Why Reps Ignore Most of the Content You Create

Eric Doty: Welcome everybody to another episode of Grow and Tell. I'm Eric Doty, Head of Marketing at Dock, here with Alex Kracov, CEO and co-founder of Dock. Hello Alex, how are you?

Alex Kracov: Good to see you.

Eric Doty: Today we're gonna talk about everyone's favorite topic, content management. So if you're in enablement, you're probably dealing with a few recurring content challenges. Reps don't use most of the content you create. It's really hard to keep everything up to date. And even when you do build something great, it tends to disappear into a shared drive, never to be seen or used again. And to make this all more complicated, AI is here, which will make creating content easier. It might make it easier to find, but it also adds all these new challenges of like this infinite content problem and all kinds of new content management problems to overcome. So let's get into it.

Okay, Alex, let's just start with that main pain point I brought up, which is companies spend a lot of time and money creating content, reps ignore most of it. Most people end up with like one sales deck they like using, one case study they like sending to customers and they just rely on those. So as someone who's been building software in this category for a long time, why does that happen?

Alex Kracov: Yeah, I mean, this is like the classic thing that frustrates marketing and even the frustrating thing that led me to start Dock in the first place, right? Like just every marketer has been there. Like you're getting a million requests from sales to make this thing or this case study. We need X, Y and Z. And then when you notice the sales rep's pattern, they just use the same stuff over and over again and they just struggle to find things. And that insight led me to build a shitty version of Dock when I was at Lattice and eventually turned into a company because I thought it was easier to kind of organize it all in a deal room structure.

So I don't know, that's a little of the company history, but why does that actually happen? I think reps are creatures of habit, right? They have a million things to do, they're working all the deals, what they typically do is just copy and paste their demo follow-up email or their intro email with the same four or five assets they're sharing again and again and again. And they're gonna share their pitch deck, which is like the canonical thing that has all the info. Like every sales motion has a pitch deck for the most part. And then there's like the one case study and pricing, right? And they'll just kind of like rinse and repeat. And that's actually a good thing. Like you want sales to be coin operated at a certain point and to feel very repeatable. Like that's a thing that every good company is striving towards.

But then what inevitably happens is they're just sharing those same things again. And then as new stuff gets created by marketing, it's hard to break that habit, right? Just as a human, just hard. And so how do you insert yourself as a marketer or the person making the content into that process from the sales rep? And some of that you can do if you use proper content management systems with syncing or use deal rooms. Like that's a great more sophisticated way to go about it.

Then the other thing I noticed is that sellers use those same things again and again until they get asked the question by the customer, right? They're like, the customer's like, how does your Salesforce integration work? Do you have a case study with another bank? Right? And then immediately they're panicking, being like, crap, I need a piece of content or a response back. And that's why all those requests happen back to the marketing team. But then once that deal closes, win or loss, they move on to the next thing and they don't need to use that thing again until the next time a question comes up. So in a lot of ways, your content strategy maps back to the questions that the customers are asking the sellers, but sellers only care when they have to respond to that question and then they just move on to the next thing. So that's the funny dynamic I think I've noticed time and time again working with a bunch of companies.

The Business Consequences of Outdated Content

Eric Doty: What is the actual business consequence of this happening? Enablement leaders always say, I want to think in outcomes, not just tactics. What is the actual downstream problem it creates for sales if reps aren't using the content that enablement makes? Why should they care at all about this? Or is it just a frustration that I'm mad that people aren't using the stuff I made?

Alex Kracov: Yeah, I mean, I think it's sort of like this and it's hard. The outcomes are close rates and velocity and things like that. But there's almost like an invisible thing around staying on message and brand theme and aligning sales with the product that's being built and the thing that's being marketed. Like what will happen, especially in a startup environment where everything's evolving so quickly, is that your pitch deck from six months ago is very different than what it should be today because the product has evolved. There's new messaging and a new way to talk about the product and the platform and different things like that. And so if sellers are using outdated content, then they might be selling an outdated product that doesn't actually reflect the actual product itself.

And you know what? It still might work. I was always surprised at Lattice, listening to sales reps kind of say the messaging from six months ago, and they're actually pretty successful in closing deals. But at some point in time, it catches up to them and it'll show up in the close rates or velocity. And then where it might even show up more is on the customer side when it comes to churn and satisfaction, because as the product evolves and your collateral doesn't really reflect what the product is today, customers might feel bait and switched, right? They might feel like what I bought is really different than what was talked about. And one of the easiest ways to standardize everything that's being said — the seller can kind of say whatever they want on a call and fib and say things on the margins, but your pitch deck and how it describes your product can sort of be canonical.

And so, I don't know, that's how I kind of think about the business impact. And I think it's really real and I think it is really important. I mean, I'm biased because I'm a marketer in my blood, but that's how I think about it.

The Stages of Content Management at a Company

Eric Doty: That makes sense. Let's talk through just how content management tends to evolve at a company. You and I have talked about this a lot. Like sort of the stages all the way from startup with the CMS or with Google Drive through maybe not quite enterprise, but what are the typical stages of content management at a company and where do those tend to break down?

Alex Kracov: Yeah, I would say the first stage is zero content management. Everything is just people making things and it's very tribal documents, right? It's like the founders doing founder sales. They just have their couple decks they might duplicate every time for a new customer. Maybe they're reusing the same PDF again and again. And they have maybe a case study — maybe they don't. Like when they get their first case study, they'll share that. It's very sort of bespoke in the early days, founder just trying to figure it out.

And then you hire your first sellers and your first group of sellers and it starts to transition from founder-led sales to, okay, we got a real sales team and we need to structure this. And it's always the first conversation is around the pitch deck. And then usually it evolves into security documents — those have become more and more important. And then case studies and pricing are kind of the next things. And so those assets start to get built out.

And then again, it's still tribal knowledge. Maybe if you're a really organized founder, you're going to have a folder with all of these things, but probably not. It's probably just the same pitch deck duplication thing, passed around Slack and email and people are just duplicating. But then eventually, the amount of content sort of increases. You have competitor battle cards. And this is usually once you start to hire more of a team — marketers and a professional sales leader, whoever it is. And then there's more requests and more questions from customers, right? Kind of going back to what we talked about before. And so you start to build competitor stuff, more case studies, more pricing things. Maybe there's really specific product questions that start coming up again and again, like how does your Salesforce integration work? And so you start to build more and more assets that are harder and harder to keep track of.

Eric Doty: I'm a spreadsheet often.

Alex Kracov: Yeah, spreadsheet, another good one. And what most companies will do, which I think is a totally great solution, is you'll either just set it up in Google Drive in a folder or SharePoint if you're Microsoft, or maybe if you're a little more advanced, you're gonna organize it in more of a wiki, like a Notion or Confluence or something like that. And that's usually where it starts. And then over time, it starts to break down in a couple different ways.

And this impacts organizations in different ways depending on what they care about. What I generally have found is one, these tools are great, but it can still be hard to find things. There's not powerful search. Like Google Drive — I was actually listening to a podcast with Sundar, the CEO of Google, and John Collison from Stripe was giving him shit for like, it's actually surprisingly hard to search things in Google Drive. You would think Google's really good at search, but it's hard. And I think it'll get better with AI, but it's hard to find documents when things are named similarly.

And so search starts to break down, the distinction between internal and external content really starts to break down — like what is appropriate to share with the customer versus which is draft mode which really shouldn't be shared with the customer. So there's no sort of content governance around that. There's no analytics in these systems. You actually have no idea how often your sales team is actually using assets or how often your customers are engaging with assets.

And then there's also the classic problem of if you're a Google shop and you try and share these documents with Microsoft users, they can't see it without a Google account and vice versa. And so everybody bumps up into that problem and it's a silly one, but it's a really big problem. So I don't know, that's usually what happens in kind of the early days of content management and different companies feel these pain points in different ways, but those are some common patterns I've noticed.

Why Deal Rooms Solve the Rep Adoption Problem

Eric Doty: That makes sense. Let's just jump to the next phase. Okay, so typically that breaks down, you feel the pain enough and then you're like, okay, I gotta buy a CMS. I think there's a few pain points that can come up there. I think one you've talked about before is that if it becomes a sales-only CMS, there are some challenges there versus being available to your whole revenue team. Can you talk about that?

Alex Kracov: Yeah, well, I think one distinction as you think about CMS and wiki and stuff like that is like, you have company-wide information, which you should still have company-wide. But what we found is revenue teams really need their own dedicated place because it's one place where they can go to find things really easily as they work with customers. The company-wide thing works for a while, but it just gets so muddy and hard. And so they need a dedicated place.

And then I think one of the problems of the last generation of enablement was it was really focused on just the sales buyer. And I get why — they actually buy software at a nice rate. Like it makes sense, that's kind of where the money was. But then it just becomes a siloed system for sales, and customer success is just not as loved in those systems, they don't use it as much. And in a world, especially for SaaS companies where just as much revenue is coming from post-sale as pre-sale — when it comes to your CS and onboarding and account management teams — it gets really challenging if that stuff is living in different places because the lines are all blurring.

I mean, we just talked to the head of enablement at Rippling and it's crazy how much post-sale stuff is going on as their different SKUs are evolving. And post-sales looks very similar to pre-sales. It's just a different stage of the life cycle. And we think these customer life cycles are not as linear. It's really a blurred thing, more roundabout. So CS teams really need a role here. And that's why it should be a revenue enablement platform, not just a sales enablement platform.

Eric Doty: Sure. And I think another challenge that comes up anyway, even if you have this beautiful CMS, that problem we talked about right off the top still happens, right? It's like you can organize the content as well as you want, but there's still this rep adoption problem. So I think one of the reasons that we went so heavy on deal rooms at Dock is that it's a way to solve the content delivery and standardization problem that isn't just a CMS. Can you talk about how Dock or any sales room sort of solves that content sharing problem?

Alex Kracov: Yeah, I think one of the problems with content management systems is there are so many assets in there oftentimes and a lot of them are irrelevant or stale — and there's a whole thing we can get into around managing your library. But it's a problem for reps to find the stuff, and as we kind of started the conversation, they don't have that much time. They want it to be repeatable. They don't want to have to think. And so what a sales room does is it packages things up really nicely. It is the couple things you need to follow up after your intro call or your demo call, and it's in a nice little package that makes it super easy for the rep to duplicate. And then it's a really nice buyer experience. So it's a win-win on both sides — less thinking for the rep, better buyer experience, higher close rates.

And so that's why it also limits the — especially in the early days of a company, you don't need to think about, God, I got to build all this crazy content. I just need to get the four or five assets in my deal room working really well. And so that's a nice aspect of it. And then as you get more sophisticated, the deal room can kind of match your entire sales process. So instead of having to deal with a thousand assets in a library, you can just think of, okay, what are the top 20 assets that I need that map to the different stages of my sales process and buyer journey? And so it adds a lot of nice structure. And then you can do more experimentation and swap things out. And it helps the marketing team also get a sense of what's actually being used again and again. So that's how I think about it.

Eric Doty: Yeah. I think there are kind of another couple of layers of problems that it solves. One is — I'm in a marketing community and someone the other day asked like, how do I share content with salespeople so that they know what we have? Like, how do I give them an ongoing feed of all the stuff we're making? And I was like, in my experience, that doesn't work at all because it's almost like when you're Google searching something — you don't search for it until you need it. And so salespeople, you can give them all the — like, hey, I made this asset, I made this asset — even I'll share it internally on Slack and our own sales team, like they won't even look at the thing. But then I'll see a month later it comes up in a deal and they use it. And so the mindshare isn't there until the asset is needed in the moment.

So you're like, how do I structure things so that it's ready for them in that moment? And this person who asked, I told them — they said we have five segments, five ICPs, all these complicated things — and like, how do I get sales to share the right thing with the right people? And the deal room, it's like, okay, you make one page in your deal room for that ICP with the right case study, the right product information that they need. And then they can just sort of click one button and turn that on versus having to have memorized, this is the case study for that customer, this is the deck I should share. You can basically make it more like flipping a switch than having to remember what's in the library.

Alex Kracov: And then the great part about deal rooms too is the syncing of the content and always having the most up-to-date stuff. Like marketing and enablement control those templates as you talked about. And so the next deal that the sales rep works is going to have the latest and greatest pitch deck and there's no problem with outdating. And then some of the cool things you can do in Dock is sync sections or sync pages. So even deals that are active or already in flight, you can actually update the content to make sure it's always up to date, on message, the latest and greatest thing. So there's a lot of power to that switching, and it's definitely a little bit of a new way to do sales, but it's definitely the best way to do sales we've found.

Eric Doty: Yeah, it's more of a lift for the enablement team to start, but it gets more adoption from sales reps in the end. Like there's almost no one-to-one sharing of assets that our reps do at this point. It's just, here's the deal room. And then as enablement or marketing, we can control the content better. So it sort of gets around that rep psychology adoption problem.

The Value of Content Analytics

Eric Doty: I really want to quickly touch on analytics as well and usage metrics. I think you touched on that as being sort of the biggest failing of a Google Drive-type system — you really don't know what reps are using, and you don't know what customers are engaging with. Like beyond the waste problem of reps aren't using the content — and then maybe you have data that you can see — what I always think is interesting is the feedback loop of the analytics and what that provides you. So can you talk a bit about the benefit of what the engagement metrics actually give you once you have them?

Alex Kracov: Yeah, I mean, I think the first thing you want to look at is team usage. Like, does the sales team actually use the thing that marketing creates? And the easiest way to track that — at least in Dock — is how many times they shared a specific asset, right? How many times did they share case study A versus case study B? How many times are they sharing this pricing SKU for this customer versus another, right? And so you really want to look at the overall team engagement and then you can slice and dice that by specific teams and get a sense of usage that way. So I think that's step one — does my team actually use this?

And then there's the customer side of things: okay, if my team uses and shares this, what kind of engagement rates do the customers have? Do they ever want to look at that thing? How often are they spending time on it? And so different assets usually have different analytics around them. Pitch decks and slides, you can get a sense of slide drop-off and how much time they're spending on specific slides. Like maybe they're always quitting on slide four and you should change that slide for some reason. Same with videos, you can do different things like that. And then others are a little more high level, like links — okay, did they just click on the link, so on and so forth.

And so it's sort of that one-two punch. And this is one of the ways you can prune your content library, right? Set up different filters in your content management system to get a sense of, okay, these are all the assets that have never been shared. And then it's like, okay, why have they never been shared? Is it because sales hates them or is it because they can't find them? And then you can kind of deduce from there. And then reverse for customers — it's like, okay, why are these assets never getting viewed? Is it because they never got shared in the first place or is it because they're just uninteresting and people don't want to engage with them? So that's how I think about it.

How AI Is Changing Content Management

Eric Doty: Cool. Let's just talk about AI, because I think that's kind of the forefront here and what's interesting and what's coming next. Maybe I'll just ask you open-ended first — how do you think AI is going to change the whole content management game?

Alex Kracov: Yeah. So I think historically and where we're at today — maybe a state of the union — it's been fairly basic stuff, right? I think it started even pre the big crazy AI thing with Highspot and Seismic searching through documents using old school ML technologies to actually not just surface the metadata around a file, but what's actually in the PDF, what's actually in the video. And that type of stuff has become table stakes today.

Solving search around the actual contents of the asset is a big thing. And AI search will continue to get better. Although one interesting dynamic is people still want old school search, we found. We arguably put AI search a little too prominently in Dock, and we need to have a better switch between quick old school search and AI search, because it's a different type of answer. So that's one interesting observation. And then the easy thing that a bunch of companies have done, including Dock, is tagging — okay, now that we understand what's in the files, can we suggest better tagging and organization and things for your library? So I think that's sort of phase one of adoption, kind of where we're at today.

I think where it starts to head in the future is maybe two-pronged. The first is using agentic editors or agents to better organize and control your library. This is happening on the coding side of things. And for folks who've used Claude Code or Cursor or things like that — Eric's using a bunch of Claude stuff for some of our own marketing — but using that sort of agent-editor experience to control your library and ask your library questions and help to tag things and move it around. We've started to scratch the surface here with Dock with things like, show me all the assets with zero views, okay, archive them, stuff like that. But there's a lot more you can do to manipulate your library from a command center, from a really simple prompt-style conversation, as opposed to what it would take to manage a Seismic or Highspot in the day — which was literally hiring somebody to set up all the views and do all the governance and click all the buttons. Like there's a lot in there and learning how that all works is a pain in the ass. And so it's much easier to just be able to talk to an AI and have that do all the running around and doing it for you.

And then the other bucket where it's also really interesting is on the AI content generation side of things. It's not just about organizing content, but also creating content. And we've started to do this in Dock with AI documents and business cases and things that you can create based off your Gong calls. But there's a lot more you can do in tools like video generation. There's all these video models. Canva's doing a lot of exciting things. There's a bunch of people coming after the creation of the content that goes in the content management system. And it'll be an interesting strategic thing for Dock even too — like how deep we go into the creating content versus storing content and the relationship between that. But I imagine a lot of companies will evolve to creating content too.

Eric Doty: Yeah, I think the other last one maybe you missed was AI suggestions, if you want to talk about that.

Alex Kracov: Yeah, good call. Thank you. Yeah, that's one of the things that we did add into Dock. And so the idea is — especially in a tool like Dock, but if you use any CRM — there's a lot of buyer context, right? What is the customer doing on that call? What did they ask for? Did they ask for a specific case study? Did they ask for pricing? And so with AI now, you can not just pull, it can be push, right? In the past, they talked on the call and now I've got to go search and find the thing. But now AI can listen to the call and be like, hey, Bob mentioned you'd send over pricing. Maybe you should send this pricing to him. And different things like that.

The delivery mechanism for that is evolving. We have that today in deal rooms, but we want to add it in more places. And so yeah, I think one of the big strategic shifts from old school enablement to new school is connecting it to that customer record. And then it's not just this passive content management library. It's something that can actually be recommended based off customer activity. And I think that's some of the things that Dock is looking to pioneer.

Will AI Generate Personalized Content One-to-One?

Eric Doty: Okay, next big question. Something I've been thinking a lot about lately is — is there still going to be a world where marketing creates assets and those get shared with the customer, or will there be some more AI-personalized future where AI documents, like we talked about at the start of this, where you make a personalized business case for the customer? Like, do you think there will be a future where the sales deck is spun up one-to-one for the customer, completely custom? Do you think that's a world we're going to get to? Do we need that world?

Alex Kracov: I think it depends on the organization and what they want. Some organizations want hardcore control over what's being shared, whether it's marketing, sales, or leadership. They really want it to be super standardized. They honestly don't trust their sales teams. I'm always surprised how often companies don't trust sales to do things, whether that's formatting, making decks, putting the right stuff together. The most common model we found is 90% of it's standardized, 10% of it's personalized. Then there's other organizations that are higher trust, or maybe they're dealing with super enterprise sellers who really need to customize things, and they're going to create more custom content — and there's sort of a spectrum there between low-trust and high-trust organizations.

I think what it evolves to is definitely more personalized content. I think that's inevitably the future. The systems will get better at personalizing the content and putting guardrails in place and giving marketing and leadership control over those guardrails — saying, hey, here's where it can be personalized, here's where it can't. And so I think that's what the future looks like — the templates and things that marketing creates start to look a little different and feel different, with a bunch of AI placeholders where sellers can fill in the parts they're allowed to.

Eric Doty: Yeah, I think we've seen this so far with the content and deal room side. Like when customers come to us and they say I want to be able to click a button and AI-generate a deal room — it's one of those things that I think you want that, but you actually want enablement or product marketing or whoever to have control over what the template looks like. And then you want to have a couple of placeholders that are AI generated. And I think figuring that out will be the balance of figuring out what the future of AI content looks like.

Alex Kracov: Yeah, it's a tricky, tricky product balance. I mean, this is literally something I'm spending a lot of my time trying to figure out — what's that right balance between AI completely generating new things or filling out templates and stuff? And the reality is, each are useful, it's just different situations and different organizations. So that makes it even trickier.

Content as a Data Layer for AI

Eric Doty: Yeah. Okay. Just a couple more questions for you. On the last episode where you and I talked about AI and sales, we talked about how content is like a data layer now for AI. And that's something I've been thinking about in these really early days of this area. For example, now your pitch decks and your battle cards and your case studies that get uploaded into this AI-powered content management system are going to be raw information that powers something like an AI chatbot that can answer rep questions. We have that built into Dock. So part of my question for you is — do you think that's going to be the role of content in the future, that it's primarily data for AI? And sort of a second question is — what will good sales and enablement content look like then? Will it be written specifically for AI? What world do you envision there?

Alex Kracov: Yeah, that's a great question. And I don't know all the answers here, but I would say yes, it's a really important data layer. I mean, what does AI need? It needs context, right? That's what makes it useful. And so the best context is in your documentation and your collateral and things like that. And so if you want the AI to answer correct questions about your competitors, the context you have in your battle card is probably better than it running around the internet trying to figure it out itself or whatever it was trained on in the model. And so that context is super important.

And that's what agents live off of — the context, some of the prompts, and the different tools it has access to. So as we think about this agentic world, the context is important. And then all of the data that you're putting in there is really important. And then to your point around how does it impact the actual content we create — I think that's fascinating. I think yes, the answer is 100% it should. We should be creating different types of content that make it more readable for agents. I know there's a lot of people experimenting with this on the website side of things, like do I create my little agent reader that the agent should read? I think that's an interesting idea, but I think the same thing can apply to competition because the way you feed AI information can be more efficient in one way versus another.

But then at the same time, I'm like, humans are visual people. And B2B sales is relationship based and people like seeing something nice. They like seeing a little pitch deck or a nice side-by-side of competitors. And so it might just mean we need to do both — content that's more readable for AI and then the human version of it. But maybe there's a future where there's no humans, it's just AIs buying from each other and then the AI version is just good enough. So we'll see.

Eric Doty: Yeah, like the version we have right now internally at Dock is I've made a Claude Code competitor database. It's basically like I worked with Claude Code to make something that it could read — like, here's all the Dock features, here's our competitors' features. And then I'm using that as input to make the assets, but it's not like that information is in our content management system yet. Like that raw code database.

Alex Kracov: Yeah, it's not client-facing enough. It's more database-y.

Eric Doty: Yeah, I still want to have the editing layer of myself before I put that in front of our sales team. So I think that's kind of where we've landed for now, but maybe it'll change in the future — that information lives in the CMS or something like that.

How to Prepare for AI-forward Content Management

Eric Doty: And I think just the last question is — okay, you're an enablement leader looking forward for the next 12 to 18 months. What are some simple things that they can do to just sort of be prepared for this AI future of content management?

Alex Kracov: Yeah, I mean, the simple thing — which is not that simple, but it's the place to start — is your data pipeline. You've got to get all of this stuff into places where whatever AI you're using, whether it's Dock AI or Glean, Claude, whatever it is, you need to get all of that data together. And so that's your customer collateral, your calls, your deal room data, your CRM data. You need to get all of that together, and probably depending on how technical you are, you're going to partner with RevOps to do that. But that's the place to start.

And that's maybe tricky, but that's the real answer. And then I would say what enablement people need to be doing is just playing around with the new tools — playing around with Claude Code, seeing what's possible, playing around with Notion agents, playing around with Dock AI. Like there's a lot of cool possibilities and things aren't quite there yet, but I think things are evolving at such a fast pace that it's this fun time for experimentation and learning and figuring things out. And you also have to be okay that the way you set it up six months ago is different now. You just need to really have that beginner's mind around all this and just play around with things and see what model works. And no matter what model works, it's gonna go back to that data. So that's where you want to start.

Eric Doty: And it's nice because we're all beginners now. So it's like a fresh start on how to do all this stuff.

Alex Kracov: Yeah, totally. And that's where I think there's opportunity, right? It's opportunities for companies like Dock, opportunities for people in their careers. The old way you did enablement is really different. And so people who can figure this stuff out are going to rise really fast. So it's a fun time for people with that beginner's mindset.

Eric Doty: Perfect. Well, that's a great place to end on that inspirational note. Thanks so much everybody for listening to Grow and Tell and listening to us talk about content management for over half an hour — probably longer than anyone needs to. But thanks for listening.