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

May 1, 2026

1:04

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

Here's something that might surprise you — many of today’s enterprise systems feel outdated, and AI is about to shake things up big time. Content+a16zpodcast@a16z.com’s Elena Burger and Joe Schmidt point out that legacy SaaS tools are hitting their limits, often feeling clunky and disconnected. Now, here’s where it gets interesting — according to Joe, AI-native platforms could fundamentally reimagine how companies handle workflows, permissions, and internal systems. Instead of being just an upgrade, these new systems could replace entire categories, making even the most defensible software vulnerable. And what does this mean for big enterprise players? They might need to replatform faster than they think, or risk getting left behind. As Elena and Joe highlight, the real game-changer isn’t just AI revenue — it’s how AI can enable smarter, more adaptable internal systems. The takeaway? The future of enterprise software isn’t just about better tech — it’s about rethinking what’s possible altogether.

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.

Resources:

Follow Joe on X: https://x.com/joeschmidtiv

Follow Elena on X: https://x.com/elenaburger

Read more from ‘Workday’s Last Workday?’: https://a16z.com/workdays-last-workday/

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Audio Transcript