You’re segmenting wrong (and it’s costing you)

ARR is NOT your strategy

Kelley’s view on segmentation? It’s not just about slicing customers into big, medium, and small. That’s a starting point… not a strategy.

At Vitally, she’s built out two segmentation models:

1. Operational segmentation: Think cost-to-serve, ARR, support needs, complexity. This is the finance lens, and yes, Kelley started her career as a controller before jumping into CS.

2. Engagement segmentation: Based on how customers want to work with you. Are they regulated or not? Are they a RevOps admin or an exec buyer? Do they want self-serve tools or 1:1 guidance?

Why does this matter? Because your enterprise champion and your startup IC do not want the same thing from you.

And more importantly…they shouldn’t get the same thing from you either.

Scale doesn’t mean spam

One of my favorite takeaways from Kelley’s team? Segmentation fuels automation.

Here’s how they do it:

1. They segment based on who the user is (IC, admin, exec).

2. They map each cohort to a value-driving feature.

3. Then, they send tailored playbook-driven messages from the CSM that speak to the WIIFM (what’s in it for me) for that person.

Same message? Nope.

• For the IC: “Here’s how I use this feature in my day-to-day.”

• For the leader: “Here’s how it shows up in your dashboard.”

• For the admin: “Here’s how to build a repeatable process.”

And guess what? It landed. They re-engaged ghosted customers with just one personalized message, sent at scale.

That’s the difference between doing segmentation and using segmentation to scale value.

The future is AI-powered (but still personal)

Segmentation is evolving fast, and AI is about to supercharge what’s possible.

Kelley shared how AI will soon:

• Predict segmentation models based on ARR, engagement, and forecasted growth

• Pull sentiment from every call so you know which champions are referenceable

• Automate playbooks based on user behavior and role-level nuance

The coolest example?

Her CSMs ghostwrite exec emails that Kelley can quickly personalize and send, so she’s not the bottleneck, and the customer gets a high-touch moment that actually matters.

That’s AI + segmentation done right. It’s not about blasting 10,000 customers. It’s about using data to craft the right message at the right time…for the right person.

And for those of you thinking, “This sounds great, but we don’t have that data,” Kelley says, just start with one feature. Identify a moment that delivers value. See who’s using it, who’s not, and build from there.

3 Takeaways

1. Segmentation is about strategy, not size

Start with ARR if you must, but evolve fast. Segment by goals, industry, maturity, and engagement preferences.

2. Personalization still scales

Use automation to amplify your team, not replace them. Speak to the person, not the persona.

3. Start simple

Pick one sticky feature and target non-users. That’s your entry point to smarter segmentation.

This episode with Kelley Turner is a must-listen for CSMs, CS leaders, and anyone trying to scale without losing that personal touch.

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Anika

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