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 trigger

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.

Key internal stakeholders

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.

Goal

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.

About this Playbook

In this playbook, you'll learn how Chris Hines used the Unicorn Framework to turn Cyera's messaging from a product-centered story into a customer-challenge-led GTM motion that Sales could actually use to create pipeline.

The playbook walks through the full process: how Chris created a brand line grounded in customer evidence, mapped the highest-urgency pains in the market, connected those pains to product proof and customer outcomes, and turned the strongest opportunities into power plays with account lists, SDR scripts, AE one-pagers, outreach copy, and CRM tracking.

The result was more than cleaner positioning. The framework gave Sales, Marketing, Product, partners, and leadership a shared operating model for deciding what Cyera should be known for, which customer problems deserved focus, and how to turn that focus into meetings and pipeline.

That GTM motion helped Cyera grow from 200 people and a $1.4B valuation to 1,500 people and a $9B valuation in under two years.

Who is this for

This playbook is for GTM leaders and PMMs who need to define or refresh messaging in a way that aligns company strategy with sales execution. It will be especially useful if your team is hearing things like:

• "We need to grow our Total Addressable Market (TAM)."

• "We need to move beyond a narrow product category."

• "Leadership wants clearer positioning."

• "Sales is not using the messaging."

• "Our product story is too feature-led."

• "We need to connect product capabilities to customer outcomes."

• "We have too many messages and don't know what to prioritize."

What you will learn

• How to create a brand line customers believe—and leadership aligns behind

• How to turn customer pain into differentiated messaging backed by product proof

• How to convert messaging into sales plays, enablement, and measurable pipeline

About This Playbook

DocuSign provides electronic signature technology and digital transaction management services. With a workforce of approximately 6,000 employees, they have established themselves as a leader in their industry. Serving over one million customers, DocuSign enables individuals and organizations to securely sign, send, and manage documents digitally, revolutionizing traditional paper-based processes. Their innovative platform has generated annual revenues reaching $1B.

In this playbook, I will share a story of my time at DocuSign (my previous employer) about how our team effectively boosted adoption rates by 50% and created stickiness through a diversified product and content marketing strategy. Targeted towards developers, our diversified campaign aimed to maximize engagement and drive widespread usage of DocuSign. By sharing our strategies and tactics, I will illustrate the impact of our focused approach on developers across all business segments, from SMBs to enterprise.

Who this is for:

While this is an example of Developer Product Marketing, this playbook is targeted to any PMM that is looking for insights and strategies to create a user-led, storytelling focused, marketing plan. As a part of the playbook, we’ll also cover how to align internal teams and secure buy-in from stakeholders, while developing a comprehensive marketing plan that caters to different user segments.

What you will learn:

• How to conduct research and analyze data for a diverse product marketing approach.

• Strategies for gaining buy-in from cross-functional teams and securing resources for execution.

• The importance of mapping the customer journey and understanding different user personas.

• How to tailor your messaging and content to meet the immediate action-oriented mindset of developers.

• How to provide tangible value and relevant information to developers.

• Methods for addressing the diverse needs of developers.

• How to adopt a drip delivery approach and focus on relevant channels and materials in developer marketing.