In a world where sales cycles are getting longer, what’s holding your business back from reaching the right person at the right time?

Today, we’re joined by Joshua Garrison, Vice President of Content Marketing and Product Education at Apollo.io, a leading go-to-market platform used by millions of sales professionals and SMBs globally. Josh is not only a sales leader but also the author of the Amazon bestseller Outbound Sales, which shares the exact strategies, templates, and frameworks that helped Apollo.io achieve unicorn status and $100M ARR. With over 2.5K purchases in its first month, Josh’s book has become a must-read in the B2B sales community.

About Joshua Garrison

Joshua Garrison leads the content marketing and customer education teams at Apollo, the leading go-to-market (GTM) solution for sales and marketing teams.

A two-time founder, he has built and sold one company. He has led sales and marketing teams everywhere from tiny businesses to multi-billion dollar publicly traded companies. From that experience, Josh developed his “full-cycle selling” framework, a data-backed perspective on what works and what doesn’t.

As a third generation entrepreneur and career salesperson, he is passionate about helping people achieve their goals and master the art of sales. He lives in the San Francisco Bay Area with his wife, baby, and cats.

Resources

Apollo website: https://www.apollo.io

The B2B Agility podcast website: https://www.b2bagility.com

Sign up for The Agile Brand newsletter here: https://www.gregkihlstrom.com

Get the latest news and updates on LinkedIn here: https://www.linkedin.com/showcase/b2b-agility/

Check out The Agile Brand Guide website with articles, insights, and Martechipedia, the wiki for marketing technology: https://www.agilebrandguide.com

Transcript

Note: This was AI-generated and only lightly edited.

Greg Kihlstrom:
In a world where sales cycles are getting longer, what’s holding your business back from reaching the right person at the right time? Today, we’re joined by Joshua Garrison, Vice President of Content Marketing at Apollo, a leading go-to-market platform used by millions of sales professionals and SMBs globally. Josh is not only a sales leader, but also the author of the Amazon bestseller, Outbound Sales, which shares the strategies, templates, and frameworks that helped Apollo achieve unicorn status and $100 million. With over 2.5 thousand purchases in its first month, Josh’s book has become a must read in the B2B sales community. Welcome to the show, Josh. Hey, thanks, Greg. Thanks so much for having me on. Yeah, looking forward to talking about this with you. Before we dive in, though, why don’t you start by telling us a little more about your background and your role at Apollo?

Joshua Garrison: Sure, absolutely. My background, the song of my people, if you will. So I think of my career arc, which is where I’ll start, in kind of like three stories. I began my career in sales. I was pretty successful there. I was fortunate to do that. and was really on the cutting edge of adopting a lot of the tools that are in market today. Tools like Apollo, Outreach, Sales Loft, Zoom Info. So I started early on 2013-2014 with Outbound Sales. Then I became an entrepreneur after several years, started a business, grew it with Outbound, sold it, started another company. It failed, took a lot of my money along with it, and I ended up getting a job at a startup managing the outreach instance for a 60-person sales team. And then kind of like worked my way into marketing, became the head of revenue at a company. And then I landed at Apollo where they were looking for someone to lead content marketing, but who had an expert background as a salesperson. So it was really this kind of unique role that fit my background. So now at Apollo, I lead our content marketing organization and our product education team. So that’s our academy, our knowledge base, our blogs, our webinars, our social media, all of that rolls into me.

Greg Kihlstrom: Wonderful. Well, yeah, let’s let’s dive in here. We’re going to talk about a few things today, but I want to start with talking about the sales process and automation and starting by just thinking about striking the right balance here. You know, as sales cycles continue to lengthen, certainly a lot of people out there listening, probably feeling the pain there. How do you determine which parts of the sales process should be automated and what requires a human touch?

Joshua Garrison: Yeah, it’s a, it’s a tricky one to figure out. And I think it, you know, depends on every business’s individual circumstances. I think for me, the way I approach this is first, you have to figure out how to do it manually. So when it comes to automation, that’s where I see a lot of people go wrong. You want to come out of the gates automating as much as you can. You’re going to prospect automatically, send emails automatically. And what you end up doing in that instance, most of the time is you just burn through a lot of otherwise quality leads before you’ve identified like what is actually going to work for you. So whether this is, you know, the most common automation that we see is at that top of the funnel where you’re finding leads and doing that initial outreach. I’ve always approached the work with the mentality of like, first you got to do it yourself, do it manually. It’s just like they teach you in school before you can use a calculator, got to use pencil and paper, right? And then the good news is you don’t have to do that for very long. Once you’ve done that and found what’s actually working for you, for your business, you take that and you scale it with automation and kind of put that piece on autopilot. And now you move to the next part of the sales process. So very concretely, you know, find leads manually, reach out to them manually, then automate that. Now you’ve got leads on the meetings on the calendar. You can start to automate parts of your deal management process as well. You know, moving people from phase to phase, sending follow up emails, that kind of thing. So it depends, I think, you know, on every company’s circumstances. But it’s really if you’re a business that’s successful, you already know what works. Start automating as much as you can right away to free your team up to do more selling. If you’re still trying to figure out what works, don’t jump to automation too quickly. It’ll bite you.

Greg Kihlstrom: Yeah, yeah, no, I love that advice because I think it’s, I mean, I know from my experience, not only doing automation, but also even just managing people. I always took the approach of like, to be a manager of people, you kind of have to know what those people are doing. You don’t have to do the work for them. You don’t have to have done it for 20 years or whatever, but like, you got to kind of know what they’re doing. So I, I look at AI and automation in a similar way. And it sounds like, sounds like that’s similar to what you’re saying is like, then, you know, once you know what success is, then yeah, like automate that you probably also know what can be automated as well as what might need human touch as well. Right. Percent. Yeah.

Joshua Garrison: And I think a valid question here maybe is like what, what do you want, why do you want to automate it, right? I think that’s something I come back to people a lot with, they’re like, hey, can I send an automated LinkedIn connection request? And I ask them like, why? And if the answer is purely to save time, like, okay, but then it’s easy to forget that on the other end of that is a real live human being and you only get one chance to make a first impression, right? So the answer is like, oh, well, I want to automate it because it’s going to be a really quality experience for them and I no longer need to do it manually myself. Like, that’s a good answer. If it’s like, cause I’m busy and I don’t want to do it. That may not be the right answer. Yeah.

Greg Kihlstrom: Yeah. So you kind of touched on this, but want to, want to dig in a little more here. You know, where do you see some of those points? I, I obviously lot, every situation is a little bit different, but like, have you seen some areas where technology can provide the highest leverage in the sales process? Are there anywhere, maybe look at it as. Where can some companies look first and ways to automate?

Joshua Garrison: Great question. I think lead scoring is what comes to mind first and foremost. So before we even get into sending emails or doing outreach or anything, you’ve got this large pool of people who you think you could sell to. The reality is only a small percentage, let’s call it 3% of your total addressable market or your ICP, however you want to phrase that, is in the market for what you’re trying to sell. So your primary goal as a salesperson, if we’re talking about outbound, is only hit up that 3% of people, right? Like that’s your, that’s your sweet spot. You’re never going to, it’s the ideal. You’ll never quite get there. But so lead scoring comes into play where let’s take that list of people. Now let’s look for, and you could do this with automation. Let’s look for the indicators that they’re in market. There’s a lot of data available to people today. So you can do things like I’m going to create and, you know, an AI agent to go look at all of their posts. on LinkedIn and all of their colleagues posts and see what the themes are. And then like, if theme X exists, I’m going to add them to my list or see what their competitors are doing. And if their competitors are, you know, moving into their territory, like add that to my list and give me a really relevant reason to reach out. So that’s where I would start. And then the second place I would say is the thing that I’ve seen kill a lot of sales teams is it’s like that old adage, like more companies die of indigestion than starvation. Yeah. So you can actually get. And this is a fortunate position to be in, but when you have opportunities coming in the door, you’ve got meetings on the calendar. You know, as well as I do, as we started the conversation, you know, sales cycles are lengthening. That might take three, four, five, six, seven, 10 meetings and many emails to bring a deal through the door. I see a lot of salespeople leaving money on the table because they forget to follow up or they forget to progress that deal. They go from one call to the next, it gets lost. You can do a lot to create automations there where, hey, if an opportunity is open and it hasn’t been touched in three days, add a task. you know, or like move them to the next phase. There’s just kind of a lot you can do to make sure you don’t let things fall apart.

Greg Kihlstrom: Yeah. Yeah. I love that. And that, and that’s something that, I mean, many times is welcome because we’re all busy. Right. And not only the people sending the emails, but the people receiving them and they may not, you know, they may have seen it and then it got buried. Like, you know, I know, I know my inbox does from time to time.

Joshua Garrison: So yeah. For sure. I mean, yeah, as a buyer, I appreciate it when the person on the other side is, you know, respectfully popping back into my inbox and be like, Oh, Hey, did I, I, and I always like to take it on myself. They’ll create the automation to send the email, be like, Hey, did I drop the ball here? And they’re like, no, it was me. I dropped the ball. Let me get you what you need. You know, move the deal forward.

Greg Kihlstrom: Yeah. Yeah. So I want to talk about your, your book a little bit. And you know, one of the things in it, you outlined some specific email automation strategies that kind of, so what we were saying earlier, you know, deliver results, not just save me a little bit of time regardless of the potential and results. So can you talk a little bit about that? You know, how can, how can startups, small businesses, others, you know, that are often constrained by resource. use automation in the right way in their, their, their email automation.

Joshua Garrison: Yeah, for sure. Oh, I think, uh, like we mentioned, where we’d start is going to be with, with research and narrowing down who the people you should reach out to are. So really tactically, I like to ask people, and if you don’t have somebody to ask you, you just write this down as like, what indicates to you that someone is looking for what you sell? If that’s, they’re doing certain Google searches or, you know, researching, hitting certain websites. That’s what they’re hiring for certain roles or their companies at a certain location. Like there’s probably, you know, depending on where you’re selling, you know, what good looks like, you know, a good lead. So then your first order of business is to plug those into a tool like Apollo, but not just Apollo. You can do this with any number of competitors and. You’re going to create what we call like a persona. So you’re going to say, Hey, I am only interested in people with these titles of companies like this, who also have these four or five criteria. So you can create an automation to automatically find new people who meet that criteria every day or every week, you know, depending on the size of your target audience. So we start with that prospecting piece. Now, once you have that, the specific strategy that I would recommend people use, we basically are going to give you two. One is you’re going to take the best of the best, your, you know, dream clients. Like if you get on the phone with the CEO, you know, that one deal can, can change your quarter. You’re going to take those people and automatically add them to what we call a sequence, right? Which is like a series of steps, automatically add them to a sequence where you’re writing the email manually. So the first email is manual, but the second email is automated and the third email is automated. So basically you do that first outreach, put as much of yourself into it as you can, but then you can let the tool do the follow-up emails for you because their job is a little different than that first email. The first email’s job is to get you in the door and explain your value prop. The second email’s job is to put that back at the top of the inbox, right? And in the book, we give templates that you can use exactly to copy this. And the templates are available on Apollo Academy in the, in the application, like wherever you want to find them. Once you’ve done that, then it becomes about, you know, for those really best fit, high quality leads, you’re going to, it’s a mix of automation and manual. You’re going to be following up with phone calls on LinkedIn, you know, kind of, or wherever you can find them on social, you want to be where they are. But for that next bucket of leads who these are pretty good leads, but, you know, they might not be like your dream clients is like, it’s a lead that you want, but it’s not like this guy’s going to make my year. Right. You can put them into a sequence that’s more automated. Maybe that first email is automated, but it’s pulling in a couple of variables that, you know, make it look pretty personalized. And I think this is a point I want to touch on is that automation. doesn’t mean that it’s not relevant. Like done well, you know, your number one goal as a salesperson is to be relevant and add value. If you do it well, automation can do that. So those four or five attributes we talked about that let people let you know somebody is a good hire. You can actually pull those into your emails as variables and craft your email around that. So it might be, Hey, Greg, I was looking at your site. I noticed B2B agility is growing. You’re hiring for a producer. I’m a producer. Can we talk? That email can actually be written completely automated fashion and it’s going to be relevant to both parties. So I kind of recommend that, you know, let’s bifurcate your list. Let’s do a high touch, higher touch sequence with a little automation. Let’s do a lower touch sequence with a lot of automation. And somewhere between those two things, you’re going to start getting meetings on the calendar. Love it. Love it.

Greg Kihlstrom: So, um, talking more about your book, Outbound Sales, you, you’ve mentioned that prioritizing your pipeline effectively can lead to booking 47% more meetings. So, you know, who doesn’t want 47% more meetings if, if that’s what their goal is, right? So can you talk about the, you know, what, what’s your, what’s your advice for sales teams looking to, to do this and, and achieve these kinds of results?

Joshua Garrison: Yeah, it’s, it really goes back to that 3%, you know, this pyramid that we talk about, the 3% who are in market, then there’s probably 10% of your ideal customers who are aware of your solution or your competitors. They’re not quite ready to buy. And then there’s everybody else. And I think the best thing you can do is ask yourself, why are you reaching out to someone right, right now? Like that’s the important part right now. I remember as a rep, a lot of the times what would happen to me was I’d log into Salesforce for the day. Sales ops or whomever had assigned me a list of leads, right? And. Why was I hitting them up? Because that’s what I got assigned to hit up, right? The difference for me being like a run of the mill sales rep to somebody who was exceeding quota and getting, you know, sizable commission checks became when I no longer accepted that as the answer. And I’d spend some time looking through that list and saying, okay, let me prioritize this. I’m only, I’m going to make sure I hit these 10 people. And I had a reason. Either it was because I’d looked at their website or, you know, I knew, I knew why they were a lead and that was quality and seasoned reps are going to do this. So that’s my first answer. And I think this goes out to the sales managers out there. Like we get, we have a tendency to become focused on activity. We’re like, I know, you know, numbers and numbers. I know if you make a number, certain number of calls, certain number of emails or whatever, we’re going to hit our metrics. But we also keep hearing from sales leaders that it’s harder than ever to hit quota. I think those two things are related. Uh, if you, you know, if you think that everything is activity-based and that’s where you’re focused, I would challenge you and your team to ask the why, and then that’s going to naturally lead you to prioritizing those best fit people first. a little worse fit next. And then if you’ve got a lot of time left over in your day, that’s when you go after that, the leads that RevOps or SalesOps gave you just because, right? Yeah.

Greg Kihlstrom: Yeah. And I think it’s, you know, and I know you talked about the. The touch points, I mean, you know, it’s like 40% of prospects require at least six touch points to secure that meeting. But to, to what you’re just saying here, there’s two components. There’s probably multiple, but there’s two components. One, it’s gotta be the right person and it’s gotta be the right touch point at the, that’s relevant. Right? So it’s, it’s not just, I know I’ve heard it a million times too. Sales is the numbers game. It’s like. And yes, I guess on a big enough timescale and with a big enough universe of people out there, it is. But I guess who needs to hear this? Is it the sales managers that kind of need to hear this? And what can they do to help their teams be more strategic about their outreach?

Joshua Garrison: For sure. Well, the first thing I would say is the phrase, I got to give credit where it’s due. I stole this from Colin Stewart at Predictable Revenue. The phrase I like to use is sales is not a numbers game. It’s a math game. And I think everybody needs to hear that. Your VP, your manager, your rep. No, no, no. There’s two sides to the equation. Who are you reaching out to and how good are you at it? So to your point, right? It’s not just about six touch points. Like we’re not automatons. It’s about which touch points. So, you know, who needs to hear it the most for me, it’s always. As a rep, your manager, like the responsibilities on you, because if you, if you do what your manager tells you and what they’re telling you to do, doesn’t get you to your number and you don’t get paid, like. you don’t get to go to your manager and be like, pay me my, I did what you said, pay me my quota or my commission, right? They’re gonna be like, no, you didn’t hit your number. So in some ways you gotta be willing to ignore what they say in order to get where you need to go. And with that, I would say, you know, I actually think that there’s a lot of commonality between the way that people buy, like when they’re buying things on the internet, like consumer goods and the way that we buy in B2B. But for whatever reason, we don’t think about them the same way because the mechanisms are different. So I’ll give an example. Like I just bought, I’m barely ever on Instagram. First of all, like you can’t, if you look up, if you look for me on Instagram, you won’t find me, but I do look occasionally on Instagram and I’ve never bought anything before. But last week I was on Instagram. I was looking at cat videos. I got an ad for a cat toy and I needed a toy for my cats for Christmas. And I bought it. Like I only saw the ad the first time I saw the ad, I bought it. So flip, flip over, right? In B2B, we’ve all had the one call close. You cold call somebody, you’re like, here’s what I got. And they’re like, actually, I need that. And then you just like, they buy it and you’re like, oh my God, how did I do that? Well, you happen to get the person who is in the market for what you needed at the right time and in the right medium. So then this becomes a question. How do I gain the system and give myself the best chances of doing that? And what I say is, first of all, you’re going to have to mix up your channels. So if you’re just sending emails or you’re just sending cold calls, and we talk about this in the book, there’s good data to support this. You’re not being as effective as you can. When you combine emails, cold calls, and social touches, you actually become way more effective. So to get some data, for people who only send automated emails as part of a sequence, 46% of them end up booking a meeting across all users of Apollo. For people who send emails one-off, not as a sequence, only 16% book a meeting. So if you’re just sending one-off emails, like pause, you gotta, you’re gonna have to do more than that. Now, the people who use all three of email, phone, and social, 70% of them book a meeting. So you can almost double your effectiveness by mixing up the mix of channels. Then to go even further than that, this is where you start to get smart. is you want to vary out the timing of when you’re hitting people up. So you don’t know, like, I don’t know you, Greg, I don’t know if you’re a morning guy, an evening guy, middle of the day guy. So as the sales are up, what am I going to do? I’m going to hit you up in the morning. Then the next time I hit you, it’s going to be in the evening. And then the next time it’s going to be in the middle of the day. And by spreading out when I’m reaching out to you and how I’m reaching out to you, I actually cast the widest possible net to give any individual prospect a chance, you know, to, for me to gain. Yeah. Yeah. Nice. Nice.

Greg Kihlstrom: Yeah. So, I mean, so then, you know, social selling it’s something, you know, I think some, some people it may come naturally to and, and things like that, but you know, what would your advice be to. somebody out there listening and they’re like, I don’t know, like I phone and email, like I got this, but like, I don’t know about, I don’t know about like, where do they start? Like what’s, what’s a way to get started there? For sure.

Joshua Garrison: Well, I think the good news is you don’t have to be an influencer to be influential. And I want everybody to like, just like hear that and let that sink into you. The reality about social is the important conversations are happening in the comments and in private messages. So if you’re not comfortable putting yourself out there as a poster, I’m with you. I’ve, I’ve spent most of my career not hardly ever posting on social, but if you’re then also not doing some, what we call social listening. So there are tools that can help you do this, where you can type in keywords and it’ll surface up threads and other people’s posts on LinkedIn or other platforms about given topics. So if you’re not doing social listening for your space, you’re leaving money on the table because what’s happening is somebody is going to post and they’re going to say, hey, I’m looking for a new podcasting platform. Does anybody have recommendations? You then can show up in the comments. And the goal here is not to sell. And I think this is something I want to like share with everybody, right? Like the less you sell, the more you’re going to sell. Your job here is to provide value, especially in social. So somebody has got a post saying, Hey, I’m looking for XYZ platform. And you’re a sales rep in that space. What you want to do is show up and say, Hey, I talked to a lot of people who are similar to you. Here’s what they find. This platform’s good at this. This platform’s good at that. My platform’s good at X, Y, and Z. If you ever want to talk more, let me know. Now you’ve just added value, you know, you’re putting yourself in the mix, you’re being an honest broker. And I’ll tell you, if you do that enough, that comment is going to lead to a comment reply to your comment. That’s going to open the door for you to send a private message. That private message might lead to a conversation that’s over the phone. Now you’ve just turned social into a value, valuable channel for you. And you never had to post ever in that whole process.

Greg Kihlstrom: I love it. So last thing I want to talk about, just trends to watch here where, you know, this is running early 2025 here. So lots of people thinking about lots of predictions, I’m sure that we’ve already read, but lots of people thinking about the year ahead. What sales trends do you see as, as being most impactful this year? And, you know, especially for those startups, small businesses looking to gain a competitive edge.

Joshua Garrison: Yeah, I think that we are well and truly going to see the, the age of AI hit the internet even more than it has already. And it’s coming to B2B sales. Like if you go to, if you’ve been in San Francisco lately, which I live just across the bay, it’s dystopia. You got billboards left, right, and center for AI sales agents. And, you know, Apollo’s on our way into that game as well with some important caveats. Here’s what I would say. If you’re a small business owner or, you know, a startup. Your one differentiator is this old startup advice, do things that don’t scale. So if you come out of the gates thinking like we talked about the start, I’m gonna automate and AI my way into success. Sure, if you’ve got really strong product market fit, I’m gonna be honest with you, it doesn’t matter what you do, you’re gonna win. Like there’s gonna be success. But if you’re out there hustling, trying to make things happen in 2025, my sincere advice is you’re gonna see a lot of people going that AI automation route. The way you stand out is go hard in the other direction. Focus on relationships and that’s in sales. That’s everything. It’s, you know, that’s your book. These are your clients that you take with you from company to company throughout your career. Focus hard on building relationships, focus hard on, if you can, in-person experiences, go to meetups, go to networking events, go to where your potential customers are in person. That’s going to be way more effective pound for pound. than just trying to jump on the bandwagon of automation and AI that everybody’s going to be with. So that’s where I see the industry going. I see it. I see it in marketing. I see it in sales. I kind of see it in both directions, not saying not to use AI, but I’m saying, if you want to stand out, be human.

Greg Kihlstrom: Well, and also, I mean, I think to that point, it’s like, if you think that automation is your differentiator, there’s probably somebody else that’s automating just as hard, right? And so, I mean, I like what you’re saying here because that’s, again, it doesn’t mean that you don’t automate. It doesn’t mean that you don’t find every way to make things more efficient, effective, all those things. But if your sole differentiator is that you can automate one thing to do another, Somebody else is probably already thinking the same thing. Is that what you’re saying as well? Yeah.

Joshua Garrison: And there are going to be people out there who have no scruples who are going to automate way more than you ever would. Right. And they’re comfortable crossing that line from outbound sales into, into spam. And so I just, yeah, to your point, I think it’s all, at the end of the day, sales has always been about relationships and about solving problems for people. The cast of characters around sales has changed in terms of the tooling and whatever, but the heart of it is the same. So I found that in, you know, in my work is just like the more I can focus on building genuine relationships with people, the more good comes from that. Like. I get referrals, I get, you know, inbound, I get, I get a lot of additional value focusing there and then using the outbound tactics and the automation around the edges where I need it. I’ll just say this, most salespeople. aren’t motivated enough to get out of their apartment after work, go to a networking event, shake hands, get people’s phone numbers and follow up with them later. 99.9% of them aren’t, but a big chunk of them are lazy enough to send a blasted automated email campaign, you know, at 8 AM in the morning or whatever. So put yourself in the 0.1%, good things will happen. I love that.

Greg Kihlstrom: I love that. Great. Well, Josh, thank you so much for joining today. I’ve got one last question for you. I like to ask everybody, what do you do to stay agile in your role and how do you find a way to do it consistently?

Joshua Garrison: Yeah. think for me, it becomes, it’s always a question of getting hands on. Like in my role, you know, I, I am in this weird position of I’m helping salespeople sell, but I no longer am carrying a quota. So I lose my credibility every passing day, unless I stay in the game somehow. So for me, that looks like I dog food Apollo to find people to talk to, to interview them, you know, kind of doing what you’re doing here to. to find appearances for me to make on, on, you know, various shows or whatever. We try and live and breathe the, the market and like the, you know, the current state of the industry. And then that keeps me relevant. So, uh, the day that I, you know, the day that I stopped doing that, I think is the day that I’ll just tell everybody to stop listening to me. Cause I want to know what I’m talking about. I love it. I love it.