The Relationship Between Sales & Marketing with Drift CRO Josh Allen

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This is a podcast episode titled, The Relationship Between Sales & Marketing with Drift CRO Josh Allen. The summary for this episode is: DG sits down with Josh Allen, Drift's Chief Revenue Officer, to go behind the scenes and talk about the sales and marketing teams at Drift, playing the long game, and what's different about marketing in 2019 vs. 2009.

Dave Gerhardt: What's up everybody? It's DG, and I'm back with another episode of Swipe File. And this is not just my bigger twin over here, Josh Allen, but...

Josh Allen: Also, with the hairdo.

Dave Gerhardt: Yeah, we got the same hairstyle. Josh is stronger than I am.

Josh Allen: You're faster than I am.

Dave Gerhardt: Yeah, I can maybe do some more pull- ups but that's about it. Anyway. I'm excited, man, because... So here's the deal, I told everybody I was going to double down on this podcast and do more of it. And I think the thing that I was screwing up is, I think what's so fun about working at Drift, for example, is I'm a marketer doing marketing to marketing people.

Josh Allen: Mm- hmm(affirmative).

Dave Gerhardt: And we're using our own product and I'm like," Wait, there's so many lessons that our best content I think here is when we just talk about what we're doing."

Josh Allen: Yeah.

Dave Gerhardt: So I was like," Shit, why have I not just texted Josh and said let's do a podcast?" So, all right. So let's do a podcast.

Josh Allen: This is overdue. It's overdue.

Dave Gerhardt: It's overdue. So I have a million things I want to ask you, but obviously this is like we take this conversation wherever.

Josh Allen: Yup.

Dave Gerhardt: So you started off, you started your career in sales, right?

Josh Allen: Mm-hmm(affirmative).

Dave Gerhardt: And I don't really want to go unpack your career, but I want to talk about the role of... So you're the CRO at Drift, right?

Josh Allen: Yeah.

Dave Gerhardt: Did you see that five years ago, if you were to say as a VP of Sales or whatever, was a CRO role a thing? Like where did this come from?

Josh Allen: Not really. You know it was funny, because you'd look at organization trees, you go back, I don't know, five to seven years ago and the highest level you got to in sales was SVP of Sales. SVP of Global Sales was what you were going for. And at my past companies, that's what the roles were and that's what you were striving for. And then as SaaS just became pervasive, there was so much more of a focus on revenue versus bookings and so I think it was a way for SaaS companies to say, remember, it's about the longterm outcomes of what's happening with revenue. So there's a bunch of different components of that, it's not just the acquisition and what you're doing for sales upfront, but it's good account management. It's customer success, it's the onboarding experience for a customer. So it was... I think the introduction of the CRO title sort of lengthened the responsibility for the whole customer journey, as opposed to just the selling aspect that happened in the middle.

Dave Gerhardt: So, to go back where you said about revenue versus booking. So in the old world, you would just book as many deals as you could?

Josh Allen: Yeah.

Dave Gerhardt: That was the job.

Josh Allen: Just get it up on the white board. That was the goal. Get the booking on the board.

Dave Gerhardt: But then, And we've had early days of Drift, we spent a lot of time with Mark Roberge for example. And he talks about his methodology and that's when with, kind of funny conversation we just came out of, which is more like Product- Led Growth stuff where sales started to be more incentivized for the success of an account. And that's where these things kind of blurred.

Josh Allen: Yeah, exactly. I think because revenue is the outcome, it's the outcome for the company, it's what the CFO is focused on, public companies is what the market is focused on. They want to know what you are actually generating for revenue as a company. So I think it was a way of kind of subtly making sure that whoever was responsible in the Sales Org was focused on a better long- term outcome, as opposed to just that moment in time where you get a booking done, because there's a lot of work that happens after that.

Dave Gerhardt: So here's what I want to talk about. Let's transition. Let's talk about marketing, this is a marketing podcast.

Josh Allen: Yes. Okay.

Dave Gerhardt: I want to know all the good relationships... How can marketing, how do we work best with you? And I don't want to talk about here at Drift, obviously there's stuff, but I want to like get real, what are the beefs that you have with marketing and what are the things that we don't often see? Because I think most people that listen to this podcast, they're marketing. They're in the weeds every day. And marketing LinkedIn, for example, we'd love to do this thing where like," Look at this shitty email I got from this dumb sales rep who..." you know, and I do it too, right, but I want to know the other side, I want to know the other side of this because I felt like, early days of Drift, I was the first marketing person here and we had one rep, then three reps, then 10 reps. And we were really close because it was easy then.

Josh Allen: You were physically close too, right?

Dave Gerhardt: Physically close. Every day, I remember, every day at five o'clock we would go and sit down. Armen had the first four or five reps, Armen is our VP of Sales, he ran the sales team in the early days of Drift. And I would just go sit with them and just listen. And every rep would go around and be like," Okay, I had three calls today" and I'd be like," Oh cool, where'd you get them from?"" Oh, that webinar that you did" and I'd be like," Cool, okay that must be working let's do more of that" And that was an amazing, amazing thing. I feel like we could write a whole book just on that experience. But as we grow, I feel less removed from that today. And it also becomes harder because then you have 30 people on the marketing team and different priorities. So how can you stay closer? How can we say closer to sales to actually make an impact? Other than just like, we generate a bunch of stuff, we punted it over the wall, go.

Josh Allen: I think you're one of these people who just has this natural curiosity about what's going on in the business, in the market. That's important and the best salespeople are wired the same way where it's like, you're just so curious about your customer and what they do and how they've built their business and why they do things the way they do and the types of people they have hired. It's the curiosity and wanting to understand what's happening. So, I think about it from a sales standpoint. It's like, we look at the leads that we get, we look at the opportunities that we've developed based on the meetings we've had. And you try to unpack and have this deep and understanding as to why. For good outcomes, for bad outcomes, and for everything in the middle, you want to deeply understand the why. Which, it's a lot harder than it sounds. You can have surface level understanding, but it's hard to go deep and truly understand that, okay, if we move this lever this way, these are the dominoes that fall afterward. I think marketing is the same way where it's like, yes, we have this big, beautiful brand. And then we have much more specific demand generation activities that are happening. We have very particular pieces of content we're building that are targeted at personas, they're targeted at types of companies. They're all these different things. It's the want to understand what each of those is generating and what types of outcomes they are generating and where we could actually develop better content, or when is the time to pivot a little bit and start to focus on a CMO or an executive of an enterprise and offer a different layer of... So I think where, where marketing teams are successful, in sales teams and frankly most types of functions is when there's that deep curiosity and want to understand the results that are happening within the business.

Dave Gerhardt: I think that I talk about this a lot on this podcast is like, I think that curiosity is the number one skill in marketing. And for me it's actually a gift and a curse because it means I can never, I can never just let something go. I need to know like, why is he using that camera and that camera. But it's just like, I can't ever turn it off. But it does push you to understand like, well, why did we do that thing? And what is the effect of that? That is the magic, right, is when you can do something that like, if I think back to the early days again, which is like, we had no attribution then, and we would literally go, I would go 20 deals and I would just," Hey, let me get the last 20 deals that close in Salesforce." And literally go one by one. And then in a spreadsheet, be like, okay we had the chat transcript so they said webinar, okay. That was a webinar. The last page they visited was the demo page. They got a demo. And then literally just out of that and make a simple pie chart that's like a 30% of people came. That's the stuff that is so fascinating, but that...

Josh Allen: Things that don't scale.

Dave Gerhardt: Things that don't scale. But do you see that even at our scale now, is it like, when you're digging in with your team ops leaders, is it still the things that don't scale that you find the real learnings from?

Josh Allen: Yeah. Yeah, I think if you're in a growth company, if you're in a true growth company, like classified as hyper- growth, if you're in a hyper- growth company you should be breaking things left and right. Which means that you have to do things that don't scale because you're not going to have the systems and the processes in place already. The learnings come from things that don't scale. And so it's, give an example of our sales process. We built a sales process for a largely inbound sales motion with the expectation that a customer was a certain percentage of the way down the buying funnel, as we've grown as a company and have moved our business up market, because that's where we're being pulled, we had to change our sales process to adapt to that. But you have to, you have to learn the breakage. You have to start to implement deal by deal pieces of a future process, and then say," All right, this is working. Let's now layer that in let's scale it across the whole team."

Dave Gerhardt: That's a super interesting learning, right? Because I think it's amazing how much you learn from being here and doing it and doing stuff. And so the learning of like, we used to just have people that would show up on our website and say," Hello, I'd like to buy now." Right?

Josh Allen: Yep.

Dave Gerhardt: Totally different sales motion than like, go to this webinar about three demand gen strategies you're going to need to know by 2025, right, one person is ready to buy now, one person is not. And it's a totally different profile of lead and person that you're going to need to work that.

Josh Allen: And it was different. Cause it was like early days, they were like, I want to test what this thing is. Like, what is this thing that Drift keeps, why do I see DG's face everywhere? I needed to go try this thing.

Dave Gerhardt: Do you know that the biggest argument Armen and I used to get in would be like, there was too many leads. Okay. So, Armen, I love you. But that was the argument that we would get into a lot. And it is funny because this is, for me, it was the first time being in a marketing leadership role and having full responsibility for that. And so it's amazing because until Drift, I'd only read in books and podcasts at the jokes about the beefs between sales and marketing. But then when I was in that seat for the first time, I'm like, holy cow, you can see how this thing that you might joke about how marketing and sales are don't have the right incentives. You can see how that totally plays out. Because we do feel like you are two totally different people, right? You're measuring me on leads, you're measuring this other person on deals. Why would I not just generate a bunch of leads and kick them over the wall and be like," Look boss, I'm doing my job."

Josh Allen: "Why aren't you doing yours?"

Dave Gerhardt: "Why aren't you doing yours?" But I think that it does take, I think the only way that I saw through that was actually sitting with the actual sales team. Because no spreadsheet, no Salesforce report is going to show you that. But then you have a rep here that's like," Look, I know you're arguing this point right now. Just come on a call with me tomorrow." And I'd be like," Okay." And that was when things changed for me as a marketer, because you get on a call and all the cute little decks and designs and taglines and stuff that I had made as a marketer, now I'm being forced to actually get on the phone and make that case. And then you hang up the phone and the sales rep is like," See why we need that deck? See why we need that updated case study?" And you feel that firsthand, which is you don't get that from a spreadsheet.

Josh Allen: No, you're absolutely right. And it's what we all appreciate about you here, and our marketing team is the willingness. It is the willingness to want to get on calls, want to talk to customers, want to really understand what they're trying to get.

Dave Gerhardt: Well I think, honestly, I would even, even if I didn't want to do that and we weren't just curious people, I would want to do that as a defense mechanism because sales people ask for a lot of stuff, like decks and this and that. And so I think it is one way, the lazy way of saying," No, we can't make that." But also the lazy-

Josh Allen: Yup. Or saying yes to everything.

Dave Gerhardt: Exactly, or also the lazy way of saying yes. Because then you just spend your day being a yes man to the sales team, but you don't actually know what's working. So to be someone who can roll up your sleeves and get on calls and listen. And now there's, we use Gong for example, it's amazing right?

Josh Allen: It is.

Dave Gerhardt: And so you don't have to, I don't have to be like I'm on calls from two to four, you can listen to them on your walk.

Josh Allen: And the exact types of calls you want to listen to.

Dave Gerhardt: And I think one of the marketing lessons that I learned from DC in the early days of Drift, just marketing in general, he always just said," You just use their words, use their words." Whatever they say, we could hire some consultant, pay him 50 grand to come in and do a messaging exercise for our company. Right. Or you could listen to five or 10 calls and you're going to hear exactly what they said. And then be able to spit that back to them.

Josh Allen: If you say it back to them, have you read'Never Split the Difference'?

Dave Gerhardt: Yeah.

Josh Allen: It's mirroring. Yeah.

Dave Gerhardt: Chris Voss, I would have no chance against that guy.

Josh Allen: No, I don't think any of us would. It's amazing.

Dave Gerhardt: But I think that is the stuff that... So I wrote this note while you're talking earlier, because I want to talk about, I want to talk about sales enablement a little bit. And the role that marketing plays in sales enablement. Because I think it's a big ask at a lot of companies, but I think what most marketers, that I know at least, we boil it down to is, sales team needs another deck. And I think it's also hard because it's harder to measure. You do something new on the website, you can pretty quickly measure lift and conversion. But in investment in sales enablement, that's going to take longer to measure the lift in close rate, or win rate. So let's talk about like, give me the... What would you have in a dream world of sales enablement from a marketing team?

Josh Allen: Something that is packaged in a way that it's repeatable, it's consistent and it's in tight form. Meaning, I think we have tons of content here, but being able to pick your prescription, that if I'm going on a call with an enterprise talking to a head of demand generation, this is what I'm going to say every single time. And that, because it's easy to take like, all right, here's what we'd recommend. And then there's 47 versions of it because it becomes doctored and somebody thinks that they're either smarter or they had this trick that worked before or whatever it is. I actually think the tighter we can make it, and I've heard this from a lot of our recent hires, is when you tighten this thing up and you put this in front of me and I can use it and I can use it the same way every single time, and I can have my metric proof points that I point to every single time to talk about what happens when you put a second net bot on a website. That is very powerful stuff.

Dave Gerhardt: I think, my wife and I have this conversation a lot, we hate going to the doctor, right. And we just went to the doctor a bunch because we just had a kid, but we hate going to the doctor and you don't get a black or white answer from your doctor. When your doctor's like," Well, you know Josh, your knee is bothering you, so you could, you know, you could do this, you could do that. You could do that." No, I'm at the doctor because I want you to tell me what to do. And I think that is a good analogy for like what you mentioned about the prescriptiveness. Tell me what I should do next.

Josh Allen: I mean, our customers ask us for that. Tell me what I'm supposed to do.

Dave Gerhardt: And that's also today how you win deals. Like even if we have the best, even if we think we have the best product in the world at Drift, the market is going to always be like, well, how is it different than this? And how is it going to be different than that? So the way that we can win more deals is by showing that you're the expert. You have to be, we did an interview maybe a year or so ago in Canada with the guy who runs sales at Shopify Plus. And he said," The best salespeople today act like tour guides in a new city." You show up in Toronto, you have never been there before. Hey, I'm Dave, by the, oh you liked steak? Okay, then you got to go to this place. That's what you want. That's what the best salespeople are today. And so I think your point is like, how can a marketing team figure out what you need to run effective tours?

Josh Allen: And the same, but if you go on that tour twice, you should hear the same thing. It should be very close. It should be 98% of the same content. And that's what the good ones do because it is, you're staying within the boundaries of what we know works. And we're prescribing what works to the team and we're staying there.

Dave Gerhardt: You own sales enablement here, have you always done it that way?

Josh Allen: Ish. I've seen it done both ways where it's centralized learning and development for the company, similar to the way we have our operations team built. And then it's kind of hub and spoke. So you have the spoke for sales development, you have marketing development, and customer success. At Drift, we have sales enablement within the sales organization today, which is very, very deliberate. I think based on where we are, because we had a team that's relatively junior and their experience. So the opportunity to really be able to affect process and change and help them develop as quickly as possible, as quickly. We have this growth curve that's happening right now in two ways. One is not only like the number of customers and the number of deals that we're selling, but the complexity of those deals is increasing pretty quickly because we have marketing involved, you have sales involved, you have the BDRs and SDRs involved, you have operations involved.

Dave Gerhardt: We sell multiple products now.

Josh Allen: Exactly, right. So we have to, we have to be able to lean on our sales enablement team to help steepen the development curve of the team to make sure that they can keep up with how we're going to market. And so I think in our current stage and state as a company, it works well to have it within the sales organization. In a future state we may get to a place where this is so repeatable and consistent that we do have a centralized learning and development function. And then you almost have classroom style and it is the same thing.

Dave Gerhardt: Yeah. It feels like it could be an extension of a good product marketing team also.

Josh Allen: It can be product marketing, it can be, I've seen it in my last place, it was in the people organization.

Dave Gerhardt: Oh, interesting. As a centralized... So they trained all teams, including sales?

Josh Allen: It was learning and development. So they were focused on leadership development and programs for the engineers. And then there was two of the top salespeople in the company had actually gone into enablement and moved into that department. I mean, they spent all their time with us, but it was a centralized function. Yeah. So I think it works both ways.

Dave Gerhardt: How do, you all right we can maybe do like five more minutes, but I want to talk about marketing. This is less about you as, less as you as like a sales leader, more just as an exec. How do you market, how do I market to somebody like you today?

Josh Allen: There's an old saying in one of my former trainings that you can't be perceived as better unless you're perceived as different. I think that's the trick. And it's saying something to me that is either unexpected or is highly targeted at something I'm thinking about. So, which sometimes you have to anticipate and sometimes it's just a math equation and if you reach out to 100 people, 30 of them are going to be thinking about this issue at any given time. So I think if it's, if you market to me with some level of understanding of some of the challenges I'm dealing with today and how you have addressed them, like if something came across my desk that was, here is how we were able to ramp reps faster at your two largest competitors, I'm going to look at that. That is pretty interesting.

Dave Gerhardt: I think there's one emotion there that works almost an in any type of marketing and it's like this, I don't know what exactly what it's called, there's probably a real name from somebody smarter than me, but I call it the keeping up with the Jones's effect, which is like, you want to know what those other two companies are doing.

Josh Allen: It is FOMO. It is pure FOMO.

Dave Gerhardt: Wait they're doing that? Why are we not doing that? Why are they using this?

Josh Allen: Yeah.

Dave Gerhardt: Yeah.

Josh Allen: It's like, what did I miss out on?

Dave Gerhardt: What did I miss out on? It might not even be right.

Josh Allen: It may not be.

Dave Gerhardt: But it's going to get you the conversation.

Josh Allen: It is going to get you to the conversation, it's going to get you to explore and understand it, yeah.

Dave Gerhardt: Do you think that, separate from exact so, do you think that, God, this is a leading question there is no other way I can ask it. I think that as a marketer, I think that marketing is getting so much harder than it used to be.

Josh Allen: Why do you think that?

Dave Gerhardt: Because I think that there is like an infinite amount of supply out there in our industry. And perception, to me as a marketer, perception is everything. And so you see the Scott Brinker's MarTech landscape slide, you see their 7, 000 SaaS companies in our space. Even though we think that we're the most differentiated company at Drift, very few people outside of the company believe that just because you look at the sheer stuff in the market, right. So there's like A, there's just so many other products and things that are claiming to do the same things similar. On top of that, we are also just bombarded by people by information on every channel, right? I am addicted to my phone in a way that I wish I could not be addicted to it. I'm on Instagram, YouTube, podcasts, email, Twitter, LinkedIn, that's all in the last 20 minutes. Then you're watching Netflix or on Amazon Prime. We're also being bombarded with information as a consumer. On top of that, then marketers, everybody has a podcast. Everybody has a blog. Everybody has events. You don't have the advantage you had 10 years ago. We were like, oh shit, that is the only SaaS company that had an event, they must be a big deal. There is no more event season anymore. Every company has an event. I think the convergence of all those things had just made it straight up noise and it's really become a hard way to, it's hard to get attention because every CRO in the world right now, especially at a fast- growing company, is getting a hundred sales pitches a week. Right. And so it's almost like trying to, I remember, you remember graduating college and you're trying to apply for a job and it's just a volume game. You can have the best resume in the world, but they might not see it because 500 other people did. So I think that's what has made marketing harder. There's fewer channels that you can, I think like 2006, if you were an early mover and you started a blog, you were going to own search for maybe a decade. And it's really interesting because I think for us growing this company, like SEO was not a strategy and there's a lot of people that blew me up for that. But I think it was the right move, yeah we're paying some debt from that now, but if four years ago if our whole marketing strategy was to rank for the terms live chat, like we would not have been very effective.

Josh Allen: And it would have been very expensive.

Dave Gerhardt: It would have been, A, it would have been very expensive. B, the quality of those people would not have been good. And C, we were trying to resegment the market and reposition the concept of live chat. So we didn't even want it.

Josh Allen: And we would not have had brand.

Dave Gerhardt: Yeah, we would not have had brand. So anyway, that's my rant to tell you marketing is harder than ever before. But I do think that-

Josh Allen: I don't know that I totally agree.

Dave Gerhardt: Go ahead, that's why you're here.

Josh Allen: I don't know that I totally agree with it being harder, I think it's different. Where it used to be, it used to be that you needed some sort of a major episode or something that was happening to capture somebody's attention. There were more big hit forums. So it's like your example, if you were one of the first ones to have a blog and somebody landed on that blog early days, it's like, whoa, that's something I haven't seen before. They're keeping it fresh. There's new content. This is valuable. It's interesting. All right, you have an event and that is a major episode at that point, because there's not a lot of other like channels.

Dave Gerhardt: Right. Or you only had, you had that big product launch once every six months.

Josh Allen: Big product launch, or you had the one time you dropped in Seattle every year, and you're going to, you were looking forward to that event because that's when you learned about what was happening whenever your industry was. I think now there are... The expectation is that if you're going to buy something, there are these micro events that happen all along the way before you go and purchase something, especially in B2B where it's more of a drip than it ever was before. And you have to be able to nurture somebody. And it's not just about content, it's about, it is about being able to see the brand on LinkedIn when I opened my feed and I'm not necessarily engaging with it, but I see it, it's there. And I start to know what it is over time. Not because I am actively trying to know, but because you've just been fed so much over time. And then you occasionally run into that bigger episode, whether it's an event or something else. And so there's... But there is a longer tail, an expectation around the content familiarity that's being built, so there's a longer courting process before somebody will buy often times. And that's okay, it makes it harder that there is more channels to manage that you have to be responsible for and how you want to feed those channels with a consistent message that is saying something similar. But I just think the expectations are different.

Dave Gerhardt: Okay. I have this, like one of my worst qualities is I changed my mind a lot based on the last thing that I heard, so I do agree with you that... No but you did, you've reframed that, it's not that marketing is harder because you could actually make the argument that in the 1950s, when there were no channels, marketing was harder.

Josh Allen: Yeah, when it was radio, early TV and billboards.

Dave Gerhardt: What is the, I forget what sales book it was there. Or maybe it was just in a... I once did a Sandler Sales Training, and the example they talked about was the vacuum salesman who would show up at your house, dump a bunch of shit on your rug and be like," How are you going to clean that up? Well, good news. I got a vacuum." So, but I do think your point is good. The thing you said about these micro events, there is not more than... And also it is like every day you can be doing something in marketing now. You don't have to wait for that on- prem update to your product every six months. And I do think that maybe it is just a mindset thing, which is like more marketers today have to accept the fact that you got to play the long game. And it is all those cuts.

Josh Allen: Yep. And it doesn't have to be this groundbreaking white paper that you develop that is like, that's good to have and it's helpful, but it is a bunch of micro events that lead up to it and happen after it that are usually going to culminate in a sale.

Dave Gerhardt: All right, Dan, we'll let him go. I think we did a good job, Josh, thank you man. Appreciate it. I appreciate it. Let's go back to selling some stuff.

Josh Allen: Let's do it.

Dave Gerhardt: All right.

Josh Allen: All right.

Dave Gerhardt: See ya.

Josh Allen: Thanks.

Dave Gerhardt: Adios. Hey, thanks for listening to another episode of The Swipe File. I'm having a lot of fun doing this podcast. And so, because it's fun for me, I hope it's fun for you. And it would mean the world if you could leave a review. Reviews really help. And so go leave a review, go to Apple Podcast, leave a review. Let me know what you liked about the show, didn't like, want to hear more of, and also if you're not already subscribed, make sure you go subscribe on Apple Podcasts, Spotify. The show is everywhere that you get your podcasts, probably where you're listening right now. But if you want more content like this, if you want to go a layer deeper, join me on Drift Insider. It's Drift. com/ insider. We're teaching courses, we're sharing videos, and we have exclusive content for people just like you in marketing that we do not share publicly. So go and check it out. Drift. com/ insider.


DG sits down with Josh Allen, Drift's Chief Revenue Officer, to go behind the scenes and talk about the sales and marketing teams at Drift, playing the long game, and what's different about marketing in 2019 vs. 2009.