Let's talk about Sales Enablement

I’ve been building sales enablement tools for years, so I feel qualified to say this: most “sales enablement content” is built for the wrong person. It’s built for the sales rep. Battlecards they reference before calls. Talk tracks they memorize. Internal training docs they skim during onboarding. Decks they present in demos. All useful. All necessary. All completely useless when the rep leaves the room and the buyer has to sell the deal internally.

Every sales rep has the same experience at least once a week: the prospect says “we’re also looking at [Competitor]” and the rep has to decide, in real time, what to say. The best reps handle this with confidence because they know the competitive landscape cold. They acknowledge the competitor’s strengths, articulate real differentiators, and plant questions that expose weaknesses without sounding like they’re trash-talking. The worst reps fumble. They say something vague like “oh, they’re a good company but we’re different because…” and then list three features that mean nothing to the prospect.

Revenue enablement is having a moment. Gartner’s talking about it. Forrester’s publishing frameworks. Every enterprise sales platform has rebranded from “sales enablement” to “revenue enablement” in their marketing copy. It sounds important. It probably is important. But the part nobody wants to talk about is the foundation that makes any of it work. Because I’ve watched companies spend six figures on revenue enablement platforms and then fail for a reason that has nothing to do with the platform.

I’ve seen a lot of sales playbooks. The good ones fit in your back pocket (metaphorically). The bad ones are 47-page PDFs that start with the company mission statement and end with an org chart nobody asked for. The thing about playbooks: the word itself is borrowed from sports, where a playbook is a collection of specific plays for specific situations. The quarterback doesn’t flip through the team’s founding story before calling a play.

There’s a workflow gap in every B2B company that nobody owns. Marketing creates content. They’re measured on traffic, leads, and brand awareness. They publish to the blog, send to the email list, and promote on social. Job done. Sales needs content. They’re measured on pipeline and revenue. They need case studies for specific deals, one-pagers for specific stakeholders, and competitive comparisons for specific situations. They need it findable in 30 seconds and shareable with tracked links.

I’ve sat through hundreds of sales decks. Most of them lost me by slide 3. Here’s the pattern: company logo, mission statement, “we serve 500+ customers”, a product screenshot that’s too small to read, and a pricing slide that shows up way too early. By the time you get to anything that matters, the prospect is checking their email. The best decks do something different. They start with the prospect’s world, not your product.

Every sales enablement tool now claims AI features. Every vendor’s website has an AI section with glowing promises about “intelligent content recommendations” and “AI powered insights.” Half of it is real. Half of it is the 2024 version of “we have machine learning”, which was the 2019 version of “we have big data.” Here’s my honest take on what’s actually delivering value, what requires way more investment than vendors admit, and how to evaluate AI features without getting sold a demo that doesn’t match production reality.

Let me save you some time. If you’re Googling “best sales content management tools” you’re probably in one of these situations: Your Google Drive / SharePoint / Box has turned into a content graveyard; folders nested in folders, outdated decks mixed with current ones, and your reps have given up trying to find anything You’re evaluating dedicated tools for the first time because your team just hit the size where “ask Marketing on Slack” stopped scaling You’re on an enterprise platform that’s overbuilt and overpriced for your team, and the recent PE consolidation has you rethinking All valid.

Let me tell you the real reason most B2B teams have fewer case studies than they need. It’s not because they can’t write. It’s not because they don’t have successful customers. It’s because the production process is broken. Here’s how it usually goes: Marketing identifies a great customer story. They ask the account manager to make an introduction. The AM says “sure, let me find the right time.” Three weeks pass.

Confluence: A great wiki, but not a sales content tool I get it. Confluence is already in your stack, your team knows it, and someone thought “why not just use it for sales content too?” Here’s why: Confluence is a wiki built for internal documentation. It’s great for process docs, meeting notes, product specs, and internal knowledge bases. It’s not great for the thing your sales team needs most; finding the right customer-facing content and sharing it with prospects in a way you can track.