them before. I advise clients to be cautious about doing this. 

What can work well is if you can mail merge something personalized for the prospect. Think of an image of a part of their website that your product can improve, a personalized demo screen, etc. 

Short GIFs are a great way to showcase a product demo right in the email itself. 

Loom

For high-value accounts and prospects with some level of interest, having the founder record a 30-second Loom video is a high ROI tactic. These can be primarily scripted but should mention the person by name, their company, and one sentence on why the product is an excellent fit for them.

Spam Trigger Words

Avoid using words like "free", "urgent", "sale", etc. HubSpot has compiled a nice, short list of 394 spam words you should avoid in your cold emails.  

Links

Too many links will impact your email deliverability negatively. Don't include more than 2 links in your entire first email. This is including any links in your email signature.

5. CTA (⭐⭐⭐)

There's a whole spectrum of CTAs — from hard CTAs that aggressively ask for a meeting to very soft CTAs, which only ask for permission to send over information. Some ICPs are notorious for avoiding sales calls (I'm looking at you, devs 💻), so play around with softer conversion options like self-serve product tours. 

For my non-native English speakers, don't use the phrase 'catch up' for a cold prospect. The connotation is that one catches up with friends and acquaintances and not with random people trying to sell them products/services on the internet. 🫡

A non-exhaustive list of CTA in increasing order of hardness:

1. Can I send over some more information on this?
2. Can I tell you more?
3. Can I share some case studies where we helped companies like [social proof] to [achieve benefit]?
4. Can I send over a personalized proposal? 
5. Can I ask you a couple of questions about this?
6. Can you point me to the right person at [company] to speak about this?
7. I made a quick Loom/video for you. Let me know your thoughts.
8. Relevant? Lmk.
9. Can we speak for 15 min on this?
10. Are you free for a quick chat sometime next week?
11. Would love to have a quick chat. My calendar link is [link].
12. Let's have a catch-up on this. My calendar link is in my signature.

Number 12 above is a case-in-point of what NOT to do. 😬

6. Sign Off (⭐)

The sign-off is a great opportunity for placing a pattern interrupt (altering a person's mental, emotional, or behavioral state to jolt them) in an outbound email. Our aspirational goal is to get someone to chuckle. This is only a one-star variable because even if you get someone to smile at your sign-off but the rest of your email doesn't deliver, you won't be getting any replies. Just stick with basic, boring sign-offs until you have the rest of your email copy dialed in.

Proceed with caution if you're dealing with high ACV B2B accounts. The last thing you want is to lose an account because of a poorly landing sign-off. This stuff works better for early-stage/SMB/mid-market. Caveat emptor! Some sign-offs to seed your imagination:

1. Best,
2. Best regards,
3. Warm regards, (works better if it's winter for your prospect)
4. Cool regards, (works better if it's summer for your prospect)
5. GTG,
6. Byeeee,
7. Hakuna Matata!
8. Live Long and Prosper
9. Live, Laugh, Love
10. Apologies, 

7. Signature (⭐)

A professional email signature is essential to your B2B cold email, providing recipients with relevant contact information and establishing credibility. An effective signature should be clean, concise, and consistent with your brand. Types of email signatures:

• Minimalist: A minimalist email signature focuses on providing the most essential information, such as your name, title, and company. This signature type is ideal for selling to early-stage businesses since it doesn't come off as salesy. It's good to include at least one link to your company website somewhere in the email.

Aditya Mehta, Founder @ Cogito Group

– Aditya

• Branded: A branded email signature incorporates your company logo, colors, and font to create a cohesive brand experience. This type of signature helps to reinforce your brand identity and make a credible impression. Plane 's emails include a great example of this.

• Social: A social email signature includes links to your professional social media profiles, such as LinkedIn and Twitter, enabling recipients to connect with you and learn more about your expertise. Commonly used by solopreneurs or startup founders who are fundraising.

Email signature best practices

1. Use a professional font: Stick to a standard, easy-to-read font, such as Arial or Calibri, to maintain a professional appearance. So as far as possible, no Comic Sans. 🤢
2. Optimize for mobile devices: Ensure your signature is easily readable on mobile devices by using legible font size and avoiding large images or complex formatting.
3. Test across email clients: Verify that your signature appears correctly in various email clients, such as Gmail, Outlook, and Apple Mail.

In Conclusion

Congratulations! You are ready to blow up your calendar with more bookings and have a healthy revenue pipeline. 🎉

If you need help with any of the above steps, we’re just a click away. We’ve done this for multiple YC and non-YC companies, who’ve gone on to generate $110K+ in new revenue from outbound emails.

What’s Next?

We’ll be releasing (the last and final) part IV of this guide shortly, which will cover everything you need to know about setting up sequences and A/B testing.