a16z Podcast - Workday’s Last Workday? AI and the Future of Enterprise Software

Episode Date: April 30, 2026

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/ Stay Updated:Find a16z on YouTube: YouTubeFind a16z on XFind a16z on LinkedInListen to the a16z Show on SpotifyListen to the a16z Show on Apple PodcastsFollow our host: https://twitter.com/eriktorenberg 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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 pot 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 Service Now or Salesforce,

it is so hard to rip them off. That's why these gross dollar retention are what they are. Like they're the most 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 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 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 Schmidt, partner on the enterprise team at A16Z. 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 A16C, 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 eulgages 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 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 out there today were kind of built in the last kind of technology shift, which is obviously the shift from on-prem to cloud. And that's really 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 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 backend system. And the reason for that is if you think about like what these systems are actually doing and if you take workday, obviously it codifies like kind of your HR business processes and a bunch of business logic internally your company inside of like one relational database. And there's a bunch of really complex stuff that happens there.

But the actual experience of that, like, you know, that an actual employee or, you know, an HR administrator or someone in IT experiences is fundamentally the same, you know, today as it was in 2005. And so if you come in and you say, hey, I'm going to rebuild workday and you tell, you know, C.H.R.R. Or you tell, you know, the CIO that. They're going to be like, okay, but like, what does it actually do differently than what workday has done previously? And you're going to say, you know, until now, it would have been very hard to say it was going to do something different. And so what many companies have been doing over the past 15, 20 years, and this has been basically all of enterprise software, has been building Little Point Solutions on top of that. So you've seen a bunch of things in recruiting, a bunch of things in finance and so on and so forth. And workday has become the home for a lot of those businesses over time. Obviously, we talked about some of their acquisitions. And so what's really interesting about this moment in time and why we're writing so many obituaries, which I hate calling them that, it's like these are opportunity pieces. And it's an opportunity for workday, just the same as it is for, you know, startups is that for the first time you can actually go to a CHRO or you can go to a CIO and say the way that this core system works for you today can be so fundamentally different.

And we can change the actual way that the work is being done by your team and the way that these platforms are actually interacted with by your employees or your customers. That's the opportunity. I see that in HR. We're seeing that in ITSM. We're seeing that in CRM. We're seeing that in the biggest and most defensible categories, historically defensible categories. And I think we're going to see every platforming. And that's why you see obviously what's happening in the stock markets happening today because a lot of investors are talking about that and are worried about that. And a lot of incumbents are too.

So that's why we're writing these pieces and that's the opportunity. Yeah. So the SaaS products of your can't get their, you know, their juicy PE ratios. They can't, you know, bank on incremental revenue. and crazy operating leverage anymore. They actually have to do real work and either pivot and adopt AI

or get out competed by, you know, the insurgents who are. So with that in mind, I feel like we should pull up your piece and, you know, chat through it. Yeah. So let's just get into it. And you can, this is a, it's called Workday's Last Workday.

We published it on A16Z, dot news this morning. And you open the piece by calling Workday the most important and least loved product in enterprise software. And I know that, you know, I think you agonized over this opening sentence a lot. So can you sort of explain the sentence? Like, what does this tell us about the nature of enterprise software? How can something be, you know, crucially important, but also like on love?

It's completely. Yeah, I mean, I think maybe it's, it goes back to what I just talked about in terms of like when, when and how these were built and maybe who these were built for. And I think, you know, I'm sure some people that are watching this have interacted with Workday in their day to day. And maybe some people are, you know, workday professionals, whether it's consultants or or HR admins that actually deal with this on a day basis. But when Workday was built, this is now a 20-year-old, like, you know, business. And the architecture is obviously 20 years old. it was a better version of, you know, kind of the PeopleSoft Oracle, you know, businesses that were, that existed back in the past. And it was built for like those internal teams, right?

And so I think it did a good job of solving for the problem that it had at the time. And I'm not going to sit here and say there's nothing good about workday. It has 97% gross dollar retention. Like it is the name in the category. But I really don't think that the user interface for employees is anything close to what great software looks like today. Right. Like I am, we are a workday shop here at Entries and Norwood. It's like I've logged into workday.

No, I'm not kidding you three times in the past. 12 months. I am the insurance person here in injuries and Horwitz. I have no idea what my benefits are. No idea. I went in actually not too long ago to like actually try to find my compensation information in workday. It took me six and a half minutes. Like I am a technology customer. So yeah. Yeah. It's just not built for that. And I think the more I talk to people, the more I realized that that experience is broken. And it, the opportunity here is to kind of, you know, build that again. So I think it's really important because it has very important information. What I just said, like my compensation information, my benefits, those are critical. But like navigating that is

extremely hard. And I've never met anyone that likes it. I had to log in considerably more times than you in the past month because I was applying for an apartment and I had the exact same pain of like, where do I find to anything? And, you know, like, why is this so difficult to you? So completely, completely resonates. I think like you also earlier were talking about platform shifts and like you have this great kind of mini history lesson right here. Like we should maybe just like touch on this for a second, but kind of like what exactly was the platform shift that created Workday? And like now let's like just be super clear cut about what this new platform shift is that we're seeing right now. Yeah. I mean, the obvious answer to the platform shift we're seeing now is, you know, kind of the shift from

businesses that weren't AI native to businesses. that are. That's the opportunity here. I actually love the workday story. Like it was, you know, a crazy kind of hostile takeover of PeopleSoft. You know, there's Larry Ellison, these, you know, these amazing entrepreneurs and Dave Duffield and then he'll be, I'm going to script his last name, but you see them come back and say, hey, we see this shift. Like, we just lost our baby. We know exactly what to build. We know all of the edge cases that you need to solve for. And solving for that in 2005 was actually a heck of a lot. You know, it's still really hard, but it's even harder back then, just considering how hard it was to build software.

And so I think these guys are amazing entrepreneurs. They saw this opportunity, and they built the cloud-native version of what they had just built at PeopleSoft. And so they were the perfect founding team. They built this incredible business. And I think it's just an amazing success story. So that's really what they wrote. And obviously there's the architectural gap. And then there's this other kind of backdrop that,

basically every, you know, leading enterprise software company of today road, which was the shift from, hey, we're going to spend a bunch of money on CAPEX and have a bunch of servers in the back, and, you know, in some back office to, you know, hey, we want something that's multi-tenant and, like, you know, kind of shifting that into OPIC spend. And so that's what they kind of designed their business to do. And, and that's what they did. So now when you look at today, there is not, to my knowledge, someone that's built like an enterprise ready, right, you know, feature parity, HR, HR, HR, or HCM. Like there's just not someone that's done that for the enterprise. I think you can actually do that.

I think you can build it. I think it's extremely challenging. And, but I think the reason for that is now companies can look at this piece of software and say, it can do things today because of the way, you know, agents allow you to work and the things that humans can do if they have an AIDA piece of software. I can do things today that the past versions of this couldn't do. And so when you think about what it takes for a large enterprise to rip and replace some piece of core technology, the experience.

the experience has to be very different. The cost growth of all of it has to be different. It has to allow you to save a bunch of money, grow, have a better, you know, employ your customer experience in a material way. And so I think that's what we're seeing with other businesses across enterprise software. We're seeing that in the other big categories

that I mentioned here. And I think we're going to see it in HR. And so that's the opportunity. Yeah. And just to maybe straw man the critics for a second because you do talk a little bit about, you know, okay, we have like gusto and we have, here, let me just find, find this, this bit right here.

So like, what would you say, what would you say to these guys who are kind of like, well, we have deal and, you know, we have, we have Gusto. We have all these other startups that are kind of, you know, in the space already. Like, like, what is? So I think there's, there's two as an answer to that question. One, there's the people that are going kind of after core HR and core payroll today. And then there's kind of the orthogonal or adjacent opportunities. Like, you know, obviously, and Dresen.

is, I think, the biggest investor in deal, and I'm an enormous deal fan. I think it's an incredible team. They're not exactly doing this, you know, play, right? So I think that, like, that's just a separate kind of category in of itself. And I think maybe the company that builds this business that we're talking about in this post could be an amazing partner with deal over time, right? So I think that there's an opportunity there. Then you talk about Gusto and the other people that are kind of building what I would call a greenfield type strategy for, you know, on HR system. that is an opportunity, right? We see that across many different categories.

Like we have businesses in our portfolio that are doing that for ERP, like Real It. There's companies that are going after that for CRM, right? There are businesses that are doing that in all these other categories. Banking, right? Think of Mercury. So there are those plays. I think that that's the only way that you can build these types of companies when it's not in the middle or beginning, or sorry, not the middle, but the beginning of a platform shift.

Because 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 Service Now or Salesforce, it is so hard to rip them off. That's why these gross dollar retention are what they are. Like they're the most standards for a reason. Should be, it should be, look at this. Yeah, we can look at them.

I mean, look at this. Beautiful chart for a second. Yeah. It's an amazing business. And so what I think the opportunity is now is, you can go after these people and go ahead to head instead of Greenfield, it's Brownfield and say, hey, you have been a hostage to work day, right? Like you have been a hostage here and you can be freed with whatever new piece of software

if someone can build this in the right way and form and fashion. So that's the opportunity. And I think that what we're going to see is enterprises now have the kinetic kind of energy buildup inside of them to go do the rip and replace. But you need to build this in the right way and you need to solve the problems intelligently. And then I think you'll do this. And there's going to be a lot of people who listen to this or read my post and say, hey, you're full out of hot air like, you know, you clearly haven't thought about this or talk to anyone.

The reality is I talked to, like, a bunch of Fortune 500 and also private companies that, like, use Workday. And I told them the kind of business that, like, I think should exist. And some of them were like, I would buy this from you if it existed right now. So it's like, it is actually already happening. 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.

So before we get super granular about what these problems are and what the opportunity spaces, like I feel like we should talk about what Workday is doing right now because like it's not like they've been sitting on their asses. Yeah. Their AI, ARR has hit like $400 million in yearly run rate. It's growing triple digits year on year. Like they're not doing nothing.

So can you talk about the products that they do have and kind of where you feel like they fall short or maybe where you feel like they're sufficient or good. Yeah. So first, like, I wrote this piece to be balanced because I do think, like, again, I said it, Workday is one of my favorite software stories ever. Like, I think the business is unbelievably defensible

until 12 months ago I would have never thought about even writing this post. And it took 12 months of me thinking about this to write this piece because I was like, I had to convince myself that it was possible. And there are like, I think what I'm seeing or like the early signs of cracks. And so one of my favorite parts of this,

and this is not just specific to workday, but there are so many different enterprise software companies now that are reporting some metric affiliated with AI revenue that I think is just like kind of ridiculous. And so when I talked to professionals about like the flex credits, like I would say flex credits and people would just start laughing. And it's interesting to get that reaction because I think it's basically, I wrote this, I think it's basically just a procurement

innovation. I don't think anything is actually, you know, fundamentally changing. It still, you know, cost $25,000 to go get like a workday extend license and then build an app. Like, you know, it's still like these flex credits are still just like a procurement innovation. There's not like actually agenic experiences that are being delivered inside people's workday instances and workday platforms. So I think that that's like a big kind of farce right now is that this AI revenue is actually AI revenue instead of just like one CIA talking to another saying, I need a I need to spend money on AI. Let's get together.

You know, and I joke, let's go to Roos Chris and celebrate. Like, you know, nothing like a buttercake and procurement innovation to make it for. Yeah, yeah. And now I think this brings us to kind of like, okay, what, you know, this is what the title of, you know, the entire second half of the piece is, what an AI Native Workday should look like. Yeah. Should we just kind of talk through a couple of these categories and kind of what you've seen, what you've heard, the kind of founders that you're talking to,

also the kind of demands that you're hearing from Fortune 500s and just kind of like, what does this look like? Yeah, I think, like, I write this because I think that these are the six very important properties. And then I talk a little bit about, like, tactically how I think you should start. I think that these were the big ones, though, of like, why do people not switch? right? And like, what could get, what could get someone to switch? I think the first one is, like, unanimously understood now to anyone who's, like, seen what coding agents can do and has, like, seen what, like, great migration businesses or, like, implementation businesses, their AI Native

are doing today. I think you can deploy a system like this in call it 30 to 60 days, whereas historically, this is 12 plus months easily, and can be much longer than that and cost you a bunch of money. Like, that is going to happen. It's going to happen across enterprise. software, and that's why, you know, like, that is the fundamental building block of, like, why these businesses now can be kind of ripped and replaced much simpler. When I talk about Workbench Native, I thought a lot about, like, what to call this. But if you talk to an HR, you know, you know, administrator, there's so many, like, random things that they have to do to make work day work on a, on a daily basis.

And, like, this can be something as simple as, like, doing payroll for, like, a certain type of role inside the company that doesn't have the exact same parameters, and so they have to do it in a G-sheet. It could be spinning up a new business unit and doing a bunch of configuration. It can be like trying to think about an employee experience where Elena, you know, you lived in New York until recently, you were coming to San Francisco and you wanted to know,

hey, who's in San Francisco? Is Joe in San Francisco? Like, how do I actually find out of that information? Right? There's like no good way of doing that inside workday. So like, how do you build that experience? So I think that like this workbench native, like allowing HR teams to,

genuinely build versus, hey, spend $25,000 to like build anything on top of workday and then also get yourself a consultant that can build it for you. Like I think the days of that in an enterprise software are gone. Like anyone who's experienced the, you know, joy and magic of like building things with cloud code is going to tell you like that is going to be everywhere at some point. So I think that's going to be really critical. This agent first piece is I think that like thinking about the way that like I talked through my, you know, issue or your issue of trying to like get anything out of workday. Like, I just think that, like, agent first is going to be the way that these systems,

you know, work in the future. You saw the sales force headless announcement. Like, they're doing as much as they possibly can to shift towards this future. And I see Workday doing this too. So I think that, like, people are going to stay inside the work, you know, the tools that they're using or, like, there's going to be an AI-Native version of this. So you can just actually allow agents to do work for you. I think you open thesis critical.

Security is, like, paramount. And permissioning is really critical. And then the compliance piece is like the last one, which is, is, you know, this is a heavily regulated space. And so just thinking through, like, how do I monitor that? And how do I'm ensure that, like, my platform is, like, enterprise ready, global ready from the start is critical. So anyway, I think that's, like, the properties, exactly what it looks like in day zero, though. Like, I think that, like, some great entrepreneur is going to have to figure out how to, like, generate that kinetic energy and that, like, urgency for the buyer with whatever that initial tool is.

Yeah. And then let's just talk about the end of the piece a little bit. So you sort of argue that, you know, this is actually about more than, you know, HR software. It's also about, you know, how humans and agents interact. And I would love to just hear you talk a little bit more about that. And here, here, we're down. Yeah, we're down here. Like, like, I would love to hear a little bit more about that and kind of, you know, what do you mean when you say that? And kind of can you help sketch out what that looks like?

Yeah, I mean, I think that like as you have more agents doing work on behalf of humans, like, understanding their roles and permission inside of the company is going to be critical. And so, like, how do you actually like use what is like one of the most critical, you know, pieces of like, or corpices of data inside the enterprise to inform that identity. future, like, you need a, in my opinion, you need an agent, like an agent first kind of core to do that. And so I think that's going to be a big problem for CIOs. And I've heard this actually from many big CIOs of just like, all right, like, how do we do permissioning? How do we do tracking across our company as we adopt more tools? And so I think that could actually be like a backdrop of this. You know, that could also mean like, hey, these, all these other third party tools that we're adopting, not just building, also need access to this information. and they need it in a clean and cohesive way that's kind of a native.

And so I think that's going to be another driver. And I think we're seeing this already in ITSM, which is like tightly related to HR. And so I think, again, we're seeing the like cracks in the most defensible, you know, businesses in the world. And it's a really exciting time. And the race is on. Like this is why work they brought a kneel back. Like this is why they, you know, done two layoffs.

This is why they're like fighting tooth and claw and, you know, buying businesses like Sana, you know, to try to find this off because it's a race and the prize is huge. So would you make the argument that HR software is like the most anthropologically salient sort of vertical in software in terms of telling us where we are? Like it tells us where we are in the software cycle. It tells us where we are, you know, socially, like, you know, people on average expect these kinds of benefits. They like their yearly function health membership and their, you know, whatever else. And, you know, like, this is acceptable in the workplace. This is not. And now, like, the AI era is going to just introduce, you know, both a completely new platform shift,

but also completely new buying and procurement norms, completely new social norms, all of these things. And if you want to see where society is going, you should look at HR software. I think so. I mean, you know, I like agree with, you know, basically all of that. I think the crazy, maybe the crazy part about it historically is that this has not been like the front foot of the organization,

you know, like at least in terms of like, you know, trying new things or adoption cycles. And so I think that we'll like, maybe it will be the, it'll be like the beacon of like AI is actually finally reaching like more mass kind of like take off. Yeah. Because like that to me feels like part of like where we are right now. It's like if I had a map of the United States and like, you know, there's like lights

in like, you know, the coasts or like I don't know how you'd say it like in the major cities. And it's like the lights indicate like who has discovered that like AI can actually dramatically transform like business processes and they're excited by it. And I think the rest of the rest of the kind of country is kind of dark. And I think what we're going to see over the next 12, 24 months is like just a dramatic brightening of that map. And, and I think as that happens, like we're going to see HR start to swing. And that will be like when we really start to see takeoff. So that maybe is a different way of saying the same thing you just said. Yeah. Yeah. When, yeah, everybody, everybody gets their AI native HR tools. So,

I think for our final question. So the last piece you wrote was on Revit. Yes. Every, every, here, let's see if this is going to, yeah, yeah, every building you've ever been in was designed by software built in 1997, which in retrospect was a bit of a controversial statement. People didn't like that. They were like, wait, there have been buildings built before 97.

I'm like, I'm aware. That was actually, that was a prerequisite for me when I was looking for. for apartments. It had to have been built in 1997 or later, just because I didn't, I didn't trust anything. I didn't trust anything prior to that. But we, we had a reference to maybe one of the greatest albums, one of the greatest songs on the greatest albums of all time. So once at a lifetime off of the album, Remain in Life by the Talking Heads. Great album. So I, we don't yet have a song for workday. So what is our workday song? I was very disappointed by this, by the way, because I'm now, you know, a kind of recurring theme and everything I've written has been

like some, you know, silly reference to a song or, uh, or like a fun movie. Um, so I think that like I was, I was trying to come up with something and I think, uh, maybe like Hotel California. Um, okay. You know, it's like you can, you can check out anytime you like, but you can never leave. Like that's good work days. That's been work days, uh, that's good. M. So I think, uh, so I think, it doesn't exactly work because obviously I think that like people are going to start leaving. Yeah. You know,

that's my obviously software for it. That's a good one. No, no, no, no, no, that's good.

I was, I was going to, like, maybe you're going to do like a meta work song. Yeah. Maybe like work it by Missy Elliott. Oh, God.

I could have gone on the work angle. I was thinking I had one. I was thinking about it actually this morning. Have you seen The Sopranos? Of course. You know, the opening theme song to the Sopranos, I feel like for some reason, it's just like very, like, woke up this morning. Yeah.

I feel like most like the Sopranos, like, I just feel like, you know, what was Tody Soprano at the end of the day, if not an HR guy? Yeah. There's this one scene in Sopranos where he's listening to Dirty Work by Steeley Dan. Oh, yeah. So that could actually work really work. That could actually really work. I don't want to do your dirty work.

Paul Thomas Anderson tie in there because there was a needle drop in one battle after another of dirty work. I think maybe it is dirty work. It's dirty work. It has to be dirty work. Should we change the title? We might have to change it. I feel like it or the subtitle. We could change the subtitle to I don't want to do your dirty work.

I don't want to do your, can we do that? Is that allowed? Someone called Denko. Get him on the horn. I can edit it. I mean, look. Look. I don't want.

I could edit it right now. Yeah. I could. Why not? Can you pull up the screen share again? Yeah. I could edit it. Yeah.

I think we have to put that right below. Um, and you put it in, put it in like the, I'll ask, I'll ask Danco before I don't want to get fired on stream. Yeah. Well, that would be, that would be like, like that would be dramatic. Um, that. That. Live stream it on work day.

Yeah. That's a situation. Uh, so. Yeah. Anyway, I feel like we've really, we've given this the treatment. Everybody like and subscribe to A16C.C. News. Everybody follow Joe Schmidt the 4th. Yes.

Is that your, yeah, it's Joe Smith. That's my handle. Yeah, don't follow my dad or my son. Don't follow his dad or his son. Yeah. And yeah, this was a ton of fun. Let's do another soon. Let's write another obituary.

It's a deal. More to come. Yeah. All right. Awesome. Thanks. Thanks for listening to this episode of the A16Z podcast. If you like this episode, be sure to like, comment, subscribe, leave us a rating or review, and share it with your friends and family. For more episodes, go to YouTube, Apple Podcast, and Spotify. Follow us on X at A16Z and subscribe to our Substack at A16Z.com. Thanks again for listening, and I'll see you in the next episode.

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