I've had this conversation dozens of times now. a revenue leader gets a referral. "she's great." "he's amazing." "they crushed it at [company]." and I don't doubt any of that. but great for what?

what stage are you? what does your motion look like? do you have PMF locked or are you still figuring out who you sell to? because the enablement person who thrives in one context can completely stall in another. not because they're bad. because the fit is wrong.

I think there are roughly four enablement personas, and most leaders hire without ever naming which one they actually need.

the charismatic creative. this is where I started. someone who energizes a room, facilitates well, builds experiential sessions that people actually remember. they love to do. they're often the person who makes SKO feel alive. but they work best when ICP, positioning, and PMF are already clear. hand them ambiguity and they'll build beautiful things on a shaky foundation.

the action-oriented analyst. they spot gaps. they can build the programs and trainings to close them. they're methodical, sometimes slower to move, but thorough. a strong fit when you have entrenched product value, systems that are already working, and you're beginning to scale what exists. less effective when the org needs someone to rally people around something new.

the verified vet. a former seller or CS professional with strong opinions earned in the field. they'll have immediate credibility with frontline managers and ICs, especially if they sold in your space or better yet at your company. but they often don't have the operational muscle yet. internal project management, stakeholder navigation, cross-functional complexity. that stuff is learnable, but they need real resources and mentorship to get there. don't just hand them the title and walk away.

the systems architect. someone who thinks in workflows, tools, and infrastructure. they're building the machine, not running the session. valuable when you're past the early chaos and need repeatability. less useful if no one has defined what good looks like yet.

the real question isn't "who's the best enablement person I know." it's which of these do I need right now. and which of these need to be full-time? some of this work is better scoped as a project with outside help. depends on your motion, your stage, your budget.

most leaders get this wrong not because they hire bad people. they hire the wrong persona for the moment they're in.

if you're thinking through your first enablement hire and want to pressure-test the fit, I'm always happy to talk through i

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