Nov. 25, 2021

5 Do’s & Don’ts of Cold Email

5 Do’s & Don’ts of Cold Email

With roughly 300 billion cold emails sent every day, how do you make your message stand out from all the outbound noise? Directly from the sales horse's mouth, our guest today is powerhouse Jeremy Donovan, who is the SVP of Revenue Strategy at Salesloft as well as the author of 5 books - including How to Deliver a Ted Talk and Predictable Prospecting. From AI, to the precise metrics that sales leaders should be using to measure effectiveness, we cover it all. We also delve into the false dichotomy of personalization and relevance, and how to strike that balance, plus the importance of keeping your finger on the pulse of changing trends that boost or reduce customer responses. Finally, Donovan shares, in plain language, his 5 top do's and don'ts that you can implement right now to have a greater reply rate and help the customer do the right thing. This includes specific language, punctuation, sentence length, and more. If you're looking for concrete, actionable tidbits of gold from one of the leading figures in the industry today, you're in the right place! Tune in now and hear what he has to say.

Key Points From This Episode:

  • Some background on Jeremy Donovan's varied experience and interests.
  • How Donovan collects and tracks cold emails for testing and analysis.
  • Talking about the effects of the pandemic on prospecting.
  • What's changed for the better and the worst in sales, and the hyper-education of buyers.
  • Talking about the concept of reciprocity and proving you're a human behind the email.
  • Donovan recommends researching Becc Holland.
  • What kind of role will AI play in prospecting?
  • How the relationship between personalization and relevance is a false dichotomy, and how to strike that balance.
  • What metrics a sales rep. should be looking at. 
  • What is a great rule of thumb for knowing when to pivot your style or strategy.
  • Examples of specific words and alternatives that can boost or reduce reply rates.
  • 5 killer do's and don't, from subject lines to punctuation marks in the first sentence.
  • Finding the sweet spot of keeping the email customer-centric while keeping it natural.
  • The importance of keeping it short and simple - plain text performs better.
  • When to leverage gifs and video, and being on top of the changing nature of trends.
  • How to craft an inviting and effortless call-to-action.


“I care so much about prospecting emails, I try to learn as much as I can. I track all the prospecting emails I can.” — Jeremy Donovan [0:02:45]

“My job officially is Revenue Strategy, but the fun part of what I do is figuring out what works email-wise and cadence-wise, and then helping out customers do the right thing .” — Jeremy Donovan [0:05:33]

“You've got to figure out ways to stand out that prove you're a human.” — Jeremy Donovan [0:11:41]

“If you wouldn't say it out loud, you shouldn't write it in an email.” — Jeremy Donovan [0:37:00]

“As things become more generic and effortful, they stop working.” — Jeremy Donovan [0:39:28]

“The more effortless you can make things for your prospect, the better.” — Jeremy Donovan [0:42:20]


Links Mentioned in Today’s Episode:

Jeremy Donovan on LinkedIn


Predictable Prospecting

How to Deliver a Ted Talk

Robert Cialdini and the Six Levers of Influence

Becc Holland on LinkedIn

Cold Email Grader

Subject Line Grader

The Sandler Selling Method 

Sam Capra on Linkedin

The Sales Samurai B2B Sales Podcast



Speaker 0    00:00:01    Coming to you from Orlando, Florida, Orlando, Florida, and streaming around the world around the world. You're not tuned in to the sales samurai podcast. The only B2B sales podcast, providing unfiltered unapologetic views and tactics directly from the sales trenches. Here's your host, Sam Capra.  
Speaker 1    00:00:27    Welcome to another episode of the sale samurai. Thanks for listening. Before we begin, do us a favor, take a moment to subscribe and download on today's show. We're going to be discussing the five do's and don'ts of cold email, and I have an amazing guest for you today by day, Jeremy Donovan is the SVP of revenue strategy at sales loft. And in his spare time, he's written five books, including how to deliver a Ted talk and predictable prospecting. Jeremy, welcome to the show, man. How are you?  
Speaker 2    00:00:56    I'm doing great. Thanks for having me,  
Speaker 1    00:00:57    Sam really excited about this. This is one of those subjects that I literally put this out to the LinkedIn and my network, and I don't think they can ever get enough of prospecting, like cold outreach, cold phone calls, cold email, all that fun stuff, because, and I think, you know, this, you know, operating a sales loft, like the statistic I saw and Jeremy, you may know this as well. I think it, HubSpot just came out with, it says 40% of salespeople say prospecting is the most challenging part of their sales job or sales process. If you will, 40%, that's a pretty good size number when  
Speaker 2    00:01:35    Yeah. I'm not surprised by that. I mean, thinking about the other things that you do, right? If, if it's account management, it's people, you know, and are happy often, not always, but often happy to take your call or, you know, sitting in one-on-ones or training or forecasting or whatever. Right. But yeah, no, that, that makes sense. And yeah. Yeah. And you get a lot of rejection during prospecting. So I would assume that's a pretty anxiety inducing sort of a thing  
Speaker 1    00:01:59    Without a doubt. And the other piece of it that, you know, and I want to hop into it because the other study I was reading it and why I think this is such a good topic and probably why everybody is so interested in it. The stat was about 300 billion emails are being sent each and every day. That's the latest study. I mean, I couldn't believe that number, but we're going to talk about it because it leads right into what we're going to be discussing the five do's and don'ts of cold email. And by do I want to circle back to it, but just kind of have it in the back of your mind, Jeremy, like what does that lead to? Like we were, we were talking about it offline, the noise of just, just outbound, making it so much difficult.  
Speaker 2    00:02:38    Sometimes I feel like I get 380 billion emails a day. I very much true. Right. As I actually, I do a funny thing because I care so much about prospecting emails and I try to learn as much as I can from prospect emails, but I actually track all the prospect emails I get and I saved them. I have a little Google label for cold email and I actually go back to them and, and look at them and try to think, why was this one bad? Why was this one good? And then I take those and then we use our kind of data science to understand. Huh? If you use like an HTML ask treatment, underlined highlight pink, flashing, whatever different font, like does that work or not. So I'd like to test these emails to figure out whether they're any good or not  
Speaker 1    00:03:24    Worth their weight in gold, if the juice is worth the squeeze for lack of better.  
Speaker 2    00:03:28    Yeah, for sure. And yeah, with that humongous number of emails, I think, I wonder if you were to look pre March of 2021 and then a few months later, I feel as though, and we actually saw it in the data that we saw an incredible increase in the volume of prospecting emails that our customers were sending. And just in folks in general, when I went to investigate why that was a, this is not rocket science diagnostics, right? It's like everyone, all the SDRs and AEs were at home and they weren't commuting. So they actually had more engaged, selling time available to them. And then, you know, we as prospects, right? I'm more on the buying side than on the selling side. We were just trying to figure things out. So we were probably less responsive and scared both for the business and for, you know, our families and our health. You saw email volumes go up, response rates dropped, same thing with call volumes and connect rates. Just think we were kind of getting back to a new normal now, but yeah, a lot of,  
Speaker 1    00:04:27    Yeah, I want to circle back to that because a lot of those numbers, that's what drew me to reaching out to have a conversation, just the data behind it. Right. Because it's one thing to talk about what's working and what's not, it's another thing next, you have the data that kind of supports what you're seeing. But before we go down that path, give the audience a little background on yourself. Kind of what you're up to. I know obviously it's sales loft, everyone knows sales loft, but kind of give everyone a kind of a quick background. If you don't mind,  
Speaker 2    00:04:52    It's hard to go quick, but I will, I will try because I have five different jobs right now. It's Jeremy fair. I mean the short answer is I, I, I joke that I'm like the biggest fraud in sales because the last thing I actually sold was mangoes from the side of the road in Florida when I was a little kid. So not like I'm a sales strategy and operations person. I'm not, not a Salesforce. I don't pretend to be at all. What I, what I do is I learn very, very, uh, aggressively, right? Like I'm, uh, I'm not smarter. I just, I just, I, I will outlearn anybody or try to outlearn anybody. And that learning comes from reading, but it also comes from going through all the data that's flowing through our systems to try to figure out what's going on. So amongst the, you know, my, my job officially is revenue strategy, but the sort of fun part of what I do is, is, well, it's all fun, I guess. But the contextually relevant part of what I do is, is like figuring out what works email wise and cadence wise, and then helping our customers do the right thing. Right.  
Speaker 1    00:05:49    It's awesome, man. I always ask this question, cause it's a fun question to ask because I know you said, listen, I'm not truly, I haven't. So I haven't really sold anything since mangoes down in Florida, how long you've been in the sales space, sales strategy type of investment.  
Speaker 2    00:06:02    Yeah, I wasn't actually, it wasn't CRO funny enough, but I would say about a decade. So I've been working 25 years, a little more, maybe 26 years. And I spent my early part of my career as an engineer. I have a semiconductor physics background and statistics background, computer science background. So pretty tactical background. And then yeah, I found my way from that into product, into marketing and then over to sales  
Speaker 1    00:06:27    In the past decade, I always ask this question because it's always fun to kind of hear these answers from different. And I liked the fact that you're coming at it from a different kind of perspective or different lens in your eyes. What has changed the most in sales in the past decade? And that's, that's the space for better, for worse each side. So what's been changed, what's changed for the better. And then on the flip side, what, in your opinion has changed maybe for the worse,  
Speaker 2    00:06:52    I guess I'll start by saying, I think things change less than people, especially the pundents right? Like there are people who are paid to make it feel and sound like everything is changing all the time and oh my goodness. If you don't spend money with me, you're going to be left behind. I actually feel as though it's like, things haven't changed that much, but what has changed? I think it's kind of obvious, right? The biggest thing is both like a plus and a minus, right. Which is I just bought, you know, I just, I just licensed for our company some software. And I went into that where I had, I had like research the space, developed a short list of companies. I had developed a punch list of required, you know, like must have a nice to have feature set. I had talked to three or four or five different colleagues at other companies.  
Speaker 2    00:07:41    I call them colleagues, but like my extended peer network. And they were users of these types of, of the platform type of platform that I ended up licensing. Right. So I, I went in there. I, you know, you hear about this from Gartner slash CEB. Like I went into it really, really educated. And then I went inbound to the two vendors who were my finalists. Right. So like, is that a good thing or a bad thing? Like, it's awesome for me as a buyer that I can be so much more educated. It sucks for the folks I ruled out because there were other, other vendors in that space. Like it sucks for them because they never even got a chance to maybe I was wrong. Like maybe I ruled some folks out and they would have been a great fit. So like, I think that's a, that's a double-edged sword, but again, it's, I think it's a relatively known thing, right? Is like this, this hyper education of the buyer  
Speaker 1    00:08:30    Catch actually. Cause Jimmy, you know, as, as much as that is a pretty evident stat, right? I mean the sheer amount of information out there, I don't remember the statistic from my Salesforce days, but more data has been created in the past three years than ever in the history of humankind, whatever. Wow. I barely tuned in for that day of school at Salesforce, but it's really you're right. It's a double-edged sword because you're right. What is the stat 70% of the buying process done before they ever talked to a salesperson and that's good. Cause you have an educated buyer. So your education process, if you have too, is, is minimal on the sales side. But to your point, you're also depending on them to understand what the requirements really should be. Right. I've never bought this before. I'm talking to a lot of people, but not everybody's business. So you're right. That is a double edge sword from a sales perspective, kind of that information overload can go both ways.  
Speaker 2    00:09:21    The other thing that strikes me, and this is again, conceptually relevant, I think to the stuff we're talking about is, is, is like, think about an arms race, arms races are so unfortunate, right? As a public society thing, a true arms race is obviously horrendously terrible, right? Cause you build up stockpiles of, you know, conventional and nuclear and biological weapons, which are all horrible, horrible things. But even in the sales, you know, sales and marketing space, you know, if you were to wind the clock back 10 years, if you wanted to say something like, you know, uh, if I were to put like your first name in the subject line of an email, I would have had to physically type your first name in there. And buyers, prospects would look at that and they would say, oh, okay. Like Jeremy actually took the effort to type the name Sam in there.  
Speaker 2    00:10:05    And it triggers what Robert Cialdini, right. Talks all hit, you know, his, his levers of, uh, of influence. And, and one of those is reciprocity, right? So I was sort of trigger a degree of reciprocity and, and, but we're in this arms race where, okay, so now the machine can do that and everyone knows the machine does that. So therefore what I see, you know, Jeremy in the subject line of an email, I instantly like, I I'm already disengaged. So this arms race has continued. It gets to now, which is interesting, right? I mean, you've got a bunch of companies out there. The space doesn't even have a name. It's like email message, content generation. I don't know what you would, you would call it. And they are there. I was joking. I was talking to someone earlier and I said, it's like, imagine you turn back Holland for those listeners who know who Beck is into a software product, you know, back has this thing where if you look at our content and flip the script, I think it's called, she's got these, I don't know, six ish levels of ways that you can personalize.  
Speaker 2    00:11:05    So now you've got companies out there who are, who are taking that concept and they'll scrape LinkedIn or they'll scrape whatever sources. But I feel as though, like, imagine, you know, imagine you start to get 10 emails a day and all of them say, Hey Sam, I saw that your company raised, you know, $50 million and its series series B, congratulations. I'd love to talk to you about how we, blah, blah, blah. You know, then the problem is, is that then the humans all realize that this is all BS and they do the same thing as when they see the first name in the subject line. So that that's the arms race kind of worries me in that space. So you gotta sort of figure out ways to stand out that prove you're a human. I don't think the people want to talk about like AI and bridging the uncanny valley that you can't tell if it's a human or a machine, as long as there's variety, I guess that's okay. But, but I fear that at least the path we're on right now with some of the rules engines and the way that natural language processing is being applied, it's like, everyone's going to be sending the same email basically, which is a problem.  
Speaker 1    00:12:08    You know, it's funny as you're caulking through that, when you've mentioned bay, Collin, cause I was just listening something, she said on a podcast, she mentioned, and we're talking about email. This is why I think it really closely related to this. We always hear personalization, personalization. You've got to personalize and you know, personalization gets a 14% lift and you know, email reading and replies and all this stuff. But she said something that was really profound and I actually really stopped and rewind the, you know, kind of wherever you call digitally, every wound it, she said, she paused and she said, stop saying, it's personalization. Like you can't personalize at scale, you can give relevance at scale, like relevance at scale is doable. Personalization at scale is, um, I'm ad libbing. She, she has  
Speaker 2    00:12:52    To agree. I agree completely with no  
Speaker 1    00:12:54    Doubt, I think every, but that goes, Jeremy, this goes to that, the email cold prospecting. I think every Salesforce keeps been beaten in their head. You kind of personalize and they spend so much time trying to craft the perfect email that doesn't exist. Right?  
Speaker 2    00:13:10    Yeah. I'm with you. I don't think it exists. I mean, it's a numbers game in a way. So let's take the following. If you personalize, we know from the data we've looked at, if you personalize up to 20% of the email, then your reply rate is going to double, but you want to personalize up to 20% of your email. Usually it's the first 20%, but we don't really distinguish. But if you personalize up to 20% of your email, then, then you will sort of double from your typical reply rate. On average,  
Speaker 1    00:13:36    When you say twin, like when you say personalized like that, isn't like putting salmon. They're like, what is, what is an example of personalization? Like a funding of 50 million? Like what, what would, what constitutes is that?  
Speaker 2    00:13:47    Yeah, I'll give you an example, but I'll just, I'll just tell you methodology here. Right? Which is when people use our platform, they start with a template and then we can determine whether or not they overwrote any portion of that template. And we know we can track that they overwrite one to 10, 20, whatever, a hundred percent of the temp blow away the whole template and override a hundred percent. So we know that they've overwritten a certain percentage of it in this case we're talking and this analysis was done on something like 300 million emails. So we're not actually making a distinction in that analysis between what you specifically did. We're just saying if you overwrote for me. Yeah. Like Beck stuff is awesome. So I would sort of start, I would start there and Beck stuff is still working because, so, you know, the machines haven't conquered that yet.  
Speaker 2    00:14:30    Personalization for me, like if someone sent me an awesome email would be like, Hey Jeremy, I heard you on Sam's podcast where you talked about X, Y, Z. We do, you know, like we do XYZ. You know, like I think that's, that's good personalization because again, what it, what it's doing is it's saying ha there's no sales machine out there yet. That is reading, you know, it's going to listen to a podcast and pull out like the right sentence at the right time. So I know that that human actually took that time. So like, I think that that would be an example of personalization or, you know, like if I said, Hey, I've been thinking a lot. If I'm pretty active on LinkedIn, I posted a lot on customer success lately. Cause I've been thinking about customer success. So if someone were to say like, Hey, I noticed, you know, you shifted from talking a lot about forecasting or whatever, to a lot about customer success, right?  
Speaker 2    00:15:20    It's like no sales machine. Isn't going to necessarily notice that context switch and where my interest lies and yet a person could do that. So I think to me, that's, that's like true personalization where I was going with that though is okay. So let's say that, you know, you do that 20% because beyond that, you don't really get a return, but you get that two X, the counterargument with, with like relevance is that, you know, if it takes me more than two times as long to personalize, then that's, that's bad. I think this is a bit of a, it's a semi false dichotomy. And it all comes down to context, which is the following. Let's say that you are an SMB seller and you have effectively an infinite pool to prospect into, I would skip personalization because it doesn't, you know what I mean? Just want to get as many out as you can as relevant as you can.  
Speaker 2    00:16:14    And, and that's, that's the way. So I think in that context, relevance is the right, is the right thing. Take enterprise selling. I know reps who have 10 accounts. I know reps with one account, but let's take the, you know, that's usually they have a Mondo account that their ups, you know, they're like maintaining and upselling, but let's say you're a rep pro an enterprise rep prospect in 10 accounts. You're not, you're no longer like time constraint, right? You effectively have a very limited pool, but you know, quote unquote, unlimited time, if you don't personalize, you could burn that account. Right? If you send the same email to 20 people in the same, in the same enterprise, you could burn that account. You have no choice, but to personalize. In fact, if I, if I were prospecting 10 accounts as a rep, I would, I would do the following.  
Speaker 2    00:16:59    I w you know, we'd sometimes refer to this as bottom up prospecting, I'd go call, like we sell sales stuff. Um, my marketing team would get mad at me for that, but we sell sales stuff. I would go, and I would call like five salespeople. And I would say, Hey, I just want to shoot the breeze with you about a day in your life. I'm not trying to sell you anything. I just want to learn. And then I'm going to go to their manager and I'm going to say, or their, you know, their boss or their boss's boss, or boss's boss's boss. And I'm going to say, Hey, I, I just talked to five of your people. And I did a study about what's working. What's not working for them. And I'd love the opportunity to present what I learned and how I think we can help.  
Speaker 2    00:17:38    That's hyper-personalized bottom up prospecting. And I can tell you I'm way, way, way, way more likely to be able to get a meeting with that senior exec by saying, I did. I know something, your team that you may not know, and I'm here to help you. And I did the work to do it, so that, so I just think it's, it's another thing that like pundits, uh, you know, they like, they need to make money and they need to get likes and whatever, plenty of pundits are my friends, but like relevance versus personalization is a, is a, a false dichotomy. And it really is all about the context of how you're selling.  
Speaker 1    00:18:10    It's perfect sense. You know, it's funny, you, you mentioned that, you know, one of the things that, you know, back in a past life at career builder, you brought up that kind of bottom up versus top down. We used to call that chair siding. You know, when we used to go, we used to sling job ads at CareerBuilder many, many moons ago. You know, we used to actually go sit by side the recruiter just to understand what their day to day was like, understand what the challenges look like. So you can go back to the manager or the chief human resource officer and say, Hey, I've chairside with 30 of your recruiters. Here's what I'm seeing. And here's how we can help. You're right. That's a much more relevant story, right? Because you're kind of up in that ivory tower and you're bringing actual, tangible information back to them.  
Speaker 1    00:18:51    So I think that, I think that's actually a lost art anymore. I think it's, I think that we need to get back that from a sales perspective. I'm curious because you are seeing a ton of email. You like what you guys do by the way sales loft is a fantastic organization, fantastic tool. I've used them in the past. So I'm just curious, because as a sales leader, you know, we look at all these sequences, these cadences, and what's performing and like, oh, the open rates are fantastic, but the reply rates suck, like, what are the metrics that we like you should be looking at as a sales rep, as a sales leader? Like, what are some of the KPIs you guys look at when you guys are evaluating, what's working and what's not,  
Speaker 2    00:19:29    Oh, yeah. Uh, so I mean, I could talk about that in the sales email, I mean more broadly, right? I think about leading indicators and lagging indicators, obviously your, your ultimate lagging indicator is, is bookings and quota attainment and win rates and all that kind of thing. But on the, on the front end, on the prospecting side, I'm going to give you sort of two-ish answers. One is what I look at the individual rep that I actually look at two things. I look at their activity level and I look at their effectiveness level. So for me, the effectiveness level is how many activities do they need in order to get a qualified op? So if I'm, and if I multiply like that number times, well it's ops per activity, times number of activities they do in a given period, then I know how many ops are going to generate.  
Speaker 2    00:20:13    And then I can apply all the rest of the funnel metrics down. So like that for me is, is really important. I actually stack rank reps on the effectiveness measure. How many activities does it take for them to get an op? I want those who spend obviously less activities to get a qualified op cause those are the better, you know, the slippers, if you will, the, the, the reps who are more, more effective. And then I try to learn what those reps, what those reps do. But if I were to go now, that's sort of one answer, and you can tell me which direction you want to go. But the other one is you mentioned open rates, click through rates, reply, you know, so I don't actually look at open rates at all because a lot of times that's a false, you get a false signal there because email spam servers open and, and, you know, and read to make sure everything's okay, data with clicks, they'll follow all your links.  
Speaker 2    00:20:59    So it makes sure that those links are safe. So I don't, I don't use that as well. The thing I look at is, is reply rates or positive reply rates. There's such a strong correlation between reply rate and positive reply rate. I don't really sweat the difference so much. Sure. You can give me an example of where somebody says unsubscribe me, but it's, it's, it's, we're talking about correlation here. If your reply rates are good, it's so unlikely that everybody told you that they were going to unsubscribe. Um, so yeah, I, I, I like reply rates as, as, as the metric I care about and, you know, a typical reply rate in B2B selling these days, probably 3%. Some people do a little better. Some people do a little worse, but that's probably about right.  
Speaker 0    00:21:45    You're listening to the sales samurai podcast. We'll be right back after this break  
Speaker 3    00:21:53    Sales samurai is excited to announce the launch of the largest database of B2B sales resources on the planet, 600 plus resources with more added every single day, searching sort and filter and leading software providers, podcasts, books, blogs, and so much more, the best part. It's absolutely free to search, go to sales, to start your search.  
Speaker 1    00:22:22    So, as you're looking at some of those, we're going to talk about some of those dudes and don'ts, as we're talking through this, but I've always, and we're going through this right now, actually, you know, you're running something and you're running multi-variant and you're you're testing, and you're doing all this fun stuff. You know, you're not getting the reply rates. All the leading indicators are well, the open rates, right? I got to look at something to say, Hey, at least people are opening. Is that like, one's getting 17 versus 40, right? What do you typically see is a good period of time to say, okay, it's time to change. Like, is it 30 days? Is it like, when do you typically see that? Hey, it's not working. You're not getting the reply rates you need to adjust course at the 30 day mark, 40 day mark, 10 day mark, is there a, is there a good rule of thumb, Jeremy, that you guys see that if you're not seeing X by this time, you need to make some course adjustments.  
Speaker 2    00:23:13    It's less time basis, more volume-based right. As like, if you send one email a day, you're never going to learn. If you send a thousand emails in a day, you're going to learn in a day or less, right? So if I, if I'm AB testing, I have a bookmark for this on my, on my browser, but I just Google the calculator for the test of two population proportions. And, you know, a lot of marketing automation platforms or things with AB testing have this built in anyway. But if it's not built in, and you're sort of doing a DIY, like can put in, you know, the response rate for your, a test and the number of emails you sent the response rate for your B tests, the number of B emails you sent, and then it will tell you whether or not the, you know, there's a statistical difference between those two different things.  
Speaker 2    00:24:01    And so, as soon as that statistical difference appears I'm going to shift, right? So if the B was better than the a statistically significantly better, I'm going to shift my beat of the eight position. And then I'm going to test something I'm going to test something new. So it really depends on, um, you know, it depends on, on volume. If anything, I think people give up because they don't actually have this, do that little thing of Googling and sticking some numbers into a online calculator. Like I think they probably give up too soon or they get one response and they, their minds explode and they say, this is better. Right. I think it's just, it's so anecdotal and not useful. What I love is, as I mentioned before, it's like, I get an email, you know, there's, there's, we actually have some utilities to do this that are like publicly, publicly available and free. But like, I don't actually have to do the AB test. What I can do is I can just go to a site, throw my content into that site. And it will tell me whether the content is good or not. So it's like, it's like doing an AB test on a hundred million emails without actually having to send a single one.  
Speaker 1    00:25:06    There was four or five that I personally went through that we're going to include in the show notes. They're a fantastic, just helping you understand some of those subject lines, what works content. Fantastic. And you're right, man. Some of those things allow you to get better, faster if you don't have the volume to quantify it in today's day.  
Speaker 2    00:25:27    Yeah. We get really goofy names to those for utilities. It's almost a joke internally, but one of them is called email. It's literally emailed and then the other one is subject line, And that's it like it's, that's it. You just so you can stick, I wonder  
Speaker 1    00:25:41    What that does the subject line grader.  
Speaker 2    00:25:44    Yeah, exactly. Yeah, yeah, yeah. There's no, no ambiguity whatsoever. I will admit to having named them and I'm not that creative. So yeah, that was, that is like, what is the stupidest domain name that I can actually buy that's available? This is my naming approach.  
Speaker 1    00:25:59    Hey, so one thing I did want to do is we went, I wanted to kind of get to the do's and don'ts, and there's just been some really cool posts that you've had. Hey, I want to lead off by saying that how I took some of those posts, uh, one of them being, and this was really subject line specific. You really put a, I think you said subject lines that contain secret, have a reply rate, 76% below average, but those with private have reply rates, 35% above average. And so I want you to maybe elaborate on that just to help us understand a little bit more context around what I just read, but what I take from that is words really matter, right? It comes down to the verbiage that we use, even if it's a tweak of a verbiage, those things matter, but help give the audience a little context and kind of that blurb that I shared. I know you do quite a bit of those on LinkedIn as well.  
Speaker 2    00:26:52    Yeah. So I think I, I forgot, I probably got an email with like secret in there and I, I put, I was curious, does that work cause conventionally people, right. If they don't have data, they'll say secret as a trigger word, that should be really positive. Right. Um, and, and then I looked, what are the synonyms for, for secrets? So yeah, the way we do it is basically, you know, we'll take whatever, a hundred million emails and we'll figure out for that a hundred million emails, what is the average reply rate, whatever 3%. And then we'll isolate just those emails that have the word secret in it, uh, or the word private in the subject line. And then we'll say, okay, what was the reply rate of those? So we're looking for the relative, like boost or reduction in the reply rate. So right in the case of, uh, of the word, private, those emails that contain the word private in the subject line, have a reply rate that's about 35% above.  
Speaker 2    00:27:45    So what does that mean? You know, if your reply rate I got, actually, I gotta bust out the calculator here because by my brain is not as fast as it was, but if your normal reply rate was a, was a 3%, um, I'm gonna multiply that by, you know, an extra 35% and I'm going to get a four, 4.05% reply rate. So if your average reply rate was a three, then those emails that have private in them would have a 4% reply rate. Yeah. Words do matter. Fewer words matter than more words. But, but yeah, but words do matter.  
Speaker 1    00:28:16    That's what I was going to ask you. That was my next IB, because there's pro and I know there, I read most of your posts. So I'm curious when we talk about, when you look at the five do's and don'ts, there's five that just almost immediately come to my mind, like just based on the analytics and based on the stats that you've seen, like, what are just five, like these are just chillers.  
Speaker 2    00:28:38    So things that don't get open, don't get read the first thing people see as a subject line. So I think the stuff that's in the subject line, you know, should constitute a few of those. The first one is, is keeping your subject lines as short as possible. So, you know, we looked at reply rate versus subject line length and emails with one word in the subject line, actually have an 87% higher reply rate than those on average. And if you do more than about four words, you're you're toast, right? Like you're, you're absolutely destroying your email response rate. People ask me what's the magic word? And there is no magic word, but what's fascinating is fairly consistently the best word you can use as is actually your own company name. So, you know, if we're going to send an email, I tell my reps over and over again, just please, please, please just put sales loft in the subject line and nothing else. I talked to companies that are smaller and they're like, but no one knows our company name. Great. Like then that's curiosity inducing. If what, if you have a two words, two word company name, two words is fine, but you know, you don't have to cut off the second word of, of your, uh, have your company name. So anyway, that, that would probably be my number one thing is like, is keep your subject line short and pro and probably use your own, uh, use your own company name in there.  
Speaker 1    00:29:51    What have you seen? Cause I've heard this questions in the subject line perform better than non questions of you. Is that true? Not true based on your,  
Speaker 2    00:30:00    I have to, you know, I probably do have that somewhere and it's like not being fed into my, into my brain. My, let me see, I'm going to punch it into our subject line, and see if I actually, I might've actually put that in there. So I'm going to do that real quick and I'll have a real-time answer for you.  
Speaker 1    00:30:15    Yeah, because you're right. I mean, like you said, you don't really look at the open rates, but when I'm looking at Hey, should we make a change? Should we not? My leading indicators typically open, right? You're right. There's a lot of systems out there that can give you false positives. But if, at least if I know the, if I could stack rank that 40% open rate, 35% open rate, then there's this outliers at 17% open rate, then I know what's underperforming. And now look at that and say, okay, well it's obviously the subject line because that's the very first thing people see the reason they're going to open it. And then to your point, try to keep it really concise. And it's funny when you say more than four words, Jeremy, because those lower performing as I'm looking at it, actually those are actually the ones that are underperforming.  
Speaker 2    00:30:57    Yeah. Yeah. It makes sense. I got the answer to your question, mark one, using a question mark in a subject line lowers response rate by 11%. And that's why I love this stuff. It's like the data it's correlation. Okay. It's not causation. You know, I'm going to get a whole bunch of trolls. Come at me saying it's not caused no, it's not cause it's correlation. But you know, the correlation is 11% lower response rate. This actually leads me to, in a way to my another tip that that hit me, which I think is a, is, is as good. A number two as any is we looked at what's the punctuation at the end of the first sentence of the email, right? Should you use a period and exclamation mark or question mark periods, basically the baseline, right? Most, most emails have have a period. It turns out that the best ending punctuation mark for the end of the first sentence is an exclamation mark.  
Speaker 2    00:31:47    My, my admonition to people is don't just stick an exclamation mark on a, nothing, you know, on a nothing sentence. It's gotta, it's gotta be like legit, legit valuable, but that that's actually the best, the best thing you can do. And this actually gets at a, an immediate kind of, if I'm, if I'm listening to me right now, and then I'm calling BS like this, there are, there are certain tips I'm going to, uh, I think about, I reference that I think are more evergreen, right? Like I think the shorter subject is an evergreen thing that that will continue to be true. Every SDR and every AAE starts to put an exclamation mark at the end of their first sentence, they're going to all F that up completely. And then, then we'll get terrible response rates when, when they do that. So, you know, that one is working now and it will, it, you know, it will continue to work until, until it goes Jeremy,  
Speaker 1    00:32:40    Isn't that the case like that's the Tibet, it's the case with everything. Right. I remember the dear Gibeah emails used to work. Fantastic. The breakup email, all these different, I used to work. Fantastic. And then it got saturated and overused. And now,  
Speaker 2    00:32:54    Yeah, I mean that, that maybe that's a tip in of itself, which is like novelty, novelty, novelty, you know, you'll hear people talk about, should I, should I use if I'm calling people, should I use, Hey, you know, Sam, that's Jeremy from sales loft, the reason for my call is blah, blah, blah. And like the first time someone hears that it's great. Like, oh, how refreshing that someone is being upfront with the reason for my call is, but then as soon as every sales person says, the reason for my call is this stops working. So I do think it's the novelty, or, you know, you hear these debates about, is this a good time to call or is this a bad time to call? If I catch you at a good time? Like whatever, as long as it's novel for a period of time, and then you try something different. I mean, I once got trained by a Sandler training. Dave Fisher is his name and he advised us to say ring, ring, Hey, this is Jeremy from whatever I was at a different company at the time. You're probably already regretting having picked up the phone. So, but that's, it's, it's novel. It's funny, it's it, it, it breaks the tension already. So I think if you do stuff like that, again, as long as not everyone's doing it, that stuff is going to be wicked effective. I'm not even from Boston, I'm using a wicked.  
Speaker 1    00:34:03    So there's, so you've given quite a few already, but I want to just boil it down. You said, let them keep it to less than four words. That's kind of an evergreen one in the subject line using the company name is very effective in the subject line. And then you said the third one, this might not be evergreen because it'll change as we keep saturating exclamation point at the end of the first sentence seems to perform better for the time being, but don't just use exclamation point for the hell of it, make it relevant. Gotcha. All right. What's next on your list, Jeremy, these tidbits.  
Speaker 2    00:34:38    Yeah, this used to be my number one, but it's losing its effectiveness, which is to use, Hey, instead of like, if you're saying hi, Hey, hello. Hey Sam. You know, it still actually works pretty well. The more it's the more ubiquitous it's become a little less effective, but it's still, you can still get an 11% boost in your reply rate. And it's just the, I think it's the formality of it, which, which I think matters. The other thing I like to dispel, I like to dispel, as you can tell sort of BS, punditry. So there was there, there was this thing decades ago, and it never really went away that, that you should minimize your use of eye and your right. Cause you should be biased. You should be customer centric, which means you should use you all the time. And so we actually looked at the percentage use of like eyes versus use.  
Speaker 2    00:35:27    And, and what we found was if you, the worst you can possibly do in an email is to exclusively use use and never the word I, and I, I it's also, I can imagine receiving, being, just thinking, you always got to whatever you hear something, even, even stuff that comes out of, you know, that I put on the post or stuff that comes out of my mouth. Like you still have to be an intelligent consumer and see if this stuff makes sense logically to you. But I asked myself if I get an email, that's like, you, you, you, that feels wrong. And the data, no, it's not natural. The data confirms it. If you do that, you get a 35% lower response rate. If you don't put a single eye on your email in contrast, if you're all self-centered and just do eyes all the time, it's still bad, but it's about a 10% lower response rate. If you don't use any use at all. And it turns out that the sweet spot is this wouldn't make sense. Logically. It's like right in the middle, and I'm not going to say it's, I can give you actually the exact percentage, but it's not the point. I think the point is that it is you should write emails naturally and conversationally the way you would to a colleague or a colleague or a friend. That's how you should write.  
Speaker 1    00:36:35    You know, it's funny, you mentioned that because as much as we try to wordsmith these things, so perfectly as a sales person at the end of the day, just talk to them. Like it's just being human. Like it's just a conversation in an email format. Like I know I'm boiling it down way further, but  
Speaker 2    00:36:55    That's it. I think that's the best rule to walk away with is, is yeah. If you wouldn't, if you wouldn't say it out loud, you shouldn't write it in an email. You know, marketers will hate me for that too, because they want to craft this stuff. And if you'd roll your eyes saying that out loud to someone, then you probably shouldn't put it in an email.  
Speaker 1    00:37:13    Awesome. So, okay. We got four now I gotta get one more. Give us the cream of the crop in your opinion,  
Speaker 2    00:37:21    I'll give you, I mean, I'll get, I'll put this in the general category of like HTML related stuff is it has to look like as much plain text as you possibly can. So what does that mean? It means no bullets. It means no underlining, no bold, no italics. You know, if you're going to use a hyperlink, but well, don't, I mean, try not to, you know, so just as, as plain text, as you, as you possibly can, I think that's, that's the last killer killer one is like short, simple, plain text stuff. Performance way, way better.  
Speaker 1    00:37:55    That's a good way. Cause you know, sometimes that that's the basic right. Cause we do know that gets caught in the spam filters, but there's a couple of questions I have for you. And whether we have the stats or not, I'm throwing these off on the 11th hour, you know, at one point using gifts was powerful. And I is that, is that, is that, is that one of those fads I stayed away? Or do you still see that that's a pretty strong I, and I know it depends on the customer. It depends if it's cold or warm, like what are you seeing when, when you see gifts,  
Speaker 2    00:38:22    I'm going to separate gifts from images. Although there's obviously related the gift thing is pretty over images. Interestingly, we know that like zero or one images actually per performance relatively similarly. So you can have an image. I think with the image, I'll give you a good example. In bad example, right. Is one of the best examples of, of someone's use of an image when they were prospecting me was they took a picture of probably like the SalesLoft home page or something and they annotated it a bit, however, you know, whatever drawing thing that they were using. And then they sent that back to me. I thought that was awesome. You know, like it, it shows they, they like, they took it's good it's it's reciprocity, right. They took the time to do this and they were making a concrete, actionable suggestion to me on something that I could improve with my own stuff, you know?  
Speaker 2    00:39:16    So I thought that was a really, really good use of an image. So I think if you can do something like that, I think it's, I think that's super powerful and there's lots of variations on that theme and that it's just, yeah. As things become less effort, less effortful and more generic than they, than they, you know, then they stop, then they stop working. Uh, I was trying, I mean, yeah, a bad example is just slow again, as Josh said, anything super like generic or, or irrelevant, we've looked at video too, by the way, what no longer works. It w it, it worked when it was new. Right. Which like you sent me a video and you're holding the little white board and it says, hi Jeremy, and whatever, like when those first came out, you just can't not watch them. Right. They were, they that you had to watch them now, you know, that, that spam.  
Speaker 2    00:40:02    So, so, uh, what works with video is to actually send it in your second email and then it can, it should be a little bit, there should be a little introductory text before, you know, five sentences or something of like relevant or personalized to pick up our conversation from earlier texts that's in there. So yeah, just don't do it on the, just don't do it on the first email, what I've been doing a lot lately internally, but I wonder if it would, I should sort of look at this is internally, I've been sending a lot of loom videos and I just send the link, right? Like, I'll say whatever, Hey, XYZ person, you know, uh, here's a, here's a demo of something I'm working on. Those seem to be working nicely, like at least for internal response. But I think that might be a good way to go is rather than the, rather than the embedded video, like say like here's a short video I made for you, but it's gotta be legit. You know, it's gotta be legitimately introduced and legitimately valuable.  
Speaker 1    00:41:02    What do you see in Jeremy? This is my last one. Just cause this is top of my, I just saw this bubbling around LinkedIn. I'm just curious if the stats, if you have those available or just in general, you know, call taction on the first email, like an ask for the meeting in the first email versus no call to action are different call to action, a Calendly link versus no Calendly link. What are you seeing in those correlations?  
Speaker 2    00:41:26    There was a thing I don't know. I, I want to say I've run this, but there was a thing on LinkedIn that was running around for awhile that said that you, you shouldn't ask for you should, you should not ask for like a specific time. I think, I think it was like the, any interest call to action was the most powerful one. I looked at that data and it was not, there was not actually statistically significant the sample size. Wasn't big enough using that test proportions. I re I responded to earlier. I mean, that passes the logical sniff test for me to just ask for any interest, as opposed to, as opposed to the cliche of asking for a specific time. So, um, I would also add that, that, you know, there was everyone knows that book, the challenger sale, right. But the same people who wrote challenge or wrote this, wrote this thing, like the effortless experience or something, it was there a third book.  
Speaker 2    00:42:12    They had the challenger customer, the challenger sale and something to the effect of like the effortless experience. And I think that that's one of those general long lived principles that the more effortless you can make things for your prospect the better. So I do think that if you send them, like, you know, the most effortless is probably times that you can just click on the second, most effortless is, is the Calendly without the times and just pulls up the calendar. And then the most effort, I mean, it feels like any interest is a little more effortful because then I got to respond and go back and forth. But I don't, I, yeah, I got to run it. I'm not a hundred percent sure one way or the other, but I think by the time you get to that point, there's like, if there's interest, they're going to respond,  
Speaker 1    00:42:57    Uh, you know, those are things that once again, those go through the ebbs and flows where something may be working for a period of time and then, then it evolves. It changes. It differs. Right. I'll never forget hearing. I think it was Brian Burns said his favorite follow-up is just any thoughts, bubbling instead of bubbling it up. It was any thoughts like in that work  
Speaker 2    00:43:17    That does that. So that does work. That's email to there, there are two killer second emails. So you do it in thread reply. Uh, and any thoughts question mark killer even better is the directive please advise.  
Speaker 1    00:43:37    I've never tried that I've done any interest question, mark, any  
Speaker 2    00:43:42    Eddie interest, any interest is like any, it's just like any thoughts that one's similar, but please advise as a little better. It's a little more aggressive. We talked about Sandler earlier. They talk about equal business stature, right? If you say, please advise, you're saying, I am at your level prospect.  
Speaker 1    00:43:55    That's a great tip. I never knew that.  
Speaker 2    00:43:57    Yeah, yeah. That one's, that one's wicked. That one works really well.  
Speaker 1    00:44:01    So I'm going to avoid reading this back. So I want to make sure I got this. I want to make sure we're giving some tangible, it's a lot of great stuff, but so less than four words in your subject line, use the company, name your company name in the subject line, exclamation point at the end of the first this sentence, if it makes sense, but that, that works HTML be conscious of. The more text is better. Doesn't get caught up in spam, leveraging video, not in the first email, in the second email. And then the last one, which I actually notated very specifically for my team as any thought is fantastic. But please advise is staggering. Now, now everyone's going to use it, Jeremy. That's awesome. That's great stuff. Any final thoughts for the audience there? You've shared a ton. So I don't want to give too much of the secret sauce away.  
Speaker 2    00:44:49    No, I think that's it. I mean, if I had one general final thing I would say to salespeople is please stop switching jobs. It's like, if you want to be successful as a salesperson, you need to learn your system. You need to learn your value proposition. You need to learn how your organization functions. And if you keep switching jobs like every year and a half or whatever, you're never going to hit your OTE. And when the economy inevitably slows down, at some point, you're going to be super out attractive. So like put some mileage in your job.  
Speaker 1    00:45:19    No, it's funny. You mentioned that. I think that in tonight in the startup environment, it's kind of been okay to keep hopping, hopping because things change, but you're right. I, and I know how heck I've been doing what I've been doing for four years. And I, I still feel I learned something new every day, just in the like, so I can't imagine hopping something new and trying to learn from scratch again and play, catch up and do all the things you have to do to be successful. That's a good piece of feedback. Hey, how do people connect with you, Jeremy? I know you're big on LinkedIn, but how do you recommend people connect with you?  
Speaker 2    00:45:50    Yeah. As long as you are a real human, I will accept your connection on LinkedIn. Although they may do. I hit my limit. There's like a limit on LinkedIn. So I, uh, you may need to press follow, unfortunately, but otherwise I would accept. I had to actually delete like 400 people in the last couple of days to free up a few slots.  
Speaker 1    00:46:07    That's awesome, man. And I know, and we'll put this in the show notes link to Jeremy's LinkedIn. We'll also put a link in there to, to learn more about SalesLoft. It is a great system. I'm not just saying that because Jeremy's on the line. It is a great system to be, to be thinking about as a sales leader and obviously as a sales rep, you know, the efficiencies that it drives for you. So Jeremy sincerely appreciate you taking some time. Thanks again.  
Speaker 2    00:46:29    Thanks for having me.  
Speaker 0    00:46:32    Thank you for listening to the sales samurai podcast with your host, Sam Capra. Be sure you subscribe to our podcast and visit sales and join the conversation. Access show notes and discover bonus content. 

Jeremey Donovan

SVP Revenue Strategy

By day Jeremey Donovan is SVP of revenue strategy at SalesLoft. In his spare time, he has written five books, including How to Deliver a TED Talk and Predictable Prospecting.