Inside HubSpot’s AI Fluency Playbook: How Kieran Flanagan Builds Teamwide Confidence, Fast
Kieran Flanagan, SVP of Marketing at HubSpot, doesn’t just see AI as a tool—he sees it as a transformative force for how go-to-market teams operate.
And his approach to building AI fluency isn’t about grand pronouncements or 10-year roadmaps. It’s about curiosity, velocity, and measurable experimentation—quarter by quarter.
In a recent conversation with Pocus, Kieran outlined a pragmatic yet provocative vision for how AI is reshaping B2B marketing and sales—and what it takes to build a truly AI-literate team.
A Two-Track Transformation: How AI Is Rewiring Teams and Talent
- On the team level: AI is already accelerating productivity across go-to-market functions—from automating prospecting to enhancing customer support and content creation.
- On the individual level: The shift may be most profound. According to Kieran, we’re entering a phase where AI fluency will become a core competency—not a nice-to-have. Roles that rely on speed, judgment, and creativity will increasingly favor those who know how to harness AI effectively. In many cases, AI-fluent employees aren’t just a bit faster—they’re operating at an entirely different level of output and leverage.
Forget 5-Year Plans—Think in Quarters
Kieran resists the temptation to build AI plans that stretch into the distant future. "I think in quarterly increments," he says. “The space is moving so fast that long-term planning feels naive. Instead, I look for short-term signals, test fast, and place deliberate bets where I see traction.”
This mindset shift—fast cycles over fixed roadmaps—is baked into how he structures AI initiatives at HubSpot.
The ‘Do and Deliberate’ Model
To enable meaningful AI adoption across teams, Kieran introduced a simple but powerful framework:
- Do: Encourage experimentation at the edges. Give employees access to tools like ChatGPT, host internal hackathons, and foster curiosity. “This is where the learning happens,” he notes. “The teams that play with AI daily are becoming significantly more productive than those that don’t.”
- Deliberate: Set company-level goals for AI adoption. HubSpot identifies a few high-leverage areas—like customer support or sales outreach—where AI can have measurable impact. They stand up small cross-functional teams, define KPIs, and track progress weekly. “It’s not an IT project. It has to be run like a growth experiment.”
AI in the Hiring Process
One of the clearest signs that HubSpot is taking AI fluency seriously? It’s now a factor in how they evaluate candidates.
“If I’m interviewing someone and they can’t name a single way AI might change their role—I won’t move forward,” Kieran shares. “You don’t need a portfolio, but you need curiosity. You need to be playing with the tools in your personal time.”
Beyond Cost Savings: AI as a Customer Experience Multiplier
While many companies talk about AI in terms of efficiency gains, Kieran starts with a different question: “Where does AI improve the customer experience?”
For him, that’s the true north. If AI can handle simple tasks, it frees up humans to focus on higher-order work—leading to better service, faster response times, and new revenue opportunities. “It’s up to the company whether to use those gains for efficiency or to reinvest in growth,” he explains.
Why This Matters for People and L&D Leaders
Kieran’s approach isn’t just for marketing leaders—it’s a blueprint People and L&D teams can learn from. His model isn’t about company-wide mandates. It’s about creating the conditions for curiosity, experimentation, and team-driven fluency to thrive.
Here’s how People leaders can adapt it:
- Codify fluency in hiring: Build a framework to identify curiosity in the hiring process.
- Encourage edge experimentation: Support hackathons and pilots across the org.
- Spot high-leverage teams: Identify where AI can improve productivity and experience
- Treat upskilling like product development: Start small, test fast, and scale what sticks
This is team-based fluency in action—and it works because it builds confidence where it matters most: in the flow of work.
