Workday’s Last Workday? AI and the Future of Enterprise Software
4/30/202629 min
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.
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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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Clips
Transcript preview
First 90 secondsJoe Schmitt· Guest0:00
No one likes doing, like, these crazy tasks inside of Workday. No employee likes interacting with Workday. No one wants to go into this portal. And so if you can go out there and solve these problems, there's a huge pie to go after. If you think about where you have to go capture these customers, if someone has already become a customer of Workday or already become a customer of ServiceNow or Salesforce, it is so hard to rip them off. That's why these gross dollar retentions are what they are. Like- Yeah ... they're the gold standards for a reason. We're seeing the, like, cracks in the most defensible businesses in the world, and it's a really exciting time and, and the race is on.
Speaker 20:34
What does it take to replace one of the most entrenched systems in enterprise software? For the past two decades, platforms like Workday have become the backbone of how companies manage people, data, and operations. They're deeply embedded, highly defensible, and nearly impossible to rip out. But platform shifts change the rules. Just as cloud transformed enterprise software in the 2000s, AI is creating a new opportunity to rethink how these systems work and whether they should exist in their current form at all. The question now is not whether these systems are valuable, but whether they can evolve fast enough. Elena Berger speaks with Joe Schmitt, partner on the enterprise team at A16Z.
Elena Burger· Host1:19
Hello, everyone, and welcome to Monitoring the Situation. [chuckles] I am here with Joe Schmitt