I began programming around the age of 12, in the early 1980s, primarily on the Apple ][, where I developed extensively in 6502 assembly language. My passion for coding led me to interact with professional programmers at a young age, exposing me to advanced concepts like sorting algorithms and graph theory. By the time I was a teenager, I had access to nearly every compiler available.
In the early 1990s, I worked as a mentor and trainer for Sun Microsystems, focusing on Object-Oriented Software Engineering, Object-Oriented Design, and Iterative and Incremental Development Processes—and, of course, Java. As an object mentor, I was often sent into failing client projects with the mission of turning them around.
By the late 1990s, I became deeply interested in something new: eXtreme Programming (XP) and Test-Driven Development (TDD). In December 1999, I became the first person from continental Europe to attend the inaugural XP Immersion.
In 2000, after working for six months at one of the XP case study companies, I founded XPLabs, the first and only company in the world to fully focus on XP practices. Based in a villa 50 km north of Rome, XPLabs specialized in software development, training, mentoring, and events centered around eXtreme Programming. Our work emphasized Test-Driven Development (TDD) and emergent design, pushing the boundaries of software craftsmanship.
Kent Beck selected me to help spread eXtreme Programming (XP) across Europe. I also became one of the editors for the second edition of Extreme Programming Explained.
Around 2007, I launched the Anti-IF Campaign, a movement focused on raising awareness about the hidden costs of excessive IF statements in software design. The campaign promoted reducing complexity through refactoring and evolutionary design, garnering support from notable figures in the software industry like Kent Beck and Craig Larman. Through talks, workshops, and university collaborations, the Anti-IF Campaign encouraged developers to rethink the role of conditional logic in creating maintainable software.
In 2008, I began developing my new design and development methodology.
My journey with Agile methodologies came to an end around 2009–2010 when I announced at an Agile conference my disinterest in the direction Agile was taking.
In 2010, my side project, the Pomodoro Technique, gained significant traction. My small team and I relocated to Berlin, where I founded Cirillo Consulting and published my book, first independently and later with Penguin. We also established a network of certified trainers.
In 2025, I moved to the United Arab Emirates with the goal of finalizing and launching my new software development methodology.
A Legacy of Innovation
From my early work in assembly language to shaping software practices and creating the world-renowned Pomodoro Technique, my career has been driven by a single mission: finding better, simpler ways to achieve results. Now, with Defuse the IF Strategy, I continue this journey, exploring innovative ways to tackle software complexity and empower developers worldwide.