The Dave Gerhardt Show: The Future of B2B Marketing with Kieran Flanagan

Date: January 5, 2026
Host: Dave Gerhardt (Exit Five)
Guest: Kieran Flanagan (HubSpot)

Episode Overview

This episode dives deep into the future of B2B marketing, the transformational impact of AI on the industry, and what marketers and leaders should focus on to stay ahead. Dave Gerhardt welcomes Kieran Flanagan—marketing executive at HubSpot (and former CMO at Zapier)—to explore how marketing roles, skills, and teams are evolving. The conversation is equal parts tactical advice and reflection on craft, creativity, and leadership in an AI-driven world.

Key Discussion Points & Insights

1. Kieran’s Career and Approach (03:02–09:37)

• Background: Started as a developer, found software development wasn’t a strength, pivoted to marketing as the discipline became more technical.
• Varied Roles: Focused on unique “two-year missions” (06:14), including building international growth at HubSpot, transitioning to product-led growth, and leading AI transformation.
  • “I work on two year increments... anything impactful takes some time, but two years is enough for me to stay motivated and see the impact.” (06:14 – C)
• Advice for Career Growth: Even if you’re in an unpreferred role, give yourself a two-year mission to build skills and open future opportunities.

2. Balancing Operator and Leader: The “Maker–Manager” Dilemma (10:07–13:54)

• Dave’s Struggle: Moving from hands-on marketer to manager/team lead (“This is not what I signed up for... I want to write some headlines.” 11:09 – B)
• Kieran’s Approach:
  • Relies on trusted teammates to alert him to people-management needs.
  • Uses “push and pull” framework: he’s deeply involved (“push”) in a handful of areas, expects his team to “pull” him in elsewhere.
• AI’s Impact: Predicts AI will make teams smaller and allow leaders to practice their craft more directly.

Memorable Quote:
“He could... be mentally 10 steps ahead and emotionally 10 steps removed. Kieran thinks in systems and long-term leverage, not entrepreneurial minutiae...” (13:01 – C, as diagnosed by AI)

3. Directness in Creative Leadership (16:32–20:33)

• Strong Points of View: Both agree that the best marketing leaders increasingly need clear, direct guidance. Probing, indirect management is less effective than direct feedback.
  • “Teams want to work for craftspeople who actually do the craft and have a really high standard.” (16:32 – C)
• Learning by Doing: Both cite tough feedback as key to creative growth.
  • Kieran recounts being told a presentation "sucked"—the directness led to fast improvement.

4. The Shift from Answers to Actions in B2B Marketing (28:24–33:10)

• AI is Changing the Buyer Journey:

  • Legacy playbooks (SEO, traffic via informational content) are being disrupted.
    • “We are going to get rid of the era of informational content... what we're moving from is answers to action.” (28:24 – C)
  • LLMs (like ChatGPT) will provide direct actions instead of just information.
    • Gartner predicts that by 2027, 95% of B2B journeys start within an LLM assistant.

• Segmentation to Personalization:

  • AI removes the constraint of one-to-many campaigns—websites, emails, and even newsletters can be uniquely tailored to individuals or companies at scale.

Memorable Quote:
“The value from AI is accruing in what happens when you capture the contact... we move towards micro audiences and much more tailored campaigns.” (29:50 – C)

5. New Opportunities and the Joy of Craft (33:10–36:15)

• AI Enables Marketers to Return to Craft:

  • Tools like Canva AI, Gamma, GenSpark let creative marketers execute ideas directly, bypassing operational bottlenecks.

• Career Renewal: Both Dave and Kieran say AI revived their enthusiasm for marketing:

  • “I've never been so happy to be a marketer… I love doing the craft. I can actually do all the things... I think this is amazing.” (33:43 – C)
  • “The last two years have re-lit my candle, because I'm like all the things that I like.” (34:07 – B)

• Warning About AI Fatigue:

  • The burst in productivity can also lead to being overwhelmed if boundaries aren’t set—humans are not meant for endless multitasking.

6. Technical Fluency and Creativity—The Two Paths (37:57–39:23)

• Rise of Technical Marketers:
  • You need to be either very technical (turning workflows into automations) or ultra-creative (“at the outer edges of creativity”).
• AI Threatens the “Messy Middle”:
  • Jobs that are merely “good enough” are at risk—pick a lane and excel.

7. Prompting as a New Literacy (41:16–44:24)

• How Kieran Develops Prompts:
  • Collects prompt frameworks and builds custom GPTs, iterating continuously.
  • Recommends treating prompt-writing like having a “swipe file”—collect good ideas and prompts everywhere.
• Encourages experimentation and adaptation:
  • “Everything I see, I'm like—that, I could take that and turn it into some sort of prompt in GPT.” (44:15 – C)

8. AI’s Impact on Teams, Agencies, and the CMO Role (45:03–47:10)

• CMO of the Future:
  • “A craftsperson, practitioner, smaller team, less people management, more actually doing the job.” (45:09 – C)
• Agencies/Service Businesses:
  • Agencies will increasingly build agentic workflows—custom AI automations tailored for each client.

9. The Human Touch in a Polarized World (46:00–47:58)

• Rise of In-Person and Community:
  • As AI takes more “informational” work, real-life experiences and tight communities become more valuable.
  • “If the bet I was making: in-person events, communities, mastermind groups... are going to be way more in demand.” (46:35 – C)

Notable Quotes & Memorable Moments

• Directness in Managing Creatives:
  “Just tell them what you want them to do. Like, they'll agree or disagree.” (17:33 – C)

• AI as a Creative Multiplier:
  “All the things that I like—the making ads, I want to make videos, I want to do creative, I want to do story... AI has re-lit my candle.” (34:07 – B)

• Dangers of Mediocrity:
  “You have to now be at the opposite... either incredibly technical, or at the outer edges of creativity. All the good enough stuff... is going to be problematic.” (37:57 – C)

• On Prompting:
  “Prompting is a new literacy... wherever I find something that works, I’ll create a custom GPT so I can conversate with that GPT and it will turn that conversation into a prompt.” (41:16 – C)

• Personal Time & Perspective:
  “None of this is that serious. You know what I mean? There's just more important things—like, I try to have fun with it.” (53:03 – C on becoming a father)

Key Timestamps

| Segment | Timestamp | |---------------------------------------------------------------|------------| | Kieran’s background and approach | 03:02–09:37| | Managing as a maker & team leader (“push & pull” framework) | 10:07–13:54| | The role of direct creative feedback | 16:32–20:33| | AI shifting marketing from answers to actions | 28:24–33:10| | The return to marketing craft, AI-powered creativity | 33:10–36:15| | Technical fluency vs. creativity—the two paths | 37:57–39:23| | Prompting as a new essential skill | 41:16–44:24| | Future of CMOs/agencies in an AI world | 45:03–47:10| | The continued importance of in-person and community | 46:00–47:58| | Hot takes & rapid-fire (tool recommendations, AI copy, etc.) | 48:25–51:30| | Reflections on time, family, and keeping perspective | 52:36–53:35|

Recommendations & Takeaways

• Marketers need to push toward one edge: deep technical/AI fluency or bold creative leadership. The “average” is at risk.
• Direct, strong feedback and creative direction are essential—don’t shy away from being a decisive leader/creator.
• Mastering prompting, and maintaining a growing “swipe file” of ideas, prompts, and use cases, is the new career superpower.
• Use AI to maximize your time spent on craft, not just process—creative energy and technical acumen are now the keys to thriving marketing teams.
• Don’t forget the human factor: as more work goes digital/automated, real-world interaction and camaraderie are more valuable than ever.

Tool & Resource Mentions

• AI Tools: ChatGPT (O and O3 models), Claude, Gemini, Canva AI, Gamma, GenSpark, Lovable, Air Ops
• Prompting & Custom GPTs: Kieran keeps a dozen+ custom-trained GPTs, often building prompts by analyzing industry leaks and frameworks, then iterating using a “swipe file” approach.
• Events, Community: Importance of in-person events, community building, and mastermind peer groups as AI automates routine informational interactions.

For more inspiration and in-depth AI/marketing insight, check out Kieran and Kip’s “Marketing Against the Grain” on YouTube.