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

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, they're the best 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. 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 February, 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 Schmidt, partner on the enterprise team at a sixteen z. Hello, everyone, and welcome to monitoring the situation. I am here with Joe Schmidt, the fourth. Joe is a Thank you for making that delineation. I appreciate it. Joe is a partner on the enterprise team at a sixteen z, and we are here to actually, I think, first just answer a big important question, which is why has the enterprise team been writing so many obituaries lately, so many eulogies lately? And what have these eulogies been for? Yeah. No. Thanks for having me on. Excited to be here. Yeah. It's funny calling them eulogies. And I think that this piece was intended to be much more balanced than maybe people have have taken it to be. But I think that, you know, if you just think about where we are in the cycle right now, with enterprise software, a lot of the biggest, businesses that are that are out there today were kind of built in the last kind of technology shift, which was obviously a shift from on prem to cloud. And that's really the the big opportunity for most companies that are being built. Selling to big enterprise buyers is basically adopting some big, shift and then building their their platform around it. Once those kind of core primitives have been set, you know, basically, these markets end up moving into, a different type of innovation, which ends up being, like, point solutions that are built on top of some kind of core back end system. And the reason for that is if you think …