Why the sudden shift in sales enablement?

The most significant change I’ve seen in my career is a fundamental shift in how we think about enablement jobs. We no longer focus on imparting knowledge months in advance. Rather, our purpose is to drive enablement and productivity in the moment. This real-time shift is being driven by AI, and it’s reframing enablement’s contribution to revenue organizations.

Now consider that enablement is simultaneously being reshaped by two powerful external forces: relentless competition with the attention economy and the dizzying tool tornado. Understanding and adapting to all these changes isn't just about staying competitive; it's about survival and growth.

How should you respond? We built our successful strategy around the tactics outlined below.

Our collective attention span has shrunk dramatically. I see it in myself, in sales reps, and in customers. It’s affecting how we enable our sales teams, and is a primary external force in the sales enablement world.

For example, I used to think about training as a hammock: You start off with a good level of interest, dip into a relaxed learning phase, and then rise for a “wow” moment at the end. That hammock used to stretch over a one-hour training course, then a 30-minute one. But now, even snackable content needs constant bursts of energy to keep people engaged.

This means rethinking how we design everything from customer demos to internal training sessions. We strive to create magic with unexpected dashes of humor, compelling visuals, and relevant pop culture references. (Taylor Swift figures prominently!) These aren't superficial additions. They're strategic interventions designed to momentarily break cognitive patterns, re-engage attention, and make information stick.

The second force — what my team named “the tool tornado” — is a whirlwind of new technologies, each promising to be a one-stop solution. It’s overwhelming. Teams suffer from technology fatigue, and are constantly asking if one tool is better than another, or wonder if we should use an all-in-one ecosystem or a collection of 20 purpose-built tools. These types of questions can lead to decision paralysis.

I’m on the Customer Advisory Board at Gong, where we all agree that generic AI and disparate solutions aren’t the solution. We can't let our teams get distracted by “tourist traps” that look good and take us nowhere. AI needs to be unified and customized to give your workflows a real boost.

My goal, therefore, is to simplify this situation by promoting a more unified environment, then building pipes and writing custom components so our managers can self-create custom content, like playbooks, quickly.

We also spend a lot of time thinking about our sellers and where they start their day. We want to ensure that they're using their core systems effectively without getting lost in a labyrinth of applications. We work hard to promote technology that feels like real-time GPS, not print outs of MapQuest, so they’re intuitively guided to the best use of their time.

(In the interest of time-savings and focusing where it matters most, my team recently spent an hour recently writing our “not-to-do list,” and it’s been brilliant for refocusing our attention. It’s an exercise I’d recommend as it allows you to say no so you can also says yes to your most strategic and most important work.)

To counter these external pressures, our internal enablement strategy is built on two pillars: a solid organizational structure and a focused approach to measurement.

The best thing we’ve done structure-wise is organize our enablement team around the lifetime value of the employee. Our mission is to shorten ramp times, extend tenure, invest in advanced skills, and make every employee more effective and productive. This unifying mission makes every decision clearer.

When it comes to measurement, we rely on the four-level Kirkpatrick model:

• Level 1: Reaction. How did reps feel about the content?
• Level 2: Learning. Did they acquire the knowledge or skill? Are they certified?
• Level 3: Behavior. Are we seeing the desired changes in action? (The Gong Revenue AI Operating System is our go-to for checking in on this.)
• Level 4: Impact. Are the changes affecting our targeted business metrics?

A word of caution if you use this model: Resist the urge to measure everything. Your strategy should be simple enough to write on a napkin, and three to five critical metrics are all you should need to focus your work.

Underpinning all of this is the critical foundation of trust. While everyone wants high-trust, high-performance teammates, an HBR study showed that in high-stakes environments, high trust, even with lower performance, is preferred over low trust, high performance. Why? Because trust creates psychological safety.

On our team, we aspire to be a “greenhouse” — a place where people can grow, be their best selves, and handle the "fertilizer" (constructive feedback) because they know it's coming from a place of genuine care.

In this rapidly evolving landscape, these are the strongest ways for an enablement team to thrive. Being smarter, more agile, and deeply connected is how we empower our sellers to perform at their highest level, despite sales' new reality.