ClickUp lays off hundreds of employees: AI agents are coming

What happened in ClickUp: The Timeline

At the end of May 2026, TechCrunch reported on the mass layoffs at ClickUp. The startup, founded in 2017, has chosen to replace hundreds of employees with thousands of AI agents. In nine years, ClickUp had become one of the most popular project management platforms in the world. However, management decided to radically accelerate towards intelligent automation.

The process didn't happen overnight. Over the past two years, ClickUp had progressively integrated AI features into its internal workflows. Additionally, it had invested in developing autonomous agents capable of handling repetitive tasks, responding to support requests, and coordinating operational activities. Consequently, the need for human personnel for certain functions was drastically reduced.

This case represents one of the first documented examples of the large-scale replacement of cognitive work with AI agents at a medium-sized tech company. As such, it warrants a thorough analysis.

Who wins and who loses in this transition

The answer isn't simple. There are winners and losers on multiple levels. Therefore, it's helpful to distinguish between the different perspectives.

The winners in the short term Clearly, the shareholders and management of ClickUp. The reduction in labor costs is immediate. AI agents, once configured, scale without significant marginal costs. Furthermore, the execution speed on standardized tasks increases significantly.

The immediate losers These are the employees affected by the layoffs. However, the phenomenon has broader implications. Even workers who keep their jobs are facing increasing pressure. They must demonstrate added value that agents cannot replicate: critical judgment, customer relations, and strategic creativity.

On the market floor, ClickUp’s competitors now face a choice. Unlike those who wait, those who embrace the integration of AI agents gain a structural competitive advantage. According to research by McKinsey on the economic potential of generative AI, the proportion of tasks that can be automated in knowledge worker roles could reach 60–70% by 2027.

AI agents: not chatbots, but autonomous operators

It is important to clarify what is meant by an AI agent. These are not simply chatbots or virtual assistants. AI agents are systems capable of planning sequences of actions, utilizing external tools, and independently accomplishing complex tasks. As a result, their impact on the workplace is qualitatively different from that of previous waves of automation.

In a project management platform like ClickUp, an AI agent can assign tasks based on priority, update progress statuses, generate reports, answer the team’s operational questions, and even reorganize the roadmap based on new input. What’s more, it can do all of this simultaneously across hundreds of projects. No human team can compete in terms of volume.

However, there are clear limitations. AI agents struggle with strategic ambiguity, interpersonal negotiation, and handling unforeseen exceptions. Therefore, the value of human work shifts towards these cognitively and relationally intensive skills. Harvard Business Review has analyzed in detail this division of labor between humans and AI.

SHM Studio’s interpretation: a signal, not an anomaly

The ClickUp case is not an isolated incident. We at SHM Studio We see this as an early sign of a trend that is set to grow. Tech companies are the first to act because they have the culture and resources to do so. However, the phenomenon will quickly spread to other sectors.

In particular, Italian SMEs in the B2B and retail sectors find themselves in a delicate position. On one hand, they cannot afford to ignore the efficiency that AI agents guarantee. On the other, they often lack the internal expertise to implement these solutions safely and sustainably. Therefore, the risk is twofold: falling behind or adopting tools hastily and in a disorganized manner.

Our position is clear: workflow automation is not a threat to be avoided, but a lever to be managed. Our services for AI consulting for SMEs are born precisely from this conviction. Analogously, our approach to digital marketing already incorporates smart automation features into its campaigns.

Operational Implications for SMEs: Three Areas of Impact

Analyzing the ClickUp case, three operational areas of immediate relevance for Italian SMEs emerge.

• Internal workflow management: Many SMEs use tools like ClickUp, Asana, or Monday to coordinate their teams. The integration of AI agents into these environments is already available. However, it requires a precise mapping of processes prior to implementation. Without this step, automation amplifies existing inefficiencies rather than eliminating them.
• Customer support and communication: AI agents can handle a significant portion of incoming requests. As a result, the human team can focus on complex, high-value cases. This hybrid model is already being adopted by medium-sized companies with measurable results.
• Content production and SEO: also in the field SEO e copywriting, AI agents are taking on an increasing role in content generation and optimization. However, human editorial oversight remains indispensable to ensure quality and strategic consistency.

Finally, there is a fourth area that is often overlooked: organizational culture. Introducing AI agents without preparing the team leads to resistance and a loss of trust. Therefore, change management is an integral part of any serious automation project.

The construction site still open: what remains to be resolved

The ClickUp case raises questions that the industry has yet to resolve. First, who is liable when an AI agent makes an operational error? The legal landscape is still evolving. Furthermore, how do you measure the performance of an AI agent compared to that of a human employee? Traditional KPIs are not always adequate.

According to According to Gartner, AI agents are among the top technologies for 2026–2027. However, the maturity of the available tools remains uneven. Agents handle certain categories of tasks exceptionally well. Others still have error rates that are too high for unsupervised deployment.

For SMEs, this means that the most prudent approach is an incremental one. You start by automating the most standardized and measurable processes. Subsequently, you extend automation based on the observed results. This approach reduces risk and allows for the development of internal expertise over time.

Next moves: how to prepare now

The ClickUp case study offers some practical steps for SMEs looking to navigate this transition in a structured way.

• Audit of repetitive processes: Identify which internal activities are most time-consuming and have the least variability. These are the ideal candidates for the first phase of automation.
• Tool Evaluation: Not all AI agents are equal. It is necessary to evaluate the available platforms based on your existing technology stack. Our experts web development e AI support this selection phase.
• Team building: investing in the training of people who will work with AI agents. The role of automated process supervisor is a new and increasingly in-demand skill.
• Continuous monitoring Define clear metrics to evaluate agent effectiveness. Google Ads campaigns and the LinkedIn campaign already automated are a good methodological benchmark.

Finally, it is useful not to isolate yourself. Comparing notes with other SMEs undergoing the same transition speeds up learning. SHM Studio Blog regularly publishes analyses and case studies on these topics. For a direct comparison, it is possible Contact our team.

The future of work is not yet written. However, companies that start writing it today will have a significant advantage tomorrow. The ClickUp case is a powerful reminder: automation doesn't wait. The question isn't whether to adopt it, but how to do so intelligently. We at SHM Studio we are available to support Italian SMEs on this journey, with method, experience, and a concrete market vision. To explore our digital services, the starting point is always an open conversation.