Q&A: Box CEO embraces shift to ‘headless’ software in the agentic AI era

The rise of generative AI (genAI) technology has prompted a growing debate about the future of software-as-a-service (SaaS) business models. Some of the fears are overblown: enterprises are unlikely to vibe-code their own applications to replace their SaaS suppliers anytime soon, while software vendors have yet to see per-seat sales fall off due to mass automation of white-collar jobs. (In fact, some now predict the opposite will happen.) At the same time, AI has the potential to change the way work is carried out, with AI agents empowered to interact with software applications on behalf of users. For software vendors, that could mean a future where applications are accessed less through traditional user interfaces as AI agents connect via APIs. It’s an inevitable shift, says Box CEO Aaron Levie, and one that requires software vendors to adapt their existing products and business models to prepare for agent workflows. Computerworld recently spoke with Levie about how Box — and other SaaS vendors — can adapt as agentic AI threatens to upend existing business models. (This interview has been edited for clarity.) Discussion about a “SaaS-pocalypse” has died down recently, and software stocks have rebounded. At the same time, it seems clear the adoption of AI agents could change how workers interact with software. How can companies like Box adapt to this new environment? If AI increasingly becomes the interface users interact with, where does the long-term value lie? “People are realizing that you’re not going to rebuild a lot of the systems that people were kind of claiming you would [with vibe-coding]; it just doesn’t make sense. So, that part is sort of dissipating. However, headless software and the ability to use your systems via AI is obviously going to happen, there’s no question. “So, I think the conversation is shifting from ‘AI disrupts software’ to ‘AI is going to be the biggest consumer and user of software going forward.’ And for that, the main thing is: can you have a business model that allows you to actually monetize the consumption of those agents using your underlying tools? We’re fortunately built for that; we’ve had an API business model basically forever, so we’re well prepared. “There’ll be some companies that have to pivot a little bit more significantly over time — there’s no question that will happen in a bunch of organizations. We’re big believers that AI will be the biggest user and interface for the future of software.” How important is it for Box to retain that interaction with human workers, rather than becoming more of the underlying layer AI agents interact with? “I would say that we’re totally comfortable with that shift. When you have AI agents, you still need a place to be able to secure the data — you need to protect it, you need to govern it, you need to make sure you know who’s accessing it. None of that changes in the world of AI. In fact, if anything, it actually increases. “We don’t really care if it’s an agent using the data, an application using the data, a person using the data — we want to be the best content management system that connects your information to all of those applications.” How does that perspective feed into your product development and roadmap “It basically means that we need to be a headless platform. That means customers need to be able to access their data via MCP inside of ChatGPT, inside of Claude, inside of all these systems. It means that we care as much about our APIs and access to those APIs as we now do our user experience. We have to make sure that both of those environments are as simple and clean as possible, and as usable as possible. “It’s basically as if there’s another constituent now in our ecosystem that we have to go and pay attention to. “We need to be the best place to manage your content, and then wherever you want to work with it from, we’re totally fine. So, if you want to work with your files from your desktop, from Claude Cowork, from ChatGPT Codex — we just want to make sure we are universally accessible across every single place that people want to work with their data.” Could that mean changes around how you price access to your software? Do you expect a shift to usage-based pricing? “Not as much as is probably being talked about online, because seats still make sense for the employee and the end user. Even when an agent is doing work on your data, it’s still you invoking that agent. It sort of makes sense that the seat is still attached to the underlying end user employee, even though an agent is going to be doing work on your data. “We think the seat model will be quite durable over time. What this does is just add another business model, where you have agent-only interactions; those will be primarily coming through the API, and then that will be a consumption model.” What are your thoughts on outcome-based pricing? Is that something you look at? “We do one thing that’s close to that — we have the Box Agent that does things like data extraction. It extracts your data and we charge based on the number of pages that you want to extract data from. So there are some things that approximate outcomes, but not at the level of resolving a customer service ticket or something like that, that maybe has been talked about. We’re probably going to be more aligned tothe amount of compute that that is used.” What are your conversations with customers around moving to a usage-based model? A lot of organizations are used to fixed monthly subscriptions — can metered AI agents become problematic? “I think it definitely can be. This is sort of a common tension in general. We saw this with cloud computing, for instance. The difference with cloud computing is that cloud was relatively centralized, versus the use of AI and tokens are much more diffuse. That’s a big difference that companies have to think about. “There’s always this tension: you can pre-buy and have a subscription, but then you might be overpaying for periods where you’re not using it as much. Or you can only pay for what you use, in which case you might have some volatility in the pricing of what happens.” How are customers progressing in adopting AI agents — particularly, the move from pilot projects to production. What are some of the biggest barriers to wider deployment of agents? “We’re very much moving from coding agents to the rest of knowledge work: this is the jump that’s starting to occur. In that, one of the big questions and challenges is how companies get agents the right context and information to work with — how do they enable agents with the right level of constraints in their organization from a security and compliance standpoint? This is our kind of reason to exist, and what we’re helping our customers on. “Overall, it’s just a transformational moment in the enterprise. Every customer that I talk to, every dinner that we have with customers, every CIO meeting I’m in, every CEO meeting I’m in, it’s all about agents. “Agents have thrown the whole world into this kind of dynamic period of, ‘What does the shape of your organization look like? What’s the future of a manager versus an individual contributor? What are the workflows that you can go and execute on?’ There are so many different ways that this is starting to change.” You were part of another major industry transition with the adoption of cloud computing. Are there similarities you see or major differences that customers can learn from? “The big difference between [them] is that, with cloud, you could centralize the deployment of and management of.Cloud really only affected 3 of your organization that was moving from the data center to the cloud, and then every employee got better products and experience as a result of that. The change was really kind of fairly concentrated. AI affects every single employee in the company. It’s a radically different type of transformation of what work looks like. “There are only so many analogies you can make to cloud before quickly you realize, no, this is actually a different transformation. Maybe it’s even closer to the PC, in the sense of every single worker has to change what they’re doing to be productive. It’s not a technology delivery shift, it’s a fundamental reworking of every workflow in the enterprise. And so that’s I think what most companies are going through right now.”