Introduction

Eric Doty: Welcome back everybody to another episode of Grow and Tell, the show where we tell the growth stories of revenue leaders behind successful companies. I'm Eric Doty, Head of Marketing at Dock, joined as always by Alex Kracov, CEO and co-founder of Dock. And today we're also joined by an extra special Dock guest, Joey Wright, who's our Head of Sales. Hey, Joey.

Joey Wright: Hey, how are ya?

Eric Doty: Doing good. Just a little more background on Joey. Joey was an AE at Yelp and LinkedIn, then spent four years at Modern Health where he worked his way up from AE to Head of SMB and Mid-Market Sales before joining Dock. And so today we're going to reflect on sales lessons from Joey's just about three years that he's been at Dock, including like what we've learned transitioning away from founder-led sales, moving up market, and just figuring out our GTM motion through trial and error. So Joey, Alex, welcome to the show today.

Joey Wright: Thank you. What's up? I know, so fun.

Alex Kracov: What's up? We get to talk about Dock today. This is gonna be fun.

Eric Doty: I know. It's been a bit of a travesty. We haven't had you on yet, Joey. We need to pick your brain here.

Joey Wright: I know I've been waiting, you know, I just had to get my stripes under me before. Perfect, perfect. Almost there.

Alex Kracov: We were waiting till 100 million ARR, but we decided to cut it a little bit short. Almost there.

The State of Dock Sales When Joey Joined

Eric Doty: So Joey, you joined Dock in late 2023. Like, can you tell us like, what was the state of sales when you joined? Like, what were your first priorities? What did the first 90 days look like?

Joey Wright: Yeah, great question. It's actually funny that we're having this conversation because we're in the process of hiring more AEs. And I think a big part of that story of getting people on board, spending time with them is obviously like the transition from where we started to where we're at today. So it actually comes up a lot in the conversations that we're having with prospective candidates, which is fun to kind of think back on.

Going back is also just like a weird game because I feel like we've come so far in terms of how we sell and our motion and the way that we talk to our buyers and honestly like who we're talking to has changed a lot. I'll highlight like probably a few things and then I'm curious to get Alex's take too, but I think the number one thing that I was most afraid of when coming to Dock is just a product-led growth motion. I had never worked at a company that you could go to a website, sign up, create an account, lean in there and then people had such early access to the solution. So for me, that was a pretty big change in terms of, okay, how do we manage this excitement? How do we drive engagement? And then really how do we use that person as a warm lead to get them engaged and to drive adoption in the platform, but more importantly, like leverage them as a champion. So that was a big challenge, I think, for me to start.

In terms of like, what do we do? Like, how do we really drive that persona to introduce their boss, get their manager involved, and really lean in there. So that's probably like the biggest one. And I think Alex would probably agree with that. That was like our first challenge is how do we take a top AE at X company and say, all right, use this a little bit and then go introduce your manager and run for more. And obviously there's been so much change since then. I think my first 90 days at Dock was all about what does this platform do? Why do people want it now? What's the challenge that we're really facing? Is it like a soft challenge in pain or can we really crystallize it until like this is our differentiator in the market and then build a pitch deck around that and our value prop and then start booking meetings while also leveraging this like really warm lead funnel to drive things forward. So I'll take a pause there and then I can go deeper but Eric, does that make sense?

Eric Doty: Yeah, for sure. And Alex, I also want to just know your perspective almost like why was it the time to hire Joey too at that point? Like why — it was you and one AE — why did we need a sales leader at that point?

Alex Kracov: Yeah, so I mean, we had one AE, but he wasn't really a salesperson by background. Like he was a fantastic guy, but he was more of a CS person sort of helping people use the product. Like my original thesis was, we don't even really need sales. Let's just get people to use the product. And if they use the product more then they'll buy. And it was too product-led growth. We were way too far on that side. And so sort of my insight was like, okay, we need to do real sales, right? Like how do we actually run a proper sales process because we were just stuck in small ACV land with these small deals and what we really need to do is drive more of like a top-down sale. And so I actually wasn't trying to hire someone like Joey, I was just trying to hire kind of another AE and did some interviews and talking to people. Like everyone I talked to sort of felt like, I don't know, too junior maybe because the role was... I don't know, it's pretty ambiguous in the early days. It's hard to tell what you got to do, where to start. There's just a big problem space and most AEs are used to a coin-operated role. That was my initial observation and then Joey DM'd me on LinkedIn and I was like, okay, this is really interesting because Joey was the first AE at Modern Health. It was like, okay, he gets what the early stage is like and then he also gets the scale because he helped grow a big team there.

And so it was like, is this, huh, is this like the perfect person who sort of like fell into Dock's lap, right? And it turned out to be true. And I think what, you know, what I guess one lesson was I was flexible with my hiring profile and that really worked out well, right? Like if I had been super dogmatic of like, I have to hire an AE and also pay for just an AE, it wouldn't have worked out well. But I think what me and Joey agreed on was like more of a player-coach role where it was like, hey, come in, figure out the sales process, lead the team. See about the current team and grow the team and that's sort of what works. So we weren't ready to hire a sales leader, but man, I'm very very very happy that we did. Joey's been awesome.

Joey Wright: Yeah, I think Eric, just to add onto that too, there's this... kind of like when you're at an earlier stage company, kind of to what Alex was speaking to, especially when you hire your first AE, there's a lot that they are taking on, right? Like they're doing follow-up for the first time, outbound for the first time, they're meeting with potential customers or like in our case, end users. And there's a blind spot in that, I think, that Alex would probably agree with. Where like that person is so focused on working with the day-to-day users of Dock, that you almost need someone to come in that can take you a step back and give you perspective of like, okay, great, you know, AE, you're talking to AE, you're trying to get them in the platform, get them engaged, get them to use it more because we want to drive that user up. But then you have to almost take a step back, which is where Alex and I spent a lot of time in the first 90 days of like, why are they using it? What's the personal pain they're facing? Why are they going onto the internet and looking for a deal room at the time, which is basically what we were. And then, you know, how do we start to identify what their pain is? Get them engaged in how they're thinking about Dock, but then really challenge them to say things like, when you're going back to your team meeting, when you're having a conversation with your manager, when you're in your one-on-one, when you're in your team all hands, like are these frustrations coming up? What's not working? Where are you blocked? What more do you need? And then that really helped us craft kind of our message.

All the things that we already knew, but now doing it at scale where we could repeat that for both the personal individual pain, the team-based pain, and build a deck around that for the first time and catch the ears of sales managers, VPs of sales, sales enablement people. And then that really helped us drive our process forward, which was the jump we needed to make. Like our first 90 days together, me and Alex, was like sitting on Zooms and putting our pitch deck together and saying, how do we take this like beautiful thing that most companies don't have, which is PLG that's working, and now scale it in a way where like that message moves up the ladder versus just staying with an end user that can come on, sign up, and it's really hard to drive an actual sale in the process.

Transitioning Away from Founder-Led Sales

Alex Kracov: Joey's hitting on like the thing that I feel like, I mean, I'm bad at and I think probably most founders and CS-focused AEs are — sales is more about like the value and the why and navigating the team and the political dynamics. It's not about like the product, right? As a founder, I'm just like, look at this cool thing I built. Let me show you all. Let me show you the buttons. Wait, you don't even care about this thing, but I built it. I want to show it to you. You know, like the demo just becomes more about me and clicking through the product and like look at all this stuff, as opposed to understanding like what's the business pain, why, and stuff. I think that's like the sort of single biggest thing that Joey, but you know, just sales in general brings to a business and it's very unintuitive because you're like, you're buying a product, like you need to make sure it works. But actually the way you close the deal is less about that. It's more about anchoring it to the why it matters and the business impact. And I think it feels uncomfortable, but that's like the really important shift that we made.

Joey Wright: Well, I think it's funny too, because I remember like some of our first one-on-ones and putting myself on blast here and maybe this will get me in trouble later, but it was like, you know, we need to get into the product more. I need to do like learning the product more. And you know, my side of it, like our duality together, it was like, that's great. Like I'm happy to learn the product more. Of course I want to be an expert in it, but like what does each part of the product do from a feature perspective? And then how do we actually identify the pain? And Eric, you were in the room for that too, right? That's like putting together a pitch deck of, okay, sales manager. If we're looking at sales manager, what the heck are they gonna care about within Dock? And then how do we actually scale that not to like the upside of it, but like what their tangible pain is every single day that they don't have with a tool like Seismic or a deal room or sending long-form emails. And like, why is their AE going behind their back to get into Dock and then how do we start to tell that story? But I'll take a pause.

Eric Doty: Yeah, and from a marketing perspective at that point too, I think we were very much telling the product story instead of like the customer story. So like the story around Dock sales rooms, for example, was like, consolidate all your content in one link. And that was very much like the pain that we thought we were leading with. But then you came in and you said, no, they want to shorten their sales cycle. They want to have an easier time working with their champions. Like you really helped us sort of uncover more of the customer pain side versus like the clicking the buttons pain that we were thinking through. And that leads me to my next question actually, because I was going to ask you like, what was one of the easy things about transitioning from founder-led sales? And I think that was kind of like lesson one is that you helped us evolve our messaging more towards being more like pain-focused. What was maybe one of the harder things of like once Alex wasn't the one leading the sale, like maybe from a product demo perspective or something like that. Like what was it like once Alex was off the sales calls, what was the hardest challenge at first?

Joey Wright: Yeah, that's a great question. I'll answer it in two ways, first kind of speaking to like a strength and then a weakness. So I came from a world where I was selling like very complex healthcare. So like, you know, we were working with companies like Match.com and Electronic Arts and Sonos and all of these bigger organizations where we were dissecting and trying to understand their populations and really where their gaps were in their mental healthcare. And the hard part of that is there's a lot of features within that platform that you can solve for, whether it's on-demand therapy, 24-hour crisis access support, coaching, meditation, all of these things, which I actually think worked in my favor when I came to Dock, because it challenged me always to have really active discovery on the phone, to understand like what's the high impact point where we can start to drive a lot of momentum in this deal. And then once we get their attention, we can either choose to knock it down or we can run more of a comprehensive solution and try to get a bigger deal out of the mix. I think that translates really well to Dock, because one of the things that I love about Dock is we continue to build product, right? Like when I started, we obviously had deal rooms as a main component of our selling process. We were building and cultivating our CMS, talking through analytics and dashboards, there's a lot of pieces of it. But when you're working with an AE that comes in, signs up for an account, you get a meeting with them, you get them really excited about how to use a deal room in their own deals. And then you try to leverage that to a larger conversation. That conversation is going to change so much all of a sudden when you're with their leadership, where they might not actually care about the day-to-day of like Peter who's in the deal room, but they want to focus on a different part of the platform. And I think that was probably the heaviness that we saw in like months two to seven is no, we're feature selling again and we're talking to every part of our platform. You can do client onboarding. You can do all of these things where we needed to reset, take a step back and say like, where is the pain again? How do we get them in? How do we get them focused? How do we drive engagement with them? How do we get them across the line? And then also trusting our CS team to then build out more and really drive exposure in the platform, engagement, and then usage in a new way, which is pretty typical for SaaS. But I would say that was the biggest challenge because what would happen at Dock early is we'd have an AE and a VP of sales who loved it and then a conversation and a half in they're like, you do client onboarding too? That's great, we're really excited that we can get more users out of it. But now we don't have the scope that we need to like drive that pin in our funnel. And it took a lot of refinement both in our pitch deck, the way that we were training our reps and our team to whittle that down, I guess is the best way to put it, and really tell a story of why Dock's gonna make the biggest bang for their buck in the first 60 to 90 days before they think about the bigger picture.

Eric Doty: And Alex, like from your perspective, sort of giving up the sale to like Joey and then eventually the sales team. Like what were some challenges for you or like challenges that that created that you didn't have before?

Alex Kracov: I mean, it's just scary letting go, right? Like the company is like your baby and someone else and you're just like not on the calls all the time. And that sort of feels weird. But it's also really nice to be clear, right? You don't feel like you have to like do every single thing to drive the business forward. It's like, yeah, like psychologically, I think that's like an interesting shift. And then it shifts to like, how can I be helpful to the team as opposed to talking to every single prospect and then how can I be helpful in a deal cycle? And so it's like, how do you stay close while you're naturally kind of drifting a little bit farther away is an interesting thing. I think I also kind of going back to what we talked about before, like I naturally was like, I'm doing product, look at all the cool stuff, Joey, do the product, show this thing, show that thing. And I think that conflicts with the value sell and the why buying Dock. I think all like the pain point that Joey was articulating was because of me like being like, here's all the cool stuff. Here's the new use case. Here's the new thing. Like that's the tension between, you know, shipping a bunch of new product and bringing it to market. It like, I mean, that dynamic has continued to this day when we've evolved the platform even more and building for AI. Like it's a really interesting balance of how do you keep investing into product development while bringing it to market in like a really thoughtful way that doesn't like pollute kind of your value sale.

Joey Wright: And I think that should always be the case. Like I've worked at organizations where they don't develop in product at all. And you have sales on one side that's like, I'm going to lose deals because what our customer — future customer better put — is telling us we're not getting. And then you obviously the drop off in your pipeline, your win rates, all of the things like that. And then on the other side is Dock world where, like in our conversation, my feedback always is give me more product feedback. And then the platform evolves again, and then you have to take a step back again and refine the pitch again and start to articulate again exactly who cares about what, why they care when you show it on a call, and then enable your team on it over and over again. And we're very lucky because we get to use Dock to do that, but it's always a push and pull, but I think that's where like the best companies thrive.

Alex Kracov: Yeah, and it's like, I think the tension between our product strategy and the ICP has been very interesting, right? Like I've always wanted to build kind of a big platform, but I think it got tricky when it was like, you know, let's build for sales and customer success and account management and all these different personas and use cases that we've had to kind of rein it in a little bit more and say, what are we focusing on and sort of build products? So it doesn't change the why or the value conversation, it just strengthens it. And I think that's sort of been a big shift and has sort of led to the business accelerating, which has been good.

Growing ACV and Moving Upmarket

Eric Doty: Yeah, let's dig into that a little more. Like, Joey, when you joined, I went back and looked and I think like Dock was closing $2,000 deals. And now they're like 10, 20 times that. Like what unlocked that big jump in our ACV?

Joey Wright: A lot of things. I mean, I think first, it's a continuation of what we just mentioned, right? Like I remember early days here. Like Alex did an RFP with a larger company and spent a lot of time on it. And we put a lot of work into what we had, our product roadmap, where we were going to go. Like, was that the best use of our time? Maybe it probably taught us a lot about like what we needed to build to meet the market's demand. But there's this like slow growth momentum that happens all at once, but then takes a long time where you continue to refine who you're working with, understand their needs. You get pushed really hard on a lot of these deals. You then get the product feedback to the product team and then you try to meet that demand while also pushing for more and saying that future stuff is going to be ready to get them on board. Like I think that's this constant pain that startups feel is like I want to go out and I want to work with the Apples of the world. Okay cool, like are you ready for that? And then it fosters this conversation internally where you have to make these hard decisions of like I have limited resources, I have a team that's really smart, what are we actually good at? And then rather than going after everything, how do we start to focus on, as Alex mentioned, what our ICP is and build around that and then create a moat where the opinionation isn't we need to do everything in the market, but we need to be in this spot, whatever you decide your ICP is, and then do it the best. And then once you do it the best, which is I think what we saw over and over again, whether it was getting really good at selling deal rooms and selling against point solutions early on. And then we added CMS on and then the conversation and the pitch changed again, right? We're no longer selling just to heads of sales, but we were selling to heads of sales. And then we were using those people as our mules or our champions to go and sell to sales enablement. And then we were doing a lot of challenger sale on like, this is the frustrations and pains that you have on your side of the house. And all of a sudden, very naturally, because your product now meets what the market needs and you're solving for a need and you're building something truly different, you have two audiences. So then like you have this nice organic growth of your pitch and also your ICP that then reflects in your ACV, right? So like it's this steady change over and over again. And then there's like little levers that we pull, right? Like we increased our pricing to really fit what our competitors were doing and where we thought we were valuable and we have opinionation in that space. And then we also changed our stack from working really small deals and having our AEs spend time on that to saying, hey, if you want to sign up, our product is ready and we're confident about it for our intro-level package, sign up online, get used to it, get comfortable. And then we have this rich lead funnel for later where those people spend three or six months in Dock, we can reach back out to them, they got their Series A or their Series B and then we can grow the deal too. So there's a lot of components of it. But I think like the headline is your product has to be there. And you also have to do a great job of not only focusing in on what you're already great at and selling to that, but then pushing your team to say, this is ready. How do we now go to market and challenge our future buyer on why they should make a change here too? And then it continues to grow, right? Like we went from just selling to sales, to then selling to sales and CS, to selling to sales and CS, and then really shifting our pitch to sales enablement. And then actually using that to drive the wedge between where we start, who our strongest champions are, but the product had to back it up. And I would say those are primarily some of the biggest changes. Alex, I don't know if you have anything to add.

Alex Kracov: I think it was super well said. I mean, I think we tried to build the platform for enablement. And we are still on that journey, but getting there. And then your team did an excellent job of shifting from, okay, let's work with the AE, to actually, let's drive a top-down enablement program. And we had the platform that actually those people cared about and sort of built more for that persona. And then if you do the top-down play, then you get bigger deals more naturally, because there's more seats. So I think like, and that's like a very simply put, it's really hard to kind of do that, right? Top down is a very different sales motion and you changed that completely at Dock. And then, yeah, I'm shocked. Like I think increasing pricing is also just like the easiest way to do this. You know, every VC will say every startup is undercharging, right? And it is so true. Like, you can charge way more for your product than you think. And some of it's like you need the confidence and the customers and the at-bats and then you've got to have the product to back it up, of course. But like increasing pricing just increases ACV. I mean, it's an obvious statement, but it's something that you just kind of have to embrace. And yeah, we've done it a few times and it's worked like every year. I feel like we've increased it and current customers get to keep their old pricing and we kind of just sell it forward. And what I've noticed is that our big customers will pay us giant amounts of money without ever saying a word and don't care at all. But the $60 a month customer is the loudest and most annoying and writing into billing all the time about refunding something. And so there's a big disconnect between what small companies are willing. And it makes sense for a small company, any amount of money is really important, whereas the big companies just make so much money. So yeah, that's worked really well.

Joey Wright: Yeah, I think there's like an opinionation piece on it too, and in two parts, Eric, to call it out. So the first is like, you obviously have to have the product to feel confident enough to sell. You also have to have a lot of wins under your belt to feel comfortable to make the change. But it was probably like Q2 of last year. And I think Alex and I identified something in a one-on-one where our team kept saying things like, yeah, we're like a cheaper solution than what you're looking at, right? Especially like legacy tools or power players in this space. And we had to like really intentionally change that shift to no, we're the best revenue enablement solution on the market. This is why we're different and this is why we should win your business. But you have to kind of get through that like weird, awkward teenager phase to get there. And then all of a sudden your confidence on the call is different, the way you're showing up to a customer. You're challenging them. You're an expert on that call, but you have to have the product to reflect that to get in there because you're eventually going to have to show it to them. So I think that's number one.

And then the second piece of it too, is there's opinionation in terms of the types of deals you work. Like one of the hardest parts about working at Dock early on is we had a lot of free accounts that would come in that were five or 10 users that we would want to work because we obviously want to hit our number. But then as you become a bigger company, you close more logos, you become more confident, you're bringing on the Vantas of the world, whoever it is, all of a sudden you really have to lean into your ICP and then put controls in place, like letting people sign up online for the smaller stuff where you're actually taking a step back, having a conversation internally and saying, okay, we're building pipeline. That's great. But are we actually building pipeline that reflects the ICP we want to work or are people just busy working a bunch of small things, which is not how we grow a sustainable business. So just two points to hit on there too.

Competing Against Seismic and Highspot

Eric Doty: That's great. Okay. I think for the first maybe two years you're at Dock, Joey, we were mostly positioning Dock as like a digital sales room point solution, selling against other sales rooms. It was kind of just like a bake-off against everyone trying sales rooms for the first time, more or less. Like that was our typical sales motion versus now we're increasingly — now that we're in the sales enablement category or revenue enablement category — we're more in deals against Seismic and Highspot, like very big legacy players, billion dollar companies that have like a 10-year headstart on us. And so obviously the sales pitch and process is going to be quite different there. Like obviously we're not going to give everything away, but what's our sort of — when you're not the biggest player in the room and you're going into the sales process — like what does the pitch look like?

Joey Wright: Yeah, it's a great question. I think there's like... this is something I learned in selling to HR for a decade. There's kind of two sides of the pitch, right? So there's like the soft ROI and more of the emotional sell, which I actually think works extremely well for our buyer. Because if you think about it, sales enablement people are the educators of a sales force. So their motivations intrinsically and what they're measured on are a lot different than what salespeople look at, which is hard numbers. Obviously there's a component of that. But I think when you look at players like Seismic and Highspot in the space, they have a huge TAM. They're talking to some of the biggest companies on the planet and they're hitting a lot of segments. So when you're a company like Dock and you have a more refined ICP and you know what that looks like, it becomes a lot easier to give a more tailored approach, both in terms of how you're pitching it, getting to know these people one-on-one, what their days look like, where they struggle, what they're trying to control. Understand, make repeatable within their process that they're probably not getting from that warm and fuzzy side from a bigger vendor, which I think was the first unlock for us. When we opened our arms up a little bit and gave them a virtual hug and said, just vent to us, what's not going well? Where are you at? Why are you struggling? There's this component that's really human of sales where they feel heard for the first time in a long time versus just buying a solution that they bought seven other times at the last six roles that they were at. So there's a big piece there. I think that like goes unsaid, which is probably the most important piece, like the human psychology piece behind like why we do well. And I think Alex can attest to that when we bring on champions, they're so excited and you know, we're doing a lot in the background to like introduce their client success manager early, make sure they feel set up for success, building a tailored timeline with them, getting their hands on the platform early and just making them feel like they're already users of Dock before they ever sign a contract with us, which I can say with confidence, they're probably not getting from those large legacy vendors in the space. And then the other piece of it, which I think is really important, is the product reflects 10 years of feedback that we've heard and tried to understand and research on these bigger tools that create a lot of dysfunction from things like admin controls, setup, implementation, driving adoption in bigger organizations that's really hard to do when you have an account manager at one of these companies that's getting switched out on you every six months. So like in turn I would say there's probably a few things. The first is you know less tailored support because they're working with a bigger institution. Two, working with salespeople that might be a little jaded or being at a bigger company that might not have like the drive that our reps do at Dock to go above and beyond. And then I think they're like, our product's just better. So there's a lot of ways to tell that story in terms of how we actually meet them where they're at. But I think it really starts with, you know, tell me why like you don't want to buy this thing again, or people aren't using it. And then just like driving a wedge between that and like what they're used to today. So I'll take a pause there.

Eric Doty: Yeah, Alex, what's the founder perspective on that?

Alex Kracov: Yeah, I think you got to find your wedge and sort of differentiation against these big incumbents. For us, it was like we're more buyer-centric and we're more AI-native was sort of the simplest way. We started on the deal room side of things. These companies and incumbent platforms all had a deal room, they are crappy. They are like old school, they're your parents' software. I think even those vendors would probably admit it. It's not a place where they really invested deeply. And so that was sort of our wedge in. So people who really cared about that part of the product would go with Dock. But we obviously don't — you can't compete on all the crazy enterprise features and all the giant platform. You can in the long run, but in the short term, it's really hard. So you got to kind of find your wedge in and that was, and then that kind of got some momentum under us. And then we're able to start to kind of compete on the broader platform. And that led us to strengthening our CMS platform and our LMS launching earlier this year. So we got there over time. And now the velocity of sort of the rip and replace happens much, much faster.

And then obviously the world is changing now with AI. The way SaaS is being built is completely different now. So I don't envy people who are running these 10, 15-year-old SaaS companies who are trying to change, because it's hard changing even a five-year-old SaaS company like Dock. So good luck trying to compete in this world of AI. And that's kind of our way forward from here.

Joey Wright: Yep. Yeah, Eric, I think the one other thing that I would call out in my experience of working at startups is like when you start to kind of get in the room, there's this like frantic, anxious, like detachment from what you were good at early, right? So like one thing that I think has worked really well at Dock is we didn't abandon our deal rooms. Like they're a core part of our product set and the way that we go to market, they're a huge differentiator for us. And when we're talking to a Highspot or Seismic customer, their biggest frustration over and over again is I rolled out this thing. It took me forever. It's extremely expensive. And no one's using it. Like they're still doing — they're bothering their top AE and they're going to copy a pitch deck. And that is a sales enablement or product marketing person's nightmare because they want people going back to that repository to find that. Where we can come in from a product perspective that worked early is we're still doing all of the work of creating a co-branded workspace, getting the AEs in, having them use it, share it with customers, and actually showing what that delivery method looks like of like, this is your missing piece. Of course no one's going into an old piece of shelf-ware and finding a pitch deck, downloading it and sending it through an email. It's too much work, they're not gonna do it, they're busy. Why don't you actually make it easy for them to drive that by delivering that to them through something that already works at Dock, and there's your connector between the two. And then we build around that conversation. It actually reminds me of a deal that we had pretty early on with Zip where we had an AE that was coming in and he was like, I don't use these tools because I can't find what I need. So I just do my own process, but I'm working with really large accounts and I have 20 stakeholders in here and I need a better way to showcase these assets that I can't grab from Highspot. And we were able to take what he did and actually give it back to the sales and the enablement team. And there was this big aha moment of like, of course this makes more sense and I can keep a better tab on my assets and all the other pieces of it too.

Selling AI Features

Eric Doty: Perfect. Okay. We have a few minutes left. We went 40 minutes without talking about AI before Alex said the magic words. Joey, as a sales leader, what's been different about selling and demoing AI products versus kind of your traditional predictable SaaS software? And how has that changed how our team has had to go about sales, if at all.

Joey Wright: Yeah, I'll give a very controversial answer and maybe I'll get my hands slapped later for this, but I think AI is this big buzzword that means nothing and everything all at once. So I think selling AI specifically has been really challenging in the sense that like you're getting a buyer that comes in, they're really excited about it. Maybe they have some sort of OKR to go out and find an AI solution that makes everything easier for X population. Great. But like you really have to spend time with them to understand truly like, all right, let's stop talking about AI. Like AI can mean 100 different things. What do you want to solve for? What is difficult in your day to day? Where are you getting slowed down? Where is the friction? And then we can start to bring that into the conversation with knowledge and intention and really highlight the part of the product that is going to impact that. And I think for a lot of sellers, especially now, cause you know, I'm still having conversations outside of Dock. That seems to be the number one thing I hear is like, I just hate this conversation. It goes nowhere. There's a lot to go with it. They're asking all of these questions I think they should ask. And we almost have to go back to more of like a challenger sale model where we dig in and say like, do you actually need this? And if you do need it, let's talk about like the one or two ways that we can make your life easier or your population's life easier rather than, you know, spending the next 30 minutes talking about buzzwords that they heard on, you know, Joe Rogan. So yeah.

Alex Kracov: Yeah, like, there's this giant education problem. You know, you talk to customers and they're like, ooh, I'll click the magic AI button. It'll just do all the things for me. And it's like, no, that's just not how it works. You know, like there's stuff you have to do to set it up in sort of the right way. And so that's a tricky part of the sales process, maybe even more on the CS side that sort of we deal with. But I think where it's been very helpful is every CEO is yelling at their team saying, use more AI, use more AI, use more AI, including me. And you know, like it's helpful for our buyer to be like, hey, I'm buying a tool that has AI in it. Even if they don't even use it or know about it or whatever, they're still going to — even that's not even the main reason — it's like a helpful thing for them to kind of say. I think, and look, there's real benefits of our AI tools and features and stuff, but even, you know, yeah. So like just even having that word to be part of the conversation is ginormously helpful.

Eric Doty: Yeah. What's funny is on the marketing side, like you have to dangle AI out there, like not as bait. So like that's overstating it, but people are searching for AI products specifically. Like they want to go out and buy an AI thing. And then it's almost like Joey, then you have to like, once they're in the door, you have to pump the brakes on them and say, okay, yeah, like you do want to buy an AI thing, but what you actually want to do is like be successful and let's figure out what that looks like for you.

Joey Wright: Yeah, like let's take a step back. Exactly. And I think like the most important point to mention is like you're paying these people a lot of money to sell for you and you want their brains. So like how do you want AI to supplement what they're doing day to day, not replace their work? And I think that's like the funny little marriage or like dance that we have within Dock is like when you get off of a call and you're building a workspace or you're looking for an asset, like are you actively listening on that conversation? Do you know what to highlight? And then how does AI support you in finding the right things quickly that you need to do next, right? And just doing it all for you, you sending it over to a customer and then they feel like it's inauthentic to the selling experience that they have. Which is a lot to go back to Alex's point, the education that we do in the selling process is like, yes, use this here because this is a challenge that you're looking to solve for, but you also want Johnny to still have autonomy in the way that he sells now being supported by AI so he can do his job even better.

Closing Advice for Early-Stage Sales Leaders

Eric Doty: Perfect. Okay. One last question, Joey, before we let you go. I've only asked a third of the questions I intended to ask, so we'll have to have you back on the show. Our listeners will demand you back. Just before we let you go, what's like one piece of advice you'd give to another early-stage sales leader right now who's kind of in the process of trying to figure out their sales motion?

Joey Wright: I would love to. I think it's honestly just like focus on the population's needs. Like it seems really simple, but I think the only reason that we've really been successful at Dock is we took really hard stock in who our users were and really studied what was most frustrating to them, what their friction points were, and then we built the product around how we enable them faster. And then when we got on a conversation with them, like most startups that are coming into the space today, unless you're creating something brand new that no one's ever heard of, there is some sort of replacement and a tool that you're competing in a space that maybe didn't exist before or a space that's really built out. And just spending time with your early users to understand at an IC level what's not working, but then more importantly, like what's frustrating their leadership. And I think you're going to find a lot of knowledge in how you support and build your product in that way. But most importantly, especially on the go-to-market and sales side, how you develop your pitch, going back to the first question that we mentioned in terms of like, what's the actual pain that we're solving for? There's so many products that are awesome and they get a ton of funding, but they can never find their footing because they're so feature-heavy and they're coming on and they're giving people hard cruise tours or marketing pitches of why they're better, but they're not really spending time understanding what makes that user tick and like what's the one small thing in their day that they can make better to make their life easier, especially at scale. Like if we're selling to revenue leadership, they have a thousand and fifty things on their plate. So like where's the one area when they go into their whiteboarding session, their team meeting, their all hands, their forecasting call that gives them anxiety, and then really drive your product around that because you're hitting both like an actual need and the emotional pain that I think will drive your pitch a lot forward faster. Yeah.

Eric Doty: Perfect. Well, great place to end Joey. Thanks so much for joining us. Alex, thanks always for being on the show and thanks to all of our loyal listeners, all the dozens of you out there who listened to every episode. Thank you so much. And so you can subscribe to the show on YouTube, Spotify — that's the right one, I was confused, Spotify and Shopify — Spotify, Apple Podcasts, or check out the newsletter version of the show at growthandtellshow.com. Thanks so much guys.

Joey Wright: Thanks for having me.

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