$5M ARR is a milestone worth celebrating. There's an enablement function. Reps are ramping. Content exists. Training happens on a cadence. That foundation is real — most companies at this stage don't even have it.

It's also exactly the moment where enablement gets to evolve into something bigger. The questions from leadership start getting more strategic. The GTM motion gets more complex. The opportunity in front of enablement shifts from supporting sales to designing how the entire revenue engine operates.

Here's what I've learned watching teams hit this moment: the unlock isn't about where enablement sits on the org chart. It's about what enablement is actually doing when it's there.

Let me say this plainly: the question of whether sales enablement reports to the CRO or VP of Sales is less important than the capability question not being asked. Structural authority — the kind where other functions actually defer to enablement on GTM process decisions — doesn't come from a reporting line. It comes from demonstrated capability.