“One of our salespeople keeps going rogue, and I’m doing all I can to reel him in,” shared a seasoned CMO at a tech startup. While the other CMOs in the Huddle offered guidance on gaining alignment, it made me wonder: Is it time to completely rethink Sales Enablement?

The problem isn’t just rogue reps. It’s a system that encourages chaos. One CMO shared, “We’ve got great messages that resonate, but Sales Enablement says it’s the wrong time to share them.” Another noted, “Product is producing substandard collateral because Sales went directly to them—cutting Marketing out of the loop entirely.”

It’s no wonder CMOs are frustrated. We build slick decks and elegant one-pagers—yet Sales clings to a 2019 slide with the wrong logo. We set up portals, and no one logs in. We host training sessions, and still get last-minute Slack messages: “Hey, do we have a case study for a mid-sized healthcare firm in Ohio?”

So what’s a savvy CMO to do?

1. Understand Your Rogues

Before condemning, listen. The rogue rep in question was closing deals—but not the kind you’d want. It turns out he was winning on price, undercutting the value proposition and increasing churn. As one CMO put it, “They don’t talk about our real differentiators—just a three-month discount.” If you don’t know what’s being said on sales calls, you can’t fix the funnel.

2. Collaborate, Don’t Dictate

Rather than fighting every deviation, smart CMOs co-create. One suggestion: “Treat the rogue like a partner, not a problem.” Pull them in. Learn what’s working. Then use that to shape flexible messaging frameworks—ones that adapt to buyers without fracturing the brand.

3. Think Co-Creation, Not Vending

Often, the problem isn’t the quality of the materials—it’s the disconnect between what Marketing thinks reps need and what Sales uses. As one CMO admitted, “We created great sell sheets—but one rep told me he never looked at them.” Why? Because they didn’t fit how he sold. Instead of assuming what Sales needs, ask. Sit in on calls. Shadow top performers. Then tailor your materials around real objections, use cases, and buyer personas.

4. Build Smart Systems, Not Static Assets

Sales enablement isn’t about creating more slides—it’s about architecting systems that drive revenue. From AI-powered content recommendations to dynamic digital deal rooms, today’s toolkit can turn random acts of enablement into precision plays. (Need ideas? See link in comments.)

5. Let Sales Be Sales—but Keep Score

Sometimes, the best way to prove the value of your materials is to put on your own sales hat. One CMO noted, “I started running a few calls myself to pressure-test the content.” Another shared, “We gave the events budget to Sales, along with the accountability. That ended the debate quickly.”

Bottom Line

Sales Enablement in 2025 isn’t about policing rogue reps. It’s about empowering the entire team—Sales included—with tools, insights, and guardrails that elevate performance without squashing initiative.

Written by Drew Neisser