Outbound Roundup: The Best of Matt, Jesse, Mark, Tito, and Kyle

Ready to transform your outbound sales game? 

Discover how this new AI business model era is reshaping sales and marketing for B2B software and services companies and how to drive outbound to your advantage. Join Tiana and our insightful guests Jesse, Matt, Mark, Tito, and Kyle as we uncover the secrets to competitive approaches.  

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Transcript

Gary: 0:05

Welcome to the GTM Pro Podcast, your essential audio resource for mastering go-to-market discussions in the boardroom. Here we share insights for revenue leaders at B2B software and services companies, especially those with less than $50 million in revenue. Why? Because the challenges faced by companies of this size are unique. They are too big to be small and too small to be big. This dynamic pushes revenue leaders into executive leadership without a lot of help or support. We are here to provide that support. Your journey to boardroom excellence starts now.

Tiana: 0:48

Hey everyone, this is Tiana speaking. Welcome to the Outdown May Season Roundup. This episode is going to be a little bit different than the others, since it's going to be just me guiding you through the best insights and moments from our past five guests, which would be Matt, Jesse, Mark, Tito and Kyle on all topics Outbound related. So let's get started. I'm going to begin this by pointing out the common threads of thought that most of our guests had. So I have been listening and re-listening to all of our podcasts and, for starters, all speakers emphasize the importance of automation in technologies. They all agree that leveraging technology and automation to enhance sales and marketing efforts is just fundamental for efficiency. For example, Jesse discusses using AI and automation to manage data and outreach. Let's hear what his thoughts are and outreach.

Jesse: 1:44

Let's hear what his thoughts are. If you could take that large you know the learning model and you can combine that with the tools which is what I've been doing a lot of is you can do that. You start to pull in like really unique insights and I think where there's a real opportunity for companies is the people that actually have the specialized knowledge like. I'll give you an example If you were to say like hey, headcount data, where would you get that from right? You know the person who knows like what's going to have the most

Jesse: 2:09

accurate headcount data live, real time, right now. Right, like, what is that source of data? And you really get that from actually doing it and a lot of the people who are starting to do it really, I think and I was doing it a lot before this with sort of spreadsheets but you're starting to see a lot of people use tools like Clay, which is one that I'll call out. Yeah, you know, great, great company, great product. But you're starting to see like people are applying this to their outbound campaigns and I think it's upsetting people in some ways, because everyone used to be like well, I could write a better email than AI, but now it's like yeah, but you couldn't do the 20 minutes of research on each individual person, so you're going to lose that more anyway, On this topic.

Tiana: 2:50

Matt McPhee and Mara Cosiglo both mentioned building tools that cater to specific market needs and using automation to improve those processes. Let's hear what they have to think about it.

Matt: 3:03

So there's a few tools that are good for kind of one off searches. If you're communicating, a great majority of your outbound emails go to a handful of corporations you can do some one off searches and check, you know, check out which tools those corporations use. We built some tooling that really more enables our user base which, again, as I mentioned up front, is more of the enterprise ICP to do a more kind of higher volume search across their entire data set. Right? So we'll provide a tool where a data set can be loaded of domains and we roll them all up to their respective mail system, the mail exchange records, so we can tell you which percentage of your data set or your segment rolls up to each respective mail system. So Proofpoint may be 50% or 60% of somebody's data set, or Gmail may be 50% or 60% of someone's data set. With B2C it's a little easier because you can sort your domains by Gmail and run account and say, okay, this percent of my data set rolls through the Gmail mail system. With B2B it's much more difficult.

Matt: 4:02

You can't look at inboxmonstercom and know where I'm backbone, where our company is backbone. So it's really important to have those insights at volume. That's what tools like ours help enable. And then it's it's as, depending on who the customer is really it's it's as important to tell them which percentage of their data set rolls up to each respective mail system. It's just as important to then list out all the domains that are a part of their segment that are being blocked. So if, for example, mail system or security tool A is blocking your messages, what are all the domains in your list that you're not reaching? And those are just some great additional insights for the average B2B sender. So they can really not just say, oh, we're having trouble mailing to corporations protected by security tool A, it's no, here are the hundred domains we're not getting messages to. We need to fix that.

Mark: 4:53

I have come to the conclusion that basic account and contact data is worthless. It is nothing, it's salt, it's a commodity. It doesn't matter. If I could give you 100 email addresses that are 100% accurate and 100 phone numbers that are 100% accurate, you would get X results and it wouldn't be that good because everybody else on the planet has that information.

Mark: 5:16

But if I can enrich, if I can see what growth hackers are doing and there's growth hackers that can take the same exact list that you do and they can get it to do five to 10, x the results, and so that kind of what those growth hackers are doing, the enrichment, the approach, the creativity that to me is the secret sauce. So most people are worried about accurate data. I would argue, if a list was a hundred percent accurate but didn't have growth hacker principles and methodologies applied to it, that it will perform at 10 to 20% of what a list that is half accurate does with that information. I think that it's exponentially better to have a less accurate list that is highly enriched with information than it is to have a highly accurate list that has no enrichment.

Tiana: 6:06

Now that we've heard Marek touch on the subject of nurturing, let's hear what Kyle actually does about it in his company.

Kyle: 6:14

So we manage the leads that the BDRs touch through RevOps and data, so the BDRs aren't surfing through sort of lists of leads and choosing who they call. We take an entire database, we pull it into our system, scrape a bunch of stuff online, enrich that information and we've got two scoring algorithms that our data team has built. One is their estimated GMV. So how much gross merchandise volume are they going to do on our platform? That's like a proxy for deal size, and we know that higher GMV customers are going to churn at a lower rate, so we are really interested in targeting those accounts. And then we also have this thing called EWIN, which is our estimated win rate, and those two numbers define what leads get routed to the BDR team. And so we're constantly like we have a lot of. There's a lot of head count expense that goes into just managing these lists.

Gary: 7:23

Right.

Kyle: 7:23

And we use a data provider to get us to a contact accuracy that we feel really good about. It's like 90% contact accuracy, so our team's calling cell phones almost exclusively Right, and so the sales team doesn't really have a chance to stray from ICP. And then, every single month, what we're doing to sort of stay as tightly built around our best potential customers we do a monthly business review and one of the sections is customer quality, and in the customer quality section we're cutting a bunch of our term data by a bunch of firmographic or product criteria so we can tell oh, companies that look like this churn higher or lower, and then we feed that back into our scoring algorithms. And so actually, like at the beginning of May, we made a fairly significant change to our scoring mechanism and we're essentially so. We took 40% of what was formerly considered our ICP and just and just completely deprioritized it because the churn rates were mediocre.

Kyle: 8:38

The churn rates in this, in these other cohorts, are incredible for an SMB business, and then they're only okay for these customers. But the BDRs our market is not infinite but it's really big. So we don't need this other part of our previous TAM in order to supply our BDRs with enough things to hit every single week and month. So we're constantly fine tuning and we've made multiple fairly big changes to targeting, to just like continue to tune. And that's the beauty of my role owning pre and post sales is the churn number is just as much my problem as the close one number, yeah, and so I'm heavily incentivized to make sure that there's this closed loop and and making sure that we're addressing customer churn at the BDR stage, which is a little different.

Tiana: 9:31

So we talked about prospects and nurturing, but what does the model look like? Let's see what it looks like for Tito. He gave a pretty clear example of what it should look like for him if your average feels is over 30k annual recurring revenue.

Tito: 9:49

This is very targeted at you on how you do it. So what are we trying to achieve? What we're trying to achieve is, every month, have an employee or a set of employees dedicated to the following motion. We're gonna grab a 100 target accounts which have been defined as our ideal customer profile due to certain characteristics of them. Those can be thermographic or technographic, if you want me to go deeper into that. That means they have a certain number of employees in industry, certain technologies they use. We've defined who they are.

Tito: 10:21

Now we put a list of 100 accounts and we assign that to an employee who we might call a sales development representative, and their goal is to grab those 100 accounts and do calls, emails, linkedin, direct mail, whatever they can, to get 10 meetings with the right person of that account. And the right person is somebody who is above the line, meaning they have power to start an initiative and create internal change of the company. Usually that means director level or above in the area where your product makes an impact. You sell to sales leaders cool. You need a CRO or a head of sales or whatever else Cool. That's step number one 100 accounts into 10 meetings.

Tito: 11:02

Step number two we need a process that turns those 10 meetings with the right people, the right account, into five and a half to seven opportunities. That means we meet with this prospect who has agreed to meet with us. They're not necessarily interested, but they're at least curious and we grab that curious prospect and in a 30-minute meeting we turn them from yeah you know, I'm open to learn some stuff to holy cow, I get to start working on this ASAP. Now we have five and a half in pipeline or up to seven if you're doing an incredible job and our final step is to turn those five and a half in pipeline into 1.6 customers. So 30% conversion from pipeline to customer. If you can do that, you have just created an outbound revenue machine that will take your company on IPO. And I am not joking. If you figure out this machine, this is worth hundreds of millions of dollars and there's no question about it worth hundreds of millions of dollars, and there's no question about it.

Tiana: 12:12

Oh, you're back, Just kidding. The need for affecting prospecting techniques is also a recurring theme between our guests. Kyle and Mark discuss various strategies for prospecting, including the use of cold calls, email outreach and leveraging existing customer relationships. Let's hear what they had to say about it.

Kyle: 12:28

So in terms of the key insights, like most companies, you start your BDR XDR efforts with the easiest stuff possible, and so for us there was a pretty healthy inbound funnel that hadn't really been tapped in the way that it could have. So the first BDR was a guy who came from Restaurant Tech. He was a former restaurant owner himself. He had to talk to restaurant owners and knew the craft of BDRing, and so we basically just pointed him at. All of our former inbounds. There were like thousands of former leads that we hadn't got to, because you've got AEs trying to sell and prospect that they're just not going to do the prospecting with the same efficiency. And so in Braden's first month I think, he booked like 30 or 40 qualified ops and tons and tons of close ones and we knew that was not long term sustainable because you're you're going to deplete that reservoir of leads. So we started to think about OK, how do we go pure, cold outbound, and what are the concentric circles?

Kyle: 13:39

And I think the advice I give to founders frequently is everybody talks about pure outbound or cold outbound, like, oh, you got to have an outbound motion. But if you're a half a million ARR company or you're $2 million ARR, going pure cold outbound is probably not your path to success. You want to start with those concentric circles of who are the prospects closest to you that will take meetings with you today, of who are the prospects closest to you that will take meetings with you today, and then, over time, how do you stretch to a market that knows who you are? Less and less and less.

Kyle: 14:11

And so your first customers are people that are either friends of the founder we used to call them FOMs at League, which was friends of Mike, foms were the best people to go after or friends of the investors, friends of the board, people that you had personal connections to, or, and then, once you start to have some customers, friends of your customers. And then how do you, how do you, find pockets of customers, pockets of prospects that are two degrees related to you, that will take a call, much easier than you showing up cold on the doorstep of some CRO that, like, has no idea who you are Right, and so that's a. That's a much better approach to building your cold outbound motion is start with you can call it near bound or whatever terminology you want to use but like prospects that are really close to you, that are high of high likelihood to take, take meetings and then, over time, do the harder and harder things, which is pure cold outbound, and that's what we graduated in.

Mark: 15:13

We did see the proliferation of SDRs. I think that was in a time when capital was cheap and you know you could buy your way to growth and that was, that was what investors wanted. So you can't, we can talk about how stupid it was and all that, but guess what? You know whose idea it was Investors that put money into the companies that did that. I'm not just talking about VC. Everybody was doing it no-transcript, and the interest rates and all that kind of stuff helped with that. And then they started to say all right, what can we cut?

Mark: 16:00

And SDRs in a lot of companies, when you start to do the economics aren't providing enough value to invest in that, and there's other avenues with greater value and, like you said, we saw that go away. Listen, though, here's the problem is is, if you take away an outbound channel, where do you put it? You put it on your AEs, and AEs now have lost the skill to prospect because they haven't done it for so long. They also don't want to do it. So there's a huge change management and a resistance to it. And the last thing is is what all they're going to do is, if they, if they have the time to do it is. They're going to take it down to the least common denominator, which basically means that we're going to do worse than what SDRs were doing, but expect the same results with people that don't have it as their full-time job.

Gary: 16:43

It's kind of insane when you think about when you say it out loud, it's like how do you think that's going to work out?

Mark: 16:49

I know, but I talk to everybody. It's like, oh, we're going to have our AEs prospect again. I'm like I had an AE that used to work for me that said, hey, I'm thinking about this job, I like the company, the accelerators. They want me to prospect. So we looked deal cycle time, her average deal size, the win rate and a few other metrics and I calculated out based on how much work you have to do to get into an account. And then that down feels she's going to have to work 82 hours a week to do enough activity. And if she didn't want to work 82 hours a week, guess what she has to do. She has to automate. And if we automate, guess what we're doing now. We're now getting down to the least common denominator and we actually have to do so. We're like doing the school, church stuff. So what do we do instead?

Mark: 17:30

I think there's two things that I'm exploring really deeply right now. One is a refactoring of the SDR function and into like, more of like a football team. So think about a football team. Get your offensive offensive coordinator, your defensive coordinator and your special teams coordinator. They'll roll up to the head coach that has an overall vision and how he wants to build out the team, but it's the offensive coordinator's job to score. If he doesn't score, the head coach gets some of the blame, but the offensive coordinator gets fired. So I believe str teams of the future are going to unite around channels.

Mark: 18:05

So email coordinator, phone coordinator, social coordinator the email coordinator's job is to send out all the emails, every single one of them. Like, if we have a fifth, if we want to approximate a 50 SDR team, they send out the emails of 50 SDRs and they use that using, you know, enrichment and data sources that they can automate and then warming up inboxes using automation and doing all that kind of stuff. And that's the problem right now is that we're trying to teach SDRs how to do email, how to do cold calls, how to do social, how to be corporate citizens. Because they're young, they're asking about their promotion path. It's too many things, right, right, so let's take it down Make one person in charge. When I go into companies, the amount of times that they have somebody that's in charge of monitoring their messaging is almost zero. There's nobody who's on the line for poor performing email. So guess what? Every email is poor performing or everybody's doing their own experiment.

Mark: 19:06

So imagine if one person their whole butt on the line is are you sending a volume and is that volume a converting or not? That's in that one thing. Then you can take that list and move it to your call coordinator, your phone coordinator. With parallel dialing, one person can make 2000 dials a day. Do you know how many meetings? I would say if I've made 2,000 dials a day with a 10% connect rate, I get 100 to 200 people with a meeting connect. I think I can connect or I can book meetings. At 15%, I could probably book 30 meetings a day on the phone with 2,000 dials. Yeah, now it would be exhausting, it'd be hard, but there's people that love it and you got to find those people and that's one that doesn't necessarily scale, like the email one you need to like at about 2,000 to 2,000 dollars. You need to hire somebody else, but the volume is so good and their only job is to be awesome on the phone.

Mark: 19:54

I just met an SDR and he's so good on the phone. He outperforms his peers by 4X and he spends half the time doing the job. He has a couple of kids. He spends and he spends half the time doing the job. He has a couple kids. He spends most of time playing with his kids and he just hops on the phone two or three hours a day, books a ton of meetings and so like that. That's the way.

Mark: 20:10

And then you have a social coordinator, and at catalyst we actually created this role. We called it a marketing projects specialist or so I can't remember we called it. But what they would do is they had access to my LinkedIn and I. They didn't do any content for me I wouldn wouldn't allow that because that's kind of like my voice. But what they would do is go in and look at all the likes and all the comments. They would then parse that against a list of targeted accounts and key personas and then they would DM those people on behalf of me and then they would set up meetings. And that person was setting up more outbound meetings and my other four SDRs were combined twice as many.

Tiana: 20:46

Another common thought between our guests was the importance of nurturing leads and understanding the buyer's journey. You have heard a little bit about nurturing leads the way Mark has mentioned it earlier. Now we're going to listen to Tito and Kyle talk about the buyer's journey and how to talk and message prospects according to the stage they're at.

Tito: 21:08

It's usually when they buy something, unless it's absolutely broken, they try to stick around with it for two or three years at a minimum. After three years they're going to be open to evaluating something new and if they are really not stoked, super happy they will actually start taking demos and looking at alternative solutions. Only if they are really not stoked, super happy, they will actually start taking demos and looking at alternative solutions. Only if they are like incredibly happy will they not go do that purposefully. But I think people are in one of four mindsets on any given point. People are either in market, which is I'm looking forward to taking demos. Let me do some quick math for you. People do that approximately every three years, from the moment they say I want to go look at demos to the moment they schedule those demos, start taking the demos and select their preferred vendor, which is quite quick. I think it's about a month. I go do demo requests, take a bunch of demos and pick my favorite. That takes a month, a month every 36. What does that mean? One out of every 36 people or one out of every 36 companies really is in the market 3%.

Tito: 22:16

There's a lot of other people that are what I call open to change. They're a little frustrated with their solution. They kind of know that their renewal is going to come up eventually. They haven't really prioritized a project to change it. But if you tell them that you've got something new, better, easier, faster, more user-friendly, whatever it might be they'll be like yes, I'll take a look at that. I'm using Sales Loft. You're reaching out to me from outreach. Outreach is better, easier, faster, better data, more sure. How many people are there?

Tito: 22:49

I think about 10% of the market are frustrated with their current solution, to the point where you say, do you want to look at an alternative to your current solution? And they'll be like, yes, well, we only have 13% of the market. Where's everybody else? I think about 40 or 50% of the market is open to learn, and this is the key. This is who you really need to learn to sell to. These are the people who I use sales loft and I'm like, yeah, it's good, whatever. And I say, hey, do you want to look at a better product? And they're like, nah, not really.

Tito: 23:28

But if you change the way that you sell and you sell the problem, not the product, and you say, hey, we're talking to SDR leaders about how to increase efficiency for their SDR teams and how to get them to produce 10 meetings a month. Would you like to learn some secrets? This STR leader is going to be like yes, I want to learn to be better. I'm open to learning. I'm not interested in buying product Don't even talk to me about outreach. But if you can sell me a better process, a better system, a better idea conceptually, I want to hear about it. And if you can convince me that that's much better, and then you can convince me that my current tool is not good enough, I'll be open to change. I'll move from open to learn to open to change. So now we have 3% in market, 10% open to change, about 40 or 50% open to learn. The rest they're detractors. You can tell them anything you want. They'll be like I don't want to talk to you, I'm not buying. I don't talk to vendors unless I'm buying.

Kyle: 24:35

But then when you're in a cold outbound environment, the whole front of the call has to change fairly drastically. That's when I start teaching pattern, interrupt so that people actually stop what they're doing and pay attention, establishing credibility. So that's where we use a local name drop. Hey Gary, I know that you're actually just a town over from one of our customers, pete from Pete's Pizzeria. Do you know them? Oh, no, but I have some friends who love it. Okay, awesome. The reason for the call is and then I'm establishing relevance, and in a cold environment that structure is so much more important.

Mark: 25:10

If it's a former inbound.

Kyle: 25:11

You'd be like, hey, you wanted to talk to us, I'm here again and you get right into your value prop In a cold, outbound environment. Your craft and precision has to be so much better as you really have to be testing your scripts. We can have a whole conversation about scripting. I'm a firm believer that your BDR should be quite heavily scripted and that scripting is going to enable you to understand what's working and what's not and then A-B test your way to something great.

Kyle: 25:47

When you introduce a local name drop, is that allowing you to have more over 30 second cold calls? So I can look at a chart of all decision maker connects bucket it by over under 30 seconds and I can see, once I've introduced this new thing, am I having more or less Okay, Because I know that credibility and relevance are the things that will unlock the gate for me to get into the value prop, which happens around 30 seconds in. I have to have a lot better craft at the beginning of the call just to earn the right to get to a value prop as you start to stretch into a cold, outbound environment.

Tiana: 26:36

Mark.

Mark: 26:37

Cazaglo also has some thoughts here. Let's hear him out. This is the way that I think that you approach this and that Mary Lou taught me, which is you have your aware, your unaware, your aware, your consideration and then your decision. That's your buyer's journey, and the way that you communicate to somebody in each one of those areas is drastically different, and so I think the way that you get compelling is you align to where someone is. So let's say that you write a sequence of emails that are geared towards someone in consideration phase. That means that they understand they have a problem and they're considering solutions to move into an evaluation with. Decision is when I've decided. I'm now collecting vendors and I'm running evaluations with those vendors. Consideration is still. I'm educating myself to do that process.

Mark: 27:22

But let's say that somebody doesn't reply. That means that they're not in consideration and they're probably not in decision. That means that they're in aware or unaware. So we need to take that message, take that person and move them back in the buyer's journey to just aware and the consideration language might be something around like here's materials that we can give you that can help you understand your problem better. You might be researching this like. Here's some third party stuff here's a podcast and you're giving that value.

Mark: 27:50

But awareness is hey, have you ever thought about the fact that your SDRs aren't performing as well as they used to?

Mark: 27:57

And so to me, what's compelling is when you find where they're at in the buyer's journey. You have a strong message that's tailored to that person's mindset in that journey, and then your job is to move them further along into the journey, hopefully into consideration and decision, where they're ready to enter your pipeline and you can run a sales evaluation. So I don't think it's like the form of the emails are like you know, hey, maybe we want to do an attention getting show me, you know me line at the beginning that gets them to read the next line. The next line is like a problem statement or something that like gets them thinking. Then you have one sentence of this is kind of how we do this, and then you have a soft CTA that's like is this worth chatting about? That seems to be like the general best practices right now. But I would suggest, if you just optimize on that format but you leave out the context of where someone's at in the buyer's journey, that you're only going to get a small percentage of the effectiveness of that email.

Mark: 28:59

Or it'll only be effective for the one area of the buyer's journey where you're targeting your messaging and most people target at consideration and if you think about it, I think the last I saw was 3% of people are in decision, 7% of people are in consideration. That means what 90% of people are in aware and unaware, and we're not actually communicating to those people the way that they need to be communicated to.

Tiana: 29:26

So to land this plane, like Gary likes to say. On similar actionable ideas, all speakers agree on the need of data-driven decision-making. Actionable steps include investing in analytic tools to better understand customer behavior and optimize your sales strategies. Mark and Kyle are advocates of segmenting sales roles to focus on specific tasks, such as having dedicated teams for different channels email, phone, social what have you? And specific functions like SDRs, focused solely on prospecting. This episode Both adapting sales techniques and understanding market changes, are interconnected. As market conditions evolve, so must the strategies employed by sales and marketing teams to remain competitive in the environment. So that would be basically all for today. Thank you so much for listening and I hope you liked the roundup of this outbound May month. All the best, bye.

Gary: 30:38

Thank you for tuning in to GTM Pro, where you become the pro. We're here to foster your growth as a revenue leader, offering the insights you need to thrive. For further guidance, visit gtmproco and continue your path to becoming board ready with us. Share this journey, subscribe, engage and elevate your go-to-market skills. Until next time, go be a pro.