EPISODE 733: Outbound Sales That Work: AI and Data-Driven Insights from Apollo’s Josh Garrison & Samuel Elliott

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Today’s show featured an interview with Josh Garrison, VP of Marketing at Apollo and the author of “Outbound Sales: A data-backed playbook for cold email, cold calling, social selling, and more,” and Samuel Elliott, Senior Account Executive.

Find Josh on LinkedIn. Find Samuel on LinkedIn.

JOSH’S TIP:  “Go leave five comments on LinkedIn, and I want you to do it in a way where you’re not selling anything. Give as much as you can in those five comments on five different posts and see what you get. Make that a habit. That’s my number one thing, that even myself, we could all do better and the rewards are going to be there.”

SAMUEL’S TIP: “Go log into ChatGPT, Perplexity, or any of the AI applications. Before your next call with someone, ask it to summarize what that company does, who they serve, and what their specific role and title cares about. You’ll be amazed at how much it can streamline your pre-call research and information and all of the possibilities beyond it.”

THE PODCAST BEGINS HERE

Fred Diamond: Josh, we’re excited because we’re going to be talking about your book, Outbound Sales: A data-backed playbook for cold email, cold calling, social selling, and more. Congratulations on being published. That’s exciting. Samuel, have you published a book?

Samuel Elliott: Not yet.

Fred Diamond: 2025 is going to be your year to publish a book, but I’m excited to get both of your insights and aspects on prospecting and what’s going on out there. As we say frequently on the Sales Game Changers Podcast, it’s getting harder for a whole bunch of different reasons, and we’re going to get deep into that. We’re going to talk about some solutions. We have sales professionals, B2B typically, or B2G, listening all around the globe, and they listen to the Sales Game Changers Podcast, or they read the transcript, for some ideas. Let’s give them some.

Josh, first off, why’d you write the book? What prompted you at this time of your career to get that book out there?

Josh Garrison: Thanks so much for having us on, Fred. For context, for those listening, I’ve spent almost my whole career in sales. 14 years and counting in the game now, all of it in B2B, but most of that in outbound, is a big part of my role. When I joined Apollo a couple years ago, I crossed the chasm a bit from being an operator in the sales space to actually working at a company creating tools for salespeople. It was actually at the prompting where our CEO came to me and said, “Hey, we’ve got several hundred thousand users. They need to learn how to do this the best in the world. Can you write a book? Can you do it in four weeks?” I said, “Yeah, I can write a book. Can’t do it in four weeks.” A few months later the book came out. It’s out now.

I think you nailed it. The game has changed pretty substantially even in the last couple of years. I think what we are finding is that you just can’t sell today, 2024, 2025, like you could in 2020 or in 2015. That’s really the reasoning behind the book. We’ve been blessed so far. It spent several weeks on the top five bestselling sales books on Amazon, and we’re hoping we’ll get it to that number one spot and keep it there to stay.

Fred Diamond: Samuel, tell us about Apollo. I should have asked you originally to give us a little bit of an overview on the company. You’re a sales leader. I’m curious on your thoughts on the state of sales. Like Josh said, things aren’t even close to what they were like in 2015. For people who are frequent listeners of the Sales Game Changers Podcast, we talk about that a lot. We talk about obviously in the old days, marketing had a role, and then in theory they handed things off to sales. We’ve done some shows about the buyer’s journey and where marketing and sales, it’s almost like a chopper. Different things happen much earlier with sales because it has to, and marketing’s role needs to be even smarter because of where the customer is. Tell us a little bit about Apollo and then give us the state of sales from your perspective.

Samuel Elliott: Apollo is an all-in-one go-to market platform. If you ask different users what Apollo is, they may give you different answers, because there’s different people at all stages of that sales pipeline, whether it’s top of funnel of prospecting and identifying leads and targeting them, to middle of funnel of being able to convert them and move them through a sales journey. Then that bottom of funnel of actually being able to close them. Apollo is that all-in-one go-to-market platform that’s able to help a multitude of sales roles do their job more effectively, driving towards that closed won revenue.

Fred Diamond: We’re going to be talking about a lot of the content in the book here. I’m going to start with one. One of the data points that you bring up in the book, Josh, “40% of respondents nowadays require at least six touch points to secure a qualified meeting.” Whenever we post something like that, someone always says, truthfully, “And most salespeople give up after three.” You’ve heard that. I’m interested in both of your thoughts. Give us some insights into that.

Josh Garrison: It’s always astonishing to me the number of people who give up after the first touch point. If you get to three, you’re probably slightly ahead of the pack. The way I think about this, there’s an old adage in advertising and marketing that it takes six or seven views of an ad for the message of the ad to stick. I think that we’ve seen really sales and marketing collide, as you were mentioning. The rules for outbound sales used to be different. You could hit an email into the inbox, nobody else was doing it, you get the reply, you get it opened. With the proliferation of outbound as a tactic, that really isn’t true anymore. The book has two main takeaways.

One is, it’s got to be more than one touch, ideally six or seven. Then the second is, and it can all be in the same channel. If you are an ad practitioner as well, you find the same thing. If you’re just running ads on TikTok and you’re not also running on Instagram, YouTube, Facebook, Reddit, and Snapchat, you’re not reaching your audience everywhere that you could. It’s the same mentality, just applied to a different set of tactics for sellers.

Fred Diamond: Samuel, give us some of your insights on that.

Samuel Elliott: With my role within the Apollo Lab services division, I’m talking with sales leaders day in and day out about outbound strategy. It’s not just about the Apollo platform and software to help them do more with less and do more and more efficiently, but it’s also around the strategy of how to use the platform. One of the analogies that I like to use is so much with outbound and going multi-channel and going multi-touch. It’s almost like when you’re trying to get in front of a prospect, you’re knocking on multiple doors, and each channel is a different door, and each touch point is a different time that you’re knocking on that specific door. You never know at what time that prospect is going to be in front of that door that you’re knocking on. It’s really about just maximizing your chances, because everyone’s busy. It’s important to have the right knock too. Let’s not just talk about activities, let’s talk about the quality of the messaging. But it’s a fun little analogy when it comes to right door, right knock, or right message at the right time to be able to make sure that you’re getting your prospect’s attention and they’re actually hearing that message.

Fred Diamond: One of the key things we talk a lot about at the Institute for Excellence in Sales and on the podcast is the whole concept of bringing value. It’s gotten so much harder to connect with people because of a whole bunch of different reasons. They can hide behind things. They don’t have to respond to you. If the sales professional isn’t bringing them value, then there’s no reason for them to even entertain your conversation, let alone an email.

Josh, you spent a lot of time in the book talking about the concept of prioritizing pipeline. One of the things we like to say, Jeb Blount has the expression, “The pipe is life.” We believe that fully. You make the statement that you could book 47% more meetings by effectively prioritizing your pipeline. Give us some insights into that, what that means. Samuel, I’m also curious from your perspective on how you work with your sales team and how you also advise customers on prioritizing pipeline.

Josh Garrison: It’s a great question and one that maybe doesn’t get enough play in the day-to-day. Because most reps log in, you’ve got Salesforce, you’ve got a list of accounts or a list of contacts, and it’s mad dash to try and get as many as you can. I think the reality of today is there’s so much data available to you that the question is how are you using the data? When we talk about prioritizing pipeline, some of the things we get into in the book are what signals are most important to you? There’s an example that I’ll give from one of Samuel’s recent deals.

We have a client who, they’re looking for companies who recently experienced an OSHA violation. If you’ve got a list of prospects, a list of companies who, maybe they’re all construction companies. When we talk about prioritizing pipeline, the question is reaching out to that, the right prospect at the right time with the right message. It’s always the game in sales. For that client, it’s, I only should be reaching out today to somebody who had an OSHA violation recently, because it’s top of mind for them. That’s just one really concrete example.

But the way I like to explain it to folks is you think about your total addressable market, or your ideal customers, only a small percentage of them, let’s call it 3%, are actively in the market for what you’re selling. The way to be most effective is to find the signals that indicate that they’re in-market and only reach out to those people. Then once you’ve exhausted that list of people, now you move to that next bucket of people who are aware of what you sell. Maybe they’re not actively buying, but they’re considering. You want to reach out to all of those people next. Then you only want to hit that big, vast pool of spray-and-pray folks who maybe are unaware and don’t have a need, that’s your last resort. You’re setting yourself up for future success, deep future success.

We just see this time and again where we start by asking, what data signals are you using to determine whether or not they’re somebody you should be reaching out to right now? The answer we get a lot of the time is, what do you mean data signals? I think the industry broadly is starting from that point where they know who their target accounts are, but it stops there. There’s a lot of opportunity for most organizations, most individual reps to get a little bit smarter with their strategy, a little bit smarter with their priority, and see a really big outcome on the other side.

Fred Diamond: We use that 3% frequently. We use the analogy of people buying mattresses. If you’re moving or if you’re having someone move in or you’ve had a flood, you’re in that 3% where you need to get a mattress this weekend, which is why there’s so many mattress stores on all the major highways. Then there’s 41%, we usually say, are people who they might be moving into a bigger house or child’s moving out, or the mattresses are 10 years old, so they’re thinking about it. Then half the marketplace isn’t going to be looking for a mattress.

Samuel, talk a little bit about that as well, about how do you prioritize pipeline? How do you work with your people to ensure that they’re paying attention to those data signals?

Samuel Elliott: I’m going to play off your mattress analogy. You talked about when people are buying a mattress, these are signals that if a mattress company could identify, they would be putting a flyer in the mail immediately. They might be going knocking on the door because it’s such a good signal of knowing that someone likely is going to be buying a mattress anytime soon.

Now, when it comes to a consumer that just experienced a flood, or is downsizing their house, or just moved into a new house, or for whatever reason needs a different bed, you can’t get that on a consumer. But when you translate this to B2B sales, if information is publicly available online and you can instruct someone how to go and find this information and where they might find the information, you’re able to use Apollo’s new Power-up feature, which is a built in AI agent, allowing you to scan your entire total addressable market of everyone who’s a good fit on paper. No matter how you splice that, tier one, tier two, tier three, to have our AI agents built into a workflow to scan for that specific signal you’re looking for, like OSHA violations, so that as soon as that person has a match for that signal, you could take that a step further of not just having them identified on a list, but they can then be entered into an autonomous workflow of fully AI personalized messaging.

Now, I know I’m suddenly throwing out a lot of AI things here, and AI is not magic. It is garbage in, garbage out if you’re not doing it right. But if you’re properly researching, following a lot of the steps that Josh talks about in the book, and you’re able to put that in a proper prompt, AI can do really, really powerful work. That’s really what the Apollo Labs division is all about, is helping work with our clients to go from current pipe gen strategies and solutions, to what is that next gen, but making sure we’re doing it right.

Fred Diamond: That’s a great way to say it, and Josh did a great job in the book going through that. I’m going to dispute you a little bit. Yeah, garbage in, garbage out. But it’s really good. As a matter of fact, before we talk to any prospect, we go into two different AI places and ask a whole bunch of different prompts to find out what might be happening to the customer a year from now. The great salespeople who don’t think forward and use the tools available, they’re not going to be providing the value that customers need.

We’re covering a lot of topics here, and Josh, you cover so many of them in the book, Outbound Sales: A data-backed playbook for cold email, cold calling, social selling, and more. Let’s talk about cold email. I remember I used to work with a guy who was a very successful entrepreneur who would always say that people think once they send the email, the day is done, even me. A couple days ago, I just sat and I sent out like a hundred emails, and then I went to the gym thinking, “Okay.” I came back and zero replies. Give us some of your insights into why you covered email in the book. What are some of your thoughts?

Josh Garrison: Even with all the changes that we’ve seen in email in terms of deliverability, changes from Google, from Microsoft, from Yahoo and others in terms of the proliferation of emails being sent, meaning each individual email has a less chance of getting opened, email is still the king. Email is still the foundation. We spent a lot of time on it in the book because if your email game isn’t strong, I think it’s really hard to be successful. I’ve met salespeople who are really good on the phone or really good at email. I think the best salespeople are really good on all three, social, email, and phone. But when we talk about email, in my experience, and I’ve sent probably in the neighborhood of 500,000 outbound emails over the last several years, for myself, for the companies I work for, for my clients. What I have always found, for the most part in the data, and I use a similar structure for most clients. The structure is similar, but the meat and potatoes may be different, or the stuffing is different, however you want to say it. That first email is about making the initial connection. The second email, the job of the second email is to reply into the same thread as the first email and bump that first email back up.

I follow a similar structure. My first email is normally four or five sentences long. My second email is one sentence, and almost every time the second email has a higher reply rate than the first email. Then we talk about a third email which is what we call our breakup email. That normally comes and it’s restating the value proposition from the first email, letting them know you’re not going to reach out again. Then we talk about the value of pattern interruption at the end.

There’s normally a PS at the end of that, which includes a joke, and it’s something completely off the wall, completely unexpected. That third email actually gets the second most replies. The second email gets the most replies, the third email gets the second most, and the first email gets the least. I think exactly what you said, you think that the job is done when you send that first email, and there you go, “I emailed them, they’re going to email me back.” The reality is, for people like myself, I’m a VP at Apollo now, right now, at this moment, I have 153 unread emails. I hit inbox zero last night.

My reality is it’s just not possible for me to get to all of the things that I have to get to in a given day. Your buyers are the same way. If they’re buyers worth their salt, if they actually can control some budget and make something happen for you. It’s not just about that first email. It’s not even just about the second and the third email. I also talk about the timing. The likelihood of me being in that I’m going to open and read your email mentality right now is pretty low. I want to make sure I hit somebody in the morning. Second email might come out several days later in the afternoon. Third email might come out later in the evening. Everybody’s got a different working style. You want to spread out the timing of when you’re delivering those emails as well so you give yourself the best chance of hitting somebody when they’re open to receiving what you’re saying.

Fred Diamond: Samuel, I want to ask you a slightly different question about contact. Do you work with salespeople and do you encourage them to send text? Is that a big part of the continuum here?

Samuel Elliott: Texting is a unique channel. I can’t say that there’s a lot of strong data that’s been published by organizations that don’t have an SMS platform themselves. Therefore, they have an incentive to publish data a certain way that may prioritize them. Some of the most successful sellers that I’ve ever managed were really good at texting in sales journey prospects, so people that they’ve already met with to further establish that relationship.

A little bit different from that top of funnel aspect. My team’s been responsible for running some SMS campaigns, adding an additional channel, a part of that top of funnel to get that initial appointment. I can’t say that I have strong data, and I’d love if any listeners have strong data that isn’t published by a company that essentially supported and paid for that SMS study and doesn’t have their own platform. I’d love to see some strong data saying whether it is something that’s effective or not, because you’re going to get people that like it, some people that will absolutely hate it.

Fred Diamond: Josh, let’s move to social selling. There’s a deeper question I want to ask after this, but you talk a lot about social selling. You say that you have some tactics that’ll make close to 60% of the sellers close deals faster. Give us some of your insights into social selling.

Josh Garrison: The first thing that I would say, maybe I’ll alleviate some concerns of our listeners, is that you do not need to be an influencer to be influential. In fact, you don’t even have to post on LinkedIn or on any social channel to be effective as a social seller. The money is in the comments. The real question here is about finding the places online where the conversations are happening that are relevant to your industry and to your product. There are actually a lot of tools you can use to do that, social listening tools. A lot of the platforms have some ability for you to do that internally or out of the box.

That’s the first thing I would say, is that there’s a pool of people in that 3% who are never going to answer your email, and they’re never going to answer your cold call, and they’re not coming to your website yet because they’re online asking other people who they think is the best. What options they’ve gone with. They’re going to get that consensus before they go and make a request from you or any of your competitors.

One of the smartest things you can do is be in those conversations. You have to realize that it is not appropriate for you to be selling in those conversations. That’s not the role that you should play. I would even say, as a seller, it’s not your role to be selling almost ever. The more selling you do, the less you’re going to sell. The less selling you do, the more you’re going to close. When it comes to social selling, it starts there. Where are the conversations happening? They’re happening in threads, they’re happening in posts, they’re happening in the comment section. Find those.

Now, the second question you have to ask yourself is, how can I bring value? If you start from that point, you’re going to be set up for success. You may find that the answer is not obvious. You’re like, “I actually don’t know.” Especially if you’re a junior rep, you’re in a new industry, you’re in a new company, you may not yet know how to bring value. Now your task becomes to go figure out a way and use those AI tools, use your skills in Google, use your colleagues, use your manager, use existing clients that you have, case studies your company has done. Not to trot that out in the comment section, but to try and give a helpful and informed response to the question somebody asks. If you do that, and you do that enough, you’re going to find natural opportunities to go from a comment to a direct message, from a direct message to a meeting on the calendar, and then that’s where your real job picks up.

Fred Diamond: Samuel, I want to ask you a slightly different question. As we’re doing a lot of conversations here, we spend a lot of time at the Institute for Excellence in Sales helping companies with their junior sales professionals. Matter of fact, I just did an interview last week with the executive director for the sales program at Kansas State University, and we talked about things that they’re teaching. What is your advice for junior sales professionals to get to the next level, to get off to a great start, to take their career? A lot of them, of course, are SDRs, BDRs, whatever you might call them. What would be some of your advice for people who are junior at sales to get their career kicked off on a nice way?

Samuel Elliott: The common advice is be hungry, and it’s a great quality of a sales professional. But I would say become obsessed with the industry that you’re in. When you can become an expert, not only in what product or service you are representing, so that you can properly understand the pain points that it’s solving and the value it’s bringing to who you are having these conversations with, but also becoming more of an expert in the industry. This goes back to Josh’s point, being involved in LinkedIn comments and social platform comments, you’re going to learn a lot too, because the comments you’re making should be thoughtful comments.

You should be reading the posts of the top people in your industry. You should be internalizing it and understanding what it actually means, reading through other people’s posts and how they’re responding to it. A great way to become obsessed and really understand what industry you play in, how your solution can solve different pain points and the value it brings, LinkedIn is a great place to learn that too. A lot of these things all connect together. If you want to crush it in a new role, be obsessed with learning and becoming really an expert, not only in your product, but also the industry.

Fred Diamond: A lot of the people that have reached success, huge success in sales, there are probably product experts at some level, but they’re also industry experts. A lot of our listeners know I’m based in Northern Virginia and there’s a lot of people here who’ve made great careers in sales selling to the government. The people who are most successful, who are living in the biggest houses, I like to say, are the ones who are selling at the highest level to the Navy or the Air Force or whatever it might be. They know everything about their mission. They know everything about where they’re going.

Josh, what is your advice to junior sales professionals? Can you top Samuel with your answer?

Josh Garrison: Samuel gave a great answer. That’s going to be hard. I can go back to my own experience, which was I looked outside the box. While LinkedIn is useful and your colleagues are useful, and Gong, if you can get in there and listen to what the best sales reps are doing, that’s useful. Believe this or not, I listened to every audio recording available of the speeches of Martin Luther King Jr., Winston Churchill, John F. Kennedy, Barack Obama, anybody that you find as a compelling speaker. Because one thing that I found in my career in sales was it didn’t matter as much what I said. It mattered a lot more how I said it. I wanted to be able to speak in a way that resonated with people and felt authentic, and I wanted to learn from the masters.

The second thing that I would say is most of your job is listening. I’ll give an anecdote here. Early in my career, I worked at a company called creditrepair.com, and my job was to sell credit repair services to people who had literally just been denied for a loan. The way that it worked is they would be on the phone with the bank, they get denied for the loan, that bank got paid to then transfer those people to us so we could try and sell them credit repair services. They had a lead gen deal with us.

I get on the phone with somebody who five minutes ago had been denied for a loan and they need a loan because they need money, and I am here trying to sell them something. I noticed that not everyone calls a loan a loan. Some of them call it a note. If they would say, “I just got denied for my car note,” and I said, “I understand you got denied for your loan,” I never would close that deal, because what I did unintentionally was I wasn’t speaking their language. They could tell immediately, whether conscious or subconsciously, “This guy’s not listening to me.”

Listening becomes the most important tool in your tool belt. Mirroring becomes very important, speaking the language your prospects speak. Then if you do go and cast that wide net, draw inspiration from the best speakers and the most persuasive people you can find, and you do that authentically in a way where you’re only speaking persuasively in a way that’s authentic, valuable, and empathetic, you’re going to win. If you can do that in a style that’s authentically your own, you’re going to be very, very successful. That’s what I’ve got for the young ones coming up.

Fred Diamond: Actually, you’re allowed to ask, “Do you refer to loans as notes?” But then you can’t do it the second time. That definitely shows listening. I agree with you a hundred percent with listening. As a matter of fact, in the early days of the Sales Game Changers Podcast, I used to ask the sales VPs, “What is your superpower?” Invariably they would say, “I’m a great listener. Two ears, one mouth, use them in that order. 66% solution.”

This has been great. We could go for another couple of hours, but I want to thank Josh Garrison. He’s the author of Outbound Sales: A data-backed playbook for cold email, cold calling, social selling, and more. I want to thank Samuel Elliott from Apollo.io as well for the great insights. Gentlemen, thank you both so much and congratulations on all your success and for giving us such great information today.

I’d like to end the podcast with you both giving us a specific action step that sales professionals listening to the show must do right now. You’ve both given us a lot of great ideas, but give us an action step that they should implement right now after listening to the podcast or reading the transcript to take their sales career to the next level. Samuel, why don’t you go first?

Samuel Elliott: If you are a sales professional and have not played around with generative AI, go log into ChatGPT, Perplexity, one of the ones that are connected to the internet. Before your next call with someone, ask it to summarize what that company does, who they serve, and what their specific role and title cares about. You’ll be amazed at how much it can streamline your pre-call research and information and all of the possibilities beyond it.

Fred Diamond: That is a great answer. Then you go into that call refreshed, knowing what the customer’s thinking about. You’re right, do a couple of prompts so you really get to specific information about what the customer will need to know. Josh, once again, congratulations on the book. Bring us home, give us a great action step.

Josh Garrison: My action step is this. I want you to go leave five comments on LinkedIn, and I want you to do it in a way where you’re not selling anything. Give as much as you can in those five comments on five different posts and see what you get. Make that a habit. That’s my number one thing, that even myself, we could all do better and the rewards are going to be there.

Fred Diamond: That is a great bit of advice. I spend a lot of time on LinkedIn. Most people don’t know how to use LinkedIn. Even my prospects, I’ll notice that maybe they’ll repurpose an event, but they won’t say anything about it. It’s just the link to the event and there’s zero comments, zero engagement. Invariably, when I see that, I’ll say something, “Wow, this looks like an event that’s going to be critical for directors of IT.” I don’t say, “Great share.” Don’t say great share. Don’t say wow. Like you just said, give a thoughtful response. Shows that you care, shows that you’re paying attention, shows that you know what they’re trying to do. Every time you see a prospect, I’m going to say 90% of the posts are just regurgitations or a company repost type of a thing, which I think have 0.0 value. If you could show the customer that you’re paying attention, it may pay dividends.

Transcribed by Mariana Badillo

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