How We Grew Our SaaS Startup to 100K ARR Using Cold Emails

Let's face it… most cold emails suck.

Cold outreach, whether through email or the phone, is one of the most difficult methods of communication. You have no relationship with your recipient and can’t receive cues to modify your approach.

Yet, it’s one of the cheapest ways to acquire your first customers as a startup.

If you’re in sales, a good chunk of your daily communications is through email. But most of your prospects will never respond because your emails are annoying, impersonal, or simply not in sight!

I decided to dig into some of my cold emails to create a summary of what I’ve learned after emailing over 1200 prospects over the summer.

One thing I should mention is that we took an aggressive spray-and-pray approach as a cheap and measurable way to do customer discovery while we were still building our product.

Our emails were also ice-cold — we did our own prospecting but didn’t include contact names and the majority of emails were sent to general inboxes.

Optimization > Personalization

Most so-called marketing gurus will tell you to spend most of your time personalizing your openers and appealing to your customer unique features. I disagree — most of your time should be spent testing.

Personalization is a great way to get someone’s attention, but as a startup with an early-stage product, our main objective was to test our messaging and discover early adopters as fast as possible.

We didn’t over-personalize our cold emails, but simply mentioned a few words that ‘felt personalized’. Mentioning the prospects’ competitors or acknowledging their product is one way to personalize without going into too much depth.

In some cases, we mentioned specific contacts or decision-makers at the company and this would increase our average reply rate by 5–10%.

Depending on your industry and target customer, your emails don’t always have to be hyper-personalized.

Most of our leads were also SMBs, so we had some confidence that a decision-maker would be seeing our emails even if we didn’t address them directly.

Always Track Emails & Follow-Ups

The important thing to remember is that cold outreach is a numbers game, and with a data-driven approach you can turn your emails into a repeatable (and somewhat predictable) sales channel.

The majority of your cold emails won’t receive a reply. If you’re not keeping track of open rates, replies, meeting rates, and follow-ups, then you’re wasting prospects.

You can use pretty much any CRM to manage your outbound communications. We use Hubspot Sales (yes, they have a free version) for automatic sequencing and tracking.

If you’re looking to execute quickly on a budget and without a CRM, you can use a tool like Woodpecker.

In our experience, most prospects reply after the 2nd and 3rd follow up, and diminishing returns came after 3 emails. We also thread all of our emails, so it’s likely that prospects are scrolling back to the original message when they receive a follow-up.

For leads that don’t reply after 2 follow-up emails, we create a reminder to try again in the next quarter.

Keep your open rate above 40%

You can easily optimize your open rate by tweaking your subject line. It doesn’t matter what’s in the contents of your email, if you have a decent subject line, you should be achieving 40%+ open rates.

If you’re not able to achieve a 40% open rate, the issue may have to do with your prospecting funnel or email deliverability.

To avoid having your emails marked as spam (by a human or the mailbox) keep your emails short and conversational. Also, be sure to include info such as the contact name or company.

85% of the US population are Gmail users, so it’s important to understand how Gmail decides the fate of your cold emails. Gmail uses over 500 different indicators to gauge the quality of your emails and they aggregate this data across all of their users to determine every senders’ email reputation.

Deliverability also varies by the email service you’re using. I don’t recommend using email marketing tools such as Mailchimp because your emails will likely end up in Gmail’s promotions inbox.

Using Hot Cognition

The oldest part of the human brain is known as the croc or reptile brain. Over thousands of years, our croc brains have developed into a fight or flight sensor that filters incoming messages to rapidly determine whether something is dangerous, docile, or interesting.

This part of our brains also control our immediate emotions, and it has a tendency to get bored fairly quickly.

Our croc brains work opposite to the neocortex, which is the part of our brains that handles complex thoughts and analyses. Given that it requires more energy and time to engage the neo-cortex with new ideas, the brain will always resort to its croc side before it tries to ‘think too hard’.

The croc is the part of the brain that assesses cold emails. Given that it takes 4 seconds to read the average email, your emails need to be novel and interesting enough for your prospect to hit ‘reply’.

Using your prospects’ immediate emotions to your advantage is known as hot-cognition. You don’t want the prospect to overthink, otherwise their brain will go to ‘flight’ mode instead of replying to your email.

Our best opener emails were no more than 4 sentences in length. That’s all we needed for prospects to reply.

Below I’ve included two separate intro emails we tested for a segment of our prospects. With a few minor tweaks, we were able to more than double our reply rate.

We also placed greater emphasis on addressing the prospect’s pains, as opposed to our own accomplishments and the customers we’ve acquired.

Social proof is great, but what prospects really want to know is why you’re emailing them.

When you place emphasis on the ‘why’, you’ll find yourself removing unnecessary fluff and writing more clearly.

Beer & Spirits Brands — Opener Template #1, 12% Reply Rate

Beer & Spirits Brands — Opener Template #2, 33% Reply Rate

Speak in Simple English

B2B and B2C are the same thing when it comes to direct emails. In the end, you’re communicating to humans — think B2H.

It’s a common mistake to sacrifice clarity in an effort to sound or appear more professional.

Don’t use jargon or be overly technical. Your goal is to open the dialogue without sounding scripted.

In her book best-selling book, Everybody Writes, Anne Handley created a list of common phrasing mistakes followed by their pro-clarity equivalents.

I regularly reference this list when I’m writing new emails.

Ways by which = Ways
Continues to be = Remains
In order to = to (especially at the beginning of a sentence)
Despite the fact = Although, though
At which time = When
In spite of = Despite
When it comes to = In, When
The majority = Most
A number of = Some, Few, Several, Various
When asked = Asked
The same level = As much
Centered around = Centered on
Try and = Try to [verb]
Utilize = Use, leverage

Closing Thoughts

• If you have a large pool of prospects, don’t spend too much time personalizing. Instead, focus on optimizing your emails with continuous testing. Your email analytics will guide you.
• Always follow-up. You can use tools like Hubspot, Zoho or WoodPecker to manage contacts and schedule follow ups.
• If your open rate is under 40%, there’s an issue with your prospecting or email deliverability.
• Keep your emails short and novel to induce a response. Target the crocodile brain and not the neo-cortex.
• Businesses are people too. Remove unnecessary jargon and speak like a human in your emails.