The Agile Brand with Greg Kihlström®: Expert Mode Marketing Technology, AI, & CX

Episode #784: Monday.com Global Creative Director Robbie Ferrara on Clarifying the Benefits of AI
Date: December 15, 2025
Guest: Robbie Ferrara, Global Creative Director @ Monday.com
Host: Greg Kihlström

Episode Overview

This episode explores how B2B brands—particularly in the evolving space of AI-driven work management—can rise above traditional, feature-heavy marketing to create emotionally resonant and culturally relevant brands. Robbie Ferrara, Global Creative Director at Monday.com, joins Greg Kihlström to discuss the value of human-centered storytelling, Monday.com’s innovative campaigns, and the practical role of AI in creativity and brand building.

Key Discussion Points & Insights

1. Moving Beyond Traditional B2B Marketing

Traditional vs. Modern B2B Branding

• Historically, B2B marketing has favored logic, features, and ROI—often resulting in bland, indistinct messaging.
• Ferrara notes the overwhelming sameness in B2B:

  “When you hear the word B2B or SaaS, you suddenly feel that you have to go into convention... it all becomes a little bit white noise.” (03:05)

• Today’s fractured, always-on media landscape requires brands—even B2B—to emotionally connect much like B2C.

Strategic Imperative for Emotional Connection

• Monday.com’s unique, intuitive platform empowers the brand to lean into emotional differentiation.
• Emotional resonance is rooted in customer testimonials—people “love to use” the product.
• Ferrara echoes the classic “definition of madness”:

  “The definition of madness is repeating the same thing and expecting different results.” (04:05)

2. The “AI Had the Time of My Life” Campaign

Addressing AI Hype and Anxiety

• Monday.com’s campaign stepped away from technical capabilities, spotlighting how AI improves human work life, not just processes.
• Ferrara on campaign insight:

  “There was a lot of AI overwhelm around Q3... we’re all feeling kind of underwhelmed by actually what the uses of AI are.” (05:38)

• Recognizing the fatigue caused by AI buzzwords, Monday leaned into humor and relatability, personified by singing llamas and a playful tone.

Insight-Driven Marketing

• Ferrara is a firm believer in “human truths”:

  “You find a human truth that travels. It doesn’t matter where you are in the world... you react to it because you’ve lived it.” (05:38)

• Monday.com’s position: The best AI is the one people actually use daily.

3. Building Creative Agility in a Global Team

Team Structure and Speed

• Monday.com operates across three time zones; autonomy and trust are essential.
• Ferrara values hiring for “modern creative thinkers” who embrace ambiguity:

  “More and more now you’ve got to deal with only having 70% of the information in front of you.” (08:26)

• A flat, peer-to-peer structure encourages quick iteration and avoids bottlenecks.

4. Navigating Creative Risk and Global Resonance

Risk-Taking and Internal Alignment

• Monday.com fosters a “forever beta” culture—fail fast, learn quickly.
• The company does minimal pre-testing; boldness is encouraged if ideas are rooted in product truths.
• Notable product features (the llama mascot and related widgets) create a cohesive and distinct asset for emotional connection.
• Externally, their creative risks feel differentiating—internally, they feel authentic and aligned.

5. Measuring Emotional Resonance

Quantitative and Qualitative Metrics

• Brand tracking (Nielsen awareness), Google search trends, social engagement, and direct customer feedback are key indicators.
• Ferrara on resonance:

  “What really blew us away was that people were going out of their way from watching the video and then tweeting us, leaving comments because I think it resonated so much.” (15:19)

• Intangible benefits—like customer enthusiasm for “plushie llamas”—also signal impact.

6. The Role of AI in the Creative Process

AI as Enabler, Not Replacement

• AI helps the team quickly iterate and visualize concepts.

  “At the moment, I feel like the benefit of AI is it’s speeding up our ability to get to a proof of concept.” (18:38)

• The “magic” of creativity comes from unpredictable human leaps and serendipitous moments AI can't yet replicate.
• Ferrara uses “four or five different AI tools” but stresses that true creative breakthroughs—like a singing llama—are uniquely human:

  “I’ve yet to see them be able to do that lateral jump... I’m sure it’ll get there, but maybe only humans can do that.” (18:38)

7. The Future of Authentic Customer Relationships in the Age of AI

Trust as Differentiation

• Ferrara cites an “AI adoption gap”—innovation outpaces user adoption.
• Brands must offer genuine reassurance and facilitate truly intuitive, lovable platforms; otherwise, customer mistrust lingers:

  “There’s so many people screaming about what AI can do, but none of it feels tangible, none of it feels real.” (21:06)

• Monday.com’s philosophy: If users love and adopt the platform, they’re future-proofed against shifts in tech.

What’s Next?

• Ferrara predicts a shift from experimentation to tangible AI implementation in marketing within a year:

  “In a year’s time, we’re going to start talking about very tangible implementation and actually what [AI is] doing.” (24:09)

Notable Quotes & Memorable Moments

• “The definition of madness is repeating the same thing and expecting different results.”
  — Robbie Ferrara (04:05)
• “You kind of have to work hard to break out and get people’s attention.”
  — Robbie Ferrara (03:05)
• “At the moment, adoption isn’t matching innovation… The best AI is the one that people use every day.”
  — Robbie Ferrara (21:06)
• “I think creatives are very intuitive beasts… becoming more adept at dealing with ambiguity and the ability of not having all the facts but having an intuition.”
  — Robbie Ferrara (25:15)

Timestamps for Important Segments

| Timestamp | Segment Description | |-----------|--------------------------------------------------------------------------| | 01:09 | Framing that AI’s adoption is a human challenge, not just technical | | 03:05 | Why emotional resonance is critical in B2B marketing | | 05:38 | Strategic insights behind “AI Had the Time of My Life” campaign | | 08:26 | How the creative team is structured for agility | | 10:48 | Approach to risk and global, bold campaign validation | | 14:49 | How to measure campaign success beyond traditional metrics | | 18:38 | How AI is currently impacting—and not replacing—creative direction | | 21:06 | The “AI adoption gap” and why trust is critical | | 24:09 | Predictions for AI’s future in marketing | | 25:15 | Advice for staying agile and creative amid ambiguity |

Conclusion: Key Takeaways

• For B2B brands, embracing emotional connection and creative differentiation is more critical than ever.
• AI is an enabler for creativity—but the most distinctive ideas still come from human intuition and serendipity.
• Building global, always-on campaigns requires agile teams empowered to move fast—and the willingness to take risks rooted in product truth.
• True brand value in a tech-driven future lies in building trust, ensuring platforms are genuinely lovable, and clarifying tangible benefits amid hype.
• The future will see a move from creative AI experimentation to visible, large-scale adoption—provided brands focus on what users truly need and love.

For more on Monday.com’s bold creative strategy and Robbie Ferrara’s perspective, follow the provided notes and explore recent campaigns.