ClickUp lays off hundreds of employees: AI agents are coming

The timeline: what happened at ClickUp

In late May 2026, TechCrunch reported the details of the mass layoffs at ClickUp . The startup, founded in 2017, chose 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. Furthermore, it had invested in the development of autonomous agents capable of handling repetitive tasks, responding to support requests, and coordinating operational activities. As a result, the need for human personnel for certain functions has drastically reduced.

This case represents one of the first documented examples of large-scale replacement of cognitive work with AI agents in a medium-sized tech company. Therefore, it deserves in-depth analysis.

Who wins and who loses in this transition

The answer is not simple. There are winners and losers on multiple levels. Therefore, it is useful to distinguish the different perspectives.

The short-term winners are 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 are the employees involved in the layoffs. However, the phenomenon has broader implications. Even workers who keep their jobs are under increasing pressure. They must demonstrate added value that agents cannot replicate: critical judgment, customer relations, strategic creativity.

On the market level , ClickUp's competitors now face a choice. Unlike those who wait, those who anticipate the integration of AI agents gain a structural competitive advantage. According to research from McKinsey on the economic potential of generative AI , automatable tasks in knowledge worker roles could reach 60-70% by 2027.

AI agents: they are not chatbots, they are autonomous operators

It's important to clarify what we mean by AI agents. These aren't just simple chatbots or virtual assistants. AI agents are systems capable of planning sequences of actions, using external tools, and achieving complex goals autonomously. Therefore, their impact on work is qualitatively different compared to previous waves of automation.

In a project management context like ClickUp, an AI agent can assign tasks based on priorities, update progress statuses, generate reports, answer operational team questions, and even reorganize the roadmap based on new inputs. Plus, it can do this simultaneously across hundreds of projects. No human team can compete in terms of volume.

However, there are clear limits. AI agents struggle with strategic ambiguity, interpersonal negotiation, and managing unforeseen exceptions. Therefore, the value of human work shifts towards these high-cognitive and relational skills. Harvard Business Review has analyzed in detail this division of labor between humans and AI .

The SHM Studio reading: a signal, not an anomaly

The ClickUp case is not an isolated incident. We at SHM Studio we interpret it as an early signal of a trend that's set to grow. Tech companies are the first to move because they have the culture and resources to do so. However, the phenomenon will quickly extend 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 hand, 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 of AI consulting for SMEs are born precisely from this conviction. Similarly, our approach to Digital marketing already integrates intelligent automation components into 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 teams. The integration of AI agents in these environments is already available. However, it requires precise process mapping before implementation. Without this phase, automation amplifies existing inefficiencies instead of eliminating them.
• Customer support and communication: AI agents can handle a significant portion of incoming requests. As a result, the human team focuses on complex, high-value cases. This hybrid model is already adopted by medium-sized companies with measurable results.
• Content production and SEO: even in the field of SEO and Copywriting , AI agents are taking on an increasing role in content generation and optimization. However, human editorial supervision remains indispensable to ensure quality and strategic consistency.

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

The work in progress: what remains to be solved

The ClickUp case raises questions that the industry hasn't yet resolved. Firstly, who is responsible when an AI agent makes an operational error? The legal issue is still evolving. Furthermore, how do you measure the performance of an AI agent compared to a human employee? Traditional KPIs aren't always adequate.

According to Gartner, agentic AI is one of the priority technologies for 2026-2027 . However, the maturity of available tools is still uneven. Some categories of tasks are handled excellently by agents. Others still have error rates that are too high for unsupervised adoption.

For SMEs, this means the most prudent approach is an incremental one. Start by automating the most standardized and measurable processes. Then, expand automation based on observed results. This approach reduces risk and allows for building internal expertise over time.

Next moves: how to prepare now

The ClickUp case suggests some concrete steps for SMEs wanting to tackle this transition in a structured way.

• Audit of repetitive processes: identify which internal tasks take up the most time and have the least variability. These are the ideal candidates for the first automation phase.
• Tool evaluation: not all AI agents are created equal. It is necessary to evaluate the available platforms based on your existing technology stack. Our experts in web development and AI support this selection phase.
• Team training: investing in training people who will work with AI agents. The role of an automated process supervisor is a new and increasingly in-demand skill.
• Continuous monitoring: define clear metrics to evaluate the effectiveness of agents. The google ads campaigns and the LinkedIn campaigns already automated are a good methodological benchmark.

Finally, it's helpful not to isolate yourself. Discussing things with other SMEs going through the same transition speeds up learning. The SHM Studio blog regularly publishes analyses and practical cases on these topics. For a direct comparison, it is possible contact our team .

The future of work isn't written yet. 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.