We’ve reached an inflection point in sales enablement. What happens next?

We’re living in a world where change isn’t just fast, it’s relentless.

Product updates no longer roll out quarterly. They’re launched weekly, sometimes daily. AI isn’t coming; it’s already embedded into how we work, communicate, and sell. And your buyers? They’re evolving just as quickly.

Yet many enablement strategies still operate like it’s 2010.

• Long onboarding sessions.

• Static LMS courses.

• Quarterly refreshes.

It’s no wonder reps are struggling to keep up.

This was the conversation we sparked in a recent webinar on my book Just-in-Time: The Future of Enablement in a World of AI.

It wasn’t just a product webinar. It was personal. A look back on eight years building Spekit. A look forward to what’s possible. And a challenge to all of us in enablement to think differently.

Because speed isn’t a luxury anymore. It’s survival.

This all started with a journal.

I didn’t set out to write a book. It started on a solo trip to the Colorado mountains—a journal, a fire, and a question I couldn’t shake: Why does enablement feel so broken?

What began as notes turned into 56 pages of raw, unfiltered insight. I showed it to a few close friends. They said, “This needs to be a book.”

And here we are.

Just-in-Time wasn’t written to sit on a bookshelf. It’s a call to action for every revenue leader who’s felt the friction. Who’s tired of launching content that gets ignored. Who wants a better way.

Because the old playbooks? They’re broken.

Let’s talk about speed.

67% of reps missed quota last year. That stat still floors me. Even more staggering? Most reps don’t expect to hit quota this year either.

So when we say speed is the advantage, it’s not hyperbole. It’s the difference between growth and stagnation.

At ZoomInfo, reps were skipping crucial steps in their outreach. Valuable pipeline was leaking. With just-in-time enablement built into their workflow, they closed that gap and recovered that lost revenue.

At Equifax, a 100-year-old institution, we saw ramp time slashed and handling time cut nearly in half, all by surfacing the right information at the right moment.

That’s the power of frictionless knowledge.

The enablement gap is growing.

In a 2025 research report by the Sales Enablement Collective & Spekit, 92% of teams said their reps use less than 60% of the content available to them.

Let that sink in. You could be creating the most brilliant, beautifully designed playbooks in the world and your reps might never even see them.

Why? Because they’re buried. Or outdated. Or irrelevant to the moment a rep is in.

We’ve normalized this. We say, “Reps don’t use content.” But maybe the better question is, are we delivering it in a way that makes it usable?

We need a different approach. One that’s:

• Contextual

• Personalized

• Effortless

That’s what just-in-time enablement unlocks.

Enablement isn’t about memory. It’s about muscle.

The science is clear: disconnected learning doesn’t stick. When you train someone in January and expect them to remember it in May, you’re setting them up to fail.

Retention improves when learning is tied to action. That’s why just-in-time enablement lives inside the workflow, not outside of it.

Think:

• Guidance that pops up during a call

• Content that shows up in Salesforce

• Coaching that adapts to deal stage

Gartner found that organizations using just-in-time learning are 2.5x more likely to exceed revenue goals. That’s not a nice-to-have. That’s your competitive edge.

It has to be personal.

Two reps. Same training. Different outcomes. Why? Because they’re different people. Different learning styles. Different deal cycles.

AI makes personalization at scale possible. Not just for Netflix recommendations—but for onboarding, sales content, and even follow-up emails.

Just-in-time AI enablement means reps don’t just get content. They get the right content, based on:

• The deal they’re working

• The competitor they’re facing

• Their past performance

• Their unique learning curve

This isn’t about treating reps like robots. It’s about empowering them as humans.

Simplicity is a strategy.

We’ve accepted complexity in our tools for too long. Ten clicks to find a case study. Five systems to remember login credentials. It’s exhausting.

“Your reps aren’t lazy. They’re busy.”

If it’s not intuitive, it won’t get used. And if it doesn’t get used, it doesn’t matter.

Enablement platforms need to feel as seamless as Spotify. As responsive as ChatGPT. As easy as sending a text.

Let’s talk about content decay.

This one’s personal for me.

The number of times I’ve seen amazing content go unused—not because it wasn’t valuable, but because it was outdated, or reps didn’t trust it—it’s frustrating.

Only 35% of reps trust the accuracy of their org’s data.

That erodes confidence. It kills velocity. And it stalls deals.

We need dynamic content systems. Ones that connect to your source of truth. Ones that automatically flag updates, suggest improvements, and track usage in real-time.

The future of content is modular, measurable, and evergreen.

Playlists > Portals

Think about how we consume music. One song can appear in multiple playlists. You don’t have to go searching. It just shows up when the moment is right.

That’s the mindset shift we need in enablement.

Break content into reusable blocks. Surface it where it matters. Curate experiences that adapt based on the role, the buyer, the moment.

Because the goal isn’t “more content.” It’s the right content, delivered just in time.

The real measure of enablement? Behavior change.

Views don’t equal impact. Completions don’t equal confidence.

Did the rep use the content in a critical moment? Did it move the deal forward? Did it change how they showed up?

Just-in-time systems can measure that—because they’re embedded in the flow of work. They tell you who used the battle card, and when. Who ignored it. What content actually led to closed-won.

So what now?

If you’re in sales, marketing, customer success, or operations, this book is for you.

If you’re navigating change, building systems, or simply trying to keep up—this is your blueprint.

Just-in-Time isn’t about theory. It’s about action. It’s a call to rethink how we work, how we learn, and how we lead in a world of constant change.

You can grab your free copy here.

Because enablement isn’t a department. It’s a design challenge. And the future belongs to the teams who solve it.