How to Measure AI Impact

You can't connect AI to revenue until you know who's using it. Here's a framework for how to think about adoption and impact.

DEAR STAGE 2: I’ve rolled out a handful of AI tools to my sales team. People seem to be using them, but I can’t tell if it’s actually moving the numbers. How do I measure whether this is working? ~MEASURING AI IMPACT

DEAR MEASURING AI IMPACT: You’re asking the right question, but it’s hard to jump from “we’re experimenting” to “measurable ROI” overnight. Start by measuring adoption. You can’t connect AI to revenue until you know who’s actually using it, for what, and how often.

Last week I chatted with Liza Rothschild, Stage 2 LP and VP of Sales at Workday. Their entire GTM organization and her team are in the thick of solving this exact question.

Start With Adoption, Not ROI

Here’s how she’s handling it:

She pulls a weekly usage report on her team that covers prompt volume and time spent in the tools, by rep and by manager. She’s not reading anyone’s individual prompts, and she’s not using it to police. The point is to see where the activity is and surface what’s working, and identify where there are gaps so coaching can happen one-on-one. The second your team thinks usage tracking is a stick, they’ll either game it or resent it.

Then she does something unique: she makes the learning social. Once a month, her top performers share the specific prompts/agents/learnings that drove results, by use case (prospecting, live meetings, expansion). Those get packaged into “plug and play” prompts and campaigns the rest of the team can run without having to recreate or build on their own. This step means you’re not waiting for everyone to figure it out alone. You’re taking what your best rep already cracked and handing it to everyone else - it’s a motion that can scale across an entire team/org.

Sequence What You Measure by Funnel Stage

On what to measure, Liza recommends sequencing it by funnel stage. She started top-of-funnel, where the lift is easiest to see, and the work is most repeatable: building account lists, running look-back analysis, pulling renewal timing, drafting value cases. Get a clear read there before you push AI into the messier middle of the funnel (discovery, negotiation, close). Trying to measure everything at once is nearly impossible.

Early on, the signal is likely going to be soft. Her read after a few months of this was “seemingly a lift, but nothing’s blown out of the water.” That is normal. You don’t want to invent a precise ROI number to make a board slide look good. What she’s doing instead is running parallel testing through rev ops to define the real KPIs over the next few months, rather than forcing a metric before the data supports one.

AI Fluency Is a Coachable Skill

One thing I want to call out is that her top AI adopters are, almost one for one, her top performers. It’s a little chicken-and-egg (do the best reps adopt because they’re already curious and coachable, or does adoption make them better?), but the same pattern shows up elsewhere too. The reps who lean into AI are the same ones who show up to every enablement session, do the practice pitches, and sell the new product first. AI proficiency is just the next tool in the toolbox, so treat it like any other coachable behavior.

Why the Tech Stack Is Shrinking, Not Growing

One last observation from our conversation, and this is a trend I’ve seen across teams, Liza’s tech stack is shrinking, not growing right now. Contracts are consolidating, redundant features and use cases are being cut to ensure budget is freed up for new experiments, and they are often leaning into the AI features of established platforms first (think Gong v. startup GTM tech). The reasoning: data integrity and single-vendor accountability matter when you’re running real customer data through these tools.

Where we landed? Measure adoption before you measure impact, learn out loud from your best rep, sequence by funnel stage, resist forcing a premature ROI number, and treat AI fluency as a coachable performance behavior. Do that for a quarter, and you’ll actually know what’s working instead of guessing.

Until next week!