Agents of Scale

Chris Savage, co-founder and CEO of Wistia, a video software leader who steered major cultural and AI-driven product shifts. He describes how a company-wide reset turned long roadmaps into biweekly shipping rhythms. They rebuilt go-to-market for rapid launches, leaned on AI to accelerate product work, and launched Remix, an agentic editor that condenses long meetings into shareable highlights.

Claire Vo, CEO of ChatPRD and former CPTO at LaunchDarkly and Optimizely, shares practical AI adoption tactics. She explains why top-down AI mandates fail. Short rituals like AI Fridays, hackathons, and hands-on exec work actually move the needle. Claire also discusses building AI-native products, hiring for learnability, and where humans still matter versus where tooling can replace roles.

Carlos Olea, CFO of Howard Hughes and a CPA who turned auditing instincts into AI-driven automation. He discusses how finance led AI adoption, the vendor-bid tool that proved value beyond price, automating lease abstraction with superior accuracy, building a startup-speed tiger team inside a public company, and winning skeptics by fixing hated tasks first.

Kristen Habacht, CEO of Elly and former Trello and Typeform revenue leader, builds AI that helps recruiters do the human work. She discusses the hiring arms race, why ATSs act like filing cabinets, the idea of an ICP for hiring, how AI can flag insights without deciding, and a vision for a universal job application. Short, vivid stories and practical takes on bias, proctoring, and product-led growth in talent tech.

Dharmesh Shah, co-founder and CTO of HubSpot and longtime entrepreneur, shares a practical take on AI and work culture. He discusses competing with AI, rituals that spark experimentation, low-risk starting points from creation to simulation, why large SaaS still matters, and when vibe-coding makes sense for niche internal tools.

Wes Schroll, Founder and CEO of Fetch, shares his journey from early entrepreneurship at 14 to leading a loyalty platform impacting significant consumer spending. He discusses Fetch's unique business model and the challenges of scaling while integrating AI. Wes emphasizes hands-on leadership over task forces for effective AI adoption and recounts a week-long AI hackathon that sparked innovation. He highlights the importance of clear AI guidelines and maintaining consumer relationships as Fetch’s core competitive advantage. With practical advice for founders, he encourages embracing AI while managing the inherent risks.

Rob T. Lee, Chief AI Officer at the SANS Institute, discusses the critical issue of shadow AI and its implications for security in organizations. He argues that a blanket 'no' on AI creates more risks and offers a 'lifeguard' approach to governance. Lee emphasizes the importance of hands-on training for executives and recommends micro-projects to foster security skills. With practical strategies like accountability partners and regular reviews, he outlines how companies can experiment safely while embracing AI, turning policy from obstruction into opportunity.

In this discussion, Jason Cottrell, CEO of Orium and new president of the MACH Alliance, shares insights on transforming enterprise AI from theory to practice. He emphasizes the power of composable architectures over monolithic solutions, highlighting a case study where a retailer achieved 5x growth in nine months. Jason argues that leveraging many specialized AI agents is more effective than relying on a single mega AI. He also delves into how brands can enhance customer experiences through personalized shopping assistants and direct chat-based commerce.

Shishir Mehrotra, a renowned technology CEO and former product lead at YouTube, discusses the game-changing rebranding of Grammarly to Superhuman. He reveals how their proactive AI assistant, Superhuman Go, transforms work by seamlessly integrating into over 1 million apps. Shishir shares insights on running products as a compound startup, the pivotal role of partnerships in expanding the agent ecosystem, and how AI is reshaping company culture through faster prototyping and ritual practices. This conversation gives a glimpse into the future of AI-driven productivity.

Ben Kus, Chief Technology Officer at Box, joins Wade Foster to discuss the evolution of AI in handling enterprise unstructured data. They delve into how AI transforms extensive data into actionable insights, making tasks manageable without needing extensive data science expertise. Ben explains the importance of trust in AI adoption, emphasizing the need for strong security and governance practices. The conversation also highlights the role of agents in streamlining workflows, ultimately transforming how businesses leverage their data effectively.