How Iterable VP of Product Marketing Gray Hardell Built an AI Sales Coach That Increased Rep Confidence by over 65%

Most PMMs want to support every important deal. The problem is that the more useful PMM becomes, the easier it is to become the bottleneck.

In this playbook, you’ll learn how Iterable’s VP of Product Marketing, Gray Hardell, built an internal AI sales coach to scale product marketing judgment across the field. The goal was not to create another content library. It was to give reps deal-ready access to the messaging, positioning, product context, proof points, and customer nuance they usually needed Gray to provide live.

But the biggest lesson was not about AI. It was about codifying PMM judgment.

You’ll learn how Gray mined repeated sales questions for product requirements, turned product and business context into modular context packs, tested the tool against real deal scenarios, drove adoption through selective access, and connected usage back to sales outcomes.

The early signal: when the tool was used, Iterable saw 42% faster sales cycles, a six-point higher win rate, and more than 65% of reps report higher confidence across AI POV, roadmap, and messaging.

If you’re trying to scale PMM support without joining every sales call, this playbook gives you a practical blueprint for turning your field knowledge into an AI coach reps can actually trust and use.

The project started because I was spending too much time on individual deals.

That was a good problem. Reps trusted me for product context, proof points, messaging, roadmap nuance, and help applying those details to specific customer situations.

But the more useful I became to Sales, the more I became a bottleneck. The business needed my focus on broader GTM initiatives, not just one deal at a time.

I needed to build a way for the field to get that product marketing context without waiting on me.

The project touched more teams than I expected. I needed input, validation, adoption, or operational support from:

• Competitive Intelligence

• Product Management

• RevOps

• Marketing Ops

• Customer Success

• Sales / Revenue leadership

• Field reps across Sales and CS

• Executive sponsors, including my CMO and CEO

• IT / internal systems support for API access and tooling

That cross-functional spread mattered because the agent had to work for the real field motion. If it only worked for one type of rep, one segment, or one use case, it would not scale.

The goal was to increase sales efficiency. I wanted reps to get faster answers, move faster within deal stages, use better assets, and apply consistent messaging and positioning without waiting for me to join a call or build something custom.

I also wanted the work to be measurable. "Reps like it" was not enough. I needed to know whether the agent was helping with sales cycle time, win rate, confidence, closed-won and closed-lost patterns, and ACV.