Insights

Integrating Automation into BlackSquare’s Structure: What BlackSquare Automation OS Looks Like in Practice

At BlackSquare, BlackSquare Automation OS is not an experiment, but an internal transformation process. We have started rebuilding, step by step, the way our team operates through automations that take over repetitive tasks, remove bottlenecks, and structure workflows in a natural, conversational way. The goal is not only efficiency, but a more coherent operational infrastructure.


Automation thus becomes an invisible layer that connects all processes: from project management, to reporting, to internal communication. And the first completed flow is perhaps the most visible in our daily activity: the ChatGPT - Jira integration.

ChatGPT + Jira: the first fully automated workflow from BlackSquare

Like many other companies, BlackSquare uses Jira, a tool used to plan, track, and deliver complex projects. While it’s a useful tool for organizing and tracking work, filling out and tracking reports in Jira is a rigid and time-consuming process. Most of us already know how energy-consuming it can be to navigate Jira when all you need is a quick status, update, report, or clarification.

Jira is an extremely powerful tool, but only if used correctly and consistently. Thus, it becomes an almost useless tool when the team does not have time to update tasks, check statuses or generate management reports, which leads to wasted time, exceeding the time allocated per project, unaccounted hours and lack of financial and administrative clarity.

The ChatGPT–Jira integration addresses

precisely this critical part of the process:

Visibility into the team’s actual workload and simplified project monitoring. Instead of opening Jira for every check, you can ask ChatGPT directly for the status of a task, the situation of a project, or a summary of the hours worked by each team member. The system can automatically calculate whether a project is approaching or exceeding its allocated hours and can generate a clear view of work distribution, without the need for manual exports or rushed spreadsheets.

Managers can receive complete reports with just a chat request, and data can be automatically sent to Google Drive in easy-to-use formats. In practice, this means less time wasted on administrative operations and a much faster understanding of how projects and team workloads are evolving.

Flow is already live internally and helps us make more informed management decisions with greater accuracy and much less effort. It is the first step towards an infrastructure where automation becomes not a one-off aid, but the foundation on which our daily processes are built.

We are already working on the next internal automations, each designed to reduce downtime, eliminate repetitive tasks, and create operational predictability. We are not building “shortcuts,” but an infrastructure.


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