I may have a minor professional obsession with sales enablement.
Probably because I’ve seen both versions of it: marketing teams producing hundreds of excellent assets, carefully organizing them into folders, and then wondering why sales can’t find anything. And I’ve seen enablement built around a much better question:
What does the salesperson need, at this exact moment, to move the conversation forward?
Those are very different operating models.
After working across technology, financial services and other complex sales environments, I’ve become convinced that the best sales enablement starts with a marketer’s mindset. Not what should we create? but what behavior are we trying to make easier?
I learned this early in my Dell days.
When you’re marketing technology to businesses, the product catalog can get complicated quickly.
Take something like a Latitude laptop. The obvious marketing approach is to give sales a product sheet, competitive comparison, presentation, customer story, promotional materials and enough specifications to make everyone involved question their life choices.
All useful.
But imagine you’re the salesperson and a small business owner tells you:
“We’re growing quickly. Half my employees travel, our laptops are getting old, and I don’t have an IT person to manage all of this.”
That’s not really a laptop conversation. That’s a business problem.
The salesperson needs to quickly understand the customer, identify the problem, connect it to the right solution and explain why that solution makes sense.
So good enablement works backward from that moment.
What questions should sales ask? Which solution fits? What’s the simplest way to explain the difference between options? What’s the likely objection? What proof point helps answer it? What should they send afterward?
Suddenly marketing isn’t just producing collateral for Latitude.
We’re helping design a better sales conversation.
That distinction has stuck with me throughout my career.
**Then I discovered **Highspot at Invesco.
And I loved it.
Full disclosure: I am not a Highspot influencer. No one is paying me for this. I just get unusually excited about organized marketing content.
Highspot solved one of those maddening marketing problems that sounds small until you’ve worked inside a large sales organization:
We could stop making salespeople figure out what was current.
Think about a large company. Multiple products. Different audiences. New campaigns. Constant updates. Compliance changes. Sales teams across markets. Marketing teams producing content from multiple directions.
Without discipline, your beautifully organized content library eventually becomes:
Which deck should I use? Is this approved? Didn’t we update this chart? Why are there three versions of this?
And my personal favorite:
“Can you just email me the latest one?”
At which point your sophisticated sales enablement strategy has become Molly emailing Bob a PowerPoint.
Highspot gave us a much better model.
Instead of expecting sales to understand how marketing organized itself, we could organize content around how sales actually worked. Current materials were easier to find, outdated versions could be managed more intentionally, and people could work with content inside a more controlled environment rather than constantly creating rogue copies.
That ability to update and work with content more dynamically matters too. The less often someone has to download something, rename it, edit it locally and send it back into the wild, the better your odds are that sales is actually using what marketing intended them to use.
And yes, this is where my inner brand-control person becomes very happy.
But the really interesting part was the data.
Content management was useful.
Knowing what happened after sales used the content was much more interesting.
Highspot can connect buyer engagement back into Salesforce records, which allows organizations to look at content views, downloads and other engagement alongside opportunities and influenced revenue.
That changes the conversation completely.
Instead of:
“We launched 37 new assets.”
You can start asking:
Did sales actually use them?
Did buyers engage with them?
Which content keeps appearing in successful opportunities?
Are certain materials showing up as deals progress?
Where are opportunities stalling?
Now we’re getting somewhere.
I would never claim that a PowerPoint caused a multimillion-dollar deal to close. Attribution gods everywhere can stand down.
But being able to connect enablement activity with opportunity data gives marketing a much better view of influence and behavior. Highspot itself describes using Salesforce data to understand which content is helping drive sales velocity and conversion.
That is a far more useful measurement conversation than counting downloads.
It creates a feedback loop:
Marketing creates something.
Sales uses it.
The buyer engages with it.
CRM data shows what happens to the opportunity.
Marketing learns from that behavior and gets smarter about what it creates next.
That’s when enablement stops being a content repository and starts becoming part of the marketing measurement system.
But Highspot wasn’t the strategy.
This distinction matters.
You can buy fantastic technology and still have terrible sales enablement.
Put 4,000 mediocre, outdated and duplicative assets into a sophisticated platform and congratulations:
You’ve created a beautifully searchable junk drawer.
The hard work still belongs to marketing.
You have to decide what sales needs, when they need it, what problem it solves and what you want them to do next.
Technology makes a strong operating model scalable.
It doesn’t create one.
Build around sales moments, not marketing assets.
Marketers naturally organize things by product, campaign and asset type.
Salespeople don’t necessarily think that way.
They’re thinking about the meeting tomorrow.
The competitor that just came up.
The objection they keep hearing.
The prospect who went quiet.
The customer who may be ready for another solution.
That’s where enablement should start.
For each of those moments, give sales the best few things they need.
Not 47 things.
A few.
If someone has to scroll through four pages of search results to figure out which piece marketing recommends, we haven’t really enabled them. We’ve assigned homework.
And not every salesperson or opportunity needs the same level of marketing support either.
Some situations warrant strategic partnership and custom marketing. Others need configurable campaigns, good training or excellent self-service.
The goal isn’t to make marketing available for everything.
It’s to make marketing incredibly useful for the things that matter.
Give content an expiration date.
This may be one of the least glamorous parts of marketing, but it matters enormously.
Every meaningful sales asset should have an owner. It should have a review date. And ideally, you should know whether anyone is actually using it.
If it’s outdated, update it.
If it’s performing, optimize it.
If sales keeps modifying it themselves, find out what they’re fixing.
And if nobody has touched it in a year?
Maybe it doesn’t deserve eternal life because six people spent three weeks creating it.
Archive it.
Otherwise, even the best enablement platform eventually becomes organizational archaeology.
And somewhere, somehow, a salesperson will still find:
FINAL_Deck_v7_ACTUALFINAL.pptx
They always do.
Measure behavior, not production.
“We created 200 new sales assets this year” isn’t a metric I’d get terribly excited about.
I’d rather know what sales is actually using. What are they searching for and not finding? Which materials consistently appear in successful opportunities? Where are people still creating their own content? How quickly can someone get from a customer question to the right answer?
Most importantly:
Is any of this helping us sell?
Because sales enablement isn’t a content factory.
It’s a system connecting customer needs, sales behavior, marketing expertise and business outcomes.
Dell taught me to think about the conversation.
Invesco showed me how technology could help scale it.
And years later, I still think the best test of a sales enablement system is remarkably simple:
Can sales find the right thing, trust that it’s the right thing and use it without calling marketing?
If yes, you’ve probably built something pretty good.
If they’re emailing you asking where the latest deck lives?
We have work to do.
