Workday’s Aneel Bhusri and Joel Hellermark break down the three make-or-break shifts leaders must make to evolve past traditional software models.
Sydney Scott
Editorial Strategist, AI
Workday
Technology market disruption is underway, and companies have an opportunity to reimagine how they work, make decisions, and grow in the era of AI. Those that do it well can transcend technology generations and be part of the next chapter of how work gets done, Workday co-founder and CEO Aneel Bhusri told a live audience May 21 at the New York Public Library.
"I think this is a chance for us to be a disruptor, not a disruptee," he said.
Bhusri appeared at the annual Sana AI Summit alongside Sana founder and Workday’s newly minted Chief AI Officer, Joel Hellermark. The two addressed ongoing market fears of a so-called “SaaS Apocalypse" and what they think AI means for their company and others.
Workday was born in a tech disruption. Bhusri and co-founder Dave Duffield saw an opportunity in 2005 to create easier-to-use enterprise software for the cloud. Now, in the midst of an even bigger disruption, many vendors are scrambling to play defense by slapping minor upgrades onto legacy tools.
Bhusri said navigating a generational technology shift requires a far more aggressive approach. In his fireside chat with Hellermark, the two laid out 3 strategies playbook that will separate market disruptors from those left behind.
“This is a fundamentally new era for software. We’re not really selling software anymore. We’re selling work itself.”
—Joel Hellermark, Chief AI Officer, Workday
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It’s natural for rapid market changes to fuel widespread industry anxiety. In that environment, playing it safe is a losing strategy.
In the case of software, traditional platforms that merely connect static tasks across different applications are facing an existential crisis. Probabilistic AI works by guessing patterns rather than following strict rules. This makes it an incredible reasoning engine, but on its own, it’s too risky for rule-based business tasks.
For example, a company cannot run payroll correctly just 95% of the time and guess who got paid and who did not. Core financial work and closing the books must be exact. They have to be right 100% of the time, every single time.
But real value lies in fusing AI with deterministic software: systems built to follow precise rules with zero room for error. Seizing the opportunity in a major technological shift will mean Workday needs to return to its startup roots and rethink every part of the employee journey.
“I do think all bets are off as it relates to what’s happening in the industry, given what we can do together,” Bhusri said, referring to the combination of Hellermark’s Sana and Workday’s deep integration in core business functions.
“It was also a big reason why we partnered with Workday and became part of Workday,” said Hellermark. “This wasn’t about playing safe. This is a fundamentally new era for software. We’re not really selling software anymore. We’re selling work itself.”
Bhusri said: “I think this is a chance for us to, you know, spread our wings.”
"I think this is a chance for us to be a disruptor, not a disruptee."
—Aneel Bhusri, Co-Founder and CEO, Workday
Technology is moving too fast for software companies to stay in their traditional lanes. The clear lines that used to separate different types of business software are starting to, as Hellermark put it,“blur.” That creates an opportunity to think bigger.
The software market is big, and Hellermark is inspired by an even bigger market: the market for labor. Building agents to handle more and different types of work, at increasing levels of autonomy, is a key expansion opportunity for Workday.
With the productivity gains it’s seeing from AI, Workday can orchestrate HR workflows, like travel, that it hasn’t participated in before. And so, he asked Hellermark in their conversation: “Why shouldn’t we?”
This won’t happen overnight. To successfully expand across these traditional software boundaries, the rollout will have to follow a proven growth model. As Bhusri explained, "You start in the lower and mid-market and work your way up as you add capabilities.”
“I think it’s a bit analogous to self-driving cars,” Hellermark said. Even when the technology existed, the transition to fully autonomous cars with humans in the back seat took a long time because we needed to make sure they could be trusted. “And during that era, you need a lot of humans in the loop,” he said. “That’s why you have a lot of humans sit alongside the self-driving car systems.”
Similarly, Workday is building a trusted world model for work, a knowledge graph for agents to run on as they gain autonomy.
This connected network changes how we think about the value of technology at work. Instead of just giving people passive tools, technology will now help finish the actual work through a shared experience where humans and digital agents cooperate.
To illustrate how this boundary-blurring network functions in practice, Hellermark pointed to IT support as a prime example.
“When you think about a domain like ITSM, a core component of that is the employee lifecycle. When that employee gets onboarded, when they get offboarded, and the journey along the way. It makes a lot of sense for a product like Workday to own those workflows.”
In this model, once an individual task connects to a core network, adjacent workflows like IT setup can handle transitions automatically.
Managing a stable, older technology generation requires one specific playbook, but inventing a brand-new AI ecosystem requires a raw startup mentality.
Steering through this transition requires an entirely different style of leadership. Managing a stable, older technology generation requires one specific playbook, but inventing a brand-new AI ecosystem requires a raw startup mentality – one that isn’t afraid to undo the past and reinvent it entirely.
For Workday, that means fixing complex user experiences. The rise of automation creates an ideal opportunity to overhaul how users interact with machines.
“The user experience is shifting, right? We've spoken about AI being the new UI (user interface),” Hellermark said. “As you could see in the demo today, I wasn't really clicking through dozens of different enterprise applications. I had it all orchestrated in a single interface for me, where I could oversee thousands of agents doing work, escalating to me when necessary as well. I think this is a very good moment in time to reimagine the user experience.”
Bhusri agreed. After 30 years, he said, users will have a whole new way of using Workday. And Sana will be that gateway.
The enterprise software landscape is undergoing a permanent rewrite. Legacy giants and fast-moving startups face the exact same choice. They can aggressively disrupt their own business models now, or they can wait for the market to do it to them.
Ultimately, a technological shift requires a fundamental rewiring of how companies organize their workflows, blend different technologies, and support their people. The old boundaries are gone and the clock is already running on the companies that don’t adapt.
“This is a story of Workday and Sana coming together where 1 plus 1 is way more than 3 or 4 or 5,” Bhusri said. “We're going to be redefining how business and work gets done.”
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