Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AEs about things like, what does it take to be a great sales manager? Or how can you go home happy month after month? So let's dive right in. 

Thank you so much folks. Welcome to “On the Flip Side” with Wingman. I'm Kushal, your host for today. And I'm super excited to introduce our guest for today's show, Stan. He was the co-founder of intro.so, a Chrome extension that gives you research right within your Google Calendar and all your prospects. I'm assuming that means less fidgeting, less stabbing around or different tabs and just more research right in your calendar. Great to have you on the show, Stan.

Stan: Excited to be here also. Yeah, perfect intro. Thanks for this.

Kushal: Okay. Stan, I know today, of course, we're gonna be talking all things cold email. And I know that both of us are sort of in the middle of cold climates. I'm, of course, based in India, you're in Warsaw. So it's pretty much cold, and all and a lot of other places in the world as well. And I think that's a perfect time to be talking about how to use cold email. So first off, there's a lot of criticism around cold email to begin with, you know, just like cold calling, it's one of those few things. Everyone's always asking, is cold email dead? Does cold email even work? How can you warm up your cold email? What's your take? Does cold email still work?

Stan: Yes, it's 100% works. I believe that cold email is my superpower. It still works. You need to do it well to make it work. But if you manage to do it, which is extremely easy, and I will be talking about how I do it, and probably you Kushal will be also talking about how you do it. It works perfectly. It's still a great tactic and great outreach method. And it was great in 2021, it will be great for 2022 also. 

Kushal: It's interesting you say that. Because even if you ask a lot of marketers, you know, what if LinkedIn went away tomorrow, what if Facebook went away tomorrow? What if all of these other platforms that we use a lot for prospecting, and Outreach really went away and a lot of marketers will still answer emails. So having a solid email strategy even for nurture is sort of a key part for most marketers as well. I guess even before we go ahead, what would you really say is a good cold email to begin with? How would you really quantify that? So a lot of folk’s will say, if you get like, 50% opens, that's good. If you get maybe a 10 to 20% reply rate, that's good. What's your take on really how to benchmark good email?

Stan: Yeah, I mean, the good email needs to make recipient take action that we want. So I wouldn't necessarily focus on those metrics like open rates and reply rates, those are extremely important, but you first need to sort of make sure that your emails are booking meetings. Of course, this could be a problem where your emails actually earn booking meetings. So then you can take a look at open rates, it's a good benchmark to keep around about 50% of people should open your emails. And then you know, depending on the quality of the email, depending on how much the personalization, how much time have you put into personalization, and how the email is personalized, then you can think about, okay, the reply rates should be around 10, to 20%, maybe another 30%, if you are extremely targeted. Meaning out of 100 emails that you sent, you should be able to see around up to maybe 5, up to even 30 emails back. So that is my benchmark. I know it's a big benchmark. You know, every email campaign is different. If you're doing extremely targeted, and the whole sort of email campaign market is 50 people, then you know, you should expect to have higher numbers, because you will spend more time actually thinking about what will make people respond.

Kushal: Got it. So Stan, here's another question while we're talking about numbers and what really benchmarks you know, to use for good cold email, how many emails do you really think it takes in today's world to get a reply? Should we be aiming for you know, what, first email at that… I get a reply or, you know, how many of you kind of suggested in a sequence 5, 6, 10?

Stan: So I think…

Kushal: When should someone give up? 

Stan: I mean, it's really like a personal thing. From I can tell what is my experience, and why I'm doing the way I'm doing, but you should really, you should test it. So I usually send one, two emails and then I respect his response. After that it is extremely, extremely low chance of getting an actual response. And you should keep the follow ups coming in if those leads are extremely important to you, but in a very wide timeframe, meaning after two emails in a span of four days. So one email on the day zero and then second email on the day two, may be three, then you should really think about a weekly emails, meaning you send one follow up every week until they respond or, you know, until you feel it's not worth it. I wouldn't necessarily go more than 7 to 10. But you should aim to get a response in the first one or two emails actually, based on how was it for you? I mean, how many do you usually get? How many follow ups who usually pull in?

Kushal: So let's talk about me as a receiver of email to begin with, because I think that gives you a really great perspective, if you kind of, you know, what do you respond to yourself. So for me, I will definitely respond to first emails if I feel they're super, super impactful, super personalized. And if they really talk to something that I'm trying to solve for at the moment, and just at that time. I will, however, also respond to email number three, or four. And I've noticed this, I'm not really proud of this, but especially in emails where the person says, okay, you know what I tried, I'm going to give up. This is the last one, you're going to hear from me. And then I’m like, “Oh no, wait, wait, you know what, I was interested in what you were saying”. But I maybe just wasn't able to respond for some reason or the other. Because even email fatigue is sort of a thing. And there's only so many days that most of us have, in our days, only so many hours. So I have, for instance, even responded, the positive two emails, three and four in a sequence as well.

Stan: Yeah. I mean, it's interesting, because normally, you know, the way I think about the follow ups is, the first email is the most important email. And then the second email is, “Hey, have you thought about this”, like, after two days. And usually, you know, after this time, they are either going to respond, or it's… the chances or you know, going almost to zero. I have seen actually this sort of, “Hey, I'm breaking up with you. I won't contact you anymore, it’s not working”. I know, I'm not a fan. But you know, as everything that we probably talked about here today, you should test it on your own and make your own assumptions and see if it actually works.

Kushal: I agree. I think it definitely is all about testing, I think different sequences, different words, I mean, a different method altogether will work for different folks and different audiences. So I think that part around testing is super key. 

Stan just going back a little bit and I shared this on LinkedIn as well, how, in fact, one of my earliest job interviews I secured by cold email, and I didn't think of it as cold email back then. I just thought about, as you know, hey, I don't know this person, I have an email id like a corporate email ID. So I was going to email them and ask for a job interview. It worked and that was the fun part. And I realized only recently that for the current position at which I’m at Wingman as well that also came to me via cold email in one sense. I knew the company was hiring, I got that information. But I didn't, you know, I had no other inroads into the company, I can just send a cold email. So I think that sort of to say, to speak to the power of cold emails, not underestimating the various uses beyond just prospecting to just kind of getting your foot into the door for so many folks, I think that's why it's so important for so many of us to pay more attention to cold email.

Stan: So going back to the example that you just gave, did you for your current position, did you send an email like to the recruiter? Or did you send an email to like jobs at Wingman, or what was the sort of the play here? Because I'm sure others are also interested.

Kushal: Yeah. So I sent this one to a careers ID. That's careers@trywingman.com. Incidentally, folks, we are still hiring, in case you're interested in joining us. So I sort of wrote into careers@trywigman.com. I think that was the email ID that was advertised, you know, from, you know, the open source, I think there was an invitation on an alum board somewhere, that's I got information, it was publicly shared, I got the email address of that. And I just wrote into the team. Did whatever research I could on the company, of course beforehand. I checked out the folks, the co-founders, the company on LinkedIn, wherever else I could, thought about whether it was a fit for me, and whether I would be a fit for them as well to begin with. So I did that research upfront. And then after all that research, I sent him that email and I got a response within a couple of hours, I think.

Stan: Yeah, you know, this is the important part. The research, you need to know who you're reaching out to, and you need to sort of gain some conviction on why actually you're reaching out to, why they should respond. This is the sort of key important part you should think about why they should respond, how we can put the stuff that you want to tell in the email making them respond in the shortest way possible. My sort of trick around managing the length of the email is, I try to think of a way where I pay $1 for every word I write, meaning that I really, really want to cut down every unnecessary word that is in the email. Meaning I can say I'm excited, I am really excited, those are too many words, this all elapsed that necessary they are not adding real value. So this is actually you know, really important, making sure that emails are short, but also like you mentioned, you know, checking if actually there is a fit and there is a worth your time sending an email to careers email or sending an email to the new prospect that you dying to get is actually, you know, there's a possible fit.

Kushal: I think that's a great point to make around really doing your research, of course beforehand. And that seems to be one of the most important things when it comes to cold email. How relevant do you make it, of course, you evaluate for yourself, whether that person makes sense for you to pursue, and, again, how relevant you make it for the other person also to respond. It seems like a large part of this is probably a lot of deep research, and maybe some personalization as well. Is it really possible to do this at scale? Or would you suggest kind of spending a lot of time on each email? And then, you know, kind of focusing on quality versus quantity? How do you, what's your approach on this?

Stan: Yeah. So I think it's, you need to find a balance, like everything. I think, if you are, you know, what you're looking for in terms of personalization, I mean, already done some email personalization in the past, you know, you can take 20 seconds actually to get that right, basically, for each recipient, which is not a lot of time. But if you're just sort of thinking about, okay, what can we include, then you possibly can take a little bit of time. And the truth is, if you can’t find anything online on the person that you're reaching out to, it may be worth it to actually skip this person and focus your efforts on people that you can find something about and you can mention and it's relevant to your page that you're making in your email. This isn't, you know, of course, a big if your market needs to be large enough, where you can actually get the permission of yourself to skip one prospect. Because, like I mentioned, if you want to reach out 100 people that you've specifically picked for some reason, you will probably spend some a little bit of time on personalization and spend a little bit of time on research on how to make every email perfect, because you know, you can, but if you're sending like 1000s of emails every month, you don't have that much time. You need to send 100 emails of few minutes in a day. So you need to keep it snappy, basically, for your own personal self-development workflow.

Kushal: Stan, going back a little bit to what you talked about earlier about thinking about why would someone want to respond to you. What's maybe and I know, this is always heavily asked and contested sort of question, what do you think really is a great way to ask for next steps? What would a great CTA email look like? Are there certain CTA that you've tested out that seem to perform better than others?

Stan: Yeah. So I mean, so you're asking about like, how should you end an email? And this is a great question that you need to think about, like, the email is not to close the deal. The email is to get you an interview, a call, a meeting and a conversation. And this is a great thinking. However, I found that asking for a meeting on the first email is not ideal. Because what you really want is you want to open a conversation, and not necessarily you want the meeting booked on your calendar. So you should always ask like, sounds interesting word for conversation, something like this is really more open minded that they can say “Yes”, to way easier than how about a meeting at 2pm next Thursday. You know, again, this is sort of my testing and my concept, you should really test them how they work for you. Because what I found that asking straight up if they're interested, or is it worth exploring further, or care to see more something around those lines is usually what works best for me. How about you? What's your take on this?

Kushal: Could you just repeat that for the top a little bit?

Stan: Yeah. So I mean, what's it, what do you think about the ending time of the email? 

Kushal: So I think when it comes to the end, when folks get an email which outright asked me to book a meeting, I think I'm fairly less likely to do that. Because 15, 20, even 30 minutes is a fair ask of someone's time, especially when they don't know you from before. There's no prior trust. There's no prior exchange of ideas. I don't know whether this is going to be worth my time. So I think I would be much less likely to book a meeting or something like that, unless I was so close to make a buying decision on something and that email just happened to pop up at the right time. And they figured that out, either maybe from what I was posting on LinkedIn, or you know, maybe I dropped in a demo request on some other tool or retargeting or in some other way that they managed to figure out that, you know, if I was for instance, really close to making a buying decision on a tool or a software then maybe I would be more open to saying, okay, you know what, I already am interested in this concept. Let's take it a step ahead. 

Stan: Yeah, I mean, so great that you're actually telling exactly what I just told which is like, it's… do not ask for a meeting straightaway. Ask for a conversation, you know, ask if they're interested, yes or no. I mean, that's the key here, because then you can actually, if you have a response, you can work with that response. And you have, I would say, like a second shot called email where you restate the value, tell them again, why this could be interesting, and then ask for a meeting . That is usually my thinking and great that we sort of you as an end recipient, thing that we think alike.

Kushal: Got it. So Stan, we have, of course, talked about personalization, we've talked about making the email relevant for the prospect as well. Are there any tips around any of these that you think we haven't covered so far? 

Stan: Yeah, I think one of the best ways to actually sort of learn about the company that you're reaching out to, is go for reviews, and you can, for example, check if you're reaching out to CEO, they usually care about their customers. So you can possibly go around looking at G2 crowd or similar review websites, where you can see what the reviews are getting, like why customers are picking them, and possibly you can tie that around into your value proposition. What is also really cool is you can see, use reviews for like personal personalization, meaning you can go to someone's LinkedIn profile and see reviews that they have received. But also the reviews that they have given out, which is even more cooler, because you can see directly what language do they use, what they care about, and what is important to them. Because they actually, you know, put that in about other people that they care about. 

So this could be an interesting way to you know, just get ideas on how can you frame the problem and the solution that you're trying to propose. But also, you know, find some ideas around personalization. Again, simple stuff like going to LinkedIn profile and seeing like description if they have like, they like some sport or they have a background of ocean, they possibly likes an ocean. So we can say mentioned some ocean, that this tool is like ocean, in ocean, red ocean strategy, or whatever it is, wherever you can make some relevant jokes and curious way to pick someone, peek someone’s interest, I will see, I would say, that's it. And yeah, for also, one idea is to go to companies’ blog, because usually, if there's a smaller company, the CEO or someone important is also posting content on there. So and of course, the usual stuff, LinkedIn content, if there's someone is posting, you can mention something that they have posted previously, or, and then use that as a relevant piece of sort of tie point where you can work around and create an email and crafting email about the value proposition.

Kushal: I think those are really interesting ideas, Stan, to sort of go into someone's LinkedIn, and go beyond what they've just posted. But actually look at the recommendations they've given other people, and not just what they've written on their own profile, but then also understand the kind of words they probably like, the kind of tone they probably write. And like you said, probably mirror that in some way your own writing, like you said, I think mirroring maybe even via words seems to be possible in some sense, that's a really interesting way to put it. I honestly can't wait to maybe get an email sequence from you to see what that looks like as well. Now, I'm curious and maybe just kind of going ahead a little bit. So we spoke initially about, you know, keeping emails super short, and kind of to the point, taking out extra words, $1 per word sort of thing. Do you think that shorter emails do actually do better? Or would you also test longer emails?

Stan: Yeah. So like, again, this is my experience, I may be wrong, you can probably find some case studies that prove otherwise, basically. So this is like my personal experience. And if you really want to have more space, you should, you can, for example, create a story with a sequence of email. Meaning the first email is like the beginning of your story. And the second email is something that you restate that you couldn't really fit in the first email, think about like six or seven emails or five emails that you send out like, one big email that at the end, they understand fully, and just keep it as a priority, meaning the first email is the most you mentioned, something that is most important. The second email is, for example, could be around your customer segment or around the previous case studies or reviews that you got. And then again, third email, keeping the story live and asking questions, asking different question in in every email, because then you have the highest chance like if the first question the first thing or doesn't, didn't really resonate, you have the second follow up email where you can ask some other questions that could unlock something in their mind that okay, this is interesting. I want to hear more. 

Kushal: So here's an interesting idea, Stan. What if we sort of took the prospect along our journey and told them upfront you know what, I will be taking on a journey of three emails. So here's what's going to happen in email one, and almost tease it and some sense and make it full of suspense and do a great job of storytelling then obviously, and kind of maybe create, like hooks for them to actually look forward to the next email. Do you think that could work? 

Stan: I don't know, I think it could work. But I also can find some arguments that it won't work. Because if, but then again, if someone… if you say something like this, and someone says, “No”, then they already sort of disqualified themselves, and you don't have to waste time on them. So I think this could be interesting. I think this could be interesting. But again, if you craft your first team as a great one, you probably won't need as many sort of follow up questions that you can ask. And also like, I'm not sure if I mentioned that, asking a lot of questions in your emails are great. So you don't have to necessarily focus on the one point and picking a one question that you want to ask for email. You can keep it three or two, maybe two questions per email, meaning, have you thought about this? What are your thoughts around this specific strategic narrative? And then the second one other question in the different part of the email also, which you just simply what I'm saying is you shouldn't be afraid of asking questions in email, because the questions are helping you create the sort of a context and get prospect to stop for a second and think and then possibly reply back to you.

Kushal: Got it. So with the goal of asking questions, is it really to get, do you really expect to get a response to those questions that you ask? Or do you simply, you know, want to kind of meet the person curious in their own time and space? And hopefully, that will lead to a response in that email was the next one?

Stan: Yeah. So I actually when I asked a couple of questions in email, I usually get a response to one of them, meaning that if I get a reply, I get the response. And then I can then work with that response to possibly craft a reply back to the prospect that just replied to me to try to book a meeting, which is great, because then you learn something about their company. And there's another piece of valuable information that you can use further along the sales development process, which is like getting them to book a call with you. So I actually, usually if you ask them two questions, they will respond to one of them, not necessarily both, because that's not sure why is that but that's how it is basically, but they will actually respond to one of the questions that you ask, which is great, because then if this question is valuable, you can use that to actually tie in your value proposition in the reply back email. 

Kushal: Got it. Stan, I think we've gone over some really interesting points over this session. I think just a few more interesting questions for you. What's maybe you know, one of the not so great feedback, you know that you've received on emails that you've sent out? I know, a lot of people can be snarky, when they're replying to email as well. Have you ever had to face any of those?

Stan: Yeah, I've been told to go to hell. I've been told, I've been sweared at or it's of course normal, it's like part of the game and someone they. Sometimes prospect even tell me, you know, unsubscribe, where actually there is no list that I have subscribed to them, which is, you know, funny because I actually took the time to focus and to, you know, to personalize the email, and they also reply to unsubscribe, it's like, it's part of a game. You are reaching out to them so you need to be, you know, prefer that they will straight up saying no, so it happens all the time. 

Kushal: Got it. And do you ever reply back to emails that you might be getting from folks who are prospecting to you? Do you ever reply back with feedback or anything else to them? 

Stan: Not necessarily. Yeah, actually, if their email is extremely bad, I will reply linking to sort of my thoughts about cold email and what you should do next. But if the email is not so bad, and I'm simply not interested reply on the first email. And the minute that they open it that I'm not interested saying, “No, thanks” and that's it. And usually, that will do just help them get to the closure and not bother me anymore, because I know that they will send more emails. So you know, if I read them, and I find nothing interested in this, I will say that I'm not interested because they will send more emails, why should bother.

Kushal: Got it. I think that's also a good way to earn good email karma to sort of faster. 

Stan: Yeah, yeah.

Kushal: All right, cool. Stan, just one more question before we wrap up the session. If you had to sort of describe cold email and the art of sending cold email, it's in a one phrase, in one line, one sentence, what would that be?

Stan: Write short, sweet emails. Think of, I mean, that's true, try to present your value in the shortest way possible. My couple of emails that I have actually sent that were extremely successful where one sentence, so one line even, so one sentence, one line, it was extremely short and they actually work because if it's once specific strategic ask question, they will respond because it's simple to respond to specific and concrete question, rather than like open-minded asking them how much revenue you want to grow or like, how big is your team? I mean, those are stupid questions. But if you ask good specific question, then you have a higher chance of getting a response.

Kushal: Got it. I love it, Stan. I like that slogan of like, short, sweet emails. I think that's a great note to end this on. Thanks so much, Stan. Appreciate your time. This has been really useful.

Stan: Yes, I'm excited too. We're super excited to talk to you. 

Kushal: Yes. Thank you.

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