The Exit Five CMO Podcast
Episode Title: The Future of B2B Marketing: AI, Execution, and Craft with Kieran Flanagan
Host: Dave Gerhardt
Guest: Kieran Flanagan, Marketing Executive at HubSpot
Release Date: June 23, 2025

1. Introduction to the Episode and Guest

In this insightful episode of The Exit Five CMO Podcast, host Dave Gerhardt welcomes Kieran Flanagan, a seasoned marketing executive currently leading a global team of 300 marketers at HubSpot. Kieran, formerly the CMO at Zapier, is renowned for his forward-thinking perspectives on AI and its intersection with marketing. The conversation delves deep into the transformative role of AI in B2B marketing, the evolving responsibilities of CMOs, and the future landscape of marketing teams.

2. Kieran Flanagan's Career Journey and AI Focus

Kieran begins by sharing his unconventional career trajectory, transitioning from a software developer frustrated with coding to a dynamic marketing leader. His passion for AI emerged as he sought to become the most knowledgeable operator in the field. This obsession with AI led him to spearhead AI transformations within HubSpot, managing cross-functional teams and integrating AI into various marketing workflows.

Kieran Flanagan [02:43]:
"I was obsessed by AI was like the only thing I really care about is being the most knowledgeable person in operator who can do AI."

Dave appreciates Kieran's diverse roles and his ability to blend different missions, emphasizing the importance of adaptability and continuous learning in a marketing career.

3. AI's Impact on the Role of CMOs and Marketing Teams

The discussion shifts to how AI is reshaping the traditional role of the CMO. Kieran envisions a future where CMOs are not just strategists but also hands-on practitioners, leveraging AI to execute campaigns more efficiently. This shift allows for smaller, more agile teams that can focus on creativity and strategic decision-making rather than being bogged down by administrative tasks.

Kieran Flanagan [05:21]:
"Anything that is impactful takes some time. But I think to actually have something that really motivates you, you should be able to do it within a, you know, a foreseeable amount of time."

Dave relates by sharing his own experience of moving from being a top marketer to a VP role, highlighting the challenges of balancing hands-on work with managerial responsibilities.

4. Managing Large Teams vs. Being a Hands-On Marketer

Kieran and Dave explore the tension between managing large teams and remaining an active contributor to marketing efforts. Kieran candidly discusses his management style, acknowledging areas where he can improve, particularly in emotional intelligence and people management. He emphasizes the importance of having proactive team members who can provide honest feedback, enabling him to focus on solving complex problems.

Kieran Flanagan [12:44]:
"I may not always sense when someone's overwhelmed, unclear or demotivated. Unless you tell me, I'm not cold, just focused."

Dave resonates with this, sharing his struggles with being a strongly opinionated marketer and his desire to balance leadership with creative execution.

5. The Importance of AI Prompts for Marketers

A significant portion of the conversation is dedicated to the art of crafting effective AI prompts. Kieran shares his approach to developing prompt frameworks, utilizing custom GPT models to refine and iterate on prompts that drive meaningful marketing outcomes. He underscores the necessity for marketers to become adept at prompting to harness AI's full potential, comparing it to a new form of literacy essential for modern marketing.

Kieran Flanagan [40:26]:
"Everything I see, I'm like, that I could take that and turn that into some sort of prompt in GPT."

Dave highlights the practical applications of this, such as using AI to enhance design processes and streamline content creation, thereby reducing dependency on external designers or developers.

6. The Future of AI in B2B Marketing

Kieran offers an optimistic view of AI's future in B2B marketing, predicting a shift from informational content to actionable insights delivered through large language models (LLMs). He envisions highly personalized marketing campaigns enabled by AI, where dynamic website optimization and tailored newsletters cater to individual company needs. This evolution promises more effective and efficient marketing strategies, allowing brands to extract greater value with fewer resources.

Kieran Flanagan [28:31]:
"We are going to get rid of the era of informational content... Instead of me saying how do I create Facebook ads that convert? I literally just go to the LLM assistant and say give me Facebook ads that convert."

He also touches on the potential challenges, such as the reliance on synthetic data and the need for marketers to focus on high-value, creative tasks that AI cannot easily replicate.

7. Listener Questions and Responses

Throughout the episode, Dave introduces several listener questions, and Kieran provides thoughtful responses:

Q1: How can marketers find white space where AI cannot replace them?

Kieran emphasizes the importance of developing strong prompt engineering skills and leveraging AI to enhance rather than replace creative and strategic efforts.

Kieran Flanagan [40:57]:
"The swipe file is a perfect analogy. It's how you train yourself to think."

Q2: How will creative shops like video production companies evolve with AI advancements?

Kieran suggests that agencies will adapt by integrating AI-driven agents to personalize and optimize their services for individual clients, thereby maintaining their relevance in a rapidly evolving landscape.

Kieran Flanagan [44:55]:
"Agencies in general will instrument agents for companies... give them agentic workflows."

Q3: Do audiences care if content is AI-generated?

Kieran remains uncertain but notes that current trends show audiences prioritize content quality over its origin. However, he advocates for transparency when AI is involved in content creation.

Kieran Flanagan [50:08]:
"You should never mimic a human with AI and not tell the person they're conversating with an AI."

8. Final Thoughts and Conclusions

As the episode wraps up, both Dave and Kieran reflect on the integration of AI in their personal and professional lives. Kieran shares his excitement about the creative possibilities AI unlocks for marketers, while also acknowledging the potential for AI-related fatigue. They both agree that AI, when used thoughtfully, can amplify human creativity and efficiency, making the role of marketers more impactful and fulfilling.

Kieran Flanagan [37:07]:
"If you can combine these things, you have a superpower... Man, Don Draper plus ChatGPT would be like the most insane thing of all time."

Dave concludes by encouraging listeners to embrace AI as a tool that complements human creativity, drawing parallels to historical technological advancements that initially faced skepticism but ultimately transformed industries.

Key Takeaways

• AI as a Strategic Asset: AI is not just a tool for automating tasks but a strategic asset that can fundamentally transform marketing strategies and team structures.

• Evolving CMO Role: The role of the CMO is shifting towards being a hybrid of strategist and practitioner, leveraging AI to drive both creativity and efficiency.

• Importance of Prompt Engineering: Mastery of AI prompting is becoming a crucial skill for marketers, enabling them to extract maximum value from AI tools.

• Personalization and Micro-Audiences: AI facilitates highly personalized marketing efforts, moving away from broad segmentation to tailored campaigns that address individual company needs.

• Balancing Leadership and Execution: Effective leadership in marketing requires balancing team management with hands-on execution, with AI serving as an enabler for both.

Notable Quotes

• Kieran Flanagan [02:43]:
  "I was obsessed by AI was like the only thing I really care about is being the most knowledgeable person in operator who can do AI."

• Kieran Flanagan [05:21]:
  "Anything that is impactful takes some time. But I think to actually have something that really motivates you, you should be able to do it within a, you know, a foreseeable amount of time."

• Kieran Flanagan [28:31]:
  "We are going to get rid of the era of informational content... Instead of me saying how do I create Facebook ads that convert? I literally just go to the LLM assistant and say give me Facebook ads that convert."

• Kieran Flanagan [37:07]:
  "If you can combine these things, you have a superpower... Man, Don Draper plus ChatGPT would be like the most insane thing of all time."

This episode offers a forward-looking perspective on the integration of AI in B2B marketing, highlighting both the opportunities and challenges it presents. Kieran Flanagan's expertise and candid insights provide valuable guidance for marketers navigating this rapidly evolving landscape.