Workday’s Last Workday? AI and the Future of Enterprise Software

About this episode

Elena Burger discusses the future of enterprise software with Joe Schmidt, focusing on AI's impact and the vulnerabilities of legacy systems.

Elena Burger speaks with Joe Schmidt, partner on the enterprise team at a16z, about the future of enterprise software in the age of AI. Using Workday as a case study, they discuss why many of today’s most important enterprise systems feel broken, how platform shifts reshape entire categories, and what an AI-native replacement might look like. The conversation covers the limits of legacy SaaS, why “AI revenue” may be overstated, and how agents could fundamentally change how companies manage workflows, permissions, and internal systems. They also explore why even the most defensible software businesses may now be vulnerable to replatforming.

People in this episode

Host: Elena Burger

Guest: Joe Schmidt

Topics covered

• enterprise software
• AI
• platform shifts
• legacy systems
• workflow management

Keywords

• enterprise software
• AI
• Workday
• legacy SaaS
• workflow management
• replatforming
• agents

Mentioned in this episode

Organizations: Workday, a16z, SaaS

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