37 min read

How To Automate Outreach Emails: 7 Things I Learned from Vukasin Vukosavljevic

A few weeks ago I was fortunate to sit down and talk to one of the most knowlegable folks on cold outreach automation, Vukasin Vukosavljevic. We discussed:

  • The four steps to building a cold email outreach campaign from scratch, including how to research and organize your audience,
  • what to have in place to maximize deliverability,
  • where and how to find emails of your prospect, and;
  • what to write in your copy and how to follow up.

Key resources mentioned:

This is a hefty episode. Listen to the interview or read the show notes below.

Lessons On Email Outreach Automation

Why Automate Cold Email Outreach?

Vuk: I think it can be summed up in one sentence. “Because you’re one message away from …”

  • Your next customer.
  • Meeting with somebody you respect or want to learn from.
  • A good content collaboration.

Everybody has a LinkedIn, and even more people are getting a Tik Tok but everybody has an email and that doesn’t cost a lot and doesn’t require reinventing the wheel.

It requires just your good research and the ability to approach another human being as a human. It’s a great way to get in touch with anybody you like.

Who should not send cold outreach emails?

Vuk: it probably depends on different businesses and different industries.

I think B2C is not as enthusiastic about email because I’m not gonna send you an email, “Hey, I got this great new microphone you can buy or some great nutritional product”.

There’s always a case that email as a channel can be used, but they use emails in different ways. It’s not outreach.

Another thing that I would say is you always wanna personalize outreach more than you wanna automate. Right, because automating the boring stuff is great. You can have more time for the things that matter, which is making sure you have a legitimate interest in approaching somebody and doing it in a personalized and relevant way.

You don’t want to automate for the sake of automating and just you know, click a button, reach thousands of people and see confetti and enjoy success. It’s not going to work that way.

Related Tools: Use Personalisation to Create High Converting Landing Pages

Where to start with outreach automation?

Vuk: You have to make this thought in your mind that this is going to be successful and I’m going to be successful no matter how long it takes.

1. Decide You Are Going To Make it Work

So, I think it’s a decision you make in mind. Like, it is going to work. It’s just a matter of time and if you have any doubts, I come back to the game plan.

2. Research Your Target Properly

Like I said before, outreach is not going to be about automating. It’s not about copy-pasting the templates that work for somebody else. It’s not going to be about having a silver bullet that’s going to help you grow your business in a week. Anybody who says it will, I honestly don’t trust them.

Number one is having done your research in the right way.

51% of success in my mind when it comes to outreach, comes from research.

How well do you know your audience? Are there qualified? Do you understand their buying signals that you can leverage?

What you’re really looking to do here is validate the target of the email so target the position or the persona, if you will and also the psychology of the things that that person is interested in.

For example, if I want to sell lemlist to somebody, there are a couple of things I can do to research.

First, go to the SaaS communities where startups and entrepreneurs are and understand their pain points. Then I can use those pain points to tell me who is the right person to reach out to and how I’m going to write the copy.

Another example. I can visit the job ads of a company that’s hiring more SDRs or a new VP of sales and I can make an assumption that the new VP of sales will probably implement some new processes in that company. Or that hiring more SDRs means that they’re investing in sales and that they need an outbound tool.

If I know the goal of the company and if I combine it with a little bit of research on LinkedIn, for example, then I can gather all the necessary detail. This will tell me, yes, this is the right person to go to and this is how I want to write my copy. Then you have the tough part done.

But most people feel like research is boring.

You know, it’s just seeing their posts on LinkedIn and writing, “Hey, what a great post about… whatever”, and it is fake flattering.

It’s like approaching somebody at the bar and complimenting them on something but you don’t really mean it. You have to mean it.

I want to start the conversation.

And so the more people feel like it’s an authentic conversation because the goal you want to achieve is to get a reply.

3. Maximize Your Email Deliverability

Step number two is making sure you have maximum email deliverability. It’s a topic we can discuss later, but email deliverability is the key.

Land in the primary tab and not to spam or promotions.

And there are different techniques that you want to do to protect your domain and to ensure that your emails are actually being opened and read and eventually, so you want to have that always in check.

4. Find Emails

Get their professional email address, not their personal one. Super important.

5. Write The Copy

And then finally you come to the most exciting stuff for most people, which is writing the email. Ask yourself:

  1. What’s my subject line?
  2. How do I write my icebreaker?
  3. How do I personalize my intro line?
  4. How do I transition?
  5. Am I going to use some cool personalized images?

The thing with this copy is making it A) personalized and B) relevant.

You need to have those two boxes ticked because the prospect needs to feel like you can understand them.

They need to relate to what you’re saying so it needs to be relevant.

You need to build some credibility in their eyes and you want to make them feel like they want to reply and find out more.

6. Follow Up

Inevitably when the person doesn’t reply, it doesn’t mean that they’re not interested. Sometimes we’re busy or sometimes we read the email at the wrong time of the day. So, having a good follow-up strategy and having a few follow-ups is also a good way to boost that reply rates.

Detailed Outreach Execution Guide

Why Do Email Outreach Research 

What’s the pain that they’re feeling or the challenge they’re facing? Is your offering solving this?

That’s what it’s called in GDPR, a legitimate interest. But this also means – you can’t sell the unsellable.

That’s why, like if you just upload and don’t qualify your audience, you’re sending something to people who maybe don’t need it and you haven’t even checked it.

So, the reason why you want to do that are all the things you said, plus you want to figure out how do you add value to that person, especially in the SaaS world. Like if I’m going to sell lemlist you need to be able to grow your business by using lelmlist and you need to do this over a period of time.

You win and then we win as a company and figuring out all those things you can only do with a solid research and research doesn’t have to last for hours and days and weeks, but it can’t last five minutes either.

Places to Research

Benjamin: Got it, makes sense. In terms of doing the research. I think the easiest tool off the top of my head would be something like LinkedIn Sales Navigator or looking around and Slack groups, but did you have any other tips on where people could go to find out more information about their targets or their psychology?

Vuk: Yeah, I think sales navigator, for sure and even free LinkedIn search is solid. Not as powerful as the navigator, but still really good, especially for B2B and I think like your audience and your industry will dictate where you go.

So, for us, like I said, the community is Facebook is about communities and groups. So, every group has that internal search filter so you can go to say SaaS growth hacks or whatever community, like that’s, you know, relevant to your people and just search things.

So, I can search like cold email, email outreach, and availability, and then I can filter and range different posts of the members and I can qualify them.

Their engagement on social media, whatever their social media is, can tell you a lot of things and I think things like buying signals.

So, if a company raised some money, you can set up Google alerts.

If you want basic stuff like it’s free to do, or you can just do a little bit of researching on the search engines themselves, or if you need the inspiration for the copy and not particular prospect, you can always go to things like, I don’t know, on top of my mind, like Reddit so you can understand what are the problems, you know, typical problems of the audience.

You might not have a specific detail on one prospect, but you can have on a segment and then that will help you create a compelling copy but, in any case, LinkedIn and any social media communities, those are always good resources and of course, company websites, like I said, their job ads, I think job ads is an underrated stuff.

You know, like job ads, it’s only used for people to apply, but the job ads will tell you a lot of things and many, many companies, especially startups are trying to differentiate themselves in their job ads. They’re being more transfer about things to attract your audience, because there’s a lot of supply when it comes to jobs so a job ad can reveal a lot of interesting things. 

Benjamin: Yeah. It definitely makes a lot of sense. The job ads, if you have to write a lot of them, all of a sudden you start wanting to cut to the chase really quickly in terms of what problems you’re trying to solve and what’s on your mind. 

Vuk: Yeah, exactly and even if you’re going to approach, I know we were building our webinars and inviting sales and the growth experts. So, you’re going to listen to the podcast they did in the past and you can leverage that as well to create a cool, personalized invitation.

So, anything they did online and it can be leveraged to personalize that copy and to send an email that you’re going to get the reply from.

How to Ensure Email Deliverability

Benjamin: Yeah. Fantastic. Cool. So, the second step was making sure that you had everything in place to ensure deliverability.

I think this is a temptation for people to sort of switch off at this point cause deliverability is often very painful.

Did you have any tips here or suggestions for things that people had to really get in place and make sure we’re all correct?

Vuk: Yeah, I think I can, later I can send you the link I had, like this step-by-step guide, like an article that anybody can leverage, whatever the tool they’re using.

Being a person who did everything with email, honestly like from burning my domain from getting blacklisted in the past to now taking good care of final vulnerability, I think gives me enough for the ability, if you will, to speak about this topic and I feel like email deliverability is a technical and can be a bit complex depending on where you’re at.

Why Use An Email Warmup Tool?

So, I think the number one step is always to audit your current situation. So where are you at right now? And there are tools that can help you give that one of such things can be the warm-up stuff.

So, as you know, the, the email warmup is the process of getting your email domain ready to send outreach campaigns.

Okay and so lemlist has, which is in full transparency, the first tool ever built for this and there are plenty of other tools that built in the meantime and in any case, the thing here is like, you can take it as an analogy from athlete.

The tool mentioned: lemwarm to warm up your email deliverability

Like they warm up before a game, so their muscles are in a good format for a training or a game, it’s the same thing for the email and you need to warm it up so you can get it ready to send campaigns and then an interesting thing that some people do is once they warm it up, they stop it and you don’t want to do that because it’s the, again, it’s the same thing, analogy from a sporting world.

Like it’s like going through the gym and getting your body in the right shape and then you stop and the muscle will go away. They won’t stay. It’s not the way it works. It would be great that it works, but it don’t. It doesn’t keeping your warmup on forever.

Should You Use a Second Domain For Emailing?

Just adapting the strategy is something that will keep your email durability maximized, but besides warmup, you also want to avoid some basic things like you don’t want to buy a domain before checking the history of the domain first.

If that domain was exchanged by a few spammers and you buy something, you die.

There’s no going back from that point and the things like if you work in a big team versus working in a small team, there’s a decision whether we want to have a separate domain for outreach and not, you know, get our primary domain, our main domain in trouble and it’s a good idea to have a second domain for outreach in general.

We have it, as soon as we start hiring more salespeople and the more marketing. You just, it’s very, very difficult to have one domain and the amount of emails and the everything involved.

You just want to have this extra level of security so my suggestion would behave like a separate domain, but to do it right, like create a domain that’s connected to the redirects.

So, they’ve had people type, I don’t know, lemlist.co, it will go to lemlist.com, things like that. So, you don’t lose people because they think your second domain is fishy or spammy and the third component that’s really important is the amount of emails that you send and the tool that you decide to use for a job.

Use a Dedicated Email Outreach Tool

Like there’s a theme a world that’s like a concept of email marketing and the concept of email outreach and the same way you never want to use lemlist to send your newsletter. You never want to use MailChimp to send outreach campaigns and both tools tell you that in there, you know, during their copy on their demos or so choosing the right tool for the job it’s because sending algorithms are different, like lemlist, for example, the unique thing about that algorithm is sends emails one after the other, and never as a blast, which is something that the email providers don’t want to see.

Another thing is the fact that this algorithm gives you your own server, so you don’t share a server with anybody else and you and you alone responsible for maintaining a clean reputation.

How Many Automated Cold Emails Should You Send Per Week?

And then finally, I would say the amount of emails that you sent, like, I always encourage people not to send more than 200 emails per campaign a week.

Some people I met in the past said like that’s too little, like 200 emails. It’s better to send the 2000 emails and get 10% reply rate here than 10% reply rate to 200.

But the fact that you’re sending 200 emails a week gives you enough time to do the research trial and to personalize the email in the right way.

So, at the end of the day, the goal is not to send as many emails, you know, be the fastest to send them, but to be the one who gets the biggest reply and the biggest conversion rate at the end of the day. In my outreach game and now Twitch game of my colleagues and a lot of longest users, it’s much better to send less, but convert more than the other ones.

So those aspects of email, deliverability are things you have to consider. You also have some additional stuff that I’ll send you this in the article, like custom tracking domain for measuring opens and clicks in the right way and there’s an interesting graph that the user shared them Twitter once. So, before and after sending a custom tracking domain, without it, a lot of emails went to spam from the day the person changed it because everything else was more or less in order that situation can completely changed and lemwarm gives you these reports to see where your Invisalign and email are going to the primary tab. So, it’s just something you have to go through for me to stop talking on this, but you just have to do the technical things right. You want to have your car legit, so you can get from point A to B and not land on a two.

What if you don’t use a warm up tool?

Benjamin: You talked about warming up your inbox with a tool like Lemlist or any of the other tools that came after, what would be the alternative? Just, hypothetically, if you want to use a tool, would you be looking at, you know, sending X number a day for a certain period and you have to sit there and pray that you’re not ending up in spam? or, what would be the alternative here? 

Vuk: You will have a tough time having first and foremost people receiving your emails in the primary tab and ultimately in replying to them and all that, the alternative, if you don’t want to use a tool and you can do it, so from the 200 emails you sent, you should get 50 replies and it’s important for people you send to reply for you to get the reply from them, maintain those conversational threads and all that.

So, you can do it manually, but that’s one of the things you can automate because it doesn’t make sense to waste your time.

Time is a resource that we all have, and it’s a super, super limited. So, why not automate that thing, but you have to choose a reliable two to do that for you. So, it does it in the right way. It doesn’t piss off the email providers. And more importantly, it gets you where you need to go, which is an optimized email. So, I will strongly recommend using landform obviously, but a warm up tool in general. It just makes sense. 

Can You Use a Subdomain for Email Outreach?

Benjamin: And in terms of separating the domains, is it the case that you can use a sub domain of your major domain? So, for example, replies or team dot your domain.com or would you have to use it a full, separate domain?

Vuk: I would use a separate domain because the sub domain would look funky, you know, and the sub domains are connected to the primary domain.

Benjamin: No difference?

Vuk: Yeah. I mean, who’s to say, because I haven’t seen the algorithm, but I’m pretty sure it impacts your primary domain.

So, for instance, we, the marketing team at lemlist have couple of domains so we have one dedicated domain for the newsletter. We have one dedicated domain for product marketing. We have our primary domain and we have our outreach domain that we share with the sales team and all are pretty similar, all have lemlist in their names and everything redirects back to the homepage.

So, I would say a separate domain, the name should be pretty much staying the same, you know, don’t just change the main extension or something like this.

How Many Emails to Send in Automated Outreach Campaigns

Benjamin: And for the amount of emails you send, you mentioned 200 per week, or was that per day?

Vuk: Per week. 

Benjamin: Per week?!

Vuk: Yeah.

Benjamin: That’s a lot less than a lot of people would say. 

Vuk: I mean, you can increase it. I’m not saying that if you send like a 500 a week, it can’t work. It can, but the truth be told, the more you send the last time, you have to make it really good like there are situations like if you have a really good list of, let’s say 400, which all share the common pain point and they can all be approached with a good copy and you just modified the icebreaker or maybe a customer.

It can work. It worked for me sometimes, but the best reply rates and best conversion rates were those where I was absolutely sure that the research was done right and research takes a lot of facts. So, sending less than converting more is something I would choose any given day of the weekend. And that’s only like if you have five people in the sales team, it means that you’ll be reaching a thousand people a week, and so, say that you have a reply rate of 20% and conversion rate of 10% converting a hundred users from a thousand people reached. It’s a benchmark that’s not so easy to hit, but the only way to hit it is by adding value and sending something that’s relevant to the person on the other side.

How To Test How Many Outreach Emails to Send Per Day? 

Benjamin: Got it. That ties in well with the next step, which is to actually program and send the emails in terms of formulating the copy. So, you mentioned 200 and you’d have the copy.

Would you break that 200 into say five tests of 40? Well, would it be 200 per week? And then you would review at the end of the week and then another 200?

Vuk: I guess it depends on the flow of everything.

Like you can send a split the 200 across five days. If you’re sending on during the work days, depending on your time and other tasks, maybe you split, maybe you do a thousand people, you research everything and it’s good and then you start sending.

I would probably go for getting to the sending part as fast as possible. I would start sending a batch or two early on, but you can program it the way it fits your work and other projects and that’s no issue just important thing to have in mind is the total amount of emails you send in timeframe, everything else is more up to you to set the way you want. 

How Many Contacts to Contact At One Account at The Same Time in ABM?

Benjamin: Some people listening will be doing a lot of ABM. Would you recommend split target account into the multiple emails and sending some of those in your initial tests and saving the rest of those contexts for a later date? Or do you find it more effective to test them all in one batch?

So, for example, if you have company A has five emails that you could contact that are on target and then company B has another five emails. So, you actually test your first batch of your campaign to only two people in company A and two people in company B rather than sending it to only company A first?

Vuk: Yeah, that’s a good question.

I think it depends like we did the interesting conversation with one guest at the webinars was whose target audience is usually like bigger enterprises with long sales cycles with the different VPs and I think different people do it in different ways.

This guy told me for instance, and what he does is he reaches all the people from one company at the same time, but he tries to be transparent about it and if you meet a CEO of the company on a demo, he will or somebody from his team will ask if they can go to their CMO, CFO and just adapting the copy to each.

Me personally, I think I always try to find the relevant person to contact in the company and then not send it to everybody. That’s the way I’ve done it in the past.

For lemlist, the primary audiences are SMBs entrepreneurs, and companies can be bigger, but only they’re agile and have their like startup vibe. So, for me, it made sense to go to the decision-maker first and depending on known results, adjust from there. But it’s the same, I guess it’s the same answer.

As in marketing sometimes what works for me, it doesn’t work for you. Sometimes an unconventional marketing strategy can work perfectly for some team and for everybody else. So, I think it comes down to testing and the only thing is if you’re reaching multiple people from one company, just make sure that you’re not shady about it and that if you’re sending, like I said, the message to a CFO and CMO, it’s a different value prop.

Programming Your Outreach Emails

Benjamin: Makes a lot of sense. Great. So, the third step was the email programming and we talked about having 200, not as a black and white rule, but as a sort of rule of thumb in terms of how much volume to send in a week. Were there any other suggestions you had around this stage of sending emails? 

Vuk: Yeah, so I would say don’t spend too much time overthinking the ideal timing or to send my email. There is a time that works better, like sending on the Monday morning.

I can see my status sometimes it’s not the best decision, but this data will tell you and another thing for that is don’t let some internal debates around what’s the best subject line or something like this stop you from sending emails. Like the idea is to let your audience tell you what works, but in terms of sending, just follow the limitations, if you want to go slightly more, like a bit more than 200, it’s fine but use lemwarm reports or any other email deliverability reports to tell you and monitor your performance based on that.

If you’re working in a team, be careful about all the tools conflicting with each other With lemlist, you can, if a prospect received something from one campaign, it can automatically exclude them from all the other.

So, you just want to sync with your team around these things, but sending them volume wise, I think this is the only thing that you have to keep in mind is picking the right tool for the job and not sending too many emails. 

How To Write Outreach Copy

Benjamin: And the last step was understanding the copy. There’s a lot of material out there on writing really good emails currently but did you have any thoughts around what is the best strategy to keep in mind or principles for writing copy that will get a response on email? 

Vuk: Yeah. I mean, like we said in the beginning, I think research reveals a lot of stuff and the better the research, the more fun writing the copies.

So, you want to start with the subject line.

This must leave them with the right expectation. So, open the email and they get what you promised.

It needs to be catchy. Don’t make it too long. Keep in mind that a lot of people will maybe see it on the mobile and you don’t have the unlimited infrastructure there and keep in mind that the Interline is also seen sometimes in the inbox before they open the email.

So, if your essential line is something boring and it’s like, “Hey, I work at Lemlist and I wanted to tell you…” it’s not going to work.

Speaking of the introductions, introductions are like the icebreaker you want lower the prospect’s guards down and you want to show them that you know them and that you come in peace that you don’t, I guess, in a selfish way, talking about you.

The less you use I, and the more you use you the better.

The introduction line can be many different things. It can be an honest compliment. It can be a comment on the recent posts, it can’t be the same way on LinkedIn.

If you leave just an emoji or you just write one word, it’s something you did in seconds and usually it’s just a plain, it’s basic, it’s nothing special. So, if you’re doing a compliment, make sure you really mean it. So, if you end up talking to this person, you can back it up.

If not that you can also elaborate different things. If I see somebody in the community, speaking about an email deliverability problem, my custom introduction can be, “Hey, we’re members of the same community. I saw your post about vulnerability and trust me, I had same feeling, but let me tell you something, I went from this to that and then something like this.”

You can play on a common reference. I had one guy I’m a massive inter? fan, which is a football club from Italy and the one guy was cheering for the CPR? and he wanted to meet for a talk and one of his introduction was around that.

It can be also funny. It can be engaging. It can be a common thing on if you don’t have anything that you found that their social activity or something like this, you can reference something recently that happened. Did they get the promotion? Did they raise money? Did they achieve something cool? Was there one of their LinkedIn posts? Did they say something interesting and you can reference something that happened in the meantime?

The only thing that you want to make is you want to make it feel genuine and you want to make it feel, how do you say, like, not basic, like it needs to feel cool.

Transitioning from Email Icebreakers to Your Pitch

And then maybe even the toughest part is how do you, how do we transition from that icebreaker to the pitch? Sometimes you can be a bit more direct.

The research will dictate.

Like we can go back to the community, for example, if I saw that the person is having a challenging increasing their reply rate or maximizing their vulnerability, my transition from the icebreaker to the pitch can be a personal story of how I got blacklisted and how I fixed my email vulnerability and then I can add, which is another, like a small sales pitch for me, a special feature of lemlist like a personalized so I can have like a cool image.

I can be like “For you Benjamin.” And it can be like logo of your company or something cool with the play button.

So, you’ll get to click and you see me, like I’m a real person, which is another benefit and then this video leads you to some really cool this like a thumbnail, if it really cool video, we’ll give you value.

So, even if you decide, like I’m not going to reply to this guy, I’m not going to use lemlist, I still brought you value in this video.

But if you’re excited, I can tell you, okay, if you want me to speak more about this, or I can show you everything in detail, let’s book a call and discuss. So, there are things that you can do.

Alternatively, if you don’t have that much of a context behind their pain, you just have the global pain, you can position your pitch in a way to start the conversation. So, it doesn’t necessarily have to be let’s book a demo or something like this. It can be to get them to start talking about things you have in common. So, you’re both figuring out outreach.

You’ll be surprised that the human copy and a question, like “How is outreach going for you? I’d be curious if we want to exchange strategies and tactics.” And then let them tell you something and then based on what they tell you can further qualify them and adjust like you don’t have to go guns blazing with sales.

You want to have, like I said, more you than I, and get them to start talking and then just adjust from there.

Types of Outreach Strategies

Benjamin: It sounds like there’s even several categories that you’d be very familiar with, which sounds like there are a lot of categories here in terms of this A) conversation starter or there’s B) the direct pitch.

Are there any other styles of outreach emails that you think are very common that people should be testing? 

Vuk: I think this is more or less the framework you can use.

I think there’s a specific sometimes if you have, we can, you can segment your list in, you know, different buckets.

So, bucket number one is pain A, bucket number two is pain B and so maybe the ice breaker. I mean, I’m always an advocate of having like an ice breaker, every single person, unique icebreaker. Just do it.

If it’s the best way I vote for that, then I can open tons of my campaigns and show the comparison. But the segments, if they’re like small and targeted and connected, you can write a compelling copy for a segment and a lot of people can relate to that.

So, you can do it like: split and have different campaigns or just have the one campaign and do it through custom tags or liquid syntax or any other feature so that you can approach them like this.

But you build credibility by telling people how you fix something that they want to fix at the moment.

And other approaches, you get them to talk and start talking, or you can go multichannel like you can combine LinkedIn with lemlist and combined cold calling with your campaign or whatever you decide. Then you can leverage your personal brand and engagement on social to reach them out on different platforms.

There are companies who are doing things like sending a cold email, and then if somebody clicks on a link, they could call people and “Hey, you clicked on my link!” in obviously in the more cooler way than this and it works.

It works because you know that they were interested about specific things and in that cold call, if you play it right, and you use your first minute or two talking to person in an interesting way, it will work.

So ultimately it comes down to getting to people, showing people that you understand their current situation, whatever that is, and yeah if you’re using the outreach for different things like inviting guests to your podcast, or wanting to put you as a guest on other podcasts that are different than strategies you can use.

Things like when we were booking podcasts. So, the first ever campaign that we did on that front was pitching Guillaume [founder of lemlist] as the founder to different podcasts back in 2019 and I was orchestrating that campaign and the framework was icebreaker, obviously, and then we had like, why could Guillaume be an interesting guest? What’s in it for the podcast host? Like mentioning that we have this like community of thousands of people that are also their target audience that we will promote it on LinkedIn, where we all already had like decent reach and you want to make like a win-win deal.

So maybe if you’re not selling, then you’re figuring out like a win-win. If you want to do a content collaboration with somebody, if you want to, if I want to go and I don’t know, meet the CMO of whatever company, like let’s say I want to meet with him solo like I need to write the copy. That’s, you know, like I need to show the collaboration and the topic will be also interesting to them the same way. It will be interesting for me. It’s like finding out those win-wins essentially. 

Should You Send a Booking Link Calendar Directly to A Prospect?

Benjamin: I think it’s a tough question to ask as well. Any thoughts around sending people, your booking links directly?

Vuk: Yeah. It’s a conversation that’s taking a lot of places on a social.

I think a lot of people are blasting that and the answer is always it depends.

In my opinion, at least like sending it to a cold prospect, it’s a mistake, nine out of 10 times.

It’s a mistake because it’s too soon. You’re asking before you gave something. However, if I qualified you and Michael in the community and I already know your pain and maybe we had, or maybe we didn’t have any contact in the past, like, I can write some story.

I can have this personalized with the thumbnail and when you click on it, you go on a specific page that I’ve built just for you and then it can be my calendar below and then the video, once I gave you my value, I can be like, “Hey, you want to discuss the issue with the deliverability and details?” You know, talk about it, let’s book a call and meet. So that works.

So, you gave some sort of value and then you ask to book the call but if you’re like just asking for a meeting without bringing value first, it’s not going to work.

So, the answer depends on really like what kind of value did you bring and where are you in the process? They’re like, after bringing some value, it’s like a, you know, negotiating a new salary. It’s a much better position. If you negotiate your new salary with the boss and you did something really good and you come after that and you say, “Hey, you know, like my or your quarterly review, like the results are nice?” It’s the same logic.

How Do You Follow Up With Prospects? How Many Follow Up Emails Should You Have?

Benjamin: Before you mentioned the follow-ups strategy, what did you have in mind here?

Vuk: I think it’s pretty simple. You have to send follow up.

I think you can send a usually having like three follow-ups it’s a good strategy. So, four emails in total, that’s my average, at least for my campaigns.

You can go even further. If you’re sending like a multi-channel campaign that consists of different channels, you can have much more steps, which makes sense.

But if we’re talking pure outreach, cold email outreach, you want to have follow-ups because of the reasons we said, initially which is sometimes people don’t reply because many of reasons, and not that they’re not interested, just they didn’t get in the find time to reply, or maybe they weren’t as convinced, but they’re still in the market and looking for things.

So, you have different tactics that you can leverage for follow-ups. You want to have your delays between emails and that’s all good, but in terms of the copy itself, usually it’s split in two ways.

You can either go for a reminder follow-up and then in the reminder follow-up you can have what I call like power sentences, rephrasing the value prop from the first email, but in a different way, like in a different, using different words or something, and, you know, doing it like this, or even like a funny reminder with Jeff can sometimes works .

You know, I’m bumping this up, but I promise after this email I’m out and then it can be like a funny meme, which is sometimes one of the last follow-ups.

But on the other hand, the different strategy can be, make sure that every follow-up adds a bit more value than the other one.

So, going back to to our video email, you might explain this strategy with maybe showing them the video.

So, maybe your follow-up, if they’re not convinced in the first email you added. If you’re selling a course, for instance, you might qualify the audience really well and in the first email they didn’t reply. So, in the second or third follow-up you can say, hey, I saw your recent LinkedIn post or whatever. I wanted to give you a special access to one of the chapters, just so you can see, 

I’m just getting like an example on top of my mind, but how do you like make sure that every follow-up adds a little bit more, so those are the two, like the second one is obviously difficult or like a bit more harder because you need to create some sort of story and all that. But on the other hand, if you’re doing like follow-up reminders, just don’t repeat basic stuff. Like if you see that your first email is not and you’ll repeat the same stuff and the follow-up didn’t work. It means that something is off and you need to tweak something to fix it better.

But sometimes it can also happen that the person will reply to the 14 email and be like, “Hey, I wanted to reply, but I couldn’t find it,” And if nobody replies to follow-up, connect with them on LinkedIn.

But don’t sell anything, just connect with them, expose them to your content, engage with their content, build a relationship and add a bit of multi-channel flavor to it.

But to go back to the primary question, I think follow-ups are really critical because it will ultimately more follow-ups it means more replies 

How Do You Coordinate Outreach Automation With Sales and Marketing Teams?

Benjamin: In terms of connecting the copy that you’re doing between sales and marketing teams. Did you have any suggestions around how they should navigate that?

So, for example, should you share all the copy that you plan to send to certain prospects to the sales team in a spreadsheet or something like this to let people know what’s being said on their behalf, or should the copy come from the sales team first with some guidelines?

What’s your suggestion? 

Vuk: I think there are different dimensions to this question.

So, it depends on the way your company is organized. So, for Lemlist, marketing stepped away from sales campaigns in most of the cases. So, we, most of our campaigns are more like related to marketing stuff, like connecting with people, inviting them from different projects, positioning gossip, different podcasts, inviting people to our staff, things like that.

Sales is more in terms of users and using outreach as a sales channel.

But what I wanted to say here, I think. You can use lemlist you can evaluate to save templates and I guess you can use the tool itself to save templates.

If you’re using a CRM, maybe you like allow exchange of information, people can see it. Like if you split your team, that one person is doing like research, the other one called calling the third one cold emailing.

You want to have this information sync somewhere, usually a CRM, so that notes and everything is streamlined that everybody can be on top of things and see it easily without having to slack other people ask them for something.

But ultimately, I feel like there shouldn’t be any competition between marketing and sales in terms of like hiding down plates or nonsense like that. Even though some companies may have like bonuses per person, it’s always a better idea like that. It’s that like Kobe Bryant’s quote, like I would wave a towel, bring a cup of water to my teammate, or should the winning the three points just to win because the ultimate idea is for you to win as a company, as a team. So, if you can create this atmosphere, it’s a much better thing and it may take off as a cliché, but it’s a much better and enjoyable environment to work in. But in a sense of the logistics side, you want to have information synced so that every person can by opening one prospect, you can have all the information here. So, if the person opened an email or reply to a LinkedIn message, reply to a cold email, or you left the note, or you’re going to send another email in 30 days because they’re changing their budget or whatever, all that information needs to be sinked, then there should be a process in place. 

Programming Outreach Campaigns

Benjamin: All right. So, we have these four steps in place. We’ve gone into the program, whichever program we’re using. If it’s something like lemlist, from memory, you go in there and you set up a campaign, you literally click create campaign.

You add in your list and you add in your copy with the variables in it.

So, it would change for name and different parts of the email and you launch you maybe get confetti depending on which program you’re using.

How To Measure Automated Email Outreach Performance?

Benjamin: What are the metrics you then say on top of, and how frequently should you be watching this for example, daily you’re checking this, weekly you’re checking that? 

Vuk: So, I think most of the campaign you’ll get the data in the 24 to 48 hours.

We usually want to check this as soon as possible.

You can do things like having like a slack lab who can, whatever reply you get a slack message so you don’t have to check it all the time if you want to do it this way.

But in terms of data, I think what matters most is the reply rate and the conversion rate.

Okay, conversion rates will come maybe after a few demos or depending how long the sales cycle for you is. But a reply rate is the most important.

You have things like open rate and click rate, considering where the industry is going. We’ll see what’s going to happen in the long run but right now, the rate is a good, I guess, pointer for your email deliverability.

Like if your open rate is lower than 50%, the problem is frequently not in a subject line. It’s in your email vulnerability it means that people are not seeing your emails and if you’re optimizing the subject line, it doesn’t matter because they’re not going to see the email.

So, if you have like an open rate, lower than 50%, you should do an audit of deliverability, make sure that everything is working properly and firing up with benchmark reports. For instance, it’s like a safe double-opt in with a strong open rate, click rate, depending on if you have clicks, we’ll see, depending on your strategy, you want to have a good click rate.

And on the negative side of things like you want to have your bounce rate, close to zero at all times, at least below, you know, things like 5%, but the closer to zero, the better.

The only thing that to make sure that it stays like this is to verify emails. So, you have email verification tools, always verify them, never send something that you previously didn’t verify. It’s just a bad idea.

Bounce rate is like a needle in the back for the deliverability. If you allow it to me to increase and obviously like other metrics, like, you know, like spam rate or things like. It’s something important, but you will see this probably being zero, if you do it the right way.

So those are the things and I would say that the last thing I would say is benchmark, right? If you’re sending like a campaign to more people and you didn’t personalize as much as you could, you should aim for something like 8% and if you send campaigns to, like I said, 200 people and you have ultra-personalization, you should aim for 20%. It should be there and then the conversion rate should be a 10% like a good result is every a hundred emails you sent having 10 people book a demo with you is a benchmark. You should be able to hit and match. I would suggest like having.

How To Source Emails of Prospects

Benjamin: Yeah, Fantastic. It’s a great rule of thumb to really hone in on your performance. It gives it a bit of scale. Something we didn’t get into earlier with the emails was sourcing the emails themselves and did you have any tips on where best to find emails and how best to do it in the clean format?

Vuk: Yeah, I think first the rule is always a professional email address. So always, always, always, never a personal one.

But in terms of tools, I think the best way to do this is to put the email finder tool in your existing funnel and to automate this as possible. Like we have this automation, I’m blessed with a tool called Dropbox that helps you do this, but you can integrate many emails finder tools with many emails outreach tools in general. So, you can do it like this.

You can go old school. Of course, have an extension, you know, go to their LinkedIn, grab an email, copy, paste it in your spreadsheet, and then upload the upload your CSV file.

If you’re doing thoughtfully, the faster way and the more joyful way, let’s say more enjoyable, is if you can automate this, like you, you can, there are things you can do, but a verification of those emails is absolutely essential and that’s most of the job. Like it’s something that should come easy.

Manually Verifying Emails

You can also do it manually. If you want to have just one person’s email and you don’t have like an email finder tool and maybe you don’t have resources to spend, like you have things like email permutators, which is where you put the name of a person the first time, the last time and their domain, and the email permutator will give you different variations of like, you know, first name@domain.com, first name dot last name@domain.com. Then you copy paste that into your Google sheet or in your sent to your Gmail or whatever using and if you cover all of it, if you see like a full name and the person’s picture, it means it’s a legit email and everything else can be deleted and if you figure out the pattern first name@domain.com, you basically have an email from anybody in that company. You just have to change the first name so you can do it manually free without anything, or you can use the tool and if possible, integrated with your flow, it’s going to be even easier. 

General Email Tool Recommendations

Benjamin: Great stuff. Second, last question, just before we go, any other tools that you recommend in this space for general email outreach?

Vuk: You know, I think obviously I’m going to say lemlist, that’s not a surprise, but I think clear out and the mailable or a bouncer are good verification tools.

If you want to use it drop contact to find emails, but you also have things like Lucia, which is another cool tool for CRMs.

I’m not that involved in, so we use Pipedrive, but that’s more of a sales thing than marketing and I would say, try to figure out your channels. It’s super important and super relevant and it works great for our users and for a lot of people.

So, I would say, think about how you can include your personal brand in outreach. And if you do, I promise you the results are really amazing.

In terms of tools, ultimately you have a pick a tool that you enjoy using and whatever that tool is, don’t think twice despite use it and see the ROI and it’s not unexpected to, for it to work in two days or in a month, try to use it properly.

Current Email Outreach Trends

Benjamin: Last question, any trends in the space that you’re noticing, what can people expect in the next six, twelve, even a couple of years from here for email outreach?

Vuk: That’s an interesting question.

I think we’ll see that email deliverability will change in the short term. I believe like you, we saw that some companies are not allowing you to track open rates the way you did before. So, for instance, this means that the warmup tool you use. We’ll be the only safe metric for you to really know whether your emails are landing, where they should, or they’re going to the dark places of email providers.

So, I believe like this is a great thing and I think in the long run with all the transparency, privacy talk, like I think spammers will have even more tougher time. Anybody who enjoys taking short cut, will have a tougher time and the people are even more sensitive than ever so you don’t sell the email. We’re great for five, six, seven years ago, you could set because people weren’t thrilled to receive an email, but I think peoples have exchanged. So, I think in outreach, if we’re talking specifically for outreach, I think this is, these are some changes that you can expect and I think world is shifting towards multi-channel outreach, no secret and I think how do you combine different channels you use in a logical way.

How to Connect with Vuk 

Benjamin: Awesome, well, thank you very much for the information that you’ve shared so far, for people who want to learn more about you and learn more about Lemlist. 

Vuk: LinkedIn is always a great choice. I think we’re all there, especially us in B2B, but lemlist.com.

If you have any question or you want to talk aobut outreach, to shoot an email, but as long as go to lemlist.com, you’ll find all the information on the website and if you want anopportunity to weigh in on opinions with other sales and the marketing experts such as you or practitioners or people figuring out outreach, there’s a community on Facebook called lemlist Family has more than 19,000 people and it’s super active and you’ll find a lot of people who are in a similar shoes such as you and there’s a most of the content is user generated and it’s a great place to be.

So type ‘lemlist family ‘on Facebook and check it out or I can send you the links later on, but those would be my go-to places.

Benjamin: Excellent. I will be sure to put all the links in the show notes, otherwise, thank you so much and have a good rest of the day. 

Vuk: Thank you for the invite. It was great to chat and all the best.