How Do Sales Teams from High-Growth SaaS Companies Write Cold Emails?

Writing cold emails is easy. Anyone can do it. Writing cold emails that get results? Now that’s a lot more of a challenge. Sending effective cold emails—emails that get opened and drive sales—is a real skill. Judging by my inbox, it’s a skill that many are yet to master. 

If cold emails are giving you cold chills, don’t panic. Simply take a look at how the pros do it and learn from them. We’ve scoured the internet for the tips and tricks that the experts use to send cold emails and get results. 

Take a look through their advice and level up your cold email game. 

Jason Lemkin, CEO and co-founder of Echosign, founder of SaaStr

Jason Lemkin is a big believer in outbound, as long as you do it right:

Take a pause, and really find the 10 best potential prospects. Really find the right stakeholder. Find a way to either get warm intros into any of them, or at least, craft the best email — and subject line — that’s ever been crafted in the history of emailkind.

Tweak it, revise it, personalize it. Make it so great it’s the best elevator pitch — ever. Get 20 folks you trust to give you feedback on it. Make it an email all of them would buy just reading the email alone — even without ever talking to you, or seeing a demo, or anything else. Make the subject line alone so compelling, you’d almost buy based on that. We call this “account-based marketing” now, to some extent. Carefully, properly targeting your very best prospects.

If your product (x) solves a real problem 10x better than anything else, and (y) you get to the right decision makers with (z) the perfect and succinct pitch on how you are solving one of their top problems — it should work. Not every time. Not even very often. But if both are true — at least once, to start.

Scott Weiss, VC at Andreessen Horowitz

Scott Weiss believes cold email is one key way entrepreneurs can get their ideas into the right hands. When you share those ideas, great things can happen:

When my co-founder and I first had the idea for IronPort, an email security company, we triangulated a list of the 20 most relevant people in email – former CEOs, open source technologists, investors and thought leaders. After we had the target list, we got resourceful in getting to them – friends of friends, cold emails and FedExed letters. One of the tactics we used was trying to get a diagram of our technology into their hands — subject matter experts just couldn’t resist correcting our analysis. Here are the huge benefits with taking the “sharing” risk:

  • Fix your compass. The experts can immediately get into the weeds and help steer you around the potholes they went through and make sure you’re not headed for a cul-de-sac. The input we received proved essential to refining our idea and setting our order of battle. We gave a number of these experts equity grants to become formal advisors to the company.
  • First employees. Two of the people on our list became employees after we went through the idea with them. One had built PayPal’s email infrastructure and the other had built Newman, the massively scalable eGroups email engine. The experts typically know where the other best-in-the-world talents are currently working and can help you recruit them in with a credible intro.
  • Investors. Our friends and family seed round became a who’s who of people who had done interesting things in email. The PayPal founders, the eGroups founders and the Hotmail founders all ended up investing. You can imagine the warm VC intros we received from a massively credible angel investor right in their subject area strike zone. In fact, on more than one occasion, a VC would say, “I’d like for you to meet with so-and-so to better understand the technology.” I would reply, “Oh, so-and-so? They are already an advisor/investor…”

It’s really hard to break through the clutter and get the attention of the top investors as they typically only look at deals that come in from a warm, credible referral. There’s absolutely nothing more credible than getting an endorsement from a well-known subject matter expert who has already put their own money into your company.

Steli Efti, CEO and Co-founder of Close.io 

Steli Efti has written extensively about how to write effective cold emails. When it comes to cold email subject lines, an essential component for getting your email opened, here’s what he recommends:

  • Use their name in the subject line when it makes sense.
  • Make the subject line as specific as possible. The more personal the subject line, the higher the open rate.
  • If you wonder if it sounds too much like a “marketing email”, then it does sound too much like a marketing email.
  • Experiment with questions in subject lines.
  • Always deliver in your email what you promise in your subject line (if the disconnect is too big, you’re going to get good open rates but bad responses).

When it comes to writing the actual cold email copy, here’s his advice…

Be brief. Give context. End with a clear and specific call to action. Every sentence is sealing the value proposition of giving you a bit more of their time and reading the next sentence you wrote. (Remember: most email clients display not just the subject line in the inbox, but also the beginning of the email copy).

For cold emails to succeed, you can’t just send one and hope it’ll do the job. Here’s Steli’s formula for following up on your cold emails.

  1. Send out the first cold email.

  1. 1 day later, at a different time of the day: Follow-up 1

This email should be a modified version of your original email. It should communicate the same message, just in a different format. For example, if your initial email was several paragraphs long, make this follow-up email just two sentences long. If your initial cold email was just two sentences long, make this email several paragraphs long. Don’t write something completely different. Don’t add attachments.

  1. 2 days after your second email: Follow-up 2

Don’t even explain anything. Just succinctly restate your call to action. You can ask your prospect to introduce you to the right person in their organization, to schedule a call, or to respond to your email—whatever your desired call to action for your initial cold email was. For example, you could say, “Hey, when would be a good time for you to discuss this on a quick 10-minute call? How about Tuesday or Wednesday 10 a.m. Pacific?”

  1. 4 to 5 days after your third email: Follow-up 3

The break-up email. It’s an email in which you say goodbye to the prospect, betting on their loss aversion, a psychological principle describing people’s tendency to strongly prefer avoiding losses to acquiring gains.

Optionally, you can add another follow-up email before the break-up email, but I wouldn’t recommend following up more than four times[…] If you’ve had a positive interaction (be it an email, a phone call, or a meeting) with someone in which they showed interest in your solution but then stopped responding to your calls and email, keep following up indefinitely. Forever. Until you get a result. Either a yes or a no.

If you haven’t gotten any response to your cold email, stop at three to four follow-ups, and move on to more receptive prospects.

Finally, Steli recommends these two tactics to improve your cold email response rate:

Acknowledge their current reality: Write with candor to demonstrate you understand that they’re getting a ton of cold emails, it’s mostly BS, and they don’t read it.

Rise above the noise: Your pitch needs to stand out from the crowd. You can’t write the same thing everybody else writes and expect different results. Customize your pitch to their business and immediately establish credibility.

Max Altschuler, VP of Marketing at Outreach and Founder/CEO of Sales Hacker inc, and Jorge Soto, Head of Sales and Partnerships at Crowdcast.io

Personalization is often recommended as a way to make your cold emails stand out, but it’s easier said than done. Here’s how Max Altschuler and Jorge Soto recommend personalizing your cold emails with segmentation:

When you do segment your lists, try to find a common denominator or variable that a bunch of the companies on the list have in common. Bucket them together so you can send them a blast that will look personalized but isn’t.

The smaller your sales team is, the more ground you’ll want to cover, so try to find a larger common denominator.

Use the common denominator to do a few things when crafting messaging:

Break the ice or build a rapport.

For example, if you have a bunch of leads that are from Boston and the Patriots just won the Super Bowl, you start the email with “Congrats on the win! Must be a fun time to be in the city. It must be buzzing!” You can be fairly confident that it will resonate with the person on the other end and not offend anyone.

Value Proposition. They all have the same issue or pain point.

For example, the common denominator could be industry. It just so happens that almost every company in the taxi and limousine industry has the same big problem (maybe it’s drunk kids messing up their cars). Your product or service just so happens to solve that problem.

Honestly, that’s all you really need in a cold email. So it basically flows like, “Hey, you’re cool/I’m cool. Here’s how I think I can help you. Let’s chat.” One flick of the thumb on a smartphone to take action, tops.

Use your research to help you nail both those points in one message to as many companies at one time as you can. But don’t force it. Segment your lists using the common denominator, and then craft the message accordingly.

Trish Bertuzzi, Author of “The Sales Development Playbook” and CEO at The Bridge Group

For Trish Bertuzzi, successful sales emails have three key sections:

  • Opening. State your ultimate value statement clearly and concisely. All you need to do here is arouse curiosity.
  • Customization. Research your prospect and write a sentence that’s specifically about them or their company. “I read a press release that you added a west coast office;” “I enjoyed your tweet about;” “I saw that your company is currently;” etc.
  • Call-to-action. Insert a request. Examples: “Are you interested in doing a quick brainstorming session?” “Have you seen our most recent research on X?” etc.

The email can literally be three sentences. Open, customize, call to action. Direct, interesting, and requests a response.

Collin Stewart, Co-Founder and Co-CEO of Predictable Revenue

Collin Stewart has seven tactics he recommends for crafting an effective cold email:

  1. It’s not about cold emailing a decision maker and getting them to respond. Rather, when cold emailing a company, aim high in an attempt to get a referral down to the right person.  You’ll eventually get referred down to the right person.

  1. The goal is to get on the phone and book a meeting. If they email you back and their number is in their signature, pick up the phone and give them a call.

  1. Use the referral approach. Accept the fact that you’re most likely starting with the wrong contact to have a sales conversation with, but know that you need to use that initial connection to get a referral to the right person. When you’re emailing and asking for a referral, the person you’re reaching out to usually doesn’t care what you do—they’re mainly trying to figure out if you’re credible and worth passing on to their colleague.`

  1. Keep emails short and sweet. If you cold email people, they’re only going to give you a couple of seconds of their time. If your email is long and convoluted, you will most likely not get a response, or if you do, it will be a no. Be clear, be concise and add value.

  1. Have a clear CTA. Don’t confuse the reader with multiple calls to action. Be as clear and direct as possible. Remember you want them to act—so get to the point.

  1. Make the email easy to answer. Because of the nature of cold emailing, people won’t give you much time because they don’t actually know you. As a result, make it really easy for them to respond. The easier the question, the more likely it is that they’ll reply. Instead of large, open-ended questions, make them quick and easy: “Do you use analytics tools?” or “How many salespeople does your company have?”

  1. Make sure you follow up. Be their polite automatic reminder system. It might take 4-5 little emails back and forth to get the meeting, so make sure you remind people that you have emailed them.

Daniel Galvin, Director of Sales at Pipedrive

Daniel Galvin recommends taking a scientific approach to writing cold emails:

  • Have someone – maybe the marketing team – create versions of emails and include the subject line, body, and call to action.
  • Provide context as to why sales needs to adopt these emails – they’re there to help them get more deals. Their commitment is essential to get data and improve performance.
  • Ensure everyone has a tracking tool – one that tracks if an email gets opened, what links were clicked, and traces the call to action.
  • Depending on the size of your team, set a clear statistical goal and test until you reach that statistical significance.
  • Analyze if the results are better, worse or the same as before.
  • Try again with the next option – be exhaustive and intentional.

Getting buy-in from the sales team will allow you to see what is effective, compared to what you think is effective because you have many more data points.

Yes, cold emails can be challenging. It can be scary, especially when you’re staring at a blank screen. Still, if you take the time to learn from the best, if you follow the advice of the experts who’ve successfully used cold emails to drive sales, then you’ll be ahead of the competition. That way, you can stand out in your prospect’s inbox for all the right reasons. 

All ready to get started on your next cold email campaign? Airborne is a sales engagement platform designed specifically to help agencies reach out to leads with relevant messaging. Talk to an Airborne Specialist today to get access! 

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