By Rob Kall, Co-Founder & CEO, Cien.ai

“Skills multiply in Sales — you don’t have to be excellent in every single one to be an over-performer, but if you are a 0 in one or two, you will always struggle.”

– Rob Kall, CEO & Co-Founder, Cien.ai

Why Is This Still So Hard

Sales performance remains one of the most opaque areas in modern RevOps. Why are some reps consistent superstars while others never ramp? What separates a promising new hire from a struggling one? And how do you even begin to measure skills like discovery, closing, or time management — let alone track improvement over time?

For too long, answering these questions has relied on tribal knowledge and elite coaching. Fine if you have it, but hard to scale. There hasn’t been a fair, objective, and repeatable way to measure individual rep skills across an entire team.

Until now.

Measuring Skills with AI: A Better Way

The core idea is simple: break each sales skill into measurable KPIs, then compare reps’ results in context to their peers. Sounds easy, but in practice, it’s full of landmines.

Take “closing ability.” Say Rep A has a 40% win rate and Rep B closes only 30% of their deals. Who’s the better closer?

It depends.

If Rep A is working easy-to-win renewals and Rep B is chasing tough, strategic new logos, the raw win rate doesn’t tell the whole story. With AI-powered propensity modeling, we can estimate the expected win rate before the deal even starts. If Rep A’s deals were expected to close at 50%, and Rep B’s at 20%, then Rep B is the one actually outperforming expectations.

That’s true skill — and now, it’s measurable.

At Cien.ai, we score reps only when there’s enough data to be statistically meaningful. This prevents misjudgments and allows for objective benchmarking across the team.

What Does Success Look Like?

With Cien.ai’s GTM analytics suite, once your CRM data is cleaned and standardized, we apply AI-driven KPIs to assess reps across six core dimensions:

• Work Effort: Are they spending time on selling, or getting lost in admin?
• Engagement Ability: Can they get prospects to reply, meet, and pick up the phone?
• Time Management: Are they prioritizing the best deals and activities?
• Discovery Skills: Can they uncover pain and align it with your product?
• Deal Maximization: Are they consistently expanding the scope and value of each deal?
• Closing Ability: Can they win, especially when the odds are against them?

These skill scores allow RevOps and sales leaders to track performance and progress in a way that’s actionable, fair, and trust-building using the latest AI. When you do, you can unlock tremendous value.

About the Practical RevOps Analysis Series

This article is part of our Practical RevOps Analytics Series, inspired by our work with B2B business leaders, growth consultants, and PE operating partners. These articles focus on the technical aspects of improving GTM performance. For business-focused strategy content, check out our companion series, Growth Essentials Series.