Is sales content management an unsolvable problem?

TABLE OF CONTENTs

TABLE OF CONTENT

It's time we finally forgive our sales teams for low content adoption—and find a better way to share sales content.

Salespeople, I owe you an apology.

For years, I’ve watched sales reps ignore the content I carefully built, organized, and announced in Slack.

Of course, a few reps would react with party parrot emojis for emotional support. But then, nothing. Three months later, I'd be watching a call recording where the rep was still sharing last year’s deck.

Let’s just say my internal monologue was not charitable. I used to think sales reps were too lazy to read, stuck in their ways, or genetically predisposed to ignoring whatever comes out of the marketing department.

Over time, I’ve come to accept that not, in fact, a rep motivation problem. It’s a systemic problem. If it were purely a motivation issue, there would be evidence of at least a few reps at every company with high content adoption rates—but I've never seen it.

In Marketing and Enablement, we try to treat the symptom—better folder structures, a Slack channel for content updates, maybe even a dedicated CMS. But we’ve never really cured the underlying problem.

Alex actually started Dock because of this exact frustration. When he was VP of Marketing at Lattice, he got so fed up with reps ignoring content that he built a scrappy internal tool just to get assets in front of buyers more reliably. That tool eventually became Dock.

This article is absolutely not a pitch for Dock. But because Alex has been thinking about how to solve the sales content management problem for 5+ years now, I asked him what “good” content management looks like in 2026 and how enablement teams can finally solve this adoption problem (with AI?). Here was his advice.

Growth Bytes

Top takeaways:

Content adoption is a timing problem, not a laziness problem. Reps pull assets when a buyer asks a question—not before. Build for that reality, and you'll get more mileage out of everything you create.
Stale content is a business risk, not just a marketing pet peeve. When your collateral doesn't reflect your current product, customers feel bait-and-switched post-sale—and that shows up in churn before it shows up in close rates.
"Never shared" and "never viewed" are two different problems. Assets that were never shared point to a rep adoption issue. Assets that were shared but never viewed point to a content quality issue. Without analytics, you're guessing at both.
Sales deal rooms templatize the content-sharing problem. Instead of asking reps to find the right asset at the right moment, you pre-package it for them—and control what's current from one place.
AI is moving content management from search to suggestion. Improved AI search made content discovery a little easier—but AI recommending exactly what to send after a call, based on what the buyer actually said, is the next big leap.
Your data pipeline is the real prerequisite for AI-powered enablement. Before any AI tool can surface the right content at the right moment, it needs context—your collateral, call recordings, deal room activity, and CRM data all in one place.

Reps don't ignore content because they're lazy

Selling is supposed to be repeatable. A rep who has a pitch deck that works, a case study that lands, and a pricing doc that closes deals isn't being lazy—they're being efficient.

"You want sales to be coin-operated at a certain point and to feel very repeatable. That's a thing that every good company is striving towards." — Alex Kracov

The problem is that "coin-operated" and "up-to-date” are in constant tension. Reps don't go looking for new content unless something forces them to. And the thing that forces them is almost always a buyer question they can't answer with what they already have.

When a prospect asks, "Do you have a case study with another healthcare company?" or "How does your Salesforce integration work?"—it triggers a search or request for that content. Once that deal closes, they go back to the usual rotation.

This is the key insight for anyone building a content library: reps aren't browsing. They're reacting.

Which means the requests you get from sales—"we need a fintech case study," "we need a better security one-pager"—are actually a reliable map of the questions buyers are asking.

Build content around what buyers ask, not around what you hope reps will remember to share.

It also explains why announcing new assets in Slack doesn't really work. The mindshare isn't there until the moment demands it. You can't push content into a rep's workflow—you have to be there when the workflow creates the need.

The hidden cost of outdated collateral

Okay, but is this actually a real business problem—or just a marketing team pet peeve?

Alex's take: it's real, but it's slow to surface. Reps using six-month-old messaging can still close deals. Alex watched it happen at Lattice—reps running the old pitch, still winning.

The problem is that it eventually catches up, and the first place it catches up is in churn.

When your pitch doesn't reflect your current product, customers feel bait-and-switched post-sale. They bought what was described in the deck. What they got is something different.

That gap shows up in onboarding friction, support tickets, and renewal conversations.

The pitch deck is one of the few things in a sales process that's actually canonical. A rep can say whatever they want on a call. But the deck that gets shared with the economic buyer's boss—the one that gets pulled up six months later during a business review—that has staying power. Keeping it current matters more than most teams treat it.

"As the product evolves and your collateral doesn't really reflect what the product is today, customers might feel bait and switched. They might feel like what I bought is really different than what was talked about." — Alex Kracov

How content management breaks at every stage

Most companies go through roughly the same content management progression as the system scales and breaks down.

Stage 1: Tribal knowledge

In the early days, there's no content management at all. Founders are doing founder-led sales with a slide deck and one case study (if they're lucky).

Tribal knowledge works at this stage because only two or three people carry all the context in their heads. Nobody needs a system when everyone already knows where everything is.

Stage 2: The shared drive

When you hire your first real sales team, you suddenly need structure. The pitch deck gets formalized. Security docs become important. Case studies get built out.

Most companies solve this with a Google Drive folder or a SharePoint. It’s the right call for a while. It's free, it's familiar, and it doesn't require buying software.

But then the content library grows, with competitor battle cards, more case studies, and product-specific FAQs.

This is where the shared drive starts breaking in predictable ways.

Search is the first thing to go. You'd think Google would be good at searching Google Drive, but it turns out it's harder than it sounds when documents have similar names and search doesn't understand what's actually inside the files.

You also have no way to distinguish what's internal-only from what's external, or which draft is okay to send to a customer, or which version is current.

There's no governance or analytics, so you have no idea which assets reps are actually sharing or whether buyers are engaging with them.

The Google-to-Microsoft problem is also more real than people admit. If you're a Google shop and your customer is on Microsoft, sending a Google Doc link creates friction because they need an account just to view it. It's a small thing, but we’ve heard it hundreds of times now.

Stage 3: The wiki

Some teams graduate to a wiki tool to manage content—Notion, Confluence, etc.

It's a step up from a shared drive. It has better organizational capabilities, cleaner navigation, and is easier to maintain. For a while, it feels like the problem is solved.

But wikis have the same core limitations. Still no analytics. Still no governance around what's appropriate to share externally versus what's an internal draft. And still no connection to the moment a rep actually needs something—which is mid-deal, not while browsing Notion on a Tuesday afternoon.

Stage 4: The dedicated CMS

Once you buy a proper content management system, most of the admin problems go away. You get better search capabilities, more governance for internal versus external content, and the ability to organize assets by stage, persona, use case, etc.

But reps still don't use most of it.

The adoption problem doesn't go away just because the library is better organized. Reps still have to remember to go there, search for the right thing, and attach it manually—in the middle of a deal, under pressure, with a buyer waiting. The habit doesn't change because the tool changed.

There's also a structural problem with most CMS tools: they were built for sales, making Customer Success teams an afterthought. In a world where post-sale motions increasingly resemble pre-sale ones—new SKUs, expansions, renewals that require a full pitch—having your pre-sale and post-sale content in different places creates real gaps.

"The last generation of enablement was really focused on just the sales buyer. But then it just becomes a siloed system for sales, and customer success is just not as loved in those systems—and in a world where just as much revenue is coming from post-sale as pre-sale, it gets really challenging." — Alex Kracov

Deal rooms partially solve the adoption problem

Deal rooms solve the content-sharing problem differently than a CMS.

Instead of asking reps to navigate a library, you pre-package the assets that belong at each stage of the sales process into a deal room template. After the intro call, the rep doesn't have to think—they just duplicate the template and send it. The deck is in there, the case study is in there, and pricing is in there.

As Alex described it:

"Instead of having to deal with a thousand assets in a library, you can just think of—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."

It's less thinking for the rep, a better experience for the buyer, and because the templates are controlled by enablement or marketing, the content stays current.

The syncing capability is what makes deal rooms work better at scale. When I update our team's sales template, I can be confident that all of our active deals are looking at the most up-to-date version of our content.

An interesting outcome we didn’t necessarily expect is that our sales team at Dock is almost never doing one-to-one asset sharing anymore. They might share the odd one-off asset like a competitor comparison that isn't in the core template, but for the most part it's just "here's your deal room."

We didn't force that process on them—we still give reps the option of sending assets one-off. But the deal room just happens to be the path of least resistance.

Without analytics, you're guessing what works

Most content libraries have no usage data at all. You put something in, you have no idea if it ever gets used. You can only make educated guesses based on how often reps ask for things and anecdotes from the field.

A CMS (or deal room) with proper analytics gives you two things that change how you operate:

1. Rep usage data. Which assets are reps actually sharing? You can slice this by team, by segment, by stage, and see which case study is getting sent versus which one is collecting dust. A never-shared asset should lead to a few follow-up questions: is it never shared because reps can't find it? Or because they don't believe in it?

2. Buyer engagement data. Of the assets that do get shared, what are buyers actually looking at? I learned that buyers were watching our case study videos but not reading the written stories, so I prioritized creating one- to two-minute highlight videos for each case study instead.

The combination of the two is how you prune your library. Filter for assets that have never been shared, then ask why. Filter for assets that get shared but never viewed, then ask whether the asset is actually useful or just something reps send out of habit.

"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?" — Alex Kracov

What AI actually changes

The early wave of AI in content management was improved search: using ML to surface what's inside a document rather than just matching on the file name. That's largely table stakes now.

What's coming next is more interesting, and it falls into two buckets.

1. Agentic library management

Instead of clicking through menus to reorganize your content, tag things, archive stale assets, and audit what's being used—you prompt it.

"Show me everything with zero views. Archive them."

This changes the operational cost of maintaining a healthy library. The old way of doing it in tools like Highspot or Seismic often meant hiring someone whose job was basically library maintenance. That's going away.

2. AI-suggested content

This is the shift from pull to push. Right now, a rep gets off a call, has to remember that the buyer asked about pricing and security, then go find those assets and attach them manually.

With AI listening to call recordings—Gong data and meeting transcripts—the system can automatically surface those assets. "Bob mentioned he wants to see pricing. Here's what you should send him."

We've built an early version of this into Dock, and the directional shift feels right: the content library stops being passive storage and becomes more like a recommendation engine.

One big question I had is whether we’ll ever get to a world where sales decks are generated one-to-one for each buyer.

Alex says maybe, for some organizations. But the more likely landing spot will be something like marketing controlling 90% of the template, with AI filling in a handful of personalization variables—like the company name, an industry-specific case study, and relevant product features.

Despite some hefty marketing claims out there, the AI-powered content library isn't fully here yet. But for the AI-impatient out there, the prep work is straightforward: consolidate your data.

Get your customer collateral, call recordings, and CRM data in order. Whatever AI layer you eventually put on top of it—Dock AI, Glean, Claude, whatever wins—is only as useful as the context it has access to.

So, salespeople—I hope we're good now. The content adoption problem was never really about you. It was about the system we put you in. Better templates, better analytics, and eventually better AI are how we fix it on our end. All you have to do is hit your number.