Mastering Sales Emails: Live Reviews and Expert Q&A.

Alex Jonathan Brown: It's 11 AM on the West Coast, 2 PM in New York City, and wherever you are, grab a caffeinated beverage, please turn off your Slack notifications if you're a person that gets distracted. It's time for a coffee break. I'm Alex Jonathan Brown, senior content strategist here at Iron Horse, and if you've joined us for a coffee break before, you know that one of our favorite topics is how sales and marketing can work a little bit closer.

You can call that alignment, if you want. That's what we often use. But, it's really just kind of the key to closing opportunities and closing them faster. And it's one of the things that we're most obsessed with here. And today, we're not talking about the theoretical ways that marketing can help sales and sales can help marketing.

We're talking really specific things. And that's specifically about some sales emails that some of y'all have been kind enough to offer up, we'll hope, for constructive feedback To keep that feedback as constructive as possible We've called in some of the big guns, from Iron Horse, our director of growth marketing Ellen's Smoley. Hi Ellen. 

Ellen Smoley: Hello everybody

Alex Jonathan Brown: And our very special guest, not from Iron Horse, from Lavender, their co-founder and COO, Will Allred. Hi, Will. 

Will Allred: Hey, hey, Alex, Ellen. Thank y'all for having me on. This is a blast. 

Ellen Smoley: Yeah, Will's Mr. Email Wizard, so we are super happy to have him on and reviewing y'all's emails. 

Alex Jonathan Brown: I said the big guns and I meant the big guns. Um, so Will, I think you're going to kind of drive the feedback portion of this largely Ellen and I will chime in where, where we have thoughts. Um, but to, to, to free your brain up, to do the magic that it does, Ellen, I do think we are going to have you do the screen share. So it's tricky. Um, so we're just going to hop right in.

Um, again, these are emails that were submitted during the registration process. Um, and thank you to everybody who submitted. We kind of picked out some that we thought would work great. Um, but the host is going to shut up and let the experts run the show. So let's dive in. Well, 

Will Allred: So, um, I love it. We're getting straight into it.

I've done a few of these and like, a lot of the times folks want to ask questions get some high level understanding And people are like, “Just get to the emails.” Uh, so I love it. I'm gonna jump in, I’m gonna read through this because it's a bit of a doozy, but I particularly liked this one for feedback in doing a rewrite because you can tell the person behind it did their research, like there's a level of thoughtfulness here, and so I want to make sure they see what it takes to turn this type of email around.

Now, looking at a subject line like this, um, this is for my marketers in the room: These are great marketing subject lines. Uh, when it comes from a seller's inbox, this is the exact opposite type of thing that you want to be doing. So Salesloft did the initial research around this. I just get to talk about it.

Um, that first name token in the subject line, it might spike your opens, but it actually crushes your chance of getting a response about 11%. And so even though. It might, like, drive some of that, like, what seems to be good engagement. It's not actually helping you out. Uh, what ends up happening, and I imagine, uh, like, Ellen, in your inbox, when you're going through and you see, “Ellen, struggling to get replies?”

Question mark? Like, what do you think that email is gonna be? 

Ellen Smoley: Probably, I hate to say it, but maybe one that's written by AI. 

Will Allred: That's a great, that's a great point. Um, but you assume that there's a pitch in there, right? For sure, yeah. Yeah, for sure. The reason being is it triggers what I like to call your mental spam filter.

Right. It might get into your inbox, but like your brain immediately associates it with being sales emails. And when your reader, ideally your buyer, is looking through their inbox, they're triaging, right? They're spending nine seconds on average reading each email. And so this type of subject line immediately raises red flags and puts you in the camp of emails that don't get replies.

Now the other big problem with the subject is way too long. Uh, beat the labor shortage with this employee benefit. The reality is like, let's say we were putting together this doc for, um, the presentation today. If I said, Yeah, uh, Will, yeah, let's say I get the email, “Will, any feedback on the doc, right?”

That's pretty normal. But if it's “Will struggling to provide feedback?” It, like, all of a sudden sounds in this, like, spammy category. So, my approach to subject lines is to do something much shorter, much, um, simpler. I'll do something like benefits, um, question. Nothing like, uh, doing, typing live in front of a studio audio.

Alex Jonathan Brown: I was just gonna say, it's the most high wire thing you could possibly do, and I applaud your bravery, sir. 

Will Allred: For sure, for sure. Um, okay, so you'll see a lot more of that. Um, so subject lines, we could also do, um, uh, retention question. You could do retention issue. Would do all caps like I just did there. Um, but the point is you're trying to make it feel like an internal email.

Um, you'll notice they're very neutral in tonality. I'm not trying to catch your attention. Um, Ellen, I believe one of the things you were asking me ahead of this was like, what's something that you could be doing to capture attention. And I'm a believer that it's like the exact opposite. Yeah.

Ellen Smoley: We want to know how to break the patterns. Like, how do you get people to just look at this and open it? But I want to hear your take on that. 

Will Allred: Yeah, it's actually, so the way you want to drive that open, and this is changing by the day, right? Somebody sent me a screenshot the other day of their Apple mail client. Yeah. Apple mail has moved to, instead of showing the first like few lines of text, it's now just summarizing the email as the preview. And when you think about, um, you know, tips and tricks that have been going on for the past couple of years, it's been like, “Oh yeah, make the subject line short, make sure you maximize that preview space to like show, make sure they know that you've personalized the email,” and then you can like throw your pitch in on the backside.

That kind of goes out the door in this world where, um, your inbox is now summarizing the message for you. It becomes more important than ever to truly craft a relevant good message. And that's just like one example of where AI is having an impact on these things like opens, right? The other issue is a lot of mail clients are cracking down on opens so Apple opens everything, Outlook by default opens nothing, and Gmail is now starting to introduce open blocking as well. Open tracking as a whole starts to become a bit of a false metric.

Ellen Smoley: Yeah, for sure. And for subject lines, um, we can move on. But for subject lines, what's your take on emoji or no emoji? Is this, I mean, is that breaking the pattern? Is that, like, two years ago? What is your thought? Yeah. 

Will Allred: Emoji in the subject line?

Ellen Smoley: Yeah. 

Will Allred: Uh, it doesn't help you. Uh, it hurts . I can't read the exact number off the top of my head. Um, yeah. Emojis hurt. Um, I believe emojis also hurt within the email itself. 

Ellen Smoley: Okay. 

Will Allred: Uh, but that could have changed with the most recent model update. So we've seen some really interesting, like, shifts in the data. Um, one of them being. This might seem ridiculous, but, how many times have you written an email and you're like, Oh, is that too many exclamation marks?

Ellen Smoley: Oof. I'm good at that. 

Will Allred: All right. Well, it turns out in a sales email, exclamations are a good thing. Um, it actually drives more response. It heightens the tonalities that make you seem more human and it's driving a lot more responses right now. Um, so. 

Alex Jonathan Brown: Millennials around the world are rejoicing.

Um, and it's actually one of the things I wanted to touch base before we move too far away from subject lines. Um, your like benefits, question, retention, question, retention issue as elder millennial, like does trigger my like the, “Oh, I, did I just get a text with the period at the end of it? What have I done wrong? How has my life falling apart?”

And I think that it's like a reverse of what we might usually expect. We're not using that kind of that flowery language in a subject line does make it feel more. important, um, in a way that kind of really just triggers that part of your, like, we love exclamation points everywhere.

So I love the idea of using them in the text and then keeping the subject lines like super clean and straightforward. Um, a couple of quick questions from the chat while we're moving through. Um, Tyler asks, “Should we be putting memes in our emails?” I'm going to guess your answer is probably no, based on your emoji standpoint.

Will Allred: So I've seen it work really well, uh, I've also received, I've been on the receiving end, right? So I always put this into the perspective of like, I also get this shit, and I look at it, and I'm like, the context is so important. So I'm scared to be like, blanket statement, memes are great, right? Because then you get this like, So cringe, like follow up email with like, you know, uh, Millhouse from the Simpsons playing Frisbee by himself, or like somebody staring out into the distance, like it might work, like, you know, whatever, test it, try it by all means.

But as a recipient on my own end, I, like, I can't condone it cause I don't like it myself. Um, and so I, I tried to, I tried to be fair with like what the data is showing us. Um, but I also want to give the caveat of there are, uh, deliverability challenges that can come if you open up your thread with an image.

Um, so I'm a big believer of plain text all the way. Um, like even check your signature line, like keep it stupid simple. Um, because spam filters are getting more aggressive than ever. And so if you're coming in hot with, um, you know, a picture of Milhouse at the start, you're, um, in trouble, but as a follow up email, it can be effective, especially if it helps demonstrate something that you're trying to, uh, explain.

Alex Jonathan Brown: And well, I do want to let you get back to this. I'll just let everybody in the chat know that I'm grabbing your questions as they come through. We'll get to them at the end. So. We're not ignoring you. We're just going to let Will be magic for the next 20 minutes. And then we'll circle back at the end. 

Will Allred: Yep. Um, we'll require keeping your people, um ,turning around for sweet green. Am I hitting on something? Something like that. 

Alex Jonathan Brown: Yeah. I think one thing that's so interesting that I just want to call out is, um, as a marketer, like that turned it around for Sweet Green sentence is such a, like, “Oh, a salesperson wrote this email,” like type of language, which is what we want in this. Right. That's what we want it to feel like.

You don't want to let Mr. Creative Writing Minor, like put together the words that he wants to use as. a creative writing manner who often does that. Um, and I think just immediately like your sense of tone and your sense of like the language that you're using is so important and good. 

Will Allred: Yeah. Um, this is actually, this is an interesting point to bring up.

You mentioned my tone, the language I use, the, like, I don't look like a creative writing minor. Um, that's very intentional. That, I've actually had to change my own style of writing in the past couple of weeks. Where, um, you know, in the past I, I would probably want to be like, uh, instead of, we turned it around for Sweet Green, be like, uh, we can help with this, Sweet Green was dealing with retention issues, half, um, took off after 90 days. Then I would say we turned it around for them, something like that. But, the problem with that structure is it's overall too formal. Um, and this has been a massive byproduct of the rise of these AI SDRs, uh, it's a bit of a hellscape in buyers inboxes right now with these like phony emails.

Um, and the reality is like the more you, uh, structure things in a way where, um, you know, they're like the, the simplest way to put it is, “Complete coherent thoughts punish you.” Uh, long winded sentences hurt. Uh, like a long sentence, for example, is going to hurt your response rate by about 17%. But now it's starting to have this impact on the level of formality in an email.

Um, where before, it used to be that you'd want to be in this like middle of the road, like not too casual, not too formal. The reason you want to stay somewhat formal is because formality creates clarity, but all the robots went that way. And like, if you ask ChatGPT to do a question, it gives you a comprehensive answer.

Right. And so when you tune it and you put it towards this like task, it writes messaging that is very, it's very cohesive, but at the same time, sometimes not. Um, but what's happening is so much of email looks the same that buyers are just tuning out. 

Ellen Smoley: Yeah, and we keep saying we need to be personal. We need to have some personalization in here. But what are your tips around being personal and maybe having a nugget in there too that like, yeah, “hey, we've done our research and it's not just about where you went to college, but we know some of your pain points.”

How do we do that, but still say. Stay really short like this concise and keep it to where they can glance at it and read it and I think what did you say like the average person somebody spends with your emails like just a couple seconds. How do we do that?

Will Allred: Yeah, so the reality is like most of folks challenges when it comes to writing starts with that they can't shut up about themselves.

Uh, Yeah, oh, yeah, probably a conversation problem, not just a email problem, but we tend to think like we've been dealing with this with like a bunch of um, you know, hyper technical products where folks are like, no, no, we're not explaining ourselves enough, we're not giving them enough context.

They don't care. Um, They just don't, they don't care at all. You are expecting them you to have the same focus and attention like they're playing a game of Scrabble. And in reality, like, you're the, like, like what's the other analogy? You'd be like a crazed person on the street, screaming at them as they try to get by and like keep their head down. Right. They're like, “Please leave me alone.” So they don't, they don't want to be bothered. Um, so the reality is like, most of it is just cutting you out of the equation. 

Ellen Smoley: Okay. 

Will Allred: The Other piece is, we write in a way where there's always redundancies or fluff and we don't always see it. And so one of the, my favorite writing exercises that I give to folks, um, and my assumption when I give this exercise is that folks do not have a premium Twitter profile because on a premium Twitter profile, you can just keep writing, but on a standard profile, you are limited to 280 characters.

And I say, take your email, paste it in there and tell me if it fits. Can you tweet it? Yeah. And there's, there's just something about, uh, I mean, obviously our own product helps with this, right. But I like to give agnostic solutions as well, but the active, just like seeing it in a new format, like you're out of your inbox, you're out of your element and all of a sudden, like half of your emails, like highlighted in red.

And you're like, “Oh man, okay. I guess I'll remove the subject line,” that helps. And then you're like, “wait, still half of it's in red.” And you're like, “What do I cut out?” And it's like, it's this forcing function of like, “How do I get stuff out of here in order to make it fit?” Um, as long as you're doing that with the lens of like, stop talking about yourself. The most important thing to them is, “Hey, I showed up and I saw you have this problem. Here's what told me you had this problem. I've seen that problem before, is that something you had, am I even, like, close to being on the nose to have a conversation with you about that?” 

Ellen Smoley: Yeah. So, I do see one thing. You ended with a question. Is that what you suggest, is to end your emails with a question rather than a book meeting link? Like, what are your thoughts on that?

Will Allred: Um, 100% question over book meeting link. And the reason being is, I don't like to send a link in my first email. That'd be like number one. Um, especially if you're using link tracking, um, big piece of advice, I don't expect to change everyone's mind on this in a webinar on a lovely Thursday afternoon where the East coast is drowning in rain, but the thing with link tracking, at least, at the very least, make sure your link tracking goes back to your own domain. So like most systems will allow you to configure this, but most people don't know to do it. And so like, let's say I use SalesLoft. If I default to using SalesLoft's link tracking, what it looks like to an IT system is I'm clicking a link that takes me here that's going to immediately take me somewhere else that I don't see. And you know what else it does, that's like a phishing attack. And so they, they don't exactly, um, not exactly kind to that. So, that's one piece on links. The other piece is just you see a hyperlink like book time with me, I'm like, “Sales email.” It just hits the nail, if it doesn't hit like the it spam filter, ot hits my spam filter and I'm just like no. Like you just showed up here, just like the focus should be because I think too many people think of it like a cold call, right, where it's like your job is to book the meeting and it's like, but they haven't opened up, like they haven't even picked up the phone yet. So you gotta start conversation first 

Ellen Smoley: So the marketer in me is like, “Okay, let's not hit them with asking for anything in the first email. Let's give them a piece of conten that's like super helpful. It's gonna be right up their alley. It talks about their pain points.” That does include a link in the first email. What are your thoughts on that? That's like, “Here, I think this piece of content might be helpful for you,” in a first cold sales email. 

Will Allred: Um, I wouldn't do it in the first, I would do it as a follow up. Um, so what I would do is I'd send something like this and then maybe I'd follow up with, um, um, “Given you're in the same, um, space as Sweet Green, thought you'd find this article useful. Um, let's see, CHRO, um, was interviewed by my colleague, whatever the colleague's name is. Big focus was on talent retention, talked about how it held back their path to growth. Yeah, let me know if you find it helpful.” And then I would do the link here and then I'd say, “PS, any thoughts on my first note?” 

Um, what I'm using here is a framework I actually learned from a lovely human, Christina Fensa, she's over at Greenhouse. Um, and she taught me to do this with, um, a third party article. So don't use your own because people's natural instinct is to believe it's biased. The challenge with that, right, is like who do you use? How do you think about that? And that's a great place where marketers can offer like a ton of help for sellers and being like, “Hey, in these scenarios, these are really good resources to send to prospects, um, to give, as opposed to take.” Especially, I'm talking to a lot of teams right now around their account based structure and thinking about these gives when you're prospecting account to account, you're yes, reaching out to the C-suites and like the reality is, is like most folks at a C-suite level aren't going to take the time to like read whatever you send them. But if you go below the line and you look for maybe someone at the IC level, you can actually spin up a conversation, um, using something like this, being like, “Hey, I was about to reach out to,” let's say the CHRO at this company is named Jennifer, right? I was like, I'm like, okay, um, I was about to reach out to Jennifer. I saw this going on in the org. Um, I thought you would find this article particularly useful. It's the CHRO at Sweet Green. They did an interview talking about blank. You know, I imagine in your role, uh, you're seeing a lot of this. Right, and it's just that reframe of like yeah persona am I sending it to? That would make a big difference. 

Ellen Smoley: Okay. Should we move on to email #2? 

Alex Jonathan Brown: Yes. I think that's, as I frantically look at the clock, I think that's a good idea. Will, are you able to go a little long? 

Will Allred: Uh, always. 

Alex Jonathan Brown:Alright. Great. Um, everybody, if you're, if you blocked off a small chunk of time, we will be sending out a recording of this afterwards. Don't worry if you have to drop, but we're gonna, we're gonna let the magician do the magic and we're gonna, 

Ellen Smoley: Okay, let's do, let's do one more, one more, and then we'll. 

Will Allred: This one, I actually, I ran this one through Lavender, um, which I would love to show y'all, but I'm on a university campus today, and so, uh, they block AI, so, uh, that's a fun thing, but I put this one through Lavender, and it got a 96.

Uh, so, It's already a really good email. I'm looking at it too and I'm like, “This is a, this is solid.” The first name, so let's say, “Will, awesome to see John posting on LinkedIn. Given you sell to HR, guessing LinkedIn is big for pipeline. We're seeing how we can help Chris, Aaron, and team post too. Question mark.Execs and sellers usually don't have time to create. They use our tool to auto generate posts from combos and sales calls. P. S., Clay is sending to a similar persona. Help edthem get 400 comments and 3,000 likes in a week.” Like, that to me is a fantastic email. Starts with an observation, um, it shows like, “Hey, like you're selling to HR. So like, I'm guessing this is part of your strategy pipeline. So like, here's why it's probably important to you. Um, I'm thinking you're like thinking about like doubling down on this.” Uh, the other piece to this is you're throwing in first names of people that like, I know. I think about like, yeah, Ellen, like if somebody is reaching out and yeah, they start referencing Alex.

In the email, your brain's immediately going to be like, okay, what is that? Right? Cause we're wired to look for names that we recognize and threads that we recognize over everything else in our inbox. So, uh, this is like my, it's like, the almost like dark magic psychology that you can use to your benefit, uh, is using names that people know within their organization is a massive benefit. Um, just because of that. 

Ellen Smoley: This is showing, too, that question with personalization of like, “how do I personalize this thing to know, to let you know, I've done my research?” This is a great example, right? Where they have done a little bit of research to see who my colleagues are, who I'm working with to then be able to put that in the email and use that psychology to, for their advantage.

Will Allred: Exactly. Yeah. Um, and this like, this alone, right, you could actually probably cut this and still have a decent email. Um, so you could probably get away with shortening it. You could probably reframe it some. The, um, the other thing that I was thinking about in this email would be, let's say, I'm going to end up reusing most of this because it's pretty darn good.

Um, but what if I wanted to do, instead, “Would it help if we could generate ideas for Chris, Aaron, etc, from your sales calls?” And so now instead of having to have those two paragraphs, I'm just simplifying that down into a single sentence. 

Ellen Smoley: Wow. And so does Lavender help you shorten and condense those sentences? I know you said Lavender scores your email because it also helps you think through some of those changes?

Will Allred: Yeah, it does. It does. Um, so, like, all of the things that would be holding your email back from a reply based on what we've historically seen perform in your inbox or your team's inbox, we'll feed that back as you're writing. So, um, let's say the way that I wrote this without the P.S., like, a P.S. is, um, like a P.S. is just like really beneficial for you, we would push to put that PS back in. 

Ellen Smoley: Okay. 

Alex Jonathan Brown: I think one thing that's worth calling out here too, just because it's, it's not something that we're going to do here, but like the work of getting these names is work. Right, in a, in a good way. Like the reason, the reason this is effective, like you said, well, is that like, to use your example, someone has to find out that I work with Ellen for that connection to like happen.

Um, and it's, it's that extra, I mean, care is like cheesy, but this isn't something that you can copy and paste to six other people at six other orgs, and like, reuse this email in that way. You can use the core, but somebody still has to go find those names. And like, people can sense that you at least did that much.

And, in addition to your, your brain dark magic, like, that's valuable. And it, it makes it feel like it's coming from a real person. Cause at least a real person figured that out or clicked around on LinkedIn for a while.

Ellen Smoley: And Charles has a good point. So Charles mentioned all the names in this email and made him dizzy. When I first read this too, same, you know, me too, but this email wasn't written for me. So I do, I do suspect if it was put in my inbox with, um, my colleagues names or the product names that made sense, it'd be like, okay, yeah, this, this works, but at first, too, Charles, I had the same, same thought.

Will Allred: Yeah. The, um, this part with the P.S. on Clay selling to a similar persona. Um, yeah, they sell it at HR, so I kind of struggled with that, because I was like, um, my understanding, maybe I'm just, yeah, I just know Clay at this point, compared to other folks, so, um, I might have, like, been more specific on, like, where in HR they play, and, like, what we've done to help them post, because if I went and looked up Clay as a recipient, I'm not saying I would, but if I did, um, then the first response I'd have is like, it's a tool for sales, like what? Obviously the first name override a lot of that, but, um, I think the big thing that they're trying to get me to focus on is like 400 comments, 3000 likes just this week, kind of thing. Um, so that would be like the way that I might reframe that a little bit. I can probably clean this up, but easy way to just think about it.

Ellen Smoley: So let's get to Alex, you maybe have been managing this better than I have, but let's get to some, uh, like one or two more questions. And then I know we're over time, so we can close it out. 

Alex Jonathan Brown: Yeah, and we'll, we'll plow through these pretty quick. Thanks everybody for, um, for being so active in the chat. This has been a delight to get to read along, um, alongside the actual conversation, um, from Paul, “What's your opinion on a full signature line? Does it create confidence that you're a real person?” 

Will Allred: A full signature line?

Alex Jonathan Brown: Uh, yeah. So for me, that'd be Alex Brown, Senior Content Strategist at Iron Horse. 

Will Allred: Oh, Oh, you mean like at the bottom of your email? 

Alex Jonathan Brown: Yeah. So this signature, not subject. 

Will Allred: The way I like to think of signature lines is, I'll do something like plain text, right?

So it'd be like, Will Allred, Co-Founder at Lavender. Um, yeah, then I would like. So like, um, helping, um, sellers write better emails faster, or maybe I would do, you know, building email intelligence, whatever it might be. Right. Depending on the persona, I might want to think about different signature lines.

Um, and then maybe I want to include like my phone number or, um, you know, our website, something like that, just to make it easy to find me. Um, that would be it. 

Ellen Smoley: I think that's a good point. I get so many emails in my inbox that you don't tell me who you are, and I literally do not know what you do, and I can't tell from your email.

So I think, um, having that little tagline of what, what is Lavender? What are, why are you contacting me? I think is really helpful at a glance.   

Will Allred: Yeah, and I think one of the things too is like this writing style that I'm showing. You lose a lot of context on what you do. And I think folks overthink about that and they're like, “Oh, I'm losing that.”

And I'm like, “Your signature line is a massive billboard for your company. Use that to your advantage.”

Alex Jonathan Brown: Yeah. Robert chimed in with maybe there, maybe throw your LinkedIn profile in. 

Will Allred: I would just do it in plain text. Don't do anything fancy with it. Like, um, so that like, you're like, you're not tracking that link. That'd be like my big key on that. 

Alex Jonathan Brown: Um, which is a nightmare for, um, orgs that have the automated, like, “Hey, here's a link to our next webinar,” that goes in your signature. If you're in sales, turn that off, just because you don't want to distract someone with literally the last thing they see in your email if they're scrolling.

Um, another question then, do you have thoughts on using a new subject line for each email or doing the like, “Hey, I'm responding to this previous email?”

Will Allred: Oh, good question. Um, cause I, it's one of these things that I take for granted and I think it's common sense, um, but I get a lot of emails where they reference the last email and then they're not like connected. And as a recipient, I'm not going to go find your thing. Um, so please thread them together. Um, it also gives you the space to build upon a story, push people back. There's two types of follow ups you could do, right? You can either expand on what came before, or you can nudge them to go check out what came before.

And that's something you can do. It actually shows up in our data too. There's either really short follow ups that do well, or really long follow ups that do well. Um, and so like a customer story might do really well as an expansion. Uh, so like maybe I go deep on like what happened with, uh, Sweet Green.

A good framework for thinking through that would be like, you know, background, action, results, you might recognize that bar framework from like job interviews when they give you a behavioral question. Uh, it works.

Alex Jonathan Brown: So yeah, and another question from Alice, and I think maybe we'll, we'll move toward wrapping it up. We talked a lot about tone. Um, is that something that you think about changing based on either the audience or like where they are in the org structure. We talked about the difference between messaging C-suite versus messaging somebody below and working up, do you factor that in when you're thinking about tone or is it just like, “Hey, this is my tone and it's going to go to the audience it goes to.”?

Will Allred: Good question. Um, so I haven't run an analysis on the split between seniority level now that the models have shifted so hard for casual. Um, but the old data used to show, “:ower in the org, more formal, higher in the org, more casual.” Um, but now we're seeing a much higher bend towards casual messaging. And so my assumption is that's starting to merge into one. Because more automated messages are going to go to folks lower in the org. 

Alex Jonathan Brown: My kind of shorthand for tone. And this is not from the chat, this is me. So if it's dumb, let me know. Um, has always been, especially for sales, like it's those emails are always most effective to me.If it feels like somebody just removed the, like, “Sent from my iPhone,” that we used to have on the bottom of emails, like when iPhones came out, like just that, like, “Hey, I'm just typing. I'm waiting on a plane thumbing my way through this thing.” Like, it's that, that's kind of my shorthand. I don't know if that lines up, but looking through notes, like that's the vibe in a lot of cases.

Will Allred: It's, um, it's a text that you're sending to a friend that you don't know yet.

The other piece that I'll add is, I've mentioned being casual and I haven't given any concrete direction on how to do that. Um, so let me give a couple of very specific points. Um, there are multiple ways to make something more casual, uh, you can shorten your sentence structure. That's one. You can, uh, imply subjects and you can imply direct objects within the sentence. So instead of saying, I was hoping to see blah, blah, blah, you just say, wanted to see, right? You just cut off like the first half of that, or like you cut off like some of these things and just make them implied.

The third piece is using more colloquial slang. That's one. So instead of writing like opportunity, maybe you say op, um, instead of, yeah, uh, writing something to its full extent, like hype, like shortening it, using something more casual that you would say in conversation, back to the text with a friend. So those are like three easy things that should help.

Alex Jonathan Brown: And just to solidify this, you're not suggesting that we say things are on fleek or fire in these emails, correct? 

Will Allred: No, no, no. Um, not yet anyways.

Alex Jonathan Brown: Glad we clarified that. Um, Ellen, I know you had some questions as well. Do you want to do, maybe do one of those and then we'll let, Will get back to his day. 

Ellen Smoley: So as a marketer, I am trying to help our sales team craft these emails. So, I'm trying to think through “How can I give you some snippets that then you can use?” What does that look like in this? What we all just talked through, like, how can I continue to help my sales team, but allow them the absolute freedom to create their email that is going to be short and concise and doesn't include all of the good things that I'm going to provide them?

So I think there, I struggle with this really is like, I want to be able to provide them this approved messaging, but in these emails, there was not very much marketing lingo. 

Will Allred: Yeah, um, there's copy that belongs on a website and there's copy that belongs in an email, right? And they're very different. The challenge that I have with marketers getting involved is marketers tend to want to use the language that they know and they want to use the brand guidelines and it's like you have to throw all of that out the door. Yeah, you have to just like talk like a normal person. 

The way that I'd like to think marketing and sales should be aligned on this, because I think it's like a general statement of like where are marketing and sales like, what does sales want from marketing and like, you know marketing wants to provide sales is pipeline. So, when I think about that, I think it's about giving sales, the context in which they came into the conversation and giving them the enablement tools and resources to action on that context, like inbound versus outbound, it's all a difference of context, right?

Inbound just means I have first party context as opposed to, you know, third party, I'm kind of guessing context. The thing with, uh, marketing in that world is, can you set up helpful, effective workflows, working alongside sales to make sure, “Hey, does this sound like something you would say?”

Right. Cause like the reality is like a lot of this messaging needs to feel like it's theirs. Otherwise they don't want to use it and they don't want to touch it. And they're going to, you're going to have this like siloing happen.

Ellen Smoley: And it doesn't work, right, like if I provide sequences that they send to everybody, it really just doesn't work. So, we've we've really tried to put ourselves in the mindset of providing a framework that has the pain points and some good content around that that we know our audience really well, so we want them to know the audience really well. So that's just some shifts that we've recently made to help.

Will Allred: Yeah, one of the I'm trying to think of examples of customers in the past and like what they've done. I think about Sindoso when they elevated Katie Penner from an SDR role, she was a top performing SDR, killer email writer, um, and they moved her into a life cycle marketing role, and just had that individual go in and adjust the copy because like that person clearly gets it, so like why not elevate them to go make that happen? Um, I've seen folks try to do content committees, uh, the only problem with content committees is they typically, um, what's the, you get too many chefs in the kitchen and like, you end up, you get this like very bland, blended, like everybody's trying to make each other happy.

So that's not also the right way to do it. But there's also different workflows that need to be accounted for in this. And like, there's a difference of who's going to own what. Um, so like if it's an ABM oriented approach where like marketing is truly just focusing on a core set of accounts, you know, it's just about what I said, like making sure they have the context, making sure like the SDR can immediately go in and action on like, whatever that signal is, it's comment, uh, to trigger that outbound.

Whereas like I see with a lot of orgs where it's like, yeah, we're running events, we're trying to do up on top of that. It's like, I would just get out of their way and be like, here's, here's what happens in this conversation. Like, here's what I think matters. Um, but I see a lot of marketing getting narrowed into very specific verticals when marketing in my mind should encompass things like sales enablement because marketing is the organization's earpiece to the market. Uh, it's not just megaphone blasting. And so, you know, you should be learning things in market, you should understand things from market, and be able to give that level of insight and communication back to sales in order to help make them more effective.

Right? So it's like, “Hey, this scenario is happening. This is usually what that means,” right? Like helping them parse through that context for them, that stuff to me is, um, much more impactful and giving them like, snippets as opposed to canned templates that they need to be using. 

Ellen Smoley: Right. And in the insights.

Will Allred: Yeah. Like our cadences, for example, are blank. Like, we just let the sellers run with it. Um, which like probably makes a marketer like, “What do you mean?” They just like do. But, like, 17 percent reply rate, like we're doing fine. Um, and it's because they understand the scenarios. They understand the problems that that entails, um, like they understand where our product fits to solve those problems. And as long as you have those ingredients, I don't care who owns what. 

Ellen Smoley: Good insights. Yeah. 

Alex Jonathan Brown: And kind of a nice overarching thing for us to wrap up on for the day. I think those of you who've stuck with us as we've blown past our time, thank you so much. This was incredibly interesting for me. Uh, I hope it was for you. Um, like I said, I'm Alex, Jonathan Brown, Senior Content Strategist and professional webinar host. I should be able to get my title out. Um, here at iron horse, uh, Ellen. You're also at Iron Horse. If people want to learn more about us, it's at ironhorse.io. But is there anything else you'd like to, any other place you'd like to direct people to? 

Ellen Smoley: Yeah. I mean, I think that this was super interesting. We talked a lot about sales and marketing alignment. We've got a really good report a couple of months ago. Um, a couple, yeah, weeks ago. So, yeah. Check that out on our website. And then our next coffee break next month is going to be around content strategies. If you're interested in that, join us again, but that's my marketing plug. 

Alex Jonathan Brown: And then will, I meant to let you do the plug at the beginning and we just hopped right into it. I get the feeling, judging by the chat, most people in the chat are familiar with you, but, uh, go ahead, let people know about Lavender and if there's anything else you want to plug, uh, go for it. 

Will Allred: Yeah, um, so, uh, Lavender, we help tens of thousands of sellers write better emails. Feel free to download our extension, reach out if you have questions, uh, we try to make ourselves readily available. Um, yeah, and follow me on LinkedIn. I post a lot of stuff. Um, that's probably where I post most of what I learned from, like digging through our data and talking to customers. 

Alex Jonathan Brown: Awesome. Well, thanks everybody so much again for joining us and until we do this next time, breaks over. I guess we’ve got to get back to work.

Ellen Smoley: Bye everybody. 

Will Allred: Bye. Thanks y'all.