You know you’re fluent in a language when you speak with confidence and clarity—not because you know every rule, but because you can communicate what matters in a way others understand.

AI is no different.

Today’s go-to-market (GTM) landscape demands fluency, not familiarity. The leaders aren’t the ones who know the most tools. They’re the ones who integrate AI seamlessly into their sales process, their GTM workflows, their coaching, and their decision-making.

I often say: “We can’t measure AI proficiency in tool understanding or adoption. It’s about fluency—skills, a mindset shift, leadership to look around corners, and the ability to integrate AI into the sales funnel and holistic workflow.”

Yet, women—especially women in GTM roles—are using AI 10–40% less than men. Not because we don’t understand it, but because too many of us still think using AI feels like “cheating.”

Let me be clear: AI is not a shortcut. It’s a skill set. The only real roadblock is not using it.

Once you start incorporating AI as a habit—not a hack—you unlock something powerful: personalization at scale, deeper emotional insight, and the ability to see patterns, preferences, and possibilities long before your competition. We’re not here to write better emails; we’re here to leverage AI to make better connections. 

Below are three pillars for building AI fluency across your GTM motion, with real examples from several key use cases.

1. Identify Valuable Micro-Segments: Move Beyond Personas to Human Insight

Traditional segmentation tells you who you’re talking to. AI allows you to understand what they care about, and even more importantly, why.

Start With Values, Not Data Points

One of the most common challenges that go-to-market leaders face is outdated ICPs; they are often stale, identified by broad sweeping data and grouped based on demographics versus any needs.

AI can be a power tool in flipping how you identify and understand your customer segments. For example, Salesforce Agentforce can identify real-time deal insights based on dynamic needs, use cases and market conditions.

Connect that detail to other tools like LinkedIn Sales Navigator for persona refinement or ZoomInfo Copilot for intent signals and you’re leveraging the power of AI to quickly surface unique segments that have relevancy to both a customer need and their intent or stage within the customer journey.

Values-based segmentation moves you from broad personas to micro-segments that actually convert.

Build a Wisdom Library From Real Buyer Conversations

Mapping the buyer journey can feel overwhelming, but AI makes it manageable and meaningful. A tactic that I’ve seen work well for a lot of clients to move micro-segmenting into motion, is to augment customer profiles with a Wisdom Library. A wisdom library turns team knowledge into shared intelligence so every team can respond with precision, not guesswork. I call this “the insights between the words.” 

For example, you can leverage a tool like Gong to record and collect customer conversations at scale. Then, embedded AI can analyze those conversations and reveal critical attributes like buyer emotions, objections, tones, and motivations—the stuff “between the words.”

You begin to understand not just what buyers say, but what they mean. And when you can understand it, you can sell to it.

In a personal example, I was able to shift the entire tone of a prospect conversation just by understanding that a company’s culture was strongly grounded in the vision of the future—it was an emotion, a value and a mission for the company and the employees. That immediately shifted what I presented, how I presented and where I met them in their journey.

A best practice is to maintain your wisdom library in your internal communication tool, like Slack, so that it is readily available to all teams, can easily be updated and is open for team members to contribute to with new insights and learnings.

Use AI to See Around Corners With Scenario Modeling

Another common challenge for GTM leaders is forecasting with precision. Tools like Einstein Predictive AI and Agentforce are powerful AI tools that predict future outcomes and can suggest ways to improve outcomes. 

A key to making these tools most helpful for you is being able to write exceptionally good prompts. 

Pro Tip: You can ask an AI tool or LLM to help you write a better prompt, simply by asking, “What am I missing from this prompt?” “What else should I be considering?”

You can then turn those predictive insights into dynamic storyboards with resources like Gamma to create stories and messages that help you address customer pain points with fluency and accuracy. Now you’re not just identifying micro-segments—you’re understanding their future needs and preparing to meet them.

2. Reach Valuable Micro-Segments with Relevance at Every Touchpoint

Once you’ve identified your most valuable micro-segments, the focus becomes reaching them with precision, empathy, and immediacy. 

AI helps you tailor the how, when, and what of your messaging so every interaction feels intentional and relevant—across every channel.

Write Messages Based on How People Prefer to Communicate

Even within the same company or buyers group, the CFO is expecting a different message than the CEO who is expecting a different message than the business leader. Tools like Crystal Knows analyze communication and social styles so you can shape value-based messaging that resonates with individual stakeholders within the micro-segment. Different people consume different information in different ways and AI can help you execute that level of precision.

Personalize the Entire GTM Motion

Email is one channel of communication. Today’s shoppers reference on average 10 channels within the buyers’ journey. AI-powered tools can extend personalization to every part of your revenue engine:

• Text.com can help you deliver real-time chat and AI agents that answer visitor questions immediately.
  
• Mutiny creates personalized or account-based website experiences.
  
• LinkedIn Campaign Manager builds hyper-targeted micro-audience ad campaigns.

Measure Relevance, Not Just Activity

We’re past the era of spray and pray messaging, just like we’re past the era of tracking standalone vanity metrics. Every GTM dashboard, can now answer questions like the following:

• “How relevant is our message to this micro-segment?”
  
• “How long is it taking us to respond?”
  
• “Is our messaging still aligned across marketing, sales, and CS?”

In today’s era, relevance is the key to building trust, and trust accelerates revenue.

Pro tip: Native AI and analytics within your GTM enablement platform, like HubSpot or Highspot can help score message alignment across all GTM teams. This keeps your motion consistent, personalized, and effective.

3. Arming the GTM Team for Execution: Building Confidence, Skills, and AI Fluency

Even the best strategies fall apart if your GTM team isn’t equipped to execute. Only 1% of companies consider themselves mature in AI adoption, and just 38% have formal governance guidelines in place.

As leaders, we must change this—not by mandating tools, but by coaching fluency.

AI Coaching Should Be a Core Capability

Every team member can know how to prompt like a pro. One way leaders can establish a baseline for their teams is to encourage each person to ask themselves: What’s my superpower? Then, challenge them to figure out how to use AI to help them amplify it.

This isn’t an exercise in tool adoption or expertise. It’s an exercise in critical thinking on how to expand one’s strengths, to consider what could be possible beyond what is readily available—it innately encourages curiosity and exploration. AI fluency is not just a productivity skill; it’s a career accelerator, especially for women in revenue roles looking to lead, influence, and advance.

The result: Sellers become better storytellers. CS teams become stronger at pattern recognition. Operations specialists gain lightning speed to insights. Marketers become unstoppable at research and creative development.

AI becomes a multiplier—not a replacement.

Practice AI as a Team Sport

One of the most impactful and easy to execute practices that I learned to incorporate AI curiosity into a culture, is to try a challenge like: “Teach me something in five minutes using AI.”

Once a week, once a month, whatever the cadence appropriate to your team is, invite a team member to teach the group a new skill or new application of AI in five minutes. In a year you could have over 50 new tips, tricks or ways to amplify your team’s work, just by leaning into the curiosity and creativity of your employees.

This type of activity builds confidence quickly and lets innovation spread laterally across the team—not just top-down.

AI Fluency Will Define the Next Era of GTM Leadership

AI fluency isn’t about learning tools—it’s about expanding capability.

It’s confidence. It’s clarity. It’s connection. And ultimately, it’s a competitive advantage.

The leaders who thrive in the next era won’t be those who adopt AI. They’ll be the ones who are confidently fluent in AI.

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Cherilynn’s presentation on AI and Personalization, was part of the Women in Revenue members-only Mini-Series: 4 Ways Leading Women are Harnessing AI to Drive Go-To-Market Impact. 

Cherilynn Castleman is a globally recognized keynote speaker, Harvard instructor, and executive sales coach with over 300 years of Fortune 500 leadership under her belt. You can connect with Cherilynn at info@cherilynncastleman.com. 

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