Pipeline Over Everything with Jed Mahrle

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Welcome to the live Better Sell Better podcast with your host, Kevin Dorsey of Inside Sales Excellence, the number one Patreon group and YouTube channel for tech sellers and tech sales leaders, where we dive in deep for tactical advice on how to book more meetings, close more deals faster, and lead sales teams to success. But we don't stop there. We also focus on the person in salesperson. We talk about mindset goals, time management, and so much more. So thank you for listening and if you're interested, head on over to patreon.com InsideSalesExcellence now with that, grab a notepad, get ready, and let's dive into the good stuff. What up, everybody? Welcome to another episode of the live Better Sell Better podcast. This is your host, Kevin Dorsey, AKA kd. And today we are talking about poe Pipeline over everything. Y' all know me. You know Pipeline is near and dear to my heart. I'm forever a prospector, which is why I get so excited when I see someone putting out great content around how to prospect the right way. Because so much prospecting advice out there is very boilerplate. Just do this, use this line, use this email without making it relevant to the prospect that you are targeting, but then also building the right systems in place to do so. You can't just send one good email, you need to send five good emails. You can't just make one call. You have to build out the whole process. And that is why I'm so excited to have Jed Marley on the show with me today. He's the head of Outbound over at Mailshake and he's going to walk us through not only his journey into SaaS, which is really fun and we're going to dive into, but how to prospect for the modern day, how to stand out, how to be relevant and be memorable. Jed, my man, welcome to the show.

What's up, kd? Thanks for having me. I like that acronym too. Poe Prospecting over Everything.

Actually, for anyone that, like, ever watches the video on this, this was a gift from my team. It's a decanter that actually says Pipeline over everything. My team bought this for me. POE was on our onboarding shirts. Poe was on the sweatshirts we made for our team. Like, it's what we lived and breathed it because the idea was if we can open it, we know we can close it, but if the pipeline isn't there, we can't grow. And so obviously, this is the world that Mailshake plays in as well. But if you think about prospecting, right, generating pipeline, I'm Gonna start this on a different angle of like, what are some of the common mistakes you see people making out there when it comes to generating pipeline? And then we'll start getting into how to solve those things.

Things for sure. Yeah. I think the biggest mistake is not understanding your ICP well enough. So one of the most powerful things you can do, whether you're an sdr, an ae, anybody who's prospecting, is take time, block time off to really study your icp, study the deals that have come inbound, study your customers and really break it down and figure out, you know, who are you having the best conversations with? What are their really like, their pain points. That's the biggest thing that helped me as well, is just diving in, figuring out what exactly are the pain points, as opposed to just reaching out to any sort of account. And so getting really niche and narrowed down is one of the biggest things to kind of stand out in that sense.

I'm so pumped. That's. No one starts there. Nobody starts there. I'm so excited that's where you went. Because we're going to unpack this a little bit. Because funny enough, in my playbooks for my reps, the first section was about what it meant to be a part of the org, right? Like just part of the org. The second part was the Personas. And I took them through this whole exercise of how to get into the mind of the Persona. So, like, go a layer deeper there. Right. No one talks about how to learn about the prospect, understanding the icp, what are the things I need to know, what are the things I need to understand, and how do I find some of that information out?

Yeah. So first of all, I feel like a lot of SDRs or new salespeople, they focus too much on the product. And definitely focusing on the ICP and the Personas is kind of the priority. There's a few ways you can do this. If you have a large enough company, just slack the people who are your ICP within your company and ask for like 30 minutes on their calendar to interview them. Ask what sort of emails do you open up? What are the day to day problems that you're focusing on? That's the number one easiest way to do it. One of the big things I did at Mailshake when I joined was I just reached out to. We sell to VPs of sales. So I reached out to 20 VPs of sales in my network and just asked, hey, like, I'm not trying to sell you or anything. I just want like 15 to 30 minutes or even just to ask you some questions over LinkedIn. And then I ask them questions related to our product. Right. I asked them about their day to day. I asked them, when do you consider looking at sales engagement tools, since that's the space we sell in. You know, the fact that I have somewhat of a brand definitely helped with them responding to that. But wherever you're at in your process, if you reach out, if you make a good enough offer, people are going to respond, you know, and whether you have a brand or not, if you reach out to enough people, you know, salespeople like helping salespeople, people especially on LinkedIn. So reach out, ask for those conversations. And that's been the biggest way for me to kind of find out about my ICP and really understand my Personas.

I love that. This was not where I thought you were going to start. I'm so glad that you did, because this is, this is everything you need to understand your prospect better. Then you figure out the product and how to attain it. But knowing the prospect, how they think, how they use your product, and for leaders listening, bonus. Record all these calls. Record every single one. Because then you put them into onboarding, where the rep, the new reps don't have to reach out to redo all this work. They can listen to 30 of these interviews. And I promise you, it's the number one place I work with companies. If they're short on resources, I say go interview 20 to 25 of your customers. I have six questions that I take them through that I've covered on other episodes. Record all those. That's what your new hires listen to.

Yeah.

You want them to level up quickly. They need to understand this fast. So I love this.

Right?

So very, very good. So then what do I do with this information, though? All right, Jed, So I went and talked to, you know, 20 people. I asked these questions. Now what, what do I do with this information to help me generate more pipeline? Do I get to ask them all for meetings now, Jed, how does this work?

Yeah, for sure. So now you kind of take that information to make your messaging a lot more targeted. So we can start with like on calls. Now you can start reprieging. Hey, I'm talking with a lot of VPs of sales or VP of marketing. And these are the top three things they're telling me. Is any of that relevant? And leading with the problem in that sense has been the most successful for me on calls. But specifically for emails, you lead with those problems in emails. So you figure out what are the Top three pain points that I'm hearing from these prospects, from these Personas, or if I listen to customer calls, what are the top things I'm hearing? And then let me create a sequence of emails. Right. But I'll reference the most. The problem that I heard the most in that first email. Hey, you know, we Talk with other VPs of sales. This is the biggest problem I'm seeing. And that's the problem. You reference the next email, you're referencing a new problem, the third email, you're referencing a third problem. So you use that to get really specific in your email and phone messaging. And the biggest thing too, is that when you're prospecting, when you're on the phone with people, they can tell when you understand them, right. When you speak their language. I was selling to it a little bit when I was at Pandadoc selling E Signatures. And it has a different way of communicating. They have different lingo. There's, you know, so if you speak their language and you start talking about things like you're one of them, they're going to tune in a little bit more when you're on the, when you're on the call or if you use those acronyms or those sort of the words that they use in your emails. Again, it's just another way for them to notice that and want to respond to your messaging a lot more than if you were a little bit more generic. So doing that alone and really spending time digging into your ICP and has been one of the biggest differentiators in any SDR that I've worked with or con executive, name it, you know, whoever it is. But that's, that's a huge thing.

Yeah. No, I love that. It's. I used to call it the long day after work test. Right. Where if you couldn't picture your prospect sitting down after a long day of work, pouring a whiskey, leaning back, taking a deep breath, and going, God, if I could just solve. Or if I only had. Right. The example I always use was actually at Patient Pop, right when I joined Patient Pop, a lot of the messaging in our outbound was, you know, practice, you know, growth platform. And I was like, how many doctors, when I did all my interviews, think said the words practice growth platform.

Yeah, None.

That's not how they talk, right? When they sit down after a long day. It's not saying, God, I wish I had a practice growth platform. It's, God, how am I going to get my next patient? Yeah, what happens if I don't meet payroll? Why am I Losing to this comp. That's how they talk. And then I love your example. Then you put that into your email messaging. Right. And you spread that out over time.

Yeah. I mean, I'll have my prospects even write my emails for me. Like, when I've had those meetings, I'm saying, hey, look at this email. And one of the biggest tests you can do to your point, Kevin, is pull up your email and say, hey, would this Persona, like, are the words in this email. Is there anything my Persona wouldn't say? Like, to your point, growth platform. If they wouldn't say that, just remove it from your email, replace it with something else. Another really easy thing to do if you sell software is go on G2 crowd and look at customer reviews. And I would literally just copy and paste snippets of how they described our product and use that for my email. Because that's literally coming straight from your customer. That's their messaging. That's what's going to resonate most.

Yeah, it's crazy to man, we could spend the entire episode on just getting to know the prospect. Because if you think back to, you know, selling, at least when I first got into sales, I think I'm a decent amount older than you. Maybe just a year. Probably a year older. But when I started selling, right. Like, that's actually where most of the training was focused. It was like industry knowledge, it was the prospect knowledge. Now in SaaS, it's so much more of, like, the product knowledge. And we just completely skip over this part of, like, getting to know the prospect and the problems that they're having. So let's keep going down this path a little bit. So I've done some of these interviews and I'm going to start trying to craft messaging. And you said something very important of using their language. Go just a little bit deeper on that because I think that's really an important call out of, like, are you using their language in your messaging?

Yeah, absolutely. I mean, there's a few different ways you can break it down. I mentioned, like, an IT Persona will use certain different acronyms. Maybe if you're talking to a VP of sales, you know, you want to talk about revenue, you want to talk about things that. I'll give you a good example. Right. So I sell sales engagement software. If I'm a VP of sales, I'm not really as concerned with the open rates of my team's emails. I'm not as concerned with the reply rates of my team's emails. I'm probably more concerned about the pipeline and the opportunities that we're booking as a result of those emails. So you can break it down by seniority level. So if I'm talking to like a C level or a VP level and I'm selling sales engagement email outreach software, I'm not going to talk to them about improving open rates or fly rates, things like that. I'm going to talk about more high level stuff that they care about that they're looking at on a day to day. Now if I'm prospecting lower, which I do to somebody like at the management level, the director level. Well, if I'm talking to an SDR manager, they do care about open rates, they do care about reply rates. That's a problem they care about. So don't just break it down by the Persona level. Figure out their lingo. Like I said, you interview them, you just write down the words that they're saying. The common things you're hearing, you know, look at G2 Crowd but also break it down by seniority level. Typically people towards the top are going to be, are going to want to be a lot more brief with your emails. They don't care as much about personalization, they just want to know what the problem is. So get more high level. There's. But then get more specific the lower you go. And that's kind of like a general rule. But again break it off, break it down by seniority level and Persona in terms of like the language you're coming up with for your messaging.

I love that. And what you're starting to get into is kind of like what I've called, right? Like ctd. And you used like relevance. You have to connect the dots like all right, maybe your product does improve open rates. If you're emailing that to a VP or a CRO, you have to be able to connect the dots back, right? Like all right, I care about revenue, right? You can't book a meeting if the email's never opened. Yeah, now we're connecting the dots, right? Of like if you need more revenue, you need more meetings. If you need more meetings. You can't book a meeting if someone never opens the email. Yeah, like in going through all that, I just think the connecting of the dots, that's how you make it relevant. And then you called out one of my, one of my favorite topics. I knew we were going to vibe on this, man. This is good shit, right? Is I talked about the three eyes of targeting, right? You target low for info, middle for insight, high for influence. And so often people are Targeting high for insight. Right. They're trying to find out what's happening. If you're reaching out to me, you better already know what's happening in my business and you find that out by targeting low. So talk to me about that, Talk to me about like targeting low and high because there's still a ton of people out there. Just like go after the decision maker, go after the decision maker. Get, you know, get the, get the CTO on the phone. You're like, what that?

No.

So talk to me about how you work the different levels differently and kind of when you work those levels.

Yeah, first of all, that three. I thing, I think I may have heard that from you in the past before, but I'm definitely writing that down again. Like that's, I know I've been using that type of strategy, but that explains it perfectly. But I, I completely agree. Right. One of the biggest things again, so I sell to salespeople. If you're fortunate enough to sell to salespeople, you need to be talking to the sales reps, the SDRs, the AES there and getting info from them because they're always going to respond to their messages. Their inbox is not as flooded. So one of the first things we do when my sdr and when an sdr, my team or myself gets a new account, I want to go after, I'm not going to talk to the director, not going to talk to VPC level. I'm going straight to the ground floor and just asking for info. And it can be as simple as just sending a quick message or if you use like a gifting software, you can say, hey, just curious, like what software you guys are using for XYZ, you know, here's a $5 coffee gift card. Thanks for the help. So something simple like that and we do that like over a three day period and then we gather all this info and then we start targeting that middle level, director level. Hey, you know, when speaking with your team, these are some things I've noticed. Is any of that relevant? Sometimes we'll book a meeting with that person, but if not we can go to the C level and really just condense down everything we've learned and say, hey, here's like the problem I think is happening in your organization. Would it make sense to chat further? But yeah, it's working your way up the ladder. And I think the problem is that a lot of people, you know, they just want to rush, they want to make the activities and it's really hard to take a step back and Work your way up and not just go directly to that C level, but take the time to actually research the account and then go to that higher level.

That's the key here. And as you mentioned it, like, you said it perfectly, man. Because so often a lot of this is the leader's fault. It's not just the sales dev REP or the AE's fault is like, we're so addicted to speed that we do things the wrong way. We're even just slowing down for a month. Just one month of intentionally restructuring and doing things the right way would pay for itself 10 times over the next three months. Because if you go low for info, right, I find out you don't have a sales engagement tool. Info that's not that hard to figure out, right? Can reach out to seven or eight different SDRs or AES at a company. Y' all use a sales engagement tool. One person responds back, says, no, now I got some info. Now I can go to the middle and go, hey, I know you don't have a sales engagement tool. So how are you managing X, Y and Z? Like, what? What does that look like? Now I'm engaging with some insight. I speak with a director. It's like, well, we manage it through this. We do this, we do this. Now I go to the top and go, hey, my guess is, as a CRO, you want more revenue in speaking with your team. There's no engagement tool, which means that they're having to do this manually, which means reps are losing time, you can't book nearly enough, and there's no tracking of the data needed to make better decisions. Could we at least have influence? Right? All because you worked through the levels to get there, and it wouldn't take that long to reset your process to do that. But everyone's just going to the CRO saying, we're going to three extra pipeline. That CRO is like, you don't even know my pipeline.

So it just doesn't sound relevant. Yeah.

Oh, perfect. And you just use the word I wanted to go into next, right? So how do you bring relevancy into prospecting? Because there's still, you know, personalization versus customization. All you know, this goes back and forth, but, like, just because you email me and say, hey, I saw you went to Wisconsin. Go badgers. It's not relevant to anything. Like, it's personalized, but it's not relevant. So talk to me about relevancy, right? That was one of the first words you mentioned to me when we were kicking this off. You brought it up again. What does that mean?

Yeah, so I'd say relevancy is the way, you know, I and my teams have been able to be a lot more efficient in terms of not having to spend a lot of time doing personalization, but just talk to the right people, get more responses. And it starts with what we just talked about, which is getting. Doing account research. And the best way to do account research, in my opinion, is just to talk to people on the ground floor. But secondly, you know, most of my messaging and the sequences in email campaigns that we build out is based around buying triggers. And so these are things like, well, first of all, it starts with looking at who are our customers and why do they buy. Why are these inbound leads coming in, for example? Are they coming in? Oh, they just hired their first sales leader, and now he came inbound and wants to look at our software. So. So that's like a buying trigger, Right? Somebody who just joined a new company or they're hiring whatever department you sell to or, I mean, funding is another example. You don't really want to use that in your messaging. But sure, that could be called a buying trigger, but you can get a lot more specific than that. Basically what we're doing is we're looking for these buying triggers on the outside, and then we're structuring our messaging around that. So, hey, saw you just got promoted to director of Sales development. Typically when know SDR directors start off, this is what they're looking for. Yada, yada, yada, going down that path. And all the messaging seems super specific to these people, even though we're not personalizing it much because we spent a lot more time on the front end kind of breaking it down by buying triggers. So that's what kind of relevance means to me is we spend more time in the front end breaking up our list and our target accounts by buying triggers. And then we load them into sequences and campaigns that align with those buying triggers. And. And we come across as a lot more relevant without having to spend time. As much time on personalization.

Yeah, I love that because the relevancy. Right. And it's funny because people always use buying triggers. And what I coach companies on is like, what are new expectation triggers? So just because I raised money is not a buying signal.

Right.

But it is a signal. I've got new expectations. Everyone seems to forget this about fundraising. When someone gives you $10 million, they want $100 million back. Yeah, there's new expectations that just anyone listening? That's how you target someone after fundraising is y' all raised money that comes with new expectations. Do you have what got you to 10 million isn't what gets you to 100 million? Do you have the things in place to get you to that next level? Right. That's, again, making it relevant. That was always what's hilarious is people, oh, congrats on the fundraise. I'm like, really?

Yeah.

Do you understand what I just got signed up for? If you understood what I got signed up for, your language would change and that would make you more relevant. Right. And so now let's talk about kind of how to build this out. So we've talked about understanding the prospect, right? Getting to know them. We've talked about understanding their language, getting that into our messaging. Right? Like how to craft that. We've talked about kind of low, middle, and high. Now start talking about, okay, well, then how do I build out, like, these sequences or how do I build out these cadences or these touch patterns in an optimal way to help get all this done? Because if you're trusting the rep to remember to do all of this.

Yeah, impossible.

Not going to happen. So how do you structure, like, your sequences or your cadences to support this type of process?

Yeah, absolutely. So like I kind of mentioned earlier, most of our. We'll just call them sequences. There's a million different ways to call it. Most of them are built around a buying trigger. Right. So we'll set it up. It's built around a buying trigger and a specific Persona. So for each Persona we're going after and each buying trigger, there's a different sequence. And then we talked about it earlier, the top three problems that you hear from that Persona. There's three different clusters within that sequence focused around a different problem. So we're not mentioning all the problems we typically hear on that first email or in that beginning messaging. We're breaking it out across the sequence. That way we can spread out the touch points and still be relevant without being redundant and just mentioning the same problems. So there's three different clusters, and typically within one cluster, it'll be one or two phone calls, a voicemail, a LinkedIn touch, and then two or three emails. So it's that email referencing the. It's like call LinkedIn, email referencing the pain point, kind of like a bump email, another call, another LinkedIn, and then maybe we'll move on to the next cluster a week later, a few days later. And so it starts by really structuring what are the top buying triggers we're seeing or to Your point expectation triggers. You have to break that down really well by looking at your customer and inbound data. And then what are the top three problems for each Persona? And that's how I break down the messaging to stay relevant across two, three weeks of touch points.

And with. And you've actually brought this up a couple times. And I want to call this out. You've referenced looking at inbound data to help your outbound process. And you're the only person I've ever spoken to that talks about this other than me. Around where I start my outbound. I start my outbound by reviewing all the inbound. That's where I start because I'm going to learn what are they searching for, what are their keywords, what ads do they like, what language do they seem to respond to? What do they download the most? Right. So talk to me about this because this is. This is gold that a lot of outbound teams miss out on is they don't pay attention to what's happening with inbound.

Yeah, it's like. It's like tracking the weather. When I first started as an sdr, my manager, he told me every inbound lead was an outbound lead yesterday. So I was like, all right, like, bet I'm going to figure out how to. How to find that.

Say that again. That was gold.

He said every inbound lead was an outbound lead yesterday. That was Troy Barter. Shout out to him. Yeah. So he. He told me that I'm like, all right, I just have to figure out how to. I'm an outbound rep. You know, I'm not going to let that lead get to inbound. I'm going to figure out what they're doing to become an inbound league. Like, what are the trends? So I went into Salesforce and I would look at all the inbound leads. I would break it down in the spreadsheet. What are all like the technographic or what is all the data I can find on. On this lead and why they came inbound? Like, what sort of trends can I start to see? And yeah, it's one of the biggest things. It's not hard to go into your CRM and find that data and then kind of work backwards from there. But you're almost like predicting what sort of things was I seeing before this inbound lead came in that cause them to go inbound and then using that for your. For your outbound targeting, that's kind of high level. We can obviously dig in. But that's. That's pretty much the Gist of it.

Yeah, no, that is very similar. I would go in, I'd meet with marketing, I say, okay, what is our number one lead source?

Yeah.

Then I'd ask, what are the long tail keywords people are using that find us, Right. Are they looking for sales engagement? Are they looking for a prospecting tool? Are they looking for a SDR tool? Like, what are the long tail phrases that they're using? Because that's, that's what I'm going to make sure my messaging is around. What ads do they click on the most? That tells me what language catches their eye. That starts to become my subject lines and my first sentences. What pages do they spend the most time on on the website? That's what I'm going to link out to in my emails. What assets do they download the most inbound? I'm going to start sending that shit outbound, right? Because all of that stuff, I want to know what do people do when there isn't a salesperson involved? I'm going to then do those things outbound, right? Like if they're searching for these types of things, I'm going to bring this out. And so that's always how I approached it too, which is like, if I'm going to do outbound, I can learn almost everything I need to from inbound and then bring that information out to outbound. Right. That was always what I found as like the best setup there. And so we're gonna take a quick pivot here as we start to wrap up about kind of this journey, right, of like where you are now, right? At a, you've been at some great startups, you're leading an outbound team now. You get to work with, you know, Sujin and the squad over there. Right. But the journey, like, I'm gonna actually work backwards. It's like, how did you get to this point? Like, some of like, and I mean this, and I do not say this lightly, some of the shit that you're talking about today I hear very, very rarely. Talking to people, interviewing people, whatever else. How did you develop these skills?

Yeah, honestly, most of it is just doing as much networking as possible on LinkedIn. I think there's different levels to how you can learn these things and consume content. You can go to the top performers at your company, which a lot of people are doing, but then you're only siloed within your company, right? You're only going to know what everybody knows at your company. You can consume content from LinkedIn podcasts, which is great, or you can Try to meet with people and ask questions. And that's where I've had the most success. And the easiest way to do that, because not everybody's going to give up time on their calendar. The easiest way to do that has been just what I call learning out loud, right? So I started creating content on LinkedIn, saying, hey, here's what I'm learning, here's what I'm sharing. And naturally, people started to gravitate towards it, and that's what allowed me to reach out to people who are experts in the industry. A lot of this stuff, I didn't come up with these things. Obviously, you're familiar with the concepts. We learned it from somebody somewhere. And so I reach out to people who are further along in my career, look for mentors in that sense. And it's just kind of having that. That goal in mind of always trying to learn new things. I'm always trying to find new things to test as an sdr, like, what's the next subject line I can try? What's the next strategy? And it's just setting a consistent goal week over week to just connect with somebody new for a quick Zoom call from LinkedIn, you know, listen to this podcast, that sort of thing, and then document, document, document, write down the notes I'm hearing, and then apply that the next week. You know, in my job.

I love that. And that's always what I've recommended to people, is like, reach out to people just a couple years ahead of you. So often when people are like, looking for mentorship, right? They're like, oh, like, who's. Who's built a billion dollar, like company? I want to go get mentored by them. Well, if you haven't built a $50 million company, maybe you should start with someone who's done that recently, right? Who's just a couple years ahead of you is where I generally recommend people look for mentors and learnings is who's done the next step recently, right? Like, I get reached out to quite often by, you know, SDRs and AES looking for mentorship. And I'm like, I'm more than happy to do that, but I would way rather you talk to someone who just got promoted in the last year from AE to enterprise or who just went from SDR to ae. Cause there's things I can give you feedback on for sure. But like, that recency effect matters, right? Because I also do the same thing. Funny enough, actually, I haven't really shared this. I like to mentor down sometimes, meaning I also like to find Mentees that have just made recent transitions, so I can learn how they did it as well, so I can help them. But I also want to learn, like, what is working, what. What is progressing. Are the things that I know still relevant, or am I already old? I'm out the game. It doesn't matter.

And so I love.

I love that you're seeking out that. That knowledge, which is going to take me to my next question here, because you shared this with me. I'm excited about this. Right. There are people that love to learn, and there are people that love school. I love to learn. School was not my favorite. Right. So I've shared this publicly. I am a college dropout. I dropped out 15 credits short of graduation because I was in a major that I knew I was never going to use, and I was miserable. Jed, talk to me about your own education journey. I think we might have some similarities here.

Yeah, so I was actually homeschooled growing up, and then I graduated. Well, so I was trying to play college basketball. Maybe I could have rode the bench at, like, a Christian college, D3, whatever. With no scholarship. I was grinding hard one summer. I couldn't get anything done. I realized, all right, I have to give up on this and transition to something else. And I was kind of like you in the sense that there wasn't, like, maybe a major that I felt like I was going to pursue a career in. Like, I wanted to do business. So I figured. I found this program called Praxis, which is not a tech sales boot camp, but it's a. It's a professional development bootcamp. They give you skills, they help you build your resume, LinkedIn profile to then look for growing startups. I went through that program. I said, hey, if it doesn't work out, then I'll go to school. But let me try this out for a year. I did that. I interviewed for, like, two or three months and then finally landed at Pandadoc for, like, an apprenticeship SDR position. But, yeah, I took the college alternative route partially because I was homeschooled. I.