Zendesk has rethought service pricing in an AI-first era beyond the evolution from seat-based to token-based pricing – the company now commits to outcome-based pricing marking one of the most important commercial shifts in the enterprise AI market.

Announced during the company’s annual Relate conference, the new model charges customers only when its AI systems have successfully revolved support interactions.

The company said every resolution would be independently verified with its own dedicated AI evaluation model, meaning that low-value exchanges would be excluded from billing.

The pioneering move reflects growing pressure across the AI industry to prove tangible business value rather than simply showcasing model capabilities for high and often wasted costs. With organisations now becoming more cautious about AI spend, vendors are increasingly being asked to demonstrate measurable ROI instead of charging for access alone, and Zendesk’s shift in pricing model holds the company accountable to pass on ROI to customers.

However, what this means in terms of revenue is less clear. For years, SaaS companies have largely relied on predictable subscription pricing tied to the number of users or licenses.

Zendesk’s approach effectively treats AI agents as digital workers whose compensation depends on measurable outcome, rather than availability. For Zendesk’s customers, it means they’ll only pay when meaningful work is completed.

As Shashi Upadhyay, President of Product, Engineering, and AI, put it in an interview at the event: “Stop thinking of agents as software… start thinking of them as a unit of labour.”

This marks the first time that a company like Zendesk could risk incurring costs without being able to recuperate them from clients, and it marks a major turning point for revenue models in general. The implications could extend far beyond customer service, as companies are expected to experiment with pricing tied to sales conversions, resolved tickets, completed workflows, productivity improvements and other outcomes.

This new strategy also reflects the growing competition within enterprise AI – looking ahead, pricing innovation may become just as important as model performance in acquiring and retaining customers.

So while Zendesk may be among the first to implement such pricing at scale, it offers a glimpse into how AI software could likely be commercialised in the future.

Workers are struggling to understand how to best use AI tools for their daily tasks due to a widening disconnect between employers and their employees, new research has claimed.

A new study from Mitel found that AI tools are often misaligned with how employees actually work, leading to widespread frustration.

This is leading many workers to bring in their own familiar tools from outside of work, potentially opening up their organisation to security threats and other risks.

The study found 71% of workers admitting to have used non-approved communication tools for work-related purposes, increasing the risk of the likes of data exposure, compliance breaches, cybersecurity threats, and a loss of visibility and control.

A similar proportion (71%) said they felt pressured to just “make it work” with tools not designed for their needs, showing the apparent disconnect or disinterest from senior management.

Overall, while just over half (51%) of workers said they regularly use AI tools, only 37% reported feeling very comfortable using them in their day-to-day work – with 70% saying they felt their organisation does not adequately support AI use.

“Organisations are making significant investments in AI, communication infrastructure, and modernisation,” said Eric Hanson, CMO at Mitel. “Yet more than half of employees report that these tools fall short at the moments that matter most.

“The challenge is not a lack of technology, but a lack of alignment with the realities of work. In fast-moving, high-pressure, and increasingly mobile environments, communication must be immediate, reliable and context-appropriate — or it risks breaking down precisely when it is needed most.”

“Closing the experience gap is now essential to reclaiming control and ensuring that communication investments translate into real-world performance and impact.”

More than 20,000 SAP customers are “stuck” on legacy ECC systems due to customisations, according to the CEO of SAP partner MyWave, Geraldine McBride, and many won’t migrate anytime soon. At Sapphire 2026, SAP offered them a path to AI, but only if they commit half their maintenance spend to the cloud first.

The offer, confirmed by SAP Chief Strategy Officer Sebastian Steinhaeuser during a media briefing, enables SAP to extend limited AI capabilities to customers still running its software on-premises during their transition to cloud ERP. But it comes with a significant condition: Customers must shift at least 50% of their maintenance spending to the cloud before they can enable Joule assistants on premises.

It’s a another small crack in SAP’s resolve: For years, it has been upsetting customers using its legacy systems by telling them the only way to access its latest innovations is to migrate to its latest platform, S/4HANA, in the cloud.

“There’s no confusion at all” about the latest change, said Steinhaeuser. “To be super clear, our Joule assistants and agents are designed for cloud. This is destiny and destiny is unchanged. […] However, we also want to meet customers where they are. We’ve put in a lot of work technically to make Joule available to ECC and S/4 customers who have committed to their journey.”

An SAP spokesperson confirmed the 50% requirement and said the company has no plans to extend the ECC end-of-service deadline beyond 2027, with extended support available through 2030 at additional cost.

For customers already on SAP’s Cloud ERP Private offering, the deal is sweeter. SAP will activate up to three Joule Assistants at no additional cost to cover common workflows in finance, HR, and the supply chain. New customers will be guided through activation during onboarding; existing customers can contact their SAP representative.

The Coalition for Fair Software Licensing has published research showing that US workers reckon Microsoft is using its productivity tools to lock their employers into the company’s AI services.

The survey data of more than 1,000 workers – out a day before the release of Microsoft’s E7 AI bundle – found that three-quarters believed Microsoft was using its dominance in productivity software to push AI. More than half (57 percent) opposed their employer buying Microsoft’s E7 bundle.

Only a third of workers questioned said they preferred Microsoft as a vendor, while 78 percent reported they could do their jobs just as well with another vendor’s AI tool.

Perhaps that other tool is Google Gemini. Though the survey makes for difficult reading for Microsoft and Copilot enthusiasts, it also opens a new front in the war for productivity hearts and minds. Google has no official affiliation with the survey or the Coalition for Fair Software Licensing – but Microsoft, for one, has its suspicions.

In a 2024 blog entitled “Google’s shadow campaigns,” Rima Alaily, Microsoft’s general counsel for Infrastructure Legal Affairs, wrote, “We understand Google is a main funder of the US-based Coalition for Fair Software Licensing.”

The Coalition for Fair Software Licensing were asked about its ties with Google. A spokesperson said, “While the Coalition does not disclose our membership, our members span a cross-section of key industries, including healthcare companies, financial services businesses, as well as cloud and cybersecurity providers – each one has experienced or been exposed to anticompetitive and abusive software licensing practices in the cloud.”

Another source grumbled about Gemini, saying there is a risk that “Google is deploying the same playbook as when they were monopolising search.”

Google were asked for comment, but the company was unable to provide a statement before publication. Other than an acknowledgement of receipt, Microsoft has also not responded.

Ryan Triplette, executive director of the Coalition for Fair Software Licensing, said, “Microsoft’s decision to launch E7 on May Day is no coincidence. It should send a clear distress signal for any organisation already locked into the Microsoft ecosystem. For years, customers have borne the cost of that lock-in, paying a premium not for innovation, but simply for the ability to maintain flexibility. E7 is the latest extension of that model, and the reaction from workers underscores a growing reality: the cost is not justified.

“Despite Microsoft facing mounting regulatory scrutiny over its anticompetitive behaviour, we fully expect the company to deploy every tool in its playbook to force existing customers into this new bundle. Regulators on both sides of the Atlantic should be watching closely and be poised to act quickly to protect customers.”

Microsoft is dominant in the office productivity space. Google Workspace has claimed a few high-profile scalps over the years, but some, such as European aerospace megcorp Airbus, have found the Microsoft habit a hard one to kick.

It is unsurprising, then, that critics have rung alarm bells over Microsoft pushing AI technology into enterprises that have already bought into its productivity ecosystem. Copilot has yet to deliver the productivity gains promised by evangelists, but Microsoft is heavily invested in the tech and determined it will be a success.

The survey data reflects wider unease among workers over AI tools being promoted through subscriptions like E7, and anxiety, perhaps, about an agentic future and what it means for their jobs. What it does not capture, however, is the thinking of those who will actually make the decisions: whether Microsoft holds its grip on office productivity into the AI age, or loses its crown to a rival.

For decades, enterprise software has acted as a digital filing cabinet or system of record where human workers painstakingly log the daily operations of a business. Now, Oracle wants to flip that dynamic, turning its software into an autonomous engine that does the work itself.

The move hinges on what the tech industry is calling agentic artificial intelligence (AI), where software agents with the ability to reason and collaborate can execute multi-step tasks with minimal human intervention.

Speaking on the sidelines of Oracle AI World Tour Singapore, Rondy Ng, Oracle’s executive vice-president for applications development, noted that enterprise resource planning (ERP) systems are evolving from passive repositories of data into autonomous systems of outcome that execute tasks based on high-level business goals.

However, Ng made it clear that Oracle’s latest AI innovations are exclusively reserved for its software-as-a-service (SaaS) products, such as Oracle Fusion, which is used by about 70% of its applications’ customer base. Legacy, on-premise product lines remain in maintenance mode.

“When people deployed those legacy applications from the past, they were heterogeneous,” he said. “They were not standard processes.

“If you have data demarcated in different ways, you can build agents to recognise all the differences, but the effort of doing that and the likelihood of making mistakes and hallucinations are higher.

“But if you’re on a relatively clean slate, you get faster results, better accuracy and more automation,” added Ng. “Our strategy is for people to go to SaaS. When you’re on SaaS, you can deploy AI much more efficiently.”

Solvimon says companies are adopting more complex pricing models as AI changes how software is billed. According to the billing platform, usage-based charges have risen sevenfold since 2025.

Its data points to a shift away from flat monthly fees and seat-based pricing towards combinations of subscriptions and consumption-based charges. The fastest-growing software and AI businesses now use nearly five pricing structures on average, up from three over the past year.

That shift is putting pressure on finance teams as AI products create value in ways that do not fit neatly into older billing systems. Businesses are trying to bill for credits, tokens, usage and outcome-based measures alongside standard subscriptions, increasing the risk of invoicing errors and missed revenue.

A Bain & Company analysis of more than 30 established SaaS vendors found that 65% have already introduced hybrid pricing, adding AI usage or outcome metrics to traditional seat-based models. Solvimon argues that the spread of these structures is making billing one of the more fragile parts of the revenue cycle for companies with expanding product lines and more tailored commercial contracts.

Research from MGI found that SaaS companies can lose between 1% and 5% of annual recurring revenue each year through billing leakage caused by errors that repeat in each billing cycle until detected. For chief financial officers, that is bringing greater scrutiny to systems once treated as back-office tools rather than strategic infrastructure.

Oracle customers have been warned to watch for changes in support and pricing as Larry Ellison’s company makes huge datacenter spending commitments to support its AI ambitions.

Advisors in Oracle negotiations said support levels are declining, while costs might increase as discounts disappear. Others have warned of a tougher approach to contract negotiations.

Oracle is aggressively expanding AI datacenter capacity to serve demand tied to customers and partners including OpenAI, xAI, Meta, Nvidia, and AMD. The deal for OpenAI alone is set to be worth about $300 billion over five years.

Widespread reports of layoffs affecting thousands of staff came as investor concerns grew over how Oracle would finance its AI datacenter build-out, while borrowing heavily to support the expansion.

In March, Oracle increased the estimated cost of its fiscal 2026 restructuring plan by $500 million, taking the total to as much as $2.1 billion, as observers anticipated broader job cuts.

Oracle previously raised $18 billion in debt and has since outlined plans to raise far more, as it funds datacenter investments aimed at meeting surging demand from AI model builders and enterprise customers. Ratings agency Moody’s warned of further borrowing and negative free cash flow as Oracle ramps up its AI infrastructure investment.

Nick Walter, CTO of professional consulting at commercial advisory firm House of Brick Technologies, said that there were plenty of anecdotal reports that Oracle support outcomes are getting worse, meaning slower service, less skilled help, and “more Oracle Support responses that were obviously written by AI.”

House of Brick had also seen a recent surge in customers asking for help in reducing Oracle Cloud Infrastructure (OCI) usage or help in negotiation with Oracle over long-term OCI deals, he said. “Many customers who adopted OCI in the last three to five years are suddenly finding out that their renewals are much more expensive because Oracle has eliminated or reduced enterprise discounts, and they are being forced close to public listed pay-as-you-go prices.”

Customers were also seeking help in response to pressure on Java, with audits and sales pushes and “scary-sounding threats.”

“This is not a new phenomenon but pressure continues and Java is the main front in Oracle’s war against their customer’s pocketbook,” he said.

Craig Guarente, founder and CEO of Palisade Compliance, said that Oracle was no longer simply putting pressure on customers to license Java; it was conducting official audits. “We’ve definitely seen in the last few months a return to classic Oracle auditing practices,” he said.

In 2023, Oracle changed its Java SE subscription model, shifting from a per-user or per-processor basis to per-employee. Critics called the move “predatory” as organisations that were using little Java but had a large number of employees could be hit hard by the cost increase. Later that year, research from Gartner showed that costs could be between two and five times greater under the new licensing model for using the same software.

Guarente also warned of price hikes at OCI contract renewal. “If you’re not adequately protected, then we’re getting 9 percent or 10 percent for long term lock in. It all goes back to that original purchase. You had some flexibility in there if you were thoughtful in how you negotiated those contracts. But if you signed the local standard agreement, there’s no price protection.”

Eric Guyer, founder of Oracle advisory and consulting firm Advizant, pointed out in a social media post that the margins in software support were much higher than in datacenters.

“This means the value to Oracle of your software support payments is increasing, desperately so, whereas the value to you is diminishing, and at an increasing rate. I mean this both technically via waning innovation and the more than 8 percent annual inflationary adjustments,” he said.

Customers are also concerned about the long-term impact of the job losses on their relationship with Oracle, Guyer said.

“The trend in license negotiations is only indirectly related to Oracle’s shift for now. The layoffs mean companies have lost one or more of their sales contacts. But for apps or the more strategic long-standing relationships, this means customers are wondering what this loss of institutional knowledge will mean for them. I’m not hearing customers wonder if Oracle is de-prioritising its legacy software business just yet, although I see this as an obvious outcome,” he said.

Does your AI agent count as an employee?

At a recent conference, Microsoft executive Rajesh Jha floated a provocative idea. In a future where companies deploy fleets of AI agents, those agents may need their own identities — logins, inboxes, and even seats inside software systems. If so, AI wouldn’t shrink software revenue. It could expand it.

“All of those embodied agents are seat opportunities,” Jha said, envisioning organisations with more agents than humans — each effectively a user that must pay for a software license, or “seat” in industry lingo.

That’s a radical twist in the SaaS pricing debate rattling companies like Microsoft, Salesforce, and Workday. Investors worry AI could hollow out seat-based pricing, the backbone of enterprise software. If one human can manage dozens of agents, why pay for dozens of licenses?

Jha’s answer: because those agents are the new users. A company with 20 employees might buy 20 Microsoft 365 licenses today. If each employee gets five AI agents, and the workforce shrinks to 10 people, that could still mean 50 paid seats.

Not everyone buys it.

Nenad Milicevic, a partner at AlixPartners, sees the opposite. AI agents will reduce the number of humans interacting with software, slashing licenses. Instead of 20 employees, you might have one person overseeing a handful of agents. That shift would pressure vendors and empower customers to push back on pricing that no longer makes sense.

Milicevic argues the winners will be open platforms. Companies could charge extra for machine-based access, but risk losing customers to software rivals that let agents operate freely.

Which brings us back to the core tension: if AI agents are just extensions of you, charging extra feels like double billing. If they’re autonomous workers, paying for them may be inevitable.

The answer could define the next decade of software economics.