In today’s episode of The Startup Chat, Steli and Hiten talk about sales and email automation. They lay out why sales automation could be a useful tool in your business and they give you some key tips for how to create great emails which get the outcome that you are looking for. Steli and Hiten also share their candid list of what not to do when creating your new email sequences.

Sales automation emails are aimed at supporting the sales team and sales process. But how can you be sure that the emails in your automation sequences, are geared towards the result that you are looking for? One of the most important points of email automation is ensuring that the copy within your emails is compelling enough to elicit a positive response. There is no ‘one size fits all’ when creating your sales automation email sequences. But there are a few success tips that we can all follow to have more success with our automated email sequences.

Tune into this week’s episode, of The Startup Chat to learn about the step by step actions to creating the kind of email sequences that crush it and how they can help the success of your business sales. Follow Steli and Hiten’s top tips to make your own email sequences, and learn how to stand out in a crowd, of all the bad emails, that your target market are receiving every day.

Time Stamped Show Notes:

00:49 The link between marketing and sales.

01:06 Introduction to automated emails.  

02:01 Automation and outbound prospecting for sales teams.

02:40 The benefit of the automation process.

05:07 The negative side of automation.

05:35 The good, the bad and the ugly of automation.

07:42 Steps to stand out from the ‘crappy’ email crowd.

09:50 What you must understand for successful automation.

10:10 How not have successful automation.

10:45 What to know about tools and templates.

3 Key Points:

  • The days of mediocre and even good email is dead, but great emails are alive because they are so rare.
  • Understand the environment in which you are competing, which is the inbox of your prospect.
  • Start manually first and then automate.


Steli Efti: Hey, everybody. This Steli Efti.


Hiten Shah: This is Hiten Shah, and today on The Startup Chat, we’re going to talk about, I think one of Steli’s favorite topics that I want to learn about a lot more, because I don’t do this right now at my companies, at least I don’t, is how to do basically email sequences when you’re doing outbound emailing for sales.


Steli Efti: Yeah, so this is a fascinating topic, and we’ll bang out some tips and try to give people a framework of how to think about this. But back in the … I think when it comes to email, marketing has always been, or in many other areas when it comes to technology in general, I feel like marketing is always kind of a little bit of a step ahead of sales. But sales is always following suit, falling behind on marketing. I know that I remember when marketing teams started to use drip emails, started to use automated emails that were personalized, depending on a person’s life cycle in the marketing funnel, or depending on their life cycle as a customer or as a user of a product. So you would set up this drip email system from a marketing perspective, and then if I as a user or as a trial user, if I visited the pricing page multiple times, you would fire off a personalized and customized email that responds to that. Or if I stop logging into the product, you might fire off another customized and personalized email that says, “Hey, we haven’t seen you around in a while. Maybe either you should watch this tutorial, or maybe we should jump on a quick demo call,” or whatever, and just use logged scale customization in an automated way, and that was kind of a brilliant trend. We might do an episode on that, specifically. Recently over the last few years, that has spilled over to the way that sales teams do outbound email prospecting. Because it used to work like this, where a sales rep, when they were doing outbound sales, a lot of sales reps would, or a sales teams would build SDR teams. And SDR teams, what they would do is, they would do a lot of manual labor of researching leads, researching their email address, and then sending them an email to try to get them to agree to a demo or an exploratory call. And then many times they would realize that one email is just not enough, because timing is of such significance. So they would create a system of going back to the same lead, and emailing them, usually six to eight times, to get them to agree or respond and start a conversation. And that’s obviously insanely labor intense, right, if you have to do this with hundreds and hundreds of new leads every month, and you have to send every lead eight emails, have to remember all that. It’s a super manual and labor intense process. And very, very repetitive. And so we started seeing the introduction of email sequences, or sales automation tools, quote, unquote, that basically mean that now, many sales people, many sales teams, what they’ll do is, they will use a piece of software that allows them to define that sequence. Say, “Hey I wanna write these eight emails to a cold prospect.” Then upload a list of leads every day, and then fire off that sequence. That sequence now is fully automated, so the prospect gets email number one on day one, and then on day three gets email number two, and then on day seven gets the email number four, and the sequence runs though automatically until the prospect replies. And the moment the prospect replies usually, the automated part of the sequence stops, and now you as a rep can start engaging with the prospect. Doesn’t matter if they say, “Not interested, please unsubscribe me,” or if they say, “Yes, I wanna schedule a call, let’s jump on it,” or if they just send you some kind of a question, “How do you guys do, X Y Z?” The automated part stops at that moment, and now a real salesperson or an SDR can engage with the prospect, and explore if they should buy or not. That is obviously, when it was first introduced became such a massive success, because it empowered sales reps and sales teams to be so much more productive, that it has exploded. So today there is hundreds and hundreds of these email sequence tools out there that people can purchase, and especially in technology and in start ups, almost every sales team today, that’s doing op-on sales is using this type of software methodology to do op-on prospecting.


Hiten Shah: Oh man, you couldn’t have said it better. There are hundreds of tools to help you do this, and they have just cropped up in literally the last two years. And it is absolutely ridiculous, how many emails I get that are so fucking shitty, Steli, so before we’re done with this, I need you to tell me, “How do I write good outbound email.” I get the sequencing, I get that these fucking tools exist, and they make it easier for me to spam other people. I get that I could get the list too, in some of these tools, so hey, everything’s easy, but now I get more email. And if I’m doing outbound, I don’t wanna send shitty email, what do I do?


Steli Efti: So, I think that, that’s a really important part, because I think step one is, the good news is, the tools are there today and it’s easy. Right? That’s the good news. So even if you are, if you’re a one person sales team, if you’re a one single founder, you could be sending hundreds of emails, send multiple followups, and you could automate the entire process. So you could act as if you had a big sales team. That’s kind of awesome, right? The flip side of that is what you just said, which is, and trust me, there’s very few people getting more shitty emails than me, because a lot of people, a lot of people, send me sales emails. On top of it, a lot of people send me their sales emails to get feedback from me about their sales emails. So I get a ton of cold emails, every single day. I think so the flip side is, because it’s so easy to automate and to scale your outbound email efforts, people take their shitty email, and they just automate it and scale it. So there’s the danger that you’re gonna take something that isn’t working or shouldn’t work, and you’re just gonna amplify it, which is a problem, right? You take something that doesn’t work and you amplify it, you’re gonna create a lot more negative noise, and negative consequences for you, and on top of that, it’s not just you now doing this, so now because everybody can scale, and automate, and amplify, you’re in a much noisier, you’ve created a much noisier environment. So now everyone’s, every prospects inbox is a lot more full with shitty cold emails, because all your competitors are also using these tools to send a lot more emails to these people. So I think the flip side is that, or the solution to this is, we’ve talked about this many times in other email related episodes, the days of mediocre or even good email are dead, but great emails are more well and alive than ever before, because they’re so rare. So I think that the way that you do great emails, great outbound emails, and you scale that, is that you first confirm and make sure, that the emails you have written, the templates you have, are truly great and stand out. How do you do that? Well number one is you don’t automate and, customize and scale immediately. You don’t do that in step number one. In step number one, you do write one email. You send it out manually. You see what the responses are. You adjust, you refine, and you improve. You talk to the people that respond to your emails, to get feedback on why they responded, what about your emails is great. You talk to the people that didn’t respond, you reach out to them to try to figure out, “Hey, I sent you an email, you ignored it. Just need two minutes to hear, what about my email sucked? What about it is not that great?” You spend time interviewing your customers, to not just hear about their needs from a product perspective, but also understand what their inbox looks like. “Hey, can you tell me, what kind of emails do you get every day? Why do you hate them? What are the good emails, what are the bad emails?” You need to understand the environment in which you compete in, which is the inbox of your prospects. And you work in the beginning, slower than you would like, on crafting, improving, and editing a great email. An email that truly is awesome. Once you have that and you have the messaging right, you work on making sure that you don’t do high quantity, but you do high quality in terms of the people you’re sending these messages to. You make sure that, these are very, very good high quality lists, where the chances are high that the persons receiving the email from you, wants to hear from you. There’s a high probability that they will need your service or product, and that they’re the right fit. So, you do those two things. You look at the result, and you see that a lot of people open your message, and a lot of people respond to your message in a positive way. That’s the moment where now you can use the power of these email sequencing tools to really scale up something that’s worth scaling, something that’s worth automating. You have to do the heavy lifting, the hard, slow, patient work in the beginning, of working on both your understanding of who you’re trying to reach, and narrowing down your niche and your ideal customer profile, and the messaging, like what is truly a message that will stand out for all the right reasons. And there’s no shortcut for that shit. I can tell you how you’re not gonna get to these two things. You’re not gonna get to it by going to and downloading our email templates, and just copy and pasting those email templates into an email sequencing tool, and then going to, or or whatever the fuck, and buying 10,000 leads in some kind of a market. And then uploading those into an email sequencing system, and then hitting, start the campaign. That’s not how you’re gonna do that, right, that’s not gonna lead you to any great results, because so many people and so many teams are using emails sequences to prospect, inboxes have become so noisy, those templates that are being shared out there are so overused, so what you have to do is you have to slow down in the beginning, be patient, do things manually. Craft your messaging, define your niche and your customer better than your competitors. Once you get these two things right, then you use the power of email sequences tools to really scale up your efforts. I think that’s both my tip and my rant on this topic for today’s episode.


Hiten Shah: Thank you for ranting on it, I love it. Start manual and then automate, that’s the key.


Steli Efti: There you go.


Hiten Shah: And make sure manual is working before you automate, that’s so simple, I love it.


Steli Efti: Boom! Got a tip from us for this episode. We’ll hear you very soon.