One thing that came up repeatedly in recent conversations with both sales and marketing leaders is how much companies are struggling with sales enablement right now.
Not because organizations don't care about enablement. Most do. They know they need their teams to ramp quickly and speak confidently about the product, the market, and the competition. The challenge is that in today's startup environment, enablement and selling often happen in parallel. Companies need a pipeline moving immediately, while salespeople are simultaneously trying to absorb product knowledge, understand positioning, learn the competitive landscape, and figure out how to communicate value effectively in live customer conversations.
How Enablement Used to Work
Years ago, when a salesperson joined a company, they would typically spend a week or more going through onboarding material, training sessions, product walkthroughs, positioning docs, recorded demos, competitive battlecards, and certification exercises. At the end of it, they were considered "enabled" and sent into the field.
Today, especially in startups, the expectation is often that salespeople begin engaging prospects much earlier in the process while continuing to learn the product and market dynamics in real time.
That's not happening because leadership wants sales teams to fail. Quite the opposite. The pressure to hit growth targets simply creates an environment where every day out of the field feels expensive. The result, though, is that salespeople increasingly need to take initiative in their own enablement while simultaneously building pipeline and progressing deals.
What Breaks When Enablement Can't Keep Up
You can argue that this approach sometimes creates the exact problems companies are trying to avoid:
- Longer sales cycles
- Inconsistent messaging
- Weak competitive positioning
- Misaligned customer expectations
- Frustrated reps
- And eventually, churn inside the sales organization itself
This is one area where strong product marketing teams can have a huge impact.
In every PMM role I've held, I've either directly led enablement initiatives or worked closely alongside enablement teams. In both cases, part of the job was building the internal training material and customer-facing content sales needed to succeed.
But creating the content is honestly the easier part.
The harder part is making sure sales teams actually absorb the material, understand how to use it in live conversations, and feel confident applying it in front of customers.
Why the Traditional Model Is Breaking Down
There's no perfect formula for this, and even the best enablement programs will still have reps who struggle to stay current, especially in fast-moving markets. But I do think the traditional "90-minute enablement session followed by a content dump" model is becoming increasingly ineffective, particularly in remote-first environments where salespeople are simultaneously trying to manage pipeline, Slack, email, forecasting, and customer calls during training sessions.
The better approach, at least from what I've seen work well, is ongoing enablement built around shorter, highly practical interactions.
Not 100 new things every session. Just a few things salespeople can actually remember and immediately apply in the field.
What a Strong Enablement Cadence Looks Like Today
A strong enablement cadence today probably looks more like:
- Recurring conversational sessions
- Short, snackable competitive updates
- Concise customer objection handling
- Quick positioning shifts
- Live deal feedback
- Fast access to PMM and product teams when questions come up
It also means treating enablement as continuous, not something completed during onboarding.
Competitors change constantly. Messaging evolves. Market conditions shift overnight. New objections appear almost immediately after major announcements, acquisitions, funding rounds, or product launches. Sales teams need a way to continuously absorb those changes without feeling buried in content.
The Simplest Thing That Actually Works
One of the simplest yet most effective things organizations can do is maintain open communication channels among sales, product marketing, and product management via dedicated Slack or Teams channels, where reps can ask questions in real time and quickly get guidance from the people closest to the market and product strategy.
Those feedback loops become incredibly valuable, especially when the market moves fast.
Long story short, good enablement is no longer about information volume. It's about consistency, accessibility, reinforcement, and relevance.
And strong product marketers can play a much bigger role in that process than many organizations realize.