Outbound Messaging that Converts: Learn the secrets of sales development pros

Whether you're a founder, a sales rep, a marketer, or just a human being looking to connect with others, you need to be able to craft an outbound email that gets a response. 

And yet, this is one of the hardest parts of everyone's job. 

How do you send emails that start a conversation and entice prospective customers, partners, or investors to take action? 

This is probably the most common question I get from clients, so I recruited a couple of friends who happen to be genuine sales development pros to share their perspective, their tips, their tricks, their secrets.

Watch the video below and soak in the wisdom (and humor) of the brilliant Niko Hughes of SDRemote and Bryce Kropf of Vacasa. 


Do you want help developing in-depth buyer personas and creating kick-ass messaging that converts?

Let A Better Jones + SDRemote give you and your team the resources and coaching you need to seriously level up your sales team performance. 


Bryce Kropf: Boston! I got peeps in Boston too!

Kasey Jones: Welcome everybody. We're gonna take a couple of minutes. There's a ton of people still kind of logging in. We'll take a couple minutes before we get started. Definitely say hello in the comments. Tell us where you're from. We're seeing people from all over the place, and Bryce happens to be the friendliest and most [inaudible 00:00:25], so he knows people in all of your cities. So, here's my challenge: name a city where Bryce doesn't have a friend. I don't know. Gormley, Ontario.

Bryce Kropf: Gormley, yeah. I don't know anyone in Gormley.

Niko Hughes: Didymo! I went to school in Canada. I've got some friends in Didymo, BC. Yeah.

Bryce Kropf: Now people lie to get up with places. Denver. I got peeps in Denver.

Kasey Jones: Whoa! Okay, Chile.

Niko Hughes: Nope.

Kasey Jones: I really want to have friends in Chile so that I can [inaudible 00:01:03].

Bryce Kropf: I actually have a friend who's from Chile. They go back every once in a while, so I guess that doesn't really qualify.

Kasey Jones: I don't know. It's pretty close.

Bryce Kropf: Alright.

Kasey Jones: Also, I wanna call out to everybody. We've put a couple of polling questions, so at the bottom of your screen you'll see a little thing that says “polls,” so definitely ... Oh, is video frozen for anyone else? I don't know. Hopefully it will come back. We included some polling questions just so we can get a better sense of kind of what you guys are dealing with. Definitely click on the little button below that says “polls” and take a second to answer some of those. I love seeing the engagement already. Obviously look weak. Our big motivation here is helping all of you, so tell us how. As we go through this conversation throw in your questions. Throw in your comments. We wanna learn from you, and the whole point is that all get better together. So, we're gonna start in just a couple of minutes here.

Kasey Jones: Oh, the other thing I will say. We are also starting to build out our community on Facebook, so this is live streaming to Facebook. If you are watching on Facebook or if you wanna open it on Facebook, definitely go for it. And would love to get your comments there, your likes, your shares. So if you know anyone in the Facebook community that is going through similar things or you think this would be relevant to, tag them in the comments, share it with them, and let's make this party even bigger. The more the merrier.

Kasey Jones: So, awesome. I mean, I feel like there's still people trickling in, but I think we'll just get started. So, welcome to Outbound Messaging That Converts. This is the first ever webinar of our “Better Growth Coaching” sessions, and I brought my pals and my legit sales development experts. They're the wunderkinds of sales development. [inaudible 00:03:22]

Bryce Kropf: High compliments. She's not paying us.

Kasey Jones: Oh, who am I? I'm Kasey Jones. I'm from A Better Jones Consulting. We help early stage startups grow, and a big part of what we do. I'm more on the marketing side, but basically my role is giving sales teams the resources they need to kick ass and also helping them fill pipeline. So, if you have questions related to marketing or early growth strategies, definitely throw those in as well. But wanted to introduce Bryce Croft and Nico Hughes. I will let them both kind of introduce themselves and give you a little synopsis on their backgrounds before we get started.

Bryce Kropf: Yeah, so thanks Kasey. I've been in sales development and sales in general in a number of different roles for about seven, eight years now. I started off like most people being, well, marketing coordinator/SDR ... know what an SDR was, but that's what I was doing. And then from there I got into the tech startup space. I had the great privilege of working with a lot of really smart and motivated sales people who kind of taught me how to learn and how to hone the craft and learn myself and build a system to keep reiterating on, so it lent itself to my success.

Bryce Kropf: Now I am heading up a team at Vacasa. We are a vacation rental management company. We're actually just surpassed Wyndham as the largest vacation rental company in the United States. We're also a tech startup because we use software and processes to maximize, essentially, the return that all of our homeowners get on our properties that we manage for them. So, even after our management fees, they still make more money and they don't have to do any work. So, pretty excited about that. It's a growing team. We recently had a large round of investments, so I've been hiring up really quickly at a team about 10 right now.

Bryce Kropf: That's pretty much my background. I also used to work with Nico. [inaudible 00:05:35] a couple different times.

Niko Hughes: Yeah, on that note I'm Nico Hughes. I run a sales development and outsourcing consultancy in Portland. I actually do wholesale cycle, but mainly coaching, training, and then outsourcing for sales development and deal closing. Work with Bryce at Lytics a few years back.

Niko Hughes: I'm not on the screen?

Kasey Jones: Um, really?

Kasey Jones: Nope!

Niko Hughes: Nope. I am on the screen.

Niko Hughes: Yes, so Bryce and I worked together a few years ago. I started out in digital marketing and then moved into sales about six years ago as well. But yeah, pretty much taken the knowledge that I learn from great leaders here in Portland and the Bay Area and bringing that to young startups, series and below trying to help them hit their revenue goals from the marketing and sales side.

Kasey Jones: So, I love this. I didn't actually realize that both of you started in marketing, 'cause I started in [inaudible 00:06:40], so we made a little flip flop.

Niko Hughes: Nice.

Kasey Jones: But that's also why I think we as a little group here, we've got a unique perspective on things because we've seen it from both sides.

Kasey Jones: So, I think to kick things off, we've got a bunch of questions. Obviously we need [inaudible 00:07:00] registered, but also that have been submitted via the little question thing at the bottom, which I encourage all of you to up vote questions, ask questions, suggest topics, all of that jazz. But I think this is one that has come up a ton is “What do you do when you're actually targeting multiple personas? So, what are your strategies for kind of understanding the difference between those multiple personas, but also how do you manage the contemplation, the pipeline generation, all of these components when you've got a product that actually appeals to multiple different types of people?”

Bryce Kropf: Well, Maybe we can kinda tag team this Nico. A good place to start is ideal world. Let's say you have all the stuff you need, but then we're gonna have to scale it back, because I'm guessing if a lot of these different folks are in the startup world like we are, or founders of their own companies, they don't have an ideal situation. They have what they have, right? Ideal situation, you would set up all of your messaging to be semi-personalized based on the persona. This is what I would see in an ideal world, because that way you can be hyper efficient while still personalizing. Let's say you have five personas. You'd have maybe five different messaging sets, then you'd have an additional layer of personalization to add in. But when you're doing all of this, the ideal situation again is that you also have custom content, so you work with marketing. You say “We have Persona A, B, C, and D. Can you set up a specific case study, 'cause we have customers already in A, B, C, and D.” I think that- [crosstalk 00:08:55]

Kasey Jones: Because we've gotten a lot of comments also about how a lot of the people that are registering don't feel like they're getting those resources from their marketing team, so one of the things that was really fascinating about the info that people were submitting was a lot of comments of “Hey, how do I write up six message sequence when I don't have any blog posts or case studies to direct people to get kinda boring, but the six message. What do I do?” So, we know in the ideal, but what would be your recommendation when you don't have those resources?

Niko Hughes: Yeah. So, working with young startups, a lot of my clients and customers ... It might just be the CEO or a Technical Co founder selling to a new market, so one, they're in a role that they're not really comfortable with. That's a whole layer of things as well if you're just starting at the [inaudible 00:09:55] in sales, how do you tackle persona development or messaging? The easiest way to have good messaging and get people to reply, get opportunities created, is taking the time. It might take a few weeks. It might take a couple months to know who you're selling to and if your product can solve the whole world's problems. It's better to start out with a couple problems, and a couple industries, and a couple persona types to double down on ... If you realized that that person and that buyer isn't willing to pay you, then you get [inaudible 00:10:25] after you understand that problem, but first start out with simple things that break down, and then dive deeper as you move along. But understanding the buyer's the number one thing. If you don't understand who you're selling to, then the likelihood that they're gonna like your messaging is probably small.

Kasey Jones: Yeah, and I am curious like everybody out there, do you feel like you have a good sense of who your buyer is at all? Because that's certainly something that I see in my work is that people ... Most of what sales teams are given when it comes to personas is a list of titles and a list of industries, and maybe one or two other additional components, but not necessarily really complex and really in depth persona information. So I'm curious from your guys' perspective what information is super valuable and what would you say makes a strong kind of persona understanding our persona profile?

Bryce Kropf: So, I think there's a couple things involved there. I think Nico and I probably both have similar or different answers, but when it comes to persona development, the key I always look for ... Titles are important, right? Titles are a key indicator, right, to get you to where you wanna go. But the key is looking for the decision maker who cares about the things that you need them to care about, right?

Niko Hughes: Mm-hmm (affirmative).

Bryce Kropf: So, if you're selling to a Director of Digital Marketing, the Director of Digital Marketing might be the VP of Content Marketing at a different company. It's understanding, right? So, it's not always just about titles. It's about understanding who you're selling your product to, but also what those needs are. What are they measured on, and what do they care about? Because- [crosstalk 00:12:15]

Kasey Jones: That's my favorite one. What are they [inaudible 00:12:17], right?

Bryce Kropf: Yeah. [inaudible 00:12:19] What are their goals?

Kasey Jones: I had an amazing sales boss. Well, he was also one of those sales bosses that was also an HR nightmare, but [inaudible 00:12:29] boss, and one of the best things he'd say is “You always wanna think of what is something that's [inaudible 00:12:35]?” Because then you'll understand what your role is in helping them look really good for their boss, and if you can do that, you're freaking golden. So I am curious, what's your ... Let's say you are only given a list of titles and industries. What's your best recommendation for figuring out some of that additional information?

Niko Hughes: Yeah. One of my thoughts on that kinda going after what Bryce is saying, you have to understand why someone's doing their job, and what they're measured on, the things that they're trying to sell. The way people talk about themselves online like on their LinkedIn, the articles they're sharing, the conversations they're having. If you're connected with them or if you're connected with someone that is connected to them, then you can see those types of interactions, and so taking the time to do some research on a type of ... Once you understand the title, like if it is a digital, go find 20 to 30 of those people and start to understand who you're trying to sell to. Then you can get some qualitative data on this is how this group of people is talking. Then you can use that to then semi-personalize and then move into tactics like I see someone said “I thought you might like this article.” and why you [inaudible 00:14:00] kind of like what John Barros talks about. Yeah, that's a great tactic, but until you understand the buyer, tactics kind of don't matter. So, if you can go back and take the couple weeks to really dive into the research, then you'll be able to do more.

Bryce Kropf: Yeah, to kind of tag off of that, on a more practical level I agree with that wholeheartedly. That's awesome advice. One of the ways that I've done that personally in the past, being in the more tech space, on some of the more complex personas that I didn't understand. Like when I was at a company called Lytics, I had no clue going in what these people were thinking about on a daily basis. So I started just reading industry articles and then finding influencers from there, going to their Twitter, finding the people that they're following or they're connected with, or they're talking to and starting a Twitter list. I am not a big social guy. Both of the people on screen with me now can tell you that. [inaudible 00:15:04]

Kasey Jones: You are very social guy. Maybe not social media.

Bryce Kropf: Not with social media. That's right.

Kasey Jones: You are the definition of a social butterfly, let's be honest.

Bryce Kropf: Yeah. But, when it comes to social media, I'm not that guy. I'm not posting pictures on Instagram every day. The point is though is Twitter is great at connecting groups of peoples and conversations. So, you can create filters, and that's what I did. I go and I create a filter say "Here's the 50 in Martech that I need to read from on a daily basis so I can start to understand the things that they care about, the things that they're talking about, and try to connect that with the definition that I'm creating of this person that I'm trying to sell to."

Bryce Kropf: A second degree to that is to also go for job postings. They're not always perfect, right? You should read several of them because some companies suck at writing job postings.

Kasey Jones: Suspenseful.

Niko Hughes: Lost you.

Bryce Kropf: Did you lose ...? Oh no! [crosstalk 00:16:16] So what I was just gonna say when you lost me, I'll distill it. Go look at job postings, take 'em with a grain of salt, because let's say the person you're looking after is a VP of Digital. Go through and find small companies and big companies and what they're looking for in a VP of Digital or something like that, because you will start to get a sense of the general idea of the things that they [inaudible 00:16:40].

Kasey Jones: Yeah. I think-

Niko Hughes: Yeah.

Kasey Jones: -the job posting idea is really, really helpful. I do a lot of similar work with my clients where you get this broader view of how they're measured, what kind of tools they're probably using, what their background is, and it can be super helpful. And, the other thing is it'll often tell you who they report to or who they manage, and that kind of stuff can be super helpful.

Kasey Jones: I'm curious to get your guys' perspective on this as well. We've had a number of questions about kind of the account based marketing strategy. Let's say you've got a particular account and it's not even these personas, it's got maybe seven or eight different people that are going to probably be involved in the decision or in using the product, and so having a good understanding of who's the influencer, who's the technical buyer, all of these things. I think job postings can be very helpful in helping you figure out the broad [inaudible 00:17:49]. But I'm curious, do you have other advice or strategies around how to learn about those sort of broader team might wind up being involved in a decision?

Bryce Kropf: I'm sorry, I lost the end of that there. I froze.

Kasey Jones: [inaudible 00:18:10] Just how do you research or how do you learn about and how do you approach reaching out to full teams that might wind up being involved in a decision?

Bryce Kropf: Oh, well I have an answer right away, but I've been talking a lot. Nico, do you wanna take this?

Niko Hughes: Yeah, sure. Yeah, kind of my approach to that question is I like to create specific campaigns based on titles. Once we narrow down who we're trying to reach out to, is writing a campaign that speaks to the “why” of that person so that the messaging relates to their pain. The company has a pain obviously, all software cells is a solution to a problem, but how it affects a VP is different than how it affects a director or manager. So, writing specific messaging that relates to their individual problems and helps them solve their goals and how it fits into the bigger picture of their company is what I like to do. I think Taylor had a question about company focused messaging versus cross [inaudible 00:19:17] specific messaging. I don't know. I kinda like to intertwine those, Have steps in my sequence that speak to the company's mission, the vision of the company, but then also how that person relates to that mission, and then match those two together. That's kind of my viewpoint. Bryce, what're your thoughts?

Bryce Kropf: Yeah, I think that the company is hard. This is just my opinion, but I think the company is getting harder and harder because "Hey I saw this article about Google wanting to x, y, z." That's noise now. That's become noise. That's not cool anymore. So, we have to be cool, guys. That's the whole idea. That you buy from cool people.

Bryce Kropf: So, when that you buy from cool people in sales, that's what it's about. So I think if you are... What's that?

Kasey Jones: It's about looking cool.

Bryce Kropf: Yeah, that's right. But no, I think that if you were to, if you had again let's talk about limited time and budget. I don't know about the people on this webinar, but for me I always had a question in my mind. Do I spend time on this or do I spend time on this? You've got to at a certain point, you have to make a decision. 

Bryce Kropf: If I were to make a decision on something that I would focus my personalization time, or even my content-creation and reiteration time on, it would be the persona-based stuff before the company. If you can find a way to automate that, there are tools out there that will do company research for you. There are things you can do to automate some of those pieces, and you can layer that in, great. But personally I would focus on the person the person themselves. Even, if you can find things like that they've shared on LinkedIn or things that they care about. That's going to have a larger impact. Even where they went to school, if you have something in common I think has more of an impact. In my experience it's had more of an impact than, 'Hey, I know your company has an initiative' or something like that. That may be related to the thing I'm selling. Maybe not. 

Bryce Kropf: It's rare. I would be shocked unless you're in a really wide persona. Some people here have large personas. So maybe every single one of those articles is gold. Because you have this product that solves everyone's problems. But most people don't. Most people have a very specific thing.

Kasey Jones: And let's be honest. Particularly when you're earlier stage, you might have a product that can appeal to a lot of different markets and different personas. But if you're not narrowly focused on one or two, you will appeal to no one. This is something I see all the time with early stage founders. They are so passionate about their product and they have such strong belief that their product has this universal application. But if you don't start more narrowly focused, so that when someone comes to your website or when somebody reads an email they feel that it was exactly for them, you're going to fucking lose them.

Kasey Jones: It's only once you've built some reputation, notoriety and you've got some oomph behind you can you do this broader appeal. It's got to be more specific in the early days.

Bryce Kropf: Yeah.

Niko Hughes: Yeah. I got it. Go ahead.

Kasey Jones: Yeah. So we're getting a couple of questions around a few things. One in particular is about, 'Okay, let's say you've got that persona information. Let's say you've got great enablement resources from your marketing team or your leadership. What if you feel like you're still sending messages that are good but you're just not getting the responses?' What, how? What are your tips for how do you actually, going back to the title of this webinar, actually creating out that messaging that converts?

Bryce Kropf: Your emails probably [crosstalk 00:23:02] 

Niko Hughes: Yeah.

Bryce Kropf: Oh, sorry. I was just going to get into it. I was like grrr.

Niko Hughes: Dropping the hammer. Go for it.

Kasey Jones: This is something that I'm interested in because what's really interesting on the marketing side, and particularly on the almost the marketing-guru side, they write really fricking long emails. That is what are emphatic works. 

Kasey Jones: But I think that there is a difference between an email that is designed to get somebody to click on something and go look at something or like you versus an email that is designed to get you to take a meeting.

Niko Hughes: Yeah.

Kasey Jones: But I don't know.

Bryce Kropf: Go ahead Niko, because I don't want to talk over you again.

Niko Hughes: No, no. Go ahead. You were saying good stuff about message length and that kind of stuff and people need to hear that.

Bryce Kropf: Yeah. So more than likely the biggest killer that I always think in my head this is a given, but for most people it's not, is that you need to make the email as short as you possibly can. And distill the information. Right?

Bryce Kropf: So every time that if you have an email sitting in front of you right now, an email in your cadence, and you can possibly take out four or five words in each sentence, more than likely you can, do it. Because [inaudible 00:24:26] in a more concise way that's going to get through.

Bryce Kropf: It's just like we're the text message generation. If you're, if you have something that's long, nobody's actually going to read the whole thing. They're going to skim it for key words. They might notice that bold headline. 

Bryce Kropf: Wow, there's a lot of stuff blowing up there. I'm getting distracted.

Bryce Kropf: Another thing to think about too is that most people are pre-reading emails. This is one of the biggest, for me, recent revelations when it comes to emails. The first sentence matters the most.

Niko Hughes: Yeah.

Bryce Kropf: Everything else below that is important and tells the story and there needs to be a structure, but that first sentence has to be engaging in some way. It should be a question or some sort of insights. Something personalized. Something unique, because as soon as they see that, that's your entry in. That's your open. You'll be surprised at how bad your open rates will be, not just based on subject line. Subject line, that's important, but as soon as they go down they see subject, quick question, because everyone's using that, and then, seriously. Then below that it says, 'Hey. I thought it would be interesting to have a conversation.' Something like that.

Niko Hughes: Yeah.

Bryce Kropf: No! You're out! You're done. 

Kasey Jones: And what someone, what you were getting distracted with, someone was also saying the big thing is not even, yes short, but it's also no blocks of text. So it's like-

Niko Hughes: Yeah. 

Kasey Jones: When you're writing an essay you might have a paragraph that has five sentences in it. You do not do that in an email, and frankly you don't do that in block content anymore either. 

Niko Hughes: Yeah.

Kasey Jones: Because people get a block and they just stop reading. We need to be able to skim and it's almost like headline after headline after headline.

Bryce Kropf: Yeah.

Niko Hughes: One of the guests, someone in here made a good point on like BDR selling meetings on products.

Kasey Jones: Yup.

Niko Hughes: A lot of the times in messaging, people are talking about their solutions and the software. All the great features and the technology that went into it. No one really cares about that. To be honest. They care about how it's fixing their day to day problems. Or, if it's a higher up like a director or VP, like, 'How is this helping me shape the vision of my organization?' Or like 'Help my team be more productive?'

Niko Hughes: So what I like to do is keep the messaging super simple and short. A cell phone screen size, you don't have to scroll or anything. Just highlight the pain point. You know? If then when you're asking for a meeting, 'If this is a problem you're trying to solve, can I have ten minutes of your time?' And if it's not, then, great. Move on to the next person. But if you are able to pull on the heart strings or get some interest there then you won. You won the meeting.

Niko Hughes: I think a lot of times people, STRs, they get in the habit of thinking that they deserve to meet with someone. It's like, 'You're earning someone's time.' So create messaging that's appealing to the pain, not necessarily to the solution you're providing.

Kasey Jones: Okay. So Eddie posted a funny question. A very, very good question. He's asking for a friend. He wanted to make that very clear. [crosstalk 00:27:42]

Kasey Jones: Okay. What if you're getting amazing open-reads, but no one is responding? So he's saying, 'Okay. If I'm getting 90% open-reads, holy moly, you've got bomb ass fricking' subject lines.' But, no one's responding. What do you think is going on there?

Bryce Kropf: Well, it depends. It could be a lot of things actually.

Niko Hughes: Yeah.

Bryce Kropf: I think there's a few things. Nice work.

Bryce Kropf: I think that I have got questions for Eddie. I really do, because Ryan is right on. Ryan, right below Eddie said, 'Calls to actions and value building will be what you should focus on for reply.' So it's kind of a given. Or playing, understanding the persona, focusing on them. Connecting with something with them. That value. Building value. Right? That is right on, boiler plate.

Bryce Kropf: One of the things I've seen a lot of SDRs do, and this could be Eddie or it could be his friend, but one of the things I've seen a lot of SDRs do is come up with something they think is an awesome subject line. But it doesn't actually help them in the long run. Or even a good opener. Because they start out with... we're all friends.

Bryce Kropf: We are all friends, Oscar. 

Bryce Kropf: It could start out with something like, let's just say you send them an email message that says, and I am using a bold example here but, 'I have your kids in my car,' or something like that. Right? That subject line is going to get a lot of opens.

Niko Hughes: It gets opens.

Bryce Kropf: Might be of concern. But when they, or maybe [crosstalk 00:29:16]

Kasey Jones: If you said it in a bar, you'd get punched in the face. You probably don't want to do it. I don't know. 

Bryce Kropf: Exactly. Yeah. I'm using an extreme example, but my point being whatever your subject line is, sometimes they can be borderline misleading. Right?

Niko Hughes: Yeah. 

Bryce Kropf: Nobody likes to be misled. So maybe it's like the good old re-strategy. Making it seem like you're replying to an email even though it's a fresh email. 

Bryce Kropf: Whatever it is, if it doesn't contain consistent professionalism, send a message, it's okay to use humor to have creativity in this process, but if at any point you find yourself going, 'This is going to get a lot of people to open this, but I don't know what taste it is going to leave in their mouth.' That's the first concern I would have with a 90% open rate. At the end of the day, if that's the case, maybe you have to, to Ryan's point, maybe you have a great opener but you're not building value. You're not connecting with the person. You aren't clearly showing you care about them and so at the end of the email maybe there's not a clear call to action at the end of the email.

Bryce Kropf: I'm a little bit different than Niko I think. In that I'm not like, 'If this is a problem you're trying to solve. Let's talk.' Sometimes I use that one. But I tend to be more forward. I tend to say something more like, 'Hey, let's connect for fifteen minutes,' or 'What's the best way for us to connect for fifteen minutes?' Or 'Are you open to have a conversation next week at 3? Or next Thursday at 3?' Something like that. Only because it's a little bit more. But again, know your persona. There's other personas that would prefer to be asked.

Niko Hughes: Yeah. It's not in the next sentence. 

Niko Hughes: Taylor had a good question. Does every email need a CTA? Or ask for a meeting? I think no, it doesn't. Sometimes I send content just to be a value add and not ask for anything from them. Other times you could be like, 'Hey. Would you like to see a report or a light paper?' And if someone replies, 'Yeah. Send it over.' Then, at that point, I would ask, 'Hey. If this is valuable, do you want to get on the phone?' 

Niko Hughes: So I think if you're adding value, they'll most likely want to talk. If you're not adding value, then they probably don't want to talk to you. At least in my experience.

Bryce Kropf: I think, just to piggyback off of that and I promise Kasey I will let you get back to some of the questions.

Kasey Jones: Okay.

Bryce Kropf: [crosstalk 00:31:42] talked about this forever. I think what it comes down to though, to your point Niko, no it doesn't always have to be a clear call to action. It doesn't have to be a pushy salesperson. In the end of the day, what is working? Measure everything you're doing. If you're not measuring it, if you can't come back and say, 'I know that Sequence A gets this type of response from this type of person and I'm going to edit this part of the sequence and see how that performs. And do AB testing.' The modern salesperson is a digital marketer who also happens to call their prospects and hunt them down and know them as a person. Not just as a persona.

Bryce Kropf: So if you're not doing that, you're not doing anything. You're spinning your wheels. 

Niko Hughes: Exactly.

Kasey Jones: There's a bunch of call outs to Gary B and [inaudible 00:32:38]. The thing that, for me, bugs me the most about Gary B's approach is if you've read Crushing It, he basically says repeatedly. He's like, 'If you aren't at least 51% altruistic, go home. Just shut up.' It isn't going to work for you. That is kind of the thing.

Kasey Jones: I think that's even more true kind of on the marketing and brand building side, but somebody needs to feel like it's not all about you. You actually have, you understand what they care about.

Bryce Kropf: Yes.

Kasey Jones: You have something to offer and your bottom line goal, your number one goal is to help make their lives a little bit easier. If that means that you get to, if that means that they give something back to you, awesome. You're stoked even if that doesn't happen. 

Kasey Jones: That's how you build trust and that's how you build a relationship. I think it can be tough when you're an SDR because it feels really transactional. And it feels, especially when it's all email, you can feel super disconnected. But if you really start to inject this human quality again, where you are acting like an actual person, your results will be better.

Kasey Jones: So the, and I kind of used this analogy jokingly earlier but I genuinely think if you're writing an email and it's the kind of email that if you said it out loud to a friend at a bar they would think you sounded like an asshole or you don't know what you're talking about, don't do it. Send a message that sounds like a fricking' person. 

Bryce Kropf: Yeah.

Kasey Jones: We're going to connect way more when you're speaking in human language. I will get prospecting emails where there will be like this long and it is full of buzzwords. I will get to the end and I'm like, 'I have no fricking clue what you were even talking about.' That happens a lot.

Kasey Jones: So talk with the person and try to make somebody's life a little bit easier.

Kasey Jones: Okay. So on the subject line question. What's your rule of thumb? What rules so that you are? Or quick question? Or 'Can I help?' Or?

Bryce Kropf: No, no, no. I didn't say that. Use those.

Bryce Kropf: So I think a good place to start is something like, 'Quick question.' 'Any thoughts?' Whatever. As long as, couple things, as long as you don't capitalize everything and you keep it short. Keep testing it. Just use whatever works. 

Kasey Jones: Yeah.

Bryce Kropf: It sounds like it may come from their coworker. Even try to make it specific to the product you're selling. You could even say, 'Sales Ops?' It sounds so cheesy, but as long as your email is relevant to sales ops and you're sending it to a sales ops person, or something like that, that is a subject line I would use.

Bryce Kropf: Again, I would just keep testing it. And coming up with new ones.

Niko Hughes: Yeah. I think the big point that he's trying to make is test. Then use the data to make decisions. So, if you're not iterating on the fact that one email is getting a 50% open rate and another one's getting a 10, and you just keep on blasting it, then you should probably make a better decision.

Niko Hughes: There's no one size fits all subject line that works for everyone. If there was, it's been used too many times so now it doesn't work anymore. So just try things out. There's a lot. HelpSpot posts a lot about different subject lines that they use that are having success. There's a lot of old articles that are six years old that people don't think to use those subject lines anymore. So now you can start using them again.

Kasey Jones: Yeah. Good call.

Niko Hughes: I've got a lot of questions on spam and stuff. If you're sending, this is why you have to AB test, if you're sending the same subject line to thousands of people a week because you're only using one campaign for five personas, you're probably going to get hit spam filters.

Niko Hughes: So use multiple things. Try things out. It's better to personalize and send less emails than send more that are just generic. Working on the phone-

Kasey Jones: So I don't want to make Eddie our continued scapegoat during all of this. But he had a question. I have my opinion about this and I'm curious about yours. That I sent this via LinkedIn to a person I am connected to. Okay. He wants our thoughts. Okay. "I was chatting with my colleague yesterday and he decided to stop using buzzwords to get folks to respond and simply asked them for their time. So, without further ado..."

Niko Hughes: Did it work?

Bryce Kropf: That's the question to ask.

Kasey Jones: So, my immediate response is way to make it all about you, Eddie.

Bryce Kropf: Yeah. Yeah. [crosstalk 00:37:38]

Niko Hughes: That's a good point. Yeah.

Bryce Kropf: Sorry.

Kasey Jones: [crosstalk 00:37:41] in it for me? That's the thing. It's like, yeah, you don't... it's a fine line. Right? But we are all really busy and we are all kind of narcissistic. Let's be honest. If I get a message and it's obvious that someone just wants something from me and they haven't told me what's in it for me, I'm a lot less likely to respond.

Niko Hughes: That's a good point. Also, it's a creative approach if you guys don't listen to the Bowery Capital Podcast. Bryce actually showed me them a few years back. The CEO of Full Contact was just on there talking about different strategies they use. One strategy is using alumni networks. Like, 'Hey. I saw you graduated from Penn State. Go Nittany Lions.' Your personalization doesn't have to be focused on the solution you're selling or the company they're in. It could be just on that person. Just to get the door open and then have the conversation. 

Niko Hughes: It's all about building rapport. As long as you're not offending anyone or being weird, you can use different strategies. Like, 'Oh. England just lost in the World Cup.' You can say something about that. Different things that is relative to the time and place, but then also to the individual.

Niko Hughes: So if you're just wanting to get conversation started, there's ways to do it outside of product.

Kasey Jones: Yeah. I think there's a couple of questions coming in about LinkedIn and LinkedIn email. I can certainly say, because I get a lot of these, when I get a LinkedIn email message and it's about connecting and it's value based, I will totally connect and I will totally engage with the person. Every single time. 

Kasey Jones: It doesn't necessarily mean I am going to take a call, but they will get a second chance. But, oh my God, I get so many LinkedIn emails that are this long. It is this super crazy long really selfish pitch. It is often like, 'Hey. Here are 800 reasons why you should help me find a job.' I'm like, 'Dude, I don't even know you.' So I think LinkedIn, because it is more social and more personal, you've got to have that strategy. It's got to be-

Kasey Jones: To you've got to have that strategy. It's got to be first about starting a conversation and not necessarily about immediately asking for something.

Niko Hughes: I agree with that.

Kasey Jones: So, the other question that we got, and we got a couple of up votes in our little questions field, is do you have any strategies, and I can offer my perspectives from a marketing standpoint, of how to get marketing to work more with your team? So, I think this happens a lot, and particularly as companies grow, that marketing is doing their own thing and they're not really focused on kind of working closely with sales. And as an individual salesperson, can you, is there something that you can do to kind of convince marketing or I don't know, just start to kind of collaborate more closely with them?

Niko Hughes: Yeah, kind of my thoughts there at least, I've been out of another company for a couple of years, but you got to do some political networking within your own organization and talk about how does it make the bottom line smaller or make the company more profitable if you guys work together? So, if there's more inbound leads coming in from marketing or if they're helping you guys get better content out to your prospects, then everyone's happy. So, you got to sell the relationship in between the organizations a little bit, if it's not already created.

Niko Hughes: Bryce, what you your thoughts?

Bryce Kropf: Well, so I think that, I mean from my perspective, especially in the company, I've worked for a few big companies now, and I think it's sometimes easier at a bigger company because you can, so I don't know. I guess that would be my question, if that question is how do I get marketing to work with me more, the first question I would have is how big is the marketing team? Do you know who owns content? Do you know what they're measured on? Do you know historically your groups have worked together if they haven't? But I mean in general, it's internal selling at that point, right? It's how do I get you guys bought into the idea that I am going to deliver value not just to our company but to you personally? 

Bryce Kropf: So why don't we, I mean the way I would approach it is I would say, "Hey, I would love to collaborate with you guys on some new content." And if you have pushback, "well, we're so busy with XYZ initiatives." Go, "Okay great. Well, I don't know if you've heard of account based marketing, but it's something that's really near and dear to my heart, and it's new way that companies are making lots of money." And so you build a case for them, and then you say, "Let's create an initiative around this. Maybe it's not your highest priority right now, but can we get it on the docket? Can we create this as an initiative down the line?" And then start building out what that looks like. Do some of the legwork yourself. And then let them put their name on it so they get credit too, and then they'll actually be more likely to engage. 

Niko Hughes: Exactly.

Kasey Jones: Yeah, so I think you guys totally nailed it. You take the same approach with marketing as you do with the people that you're trying to sell to. They're just your internal customers. You [inaudible 00:43:36] have empathy. You figure out what you can do to help make them look good internally. And one of the things I would say is go what give get. You don't always have to say, "Hey, let's do this whole separate project." What if instead you say, "Hey, okay what is a campaign that you're running, and how can a sales development team help you get more eyes on that content? Or more people to that event? Or funneling more people to that webinar?" 

Kasey Jones: So, this is something that I do a lot with my clients with webinars is instead of only publicizing webinars to an existing list, sales development teams will work with me to do outbound invitations to cold prospects for them to attend these webinars. And it's a total win-win. So, what I would really recommend is if you really want to be, you want more support from your marketing team, offer them support first, and I promise, they will give it back. But everybody's really busy, and you've got to make it a win-win and you've got to give first to get something in return. And I promise if you do it once, marketing will all of a sudden be like, "Oh shit, we got twice as many people to attend this webinar. Maybe we're on to something. And they'll start to get creative with you.

Niko Hughes: Yeah. Tie your goals to their goals, and then solve problems together. So, if you can pitch that, they'll be happy.

Kasey Jones: Yeah. 

Niko Hughes: Yeah.

Kasey Jones: Okay, so let's see. 

Bryce Kropf: Can I say one more thing about that? Because I love internal politics? I think that I have a sick, sadistic fascination with it. I think another approach that you can take with that too is if you don't feel, because some people, you can be the great person that Casey was just displaying, right? Like I'm going to provide you value. I'm going to connect with your goals. I'm going to do all these great things to you. And sometimes, you just work with a department whose not nice. That happens. Sometimes you work with people who aren't as cooperative as you'd like them to be.

Bryce Kropf: One of the things you can do is start the initiative yourself, and then basically just passive aggressively, this is going to sound terrible, but kind of passively go, "Hey, we want to push," let's say it's a webinar or something like that, we as SDRs we have a plan. We want to do this thing to push marketing. And what'll happen is because you're involving marketing;s content or maybe it's an event that they're putting on outside of their initiatives, like it's whatever, let's say it's webinar that they're putting on themselves. And you go, "Hey, we're going to incorporate that into our outreach methods." You force them to work with you. Sorry.

Niko Hughes: sounds good.

Kasey Jones: No, I think that that is super solid advice. Right? Because if you can have them get going and they sort of have to get on board, and frankly they'll do it begrudgingly. But once they've seen results from it, they'll be excited. And I just realized, because we're getting sort of close to the end, one of the things that the three of us could have sat down when we were looking at everybody kind of submitting their information [inaudible 00:46:57] register, we were astounded by how many people really expressed a desire to have help developing personas and also then auditing, or improving the content they are currently using, but having kind of a mechanism for ongoing improvement. And so, we kind of scraped together and came up with some ideas on how we could actually help you do that. And so, we put together a little bit of a kind of sample offering to help you guys improve your persona profile developments so you have a way better understanding of who you're targeting. But then also having a mechanism for having en masse messaging.

Kasey Jones: So, if you guys are at all interested in getting some of that help from us, I just a little call to action at the bottom of this. Click the link and we'll set up some time to kind of give you a little bit more info about how we might be able to help you and your team. Because we were really blown away by, I mean, easily 60% of the people that registered expressed struggle with personas and really understanding who they are targeting, and then crafting messages associated with that. So, we want to help you guys do that. So, if you're at all interested, click that link below. 

Kasey Jones: And along those lines, we've got a couple of questions around okay, are there templates for personas that you guys like to use?

Bryce Kropf: So, I think that that in itself is not a thing. I'm just going to say, sorry go ahead.

Kasey Jones: No, I was just saying that it is a thing, and it's kind of to a detriment, that it is a [inaudible 00:48:57] like a template, it doesn't work.

Bryce Kropf: Yeah, I guess that's what I was going to say. That is not a good thing about that. We don't want those. I think that you have to look at the structure. I think somebody in the message, I saw it but I didn't get a chance to shout out and say it was awesome, but somebody mentioned something about creating a structure to your messaging, and that being the way you get to "a boiler plate or a template." But it shouldn't be that. It should be different for the type of person you're reaching out to and the industry, et cetera. But you should always have a structure. My structure looks like something to the effect of entry question. I usually like to start with a question or a personalization. One or the other, depending on what level they are. 

Bryce Kropf: Let's say I do grading, so it's like C level prospect, somebody who's not necessarily the best fit, they're just getting a general. They're getting a question, something like, I don't know, have you considered doing XYZ for your sales office organization? Or something like that. Or what are your thoughts on implementing ABM this year? How far are you towards your goals? Something like that. Below that, some sort of basic explanation of why I'm reaching out to you, right? Some very clear, here are the kind of things that we're, the reasons why people work with us and how we're helping them. And then, a call to action at the end. And that should be less than five sentences. It should be around five sentences.

Niko Hughes: Bryce made a subtle good point here. You should have a tiered approach to your outreach, so A level, B level, C level. So, C is people who if you get a meeting with them or if they, they might not be the sole decision maker, but if you get a meeting with them, it's great. And B is you spend more time personalizing at that point. These are good buyers, but they're not like the 100 logos you want on your website next year. And then the A list is where you spend a ton of time cracking good messaging, getting on the phone, sending them a letter, sending them a gift. Like a lot of people are sending Starbucks gift cards or hey, we're in Portland, so maybe Barista or something. Not Starbucks. But -

Kasey Jones: Not [inaudible 00:51:08] important.

Niko Hughes: Yeah. So sending, investing, giving something away for them to get them to meet with you. So, if you have that approach, then you're going to have a good mix of super qualified, warm potential buyers. And then people who, then you get their business, then more revenue on your table, but it's not the logo that you want to post on your site kind of thing.

Kasey Jones: Well, but here's the other thing that I've seen with a ton of sales teams is that they go after the logo whether they're a good fit or not. 

Niko Hughes: Yeah, that's true.

Bryce Kropf: Yeah.

Kasey Jones: This is a whole other story and we could have a whole webinar just about this, but you really have to take a self-aware assessment of what makes a customer a good fit for your product. And one of the things that's really difficult, particularly for kind of young AEs or when you're just starting in sales, you get, I don't know, starry-eyed over a big logo, or frankly, over anyone who shows any interest in you whatsoever. And it then becomes very hard to recognize that this is not a good fit and this is a waste of my time. And the best salespeople I've ever seen are the ones that are really good at qualifying out bad opportunities and not wasting that time.

Kasey Jones: And like, I mean I have tons of stories, and I'm sure you guys do too of sales teams spending a fortune and a ton of time chasing some big fat logo, and no joke, this is a real story, where it was like they had spent seriously like a million dollars to close this client. The customer was like, "Oh yeah, we're a big logo, but you'll never use our logo on your website." And they finally close it, and three months in, the company came back and was like, "You guys aren't delivering on what you said you would, and we're walking." And they didn't pay a fricking dime. 

Kasey Jones: So, that's one thing that's, this is why we continuously go back to really understand what makes somebody a good fit, and who understand what is an ideal buyer and why. Because then you'll be, you'll spend more time going after the people that aren't shiny, but maybe they're the people that are going to close faster, they're going to love your product more, they're going to make your company look good, and they're going to be evangelists and referral partners. 

Niko Hughes: Yeah, that's a good point. I think as an SDR, as a startup, you have to know your metrics. Like how many opportunities do you need on your calendar to then close the right number of deals a month to then hit your quarterly and yearly goals? If you can calculate those things, then you can extrapolate that out to your messaging, to how many people you need to contact, how many webinars you need to do. All that kind of thing. So then, you can have data around what you're doing so then, if you're hitting your numbers, you know it's going to result in blank revenue goals. So, that's one recommendation that we do internally at my company that we recommend our clients, is really get down to the numbers so that you can predict revenue based on day-to-day results. 

Kasey Jones: Okay, so as we kind of near the end here, just wanted to call out again, if you guys are at all interested in some help on the persona and also the content creation and approaching there, click the link, we'll reach out, we can start a conversation. But as we wrap up, I'd love to hear Nico and Bryce, okay, we've billed you as these sales development wunderkinds, these -

Niko Hughes: Yes.

Kasey Jones: What would be for all of the sales development reps out there, what would be the two or three things that you would say that you focus on and are your mantra for success?

Bryce Kropf: I'm going to let Nico start because I'll talk too long.

Niko Hughes: All right. Okay. Yeah, [inaudible 00:55:09] I think Bryce and I both appeal to this is you have to be a student of your craft. So, if you're not constantly learning more about your industry, our own skillset and your company, then it's going to affect your day-to-day work and how you approach the market. So, I'm not going to tell you to work 15 hours a day, but you probably should spend a lot of time focusing on improving your own skillset and your knowledge base because that'll just make your results better. And looking back when I was MSDR full-time, my best results were when I was fully interested in the market I was in and focused on my personal goals and how those related to my company. 

Niko Hughes: So that, and then really focusing on making things relevant to the people you're reaching out to, whether that's spending time developing personas or crafting new messaging and iterating every day. I love the book by Jocko Willink called Extreme Ownership. Subtle plug. But you have to own your own business, like being an SDR and being a sales rep or marketing, whatever it is, own your responsibility and it's your job to hit your goals. If you're not getting support for marketing, like okay, write a blog yourself. So, be the best person you can be in your role and then you'll have success.

Bryce Kropf: Yeah, I think -

Kasey Jones: Close us out.

Bryce Kropf: What's that?

Kasey Jones: I said close us out.

Bryce Kropf: Well, I was going to say, I agree wholeheartedly with pretty much everything that Nico said. For me, I think it's, I'm a little bit, my wife's a therapist, so I'm always self analyzing, and I think for me the biggest hurdle for moving to being a really, truly successful salesperson, SDR, whatever, just in general, professional, was learning to let go of the little things and to focus on the big picture doing all of the things that Nico said. It's taking the time you need to do the work well, and engage in it. Depending on, yeah, a counselor here, awesome. Engaging with not just the product and the company and the messaging and your people and your prospect, but with yourself and understanding what motivates you, and using hat to get you through to consistency. 

Bryce Kropf: Because SDRs are the highest burnout, I think, of most roles out there. Don't know that the exact statistics are, but last time I checked, it's crazy high. And part of that is it's a very demanding job that requires a lot of focus and attention to do well, so a lot of people fail out of it. And I think that if you one poin two years, look at that, it's very quick. So, if you really want to do well as an SDR and you really want to make that a part of your career so you can be an amazing salesperson, you have to figure out what truly motivates you deep down, whether that's "I want to go to Cabo," or "I want to pay for my sister's college," I don't care what it is, find a center for you to focus on, and use that to fuel all of the things that Nico just said, taking the time to reiterate on that messaging, focus on the buyer to really be an expert in your industry.

Niko Hughes: Perfect.

Bryce Kropf: I hope it is.

Kasey Jones: It was awesome. Thank you guys so much. So, everybody that is listening, definitely reach out. Connect with any of us on LinkedIn, SD remote where Nico's company now has a Facebook page. So, definitely come find that. I have one at A Better Jones. Bryce already told us he's not on social media, so just ignore him.

Bryce Kropf: I have a LinkedIn. That's the only thing I do is LinkedIn.

Kasey Jones: So yeah, definitely feel free to find us on LinkedIn and connect, send any additional questions and we will be sharing the recording of this. I'll add captions and share it tomorrow. So, definitely feel free to re watch and share with any of your friends or colleagues. And let us know how we can help you guys level up your sales results and filling pipeline. That's what we're here to do. Okay?

Kasey Jones: Have a happy Thursday and talk soon.

Niko Hughes: Thanks, everyone.

Kasey Jones: Thanks.

Bryce Kropf: Thanks, guys.