At HubSpot's annual AI Summit in San Francisco, two influential tech leaders came together for an intimate fireside chat about navigating AI transformation at the CEO level. HubSpot CEO Yamini Rangan and Atlassian CEO Mike Cannon-Brookes, moderated by Mania Lab founder Sandhya Hegde, shared candid insights about steering their companies through what they describe as both an exciting and terrifying time in technology.
The Speed of Change Sets This Era Apart
While both CEOs have weathered previous technology disruptions—from mobile to cloud computing—they agree that AI represents something fundamentally different. According to Mike, who co-founded Atlassian over two decades ago, "This is a different technology disruption to the last few." The key differentiator? Speed.
Yamini, who has spent decades in go-to-market roles, emphasized this point: "The speed with which technology is developing shocks us and surprises us." She noted that developments projected to take twelve months are happening in six, creating a gap between technology advancement and organizational adoption.
From Software as a Service to Work as a Service
Both leaders highlighted a fundamental shift in how AI transforms business operations. Yamini articulated this transformation clearly: "We're going from software as a service to work as a service."
Key areas where AI is delivering actual work rather than just enabling it include:
- Support operations: AI agents now resolve tickets directly rather than just helping human agents work more efficiently
- Marketing transformation: AI is both disrupting traditional content marketing (through Google's AI overviews) and enabling new, highly personalized approaches
- Sales prospecting: AI handles account research, meeting setup, and follow-ups—tasks that previously consumed significant human time
Finding Product-Market Fit with AI
Both companies have achieved significant AI adoption, with Atlassian reporting over 1.5 million monthly AI users. However, the CEOs emphasized that true product-market fit goes beyond novelty.
Yamini distinguished between one-time use driven by curiosity and sustained adoption: "Product-market fit is when it's a necessary part of your job, and you can't do your job without it."
Three areas showing clear product-market fit:
- Customer support automation
- Content creation and distribution in marketing
- Sales prospecting and account research
Cannon-Brookes added an important perspective: users don't necessarily need to know they're using AI. "Ideally, they don't notice that we are massively invested in AI. They just think, wow, my job got a bit quicker."
Leading Organizations Through AI Adoption
Perhaps the most challenging aspect of AI transformation is managing organizational change. Both CEOs emphasized that this isn't about efficiency or headcount reduction—it's about enabling teams to achieve more.
Key leadership approaches:
Start with purpose: Yamini stressed beginning with "why"—at HubSpot, the goal is solving customer problems in new ways. AI fluency improves employee conviction, which translates to better customer communication.
Focus on joy, not just productivity: Cannon-Brookes introduced the concept of "developer joy" over pure productivity metrics. By asking teams what makes their work less enjoyable and using AI to eliminate those pain points, adoption naturally follows.
Make it about growth, not cuts: Both leaders explicitly rejected using AI for staff reduction. As Cannon-Brookes put it, "My job has never been to have less people to do a thing. My job has been to do more things or to do higher quality things."
Personal Experiments and Future Vision
The conversation concluded with both CEOs sharing personal AI experiences that illustrate the technology's transformative potential. Yamini described using Lovable to create a high-protein vegetarian recipe app for her son—despite not having coded in 28 years. Cannon-Brookes recounted creating an entire children's book with his daughter using ChatGPT, complete with storyline, images, and even mock merchandise.
These personal anecdotes underscore a crucial point: the barrier to creation is dissolving. As Cannon-Brookes reflected on his daughter's matter-of-fact reaction to their AI-powered creative session, "For her, it's like, yeah. This is pretty cool... that will become just normal."
The Path Forward
Both leaders view this as the most exciting time in technology in decades. While acknowledging the challenges—from talent development to adoption speed—they see unprecedented opportunity to transform how work gets done.
The key takeaway? Success in the AI era isn't about replacing humans or cutting costs. It's about empowering teams to work at unprecedented speed and scale, focusing on creativity and problem-solving rather than repetitive tasks. For startups and established companies alike, the message is clear: embrace AI not as a threat, but as a tool to achieve what was previously impossible.
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AI Disclaimer: AI helped us summarize the key points from these videos, and our editorial team reviewed everything to make sure it's clear and correct.
