Enable salespeolpe with AI like an Optiversal PMM

Sales enablement only looks like a messaging problem when you’re standing too far away. Up close, it’s usually something else. A missing strategy. No feedback loop. Training that happens once, then disappears into the void. Reps doing their best with whatever they can remember, while the business wonders why deals keep stalling in the same places.

I recently sat down with Michele Nieberding, a product marketing leader who’s been in the trenches of enablement transformation. She shared what it looked like at Treasure Data when enablement wasn’t driving outcomes, and how she rebuilt it into something that actually changed sales behaviour and improved results.

Step 1: Spot the Signals

Most teams wait for revenue to slip before they admit something’s off. Michele’s point was that the earlier signals are usually already there. The pipeline starts looking uneven. Certain stages become a graveyard. Losses cluster around the same objections. Deals drag longer than they should.

The first move isn’t “rewrite the deck.” It’s diagnosis. Where exactly are deals going cold, and what’s consistently happening right before they do?

Step 2: Talk, Listen, and Build a Hypothesis

Michele stressed that you can’t fix enablement from a spreadsheet alone. You’ve got to talk to reps and actually listen, not in a performative “what do you need?” way, but with questions that get to the real friction. What are they hearing in calls? Where do they feel shaky? What do they avoid because it’s too hard to explain?

From there, you build hypotheses. Not “messaging is bad,” but “we’re losing deals at this stage because reps don’t have a confident way to handle this objection,” or “we’re not creating urgency because the value story isn’t landing in the first two minutes.”

That’s the difference between enablement that feels busy and enablement that changes outcomes.

Step 3: Experiment With Purpose

Michele’s transformation wasn’t one big launch. It was a series of experiments designed to reinforce learning and make it stick. She tested different formats, including internal podcasts, AI-supported tools, and role-play approaches that helped reps practise in a low-stakes environment.

The throughline was simple. One-off trainings don’t work. Repetition does. Reinforcement does. And feedback loops that show reps what “good” sounds like, and why it works, are what actually change behaviour.

Step 4: Measure, Celebrate, Repeat

Enablement only earns trust when it’s measurable. Michele focused on tracking impact and evolving the program based on what the data and the field were saying. Even small improvements in cycle time or stage conversion mattered because they proved the system was working.

The goal isn’t a perfect enablement program. It’s a living one. Something that keeps getting sharper as the product, market, and sales motion evolve.

Messaging Critique: ClickUp

To close out our conversation, we shifted into the messaging critique and looked at ClickUp. Their positioning is bold, with “Every app, every team, unlimited AI Agents” but the trade-off is clarity. When you try to be everything to everyone, it can get harder for a specific buyer to quickly understand why you are the best choice for them.

The reminder here is simple. Big positioning still needs sharp edges. The broader your promise, the more important it is that your messaging quickly anchors on a clear use case, a clear outcome, and a clear reason to believe.

Michele’s conversation is a good reminder that great enablement is not about producing more content. It’s about changing what reps do in real conversations, and building a system that keeps improving over time.

LINKS:

Messaging Critique: ClickUp

Connect with Michelle
LinkedIn:
https://www.linkedin.com/in/michele-nieberding/


Connect with Elle:
LinkedIn:https://www.linkedin.com/in/elle3izabeth/

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