The Future of B2B Marketing with Kieran Flanagan
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier, joins Dave to discuss how AI is fundamentally reshaping B2B marketing. The conversation explores practical AI applications, the evolution of marketing teams, and how creative professionals can thrive in an AI-driven future. (15:48) Kieran emphasizes that successful marketers must position themselves at the extremes – either becoming highly technical with AI implementation or doubling down on creativity and storytelling. The discussion covers everything from prompt engineering techniques to the changing role of CMOs in smaller, more autonomous teams.
- Main themes include AI's impact on B2B marketing workflows, the shift from "answers to actions" in content strategy, and how marketing teams will become smaller but more capable through AI augmentation.
Speakers
Kieran Flanagan
Kieran is SVP of Marketing at HubSpot, where he leads a marketing team of 300+ marketers globally, and former CMO at Zapier. He's known for his expertise in AI marketing applications and operates on two-year mission frameworks, having led various transformational projects including HubSpot's international growth, PLG transition, and AI transformation initiatives.
Dave Gerhardt
Dave is the host of B2B Marketing and founder of Exit Five, a private community for B2B marketers. He's known for his expertise in creative marketing, storytelling, and copywriting, having previously worked at companies like Drift and HubSpot.
Key Takeaways
Pick Your Lane: Technical vs. Creative
Kieran emphasizes that marketers must choose to excel at either the technical side of AI implementation or the creative storytelling side – the "messy middle" of being "good enough" at both will become problematic. (38:39) He suggests marketers should think like engineers when deploying AI across workflows while also being at the outer edges of creativity for ideation and storytelling. This isn't about being average at both; it's about being exceptional at one while having competency in the other. For example, a creative marketer might use AI for technical execution but lead with their unique perspective and storytelling ability. The practical application involves auditing your current skill set and deliberately investing time in becoming exceptional at your chosen specialty while using AI to augment your weaker areas.
The Death of Informational Content
The traditional B2B content strategy of creating "10 best tools" listicles to capture search traffic is becoming obsolete as buyers move from seeking answers to taking actions. (28:53) Kieran explains that by 2027, Gartner predicts 95% of buyer journeys will start in LLM assistants rather than Google searches. Instead of researching "how to create Facebook ads that convert," buyers will simply ask AI to "create Facebook ads that convert" – moving directly from problem to solution. This shift requires marketers to focus on awareness and attention-grabbing content rather than informational SEO plays. Successful marketers will need to create content that builds trust and authority in channels where personal brands thrive, like podcasts, newsletters, and social media, rather than hoping to rank for informational keywords.
Custom GPTs for Prompt Mastery
Rather than trying to memorize perfect prompts, Kieran creates custom GPTs trained on different prompt methodologies and frameworks that can generate prompts for specific outcomes. (42:06) His approach involves finding successful prompt frameworks (like when Cursor's system prompt leaked), distilling the core learnings, and training custom GPTs to apply those learnings to marketing scenarios. For example, he can ask a custom GPT for "a campaign that should be quirky, thirty days, and generate 100 customers," and it will craft an appropriate prompt using proven methodologies. This approach treats prompting like building a swipe file – constantly collecting and systematizing what works. The practical application involves creating custom GPTs for different marketing functions (content creation, campaign planning, analysis) and continuously updating them with new frameworks you discover.
Push and Pull Management Framework
With 300+ direct reports, Kieran uses a "push and pull" system where he clearly communicates which projects he'll be deeply involved in each quarter (push) while expecting teams to pull him in when they need help on everything else. (15:13) This framework acknowledges that leaders can't be in the weeds on everything, so transparency about priorities prevents confusion and micromanagement. He tells his team upfront which problems he's obsessed with solving and will act like a team member on, while trusting them to manage other initiatives independently. This system works because it sets clear expectations and allows him to maintain his problem-solving energy while scaling across a large organization. The framework requires honest self-assessment about your capacity and clear communication about where your attention will be focused.
AI Enables the Return of the Craftsperson CMO
Kieran believes AI will enable marketing leaders to return to being practitioners rather than just people managers, as teams become smaller but more capable. (12:03) Traditional CMO roles often pulled great marketers away from doing marketing into administrative tasks, but AI's ability to automate workflows means future CMOs can lead smaller teams while staying hands-on with creative execution. This shift addresses the common career progression problem where excellent individual contributors become mediocre managers simply because they were good at the craft. With AI handling routine tasks, marketing leaders can focus on high-level strategy and creative direction while maintaining direct involvement in execution. The practical opportunity for current marketers involves positioning themselves as both strategic thinkers and skilled practitioners who can leverage AI to amplify their capabilities rather than being replaced by purely administrative managers.
Statistics & Facts
- Gartner predicts that by 2027, 95% of the B2B buyer journey will start in an LLM assistant rather than Google, compared to 80% currently starting on Google. (29:03) This statistic highlights the fundamental shift from information seeking to action-oriented queries that will reshape content marketing strategies.
- Kieran manages 300+ direct reports across HubSpot's global marketing team. (15:06) This context demonstrates the scale at which he's applying AI and management frameworks in a real enterprise environment.
- Kieran estimates that Cursor, an AI coding assistant company, is worth $300 billion and their leaked system prompt provides valuable insights into effective AI prompting strategies. (42:07) This illustrates how valuable prompt engineering has become in the AI economy.
