How to improve email deliverability? | Avoid emails landing in spam - Jesse Ouelette

This is the Sales Spin podcast. You are listening to Salespin, India's top B2B sales podcast where we bring the world's best sales experts, successful sellers and sales leaders who share their strategies to succeed in sales right now and talk about things no one else will. And now, Raul Wadhwa.

Give us your background so that people who are listening to this or probably watching this can actually relate to you.

Yeah, I spent 15 years in enterprise software covering strategic accounts for other kind of SaaS, enterprise software companies, and was selling kind of upmarket, really wanted to follow more of my passion, which was more kind of building my own business, of course, and then also really, really around modern kind of outbound lead generation data, using tools, using technology to make things better, faster, quicker.

Awesome. You know, you talk about the email delivery a lot. I'm curious to understand. And this is something which I'm now seeing on my LinkedIn a lot because now most of the leaders are talking about it. I'm curious and I'm probably coming from a place where, you know, I mentor a lot of new SDRs and they might not even be aware of this problem and might be getting fired, might be getting on pips every single day and because their leader is probably telling them, hey, it's your email delivery. It's actually your email writing skills which is at stake. But that might not be the case.

Yeah, I mean, this is a great, great question here. What really is happening right now is since delivery is such a black box in a lot of ways, right? When you, when you send an email to somebody else, where your email gets placed, placed in their inbox is really a mystery. Right. There's tactics you can use to figure out where it's going to place based on other heuristics. But what's happening is there's a lot of people that, you know, with COVID of course, there was a huge shift in email protection software threat. And remember, email is still the number one attack surface for hackers. So this is why you have to go through all those weird trainings with your company and all of that. But what's happening is all of these training or all of these emails are starting to get more into the spam folder because they're just, all you have to do is tip that number, that score up to a certain threshold depending on the organization, they're going to be a little bit more picky. Obviously the bigger, bigger, more companies that have more to lose are going to be definitely a lot harder to get through. Right. So you don't really know if it goes through. You can only really. Yes. Based on other heuristics, based on the fact that you've set things up right. Based on the fact that you've collected data. And what we're finding is it's going down a lot, but there's a lot of people who have really haven't realized that the open rates have actually changed quite a bit because of Apple. Apple's opening a lot of emails now. So your open rate should have gone up, but in the case of most people, it's gone down, which means it's really gone down. So people don't really understand the thresholds that have happened. I've been tracking this since the beginning and, you know, I have some really good data on this now.

How did you first discover that, you know, this is actually the problem? Because, like I said, a lot of STRs who are probably new, if they're not watching this or they're not following you, they might not even be aware of this. I was not aware of this about this whole concept until, you know, I spoke to you like six months ago.

Yep.

So I'm guessing someone like me, who's been into the space for five years did not know. I'm guessing that's the case with everybody.

Yeah. So the good thing about email, and this is one of the things that sets it apart, is it's not a social media website or anything. And the way that I figured it out was I was a rep and I was trying, I was failing. Right. And I saw ways to optimize. Now, I worked for some companies and they would take the feedback, they'd get me with it, and then I would fix the problem for it. Right. And then there were other companies I went to where, you know, I wanted to talk to. I guess the last and final time, I wanted to talk to the IT department, the engineering department, to get it fixed, and they put me on with HR and fired me. So, you know, that was a little bit of an uncomfortable position, but it also created the fact that now I can, you know, have resilience and not worry about that and just show people the data and show people, and hopefully they respect it. Right. I run my own business. I don't have to worry about that anymore.

So you talked about this problem. Okay. Which has been existing for a while, especially since the time you said, you know, pandemic hit. So you kind of realize this. I'm guessing few other leaders who probably know you, because now I'm seeing this on LinkedIn a lot for the last three, four, five months. So I'm guessing leaders are now getting this problem and at least paying attention. What I'm trying to understand is if I'm setting up my SDR function for the first time. All right, help me out. What, what. All I can do to make sure I'm not landing in spam.

Yep. Yeah. So let's talk about like a normal kind of organization and then we could talk about the extremes after. But let's talk about like your, your typical SaaS or sales development, possibly like an outreach or salesloft or one of the popular outplay, one of the popular CP tools. So what those teams are basically, what really needs to happen is you need to understand the concept of something called mail flow. Right. And the reputation is through the domain name. So by knowing that, you basically have to keep an eye on how many bounces you've had. Right. The number should be. You shouldn't really be over 2% bounces. Right. It's easy to validate emails. Right. You don't. Shouldn't be sending to emails that bounce. You know, that's one area. I mean, there's another couple areas like complaints. Your IT department knows if a company reports you as a complaint, do they share that with you all the time? Probably not. Right. Let's look at that. And you get put in kind of G suite jail or whatever they call it. But what's happening is you've got these groups of people that have kind of an unlimited ungoverned engagement platform. And cold email to by default is already at a 3 to 5% response rate on an even, even a good campaign. Now the mail flow systems really want you to be way above that. So it doesn't look good that your domain is getting that. And then what happens is it tips the scale the wrong way. And now most of your emails are now inside a spam filter and the response rates are dramatically. Like. It's just they don't. People don't respond if it's in your spam folder, really. Right. Unless you tell them or they find out from somebody else that it wasn't there. So even if they wanted to respond, they couldn't. That's one problem. And really what I think is going to happen is you're going to start to realize that the emphasis on messaging is going to shift to more delivery. And part of the problem is delivery is a hard thing for a sales team and a sales ops team to cover. You really need more of a market team to help out here because it gets to become more of a systems. And a lot of these companies aren't really designed to scale the same way. So it's a weird thing that's happening that kind of nobody wants to talk about right now because they know it's happening. They probably think I'm right, but they don't really know a good way to fix it. So that's kind of.

Right now, I'm guessing most of them are actually in the same mode. So you talked about your email can never get open or never get reply because they actually never landed in the primary inbox and they spam. So my next question would be how to avoid it.

Yeah, sure. So there's some things that would help you avoid it. So the number one thing right now, I think if you're going to do anything, put limits in place on your sales development team, right? Don't let them send over. I mean, we're sending 50. I mean, don't let them send over 75 a day on an inbox. I wouldn't even go that high. But like, it depends on what you're comfortable with. But you know, just stop that part of it because most of those emails are going to be copy and pasted, right? They're going to be the same email over and over with a couple of different fields merged.

Correct.

The other thing you want to do is you want to run two checks. One check you want to run is a. The checks call. It's like a mail. You can run like a, you know, like an MX toolbox diagnostic which tells you which delivery settings you have off. I have it on my LinkedIn profile of like, if you want to try to figure that out, that's kind of checking your own servers and you're going to probably find you could be in a series C or D company and you still have these problems. Like, don't think that you're, you know, I've even found publicly traded companies that did not have their records set up right. And they deteriorate over time because you add more records to the DNS. This is like the mapping of all of the services in your company so other companies could access it. What happens is those deteriorate as your company adds more services in your company and then sometimes they screw up the cold email settings. So you have to check that. The other thing you want to do is do something called a seed test. Now this is where a lot of companies aren't doing. What you do is you got to go use a service that has a seed test. There's a bunch of Them out there, just Google it, like Glock Apps has it. And this is where you test an email to like an email that you would send. You would test it to see if it lands where it lands, like in the primary inbox or wherever. Now the nice thing about seed testing is they have inbox up at all the major providers. So if you regularly do this test, you can start to see if there's a trend like, hey, we're not getting in on Outlook anymore, what's going on? Then you might know your domain's burned and that's where you start to run into a problem. Because remember, the two major providers are Google and Outlook. So if you get burned on one of the two, you could be in a real world of hurt. And sometimes it takes two to three weeks to repair a domain once it's burned. And that's really the reality. So seed testing, checking the delivery optimization settings and then really like data validation and making sure that you're using validated emails is really the next one.

All righty. I think that brings me to tons of other questions. So you talked about something like MX testing, so can you maybe elaborate on that? I have a new domain, I'm a new company, like so say C2 Series A. So my domain is not that old. And I think we would, I would love for you to talk more about the different domains. But before that, where do I go to make sure I can test how old is my domain? What's my domain reputation right now?

Sure. So really you have to start doing more. You have to start sending emails and you have to start looking at like your open rate. That's one of the good ways to kind of figure out what your reputation is. There's also a thing in Google where you can check the postmaster. You have to set that up first. A lot of people don't have that set up. It'll tell you your reputation in there depending on which service you're using. But what I would do is as a brand new domain, this is what we do. It takes about three weeks to get it up and running. Right. So what we do first is we register the domain. We make sure that it's like a top level domain. This is another thing, people are trying to register these kind of way off domains. Just register something like what you have now. Get a.com, get a.net, get a IO or if you're in a major country, like get the local country domain or whatever, wherever you're emailing. And what you want to do is Start something called an email warm up on that. There, there are a lot of tools I'll try to. I hate to recommend tools because right. If something changes like next week there could be an app, so I'll refrain from doing that. But there's a lot of tools out there that do email warmup. And what you want to do is start that out at really low number, like a three, right. That's three emails per day. And what it does is it starts emailing around the network. So there's a bunch of other people who have opted into this warmup network, typically people who send a lot of cold emails. And you want to start using that domain for three weeks with all of the right settings on. The right settings are the ones that the provider tells you to set up. And if you run those that can that for three weeks and you get it up to 40 emails and you're running it and there's no, none of those emails are going into spam, then you're in business. Now you can stop that warm up feature and you can start sending. The problem with warmup though is it's a bit of a gray hat move, right. So there's a lot of people who are like, well, you're kind of artificially. But this is what all email marketing people do anyways, right? So that's why it's starting to become more of an email marketing function and people that understand E commerce and that are getting kind of into the space as well. So hopefully that kind of sums it up. It's three week warm up and make sure the delivery settings are right.

Okay, awesome. So we got our email set up. We got our email warm up set up. What's the next step?

Next step would really be to make sure that the data that you have is validated. So we've been testing a lot of the tools out there, the major ones, and most of them have at least a 40 to 60% bounce rate. And it's funny because a lot of them even own. Won't go into the. I'm not going to name names, but some of them even own bounce validation companies, which makes it even more interesting. So it just shows you when you're structuring your contracts with your data providers, you want to keep an eye on this because there's a process called validation. Now I want to kind of dig into that because what a lot of people think it is, it's like, yeah, we know they're high quality or whatever, but validation is not like quality of the. It's a Binary decision, right? So when you get a list from, let's say any of the major providers, they're going to give you an email and they're going to say this is that person's business email. What you need to do then is you need to run something called an email validation. And you need to put this step inside your process, meaning you can't send emails that aren't validated. You'll really do damage. But what you do is you test it and then there's going to be some responses that come back. Now the responses are critical, so, so one response is valid. Go right ahead, start sending emails. In fact, if you send emails to all the valid emails, you're gonna have a good day, right? It's gonna be a lot better. You're gonna get that delivery, everything's good, start there. Now what happens is some of the emails aren't gonna come back valid. They're gonna come back as something called a catch all. Now what a catch all does, it's something set up from the IT department which they basically say, we're not gonna tell you if that email's here or not. And there's a lot of companies that won't give you that information. So you have to make a decision on that catch all and you have to think about where it came from, how you got it, and if you can find it on other kind of public sites. There's like another kind of. What I do is I cohort those and find out, all right, which one of these catch alls can I find on other websites if I can't find it, I'm going to make sure that if I'm sending to these people, I'm sending it on a completely separate domain name and I'm not doing anything. I'm not sending all those through my main primary domain name. Because if you start to send through that and you start hitting all these catch alls, you're in trouble. And then I guess there's also bouncing, which you never want to send a bounce. It's just completely unacceptable to send anything to bounced emails and you're just not checking it. And then there's another one that's a spam trap and that one's even worse because that one's the one they set up and then they report you as spam immediately.

I think one of the things you and I talked about. I'm just. Sorry, go ahead.

Yeah, no, I was just. That's what you have to look at.

I think one of the things you and I talked about some time back was for example, if I have 100 prospects I would first want to run this via these bound checkers where they tell me which one is valid, which one is catch all and which one is bounds. So your recommendation is not to send any emails to bounce or maybe basically verify again with another provider if you can get a valid one and maybe recheck until you reach like a valid or catch all.

Yeah. So the ones that are that come back balanced, just don't email those. You could double check it with another provider but some of the providers out there, what they do is they, it benefits them to not check it as long because that's how they pay their compute costs for cloud. But there's some providers that will give you a 30 to 40 second check. You basically need to wait is that's the secret. You need to wait to get the answer back from those. So go for, don't go for speed, go for accuracy of course. But if it's still coming back bounce after 30 seconds of waiting, then you base and this, the tools will do it automatically. This isn't a manual process by any means. And what you want to do is send to those ones that the validation tools will tell you to send to. And I also would not validate with the provider that you buy the data from. Do it from another provider. Just so you know, you're getting that kind of consistency there.

Got it. Another thing which I remember we talked about was not only to send these catch all emails from another domain, but also run a different sequence. That way, as you know, you can always validate whether it's impacting your original sequence or not. Because if you're sending it to all valid, your open rates could be even more higher. I mean that's what I at least realize.

Yeah, we try to get about a 70, 75% open rate across 10,000 emails. Right. Like that's our goal because what we realized is the compound impact of getting it earlier. It's just like a four, you know, it's just like investing earlier. It's just big. And what you're, what you're mentioning there is, is in terms of changing the sequence around. So there is a really. One of the other things that the spam filters will check is if you're sending to some of the same domains, if you send that same email without any, any, any of the text changed, that gets picked up pretty quickly. So what you can do is you can add these kind of like variables in it. There's something called spintax, I Mean, look it up. But a lot of these tools have multiple variables. So you'd say like hey, whatever, hello, whatever. Right. You kind of change the variables and make the sequences different every time they go out. A lot of the tools, I think pretty much every tool has that functionality. It's just a lot of people don't really take the time to do that. And you really need to now, you really need to go in and make these things unique. Right. And you want to add stuff that's unique to each person if you could. Right. Like there's ways to do that too on a spreadsheet, to mail merge it the right way. And you know, there's a lot of strategies on this and the people that figure this stuff out are going to be the ones that are successful with cold email.

Awesome. So in one of your posts you also talked about some validation using Excel. Could you maybe talk a little bit more about that?

Yeah. So there's a. So in Google Sheets there's a, there's a feature and I kind of exposed this on that LinkedIn. I kind of gave away one of the secrets here. Hopefully it doesn't get blocked or somebody. But one of the ways you can get some of those catch alls back and get a little bit more confidence level on them. Obviously it's not a hundred percent, but you can right click on Google Sheets when you put an email in and it's very similar to if you type in somebody's name in an email, but you can right click and go convert to people chip. And then what you do is you see the name turn gray if it's a real email or not on Google. Now there is a little bit of a margin of error we found. But I just talked to somebody who just, he messaged me in my DMs over the weekend and he said he just enriched 14 million emails for free. So he was pretty happy. He just saved himself like, I don't know, that might have been like 15, $20,000 of data. Right. That he just figured out he might even have a bigger database than some of these providers. But that gives you that confidence back. So if it's a catch all and you find it, there's. It'll only find people on G Suite though. So that's a catch. Yeah, there's a. So if you do it, it basically looks to see if they're on Google and if they have an email on Google, it's one of the ways to do it. Right? Like that's one of the ways to get some of your catch alls back. I exposed this on there and that that Post got like 200,000 views of course, because it was a pretty good secret. And I was surprised because usually quality posts don't really make it past the algorithm.

Yeah, I mean, believe it or not. So when you first told me I was doing this one by one until I realized that I could actually select the entire column and you know, just do it in one go.

So but it also gives you other information like cell phone sometimes, like there's a lot of information there you get. So it's definitely something you want to look at, look at on Google sheets.

Okay, help me with the next step. So let's say I find, let's say hundreds of catch all. I put that in Google Sheet. You're saying it's going to only identify the Google email addresses. It's going to turn it into gray. What's your next recommendation? Should we put this again from a different domain into a different sequence or how do you do it?

So the best strategy would be to take that and put it on one. Those emails are lower quality of course because they're not valid. You haven't validated them. There's no way to make them valid because they're catch alls. But I would say there's a pretty high confidence level that you'd want to email them. And I would probably try to isolate that to one group of domain names. Obviously like the hard part is the reputation level is driven by the domain name. This is what people. It's domain name and IP address. Now let's think through this a little bit. Nobody is blocking Google, Zoho and Microsoft's IP Pool. It has nothing to do with the IP for those providers. Maybe for DigitalOcean or somebody like that, it's going to be a little bit. They're not as they're kind of known. They have a lot of people on there that are sending a lot of emails. But for those three providers, the world has said we don't care. We know that we can't reject emails from Microsoft, Zoho and Google. So your best tactic would be to blend in. Right. So the domain name is what the reputation is based on. Right. So I think Microsoft and Google have a little bit of a war going on right now. I can tell they're starting to get a little more aggressive on putting each other's domains and spam. Let's not talk about that. What we have seen is if you can kind of stay on one of those shared platforms, you keep Your limits low. You blend in, you send relevant emails with relevant information to relevant people. You're complying with all of the laws and everything in your country. You know, obviously there's GDPR and you want to be mindful of that. But if you do this, you are going to get a good return on your cold email program. This is going to change the way that you kind of get business. Remember, cold email, you don't have to physically be there. This is one of the things that I think I argue a little bit with the cold. There's a special group of people and I have a really like these people. I respect them quite a bit, but they always fight with you. They'll tell you you're like a wimp, get on the phones. Like there's this kind of like macho, I don't know thing going on, but I don't really understand it because you physically have to be there to make cold calls. Right. If I don't physically have to be there to send cold emails, I'll take that because I can spend time with my family and I don't have to go, you know, send, you know, they send while I'm sleeping. Right. Like I don't need to be there. And that's a huge advantage to cold emails.

True. I mean one of the question I had which something I get especially from the early stage founders all the time, Even let's say SDRs who are getting into a different territory or different industry altogether where they have no experience in terms of what should be my benchmark look like. And I, I often don't have the answer because if I were them I would probably look at some sort of stats, some sort of studies. I mean if you think about this, most of the SAS studies or most of the email open rates are, you know, sort of genetic. So what do you think? For example, we're running a lot of.

Campaigns and we, we are seeing the stats and we see what a good campaign looks like and we see what a bad one looks like. Right. So let's just talk through it. So in terms of the stats, you want to watch open rate and you're going to see a lot of the gurus out there are going to tell you it's a vanity metric, don't just ignore it. Unfortunately, it really isn't, it really isn't right now. And they'll tell you, well, it's not a vanity metric. It gives you a performance of your email delivery and subject line and the timing of that email. So what we like to see for an open rate is for like a big sales organization, sales development team, like a 40% or better if you're below 40, you know. And I just did a John Barrows webinar on this and the average was like 10 or 15. And I was, you know, shaking my head a little bit because I was like, whoa, this is not good because you're not going to get the level of that. So first thing is open rate. Second thing I would look at is response rate. Now we tend to get around 5, but in kind of earlier in the campaign we'll get about three. This would be the number of people that have opened the email that we can get to respond. Now I'm talking about all the response levels, right? Negative, positive, doesn't matter right now. I know people are like, well, why do you. No, no. So you got to look at the total number of responses. Then what we do is we back that number into something we call a positive response rate. These are like, yes, I'd like to learn more. I'll take a meeting. Right. They're like one step away from that meeting or they're actually asking for the meeting. Right. Or whatever the high ticket item is, right. That you're trying to sell. Right. So we do 50 or, sorry, 40% open rate, 3% response rate. So a lot of teams are at 1 or 2. That doesn't work. Right. You're going to have to figure that out. And then the positive response rate, we like to see a 50, 15% rate. So that's. Of those 3% that kind of come back through. That's you want to see 15% of those become positive. So I can give you kind of an example. Let's say you sent out 3,750 emails that got opened. Sorry, you sent out 7,500 emails that got opened. And then your next number would be you got 113 that were responded to. That might be 16 positive responses. And then you're booking maybe out of those, you're booking about 80% of those meetings. Right? Because if they positively responded, you should be able to get the meeting. So that right there is about 13, 14 meetings. Right. So that's kind of how you have to do it. So just to recap, open rate, 40% response rate, 3%, positive response rate, 50, 15%. Sorry, the numbers get a little bit confusing here. But you know, 43, 15 and then the show rate of the people that actually show up to the meeting, 80%. Those are the numbers you have impact over.

Got it.

And you know, there's one other number, but it doesn't kind of fit into the equation. But you should be checking for under a 2% bounce rate. You should not have over a 2% bounce rate. That can severely impact your campaign as well. But it doesn't fit into the same funnel.

Got it. So I'm guessing when you talk about these number 3750 emails or whatever, the number you talked about is this specific to a particular industry or is this like common across?

So it's after sending a lot. The two industries that I've targeted or have done it with is either agency like service based agencies like digital marketing or whatever, and more like technology SaaS and maybe a little bit of IT services. So I've tried all three and I haven't seen a huge difference between the three industries. I think it could only get better if you're doing it to an industry that those are probably the harder industries to target because they've actually got more people kind of targeting them. Obviously that's where a lot of the world's going. So I think you could probably expect higher ones. I've talked to some people who are in regulatory industries that are doing cold email and they're killing it right now where they've shared a couple of their numbers and they're in some like more compliant, like where there's not a lot of people selling. They're getting their cold emails off the ground and they're really doing well. So I think there's opportunity there to get even more. But I think that's a pretty good benchmark for really everybody who would be watching this podcast.

I have one final question.

Yeah.

So some of, some of the founders, some of the SDRs might say, Hey, I only sell to CEOs, I only sell to one Persona, right? So that could be the reason why my open rate is low. Do you think that's the case or no?

And I'll tell you why. Because, you know, and I did some consulting, right? First for Winning by Design, top management consulting firm in the world really for SaaS. Right. And you know, the real strategy that you really, you know, after looking at benchmarking in 500 companies, like you really got to go into the company where the biggest emotional impact is, right? Like this is somebody who's blocked or whatever. You got to find your mobilizer. So if people are targeting the CEO, you know, what's the, the only thing I could see you'd be targeting the CEO for would be possibly, you know, funding, right? Or maybe, you know, maybe, maybe his Email's not working or their email's not working. Sorry there. But you know, I think that's the thing is like you really, when you're going into any company, for any, it doesn't matter what outreach method you're using, CEOs are going to be much lower response as you'd imagine, right? But they're not going to be lower response if you get the right, like, you get the right pain. The problem is their pain points aren't the same as like, you know, if you're an SDR manager, you need more meetings on the calendar, you need tools to help you do that, you know, you know you could go after that group, right? The emotional impact isn't as big, but for a CEO, it might be more fundraising, it might be more, you know, visibility into the market, data insights. You probably still get a pretty good, you probably still get your 3% response rate if you were relevant. But you got to go for that person who can mobilize internally and become your champion.

I think you covered everything pretty much in less than 30 minutes. Any final thoughts? No.

I mean, just take a look at this, right? Like, you don't have to change it all tomorrow. What you do have to do though is you have to start thinking like, what damage am I doing with my cold email program? Is it worth it, right? You're spending, companies are spending a ton of money on these programs. Put it on another domain name, right, and do it that way and do something to just make sure that you're getting a reasonable open rate. Like, don't just sit there and wait for it to get better. It's not going to get better, it's going to get worse, way worse, because the spam filters are picking it up. And the last thing I'll end with is another tactic that a lot of people have been thinking. They get with their IT department and then their IT department immediately tries to put them on what they call an email service provider. Like more of like an enterprise grade sending system like Amazon, Sesame, Sendgrid, Mailgun, all those. I'm going to tell you right now, you do not want to do this. And I can talk to you about why, but the real reason why is you can torch the domain in less than a day and you won't be able to send from it for months. So be very careful about that. You don't want to put your team on a dedicated ip, you don't want to put them on a dedicated sending platform that, by the way, doesn't allow cold email. You want to be on a shared provider. So I think I'll end with that. If you have any questions, you feel free to reach out. I'm always available there and then, you know, looking forward to everybody's feedback.

Wow, this was super insightful, Jesse. Thank you so much, man.

Yeah, thanks.

Have a good one.

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