Why Most Sales Enablement Fails (And What to Do About It)

Here’s a hard truth I’ve seen play out at multiple startups: You can have a solid go to market plan, a clear message, a strong product, and still fall flat because your sales enablement didn’t deliver.

Most teams treat sales enablement like a checkbox. Something to package up at the end of a launch. A few one-pagers, a new slide or two, maybe a quick Loom. Done.

But sales enablement is not just another launch deliverable. It’s one of the final levers that determines whether your entire GTM motion succeeds or stalls out.

If your enablement isn’t driving the right conversations, or worse, isn’t being used at all, it doesn’t matter how polished it looks. It failed.

And more often than not, it fails because product marketers don’t treat it with the same care they give to things like positioning or messaging. That’s a mistake.

Sales Enablement Isn’t Just for Sales

The first problem? Product marketers often think sales enablement is someone else’s domain. After all, Sales has their own leaders, their own metrics, their own language. There’s a level of protection around Sales that can feel intimidating, especially at companies where every sales motion is being watched by leadership.

But here’s the reality: if you’re driving the GTM strategy, you can’t afford to hand sales enablement off like a side project.

You need to approach it the same way you would approach any other core PMM initiative. That means:

• A/B testing sales materials

• Validating them in the field

• Layering in the voice of the customer

• Tracking whether they’re being used, and if they’re helping close deals

Sales enablement is not an asset drop. It’s an ongoing conversation.

My Framework: Sales Enablement as a Three-Way Dialogue

Most enablement strategies treat it like a handoff between Product Marketing and Sales. But the best enablement happens when you design for three parties at once:

1. What Sales says they want
   Sales will always have opinions on what works: listen to them. They’re closest to the objections, the nuances, the deal momentum. But don’t stop there.
   

2. What Product Marketing wants the sales process to communicate
   You’re responsible for shaping perception. You know how the product should be positioned, what differentiates it, and where the messaging needs to land. Your input should shape the narrative architecture behind every asset.
   

3. What the prospect actually needs to hear to feel confident and convert
   This is the piece that often gets overlooked. Sales and PMM might both agree on the best talking point, but if it doesn’t address the prospect’s buying concerns or internal objections, it won’t matter.
   

This three-way collaboration helps you move past a one-size-fits-all approach. It’s not about building one perfect deck. It’s about creating a toolkit that adapts to the messy, unpredictable, non-linear nature of real sales cycles.

The Sales Journey Isn’t Linear. Your Enablement Shouldn’t Be Either.

Here’s where most sales enablement falls short: it assumes the deal flows cleanly from awareness to interest to decision.

But in reality, deals branch out in infinite directions. Demos get rescheduled. Budgets get cut. Procurement slows down. New stakeholders show up mid funnel.

If your only asset is a pitch deck, you’re asking Sales to do a lot of heavy lifting.

That’s why I always build enablement with range. Tailored content for different steps in the funnel, and different deal scenarios.

• Short-form videos for cold outreach

• One-pagers that speak to specific use cases

• Competitive cheat sheets for objection handling

• Case studies that map to verticals or company sizes

• Personalized landing pages for high-priority accounts
  

You want your reps to have options. Because the best asset is the one that gets used in the moment it’s needed, not the one sitting in a Google Drive folder no one opens.

Real Example: Enablement as a Scalable Touchpoint

At one B2B enterprise I worked with, we were pivoting a legacy product into a self-service SaaS solution. It was a brand new motion for the sales team, especially for the rep assigned to this single offering.

We wanted to drive adoption through a self-service model, but still give early users a sense of white glove treatment. The challenge was doing that at scale with a small team.

So we built a suite of sales enablement assets that could be lightly personalized for each prospect, creating a high-touch feel without manual lift. Email scripts, follow-up sequences, intro decks, demo frameworks, all prepped with modular content the rep could tailor on the fly.

It worked. The early sales cohort hit their targets. And more importantly, those assets became reusable across future cohorts, helping build momentum instead of burning it.

Don’t Phone It In

Sales enablement is the last mile of your product marketing strategy. It’s where your positioning, your narrative, and your go to market thesis get tested in the wild.

If you treat it like a handoff, you’ll lose that moment.

If you treat it like a dialogue, something to co-create with Sales and calibrate with the prospect in mind, you give your team the tools to close.

And when that happens, the entire GTM motion starts to work the way it was meant to.