Cathal O’Neill joined Rapid7 in 2023 as a Senior Engineering Manager, and he has since advanced to the role of Engineering Director. Reflecting on his career path, he says, “My journey into senior management has been a continual evolution, driven by both personal development and the desire to lead challenging technical projects.”
Cathal credits the experiences for paving a path of continuous growth and development. Beginning his career as an intern and moving through roles from engineer to team leader, he notes, “Through each role, I’ve gained deeper insights into the technical, managerial, and strategic aspects of technology leadership. As I navigated these roles, only then did I understand the scale at which software solutions need to operate and evolve.”
We asked what his key to success was, and he shared what he sees as three critical ingredients for taking command of your career in tech:
Feedback
Connections
Continuous Learning
Below, Cathal delves into each principle and offers resources and practical tips that have helped him along the way
Feedback
“I often hear that feedback is a gift. This is something I know to be true today, but it took me a while to realise what this really meant, and get comfortable with it. Early in my career, I would get constructive feedback and feel defensive or try to prove that it wasn’t true. Once I started to embrace feedback and use it as an opportunity to learn, I was able to navigate challenges much more efficiently, and become a better leader for my team. Looking back, every major milestone in my career was shaped by feedback from team mates, managers and mentors.”
“Feedback is most effective when built on mutual trust. Early on, a mentor recommended Radical Candor, a book by Kim Scott that emphasises the importance of relationships in delivering constructive feedback. I’ve applied its principles to give and receive feedback in ways that feel authentic and lead to productive outcomes. The Software Engineering Guidebook by Gergely Orosz is another one that I have recently been reading, and using to frame my feedback and guidance to my teams. Orosz dives into both the technical aspects of the software roles, as well as providing advice on how to work within an organisation.”
Connections
“As I navigate different situations, I’ve found myself very lucky to have a number of strong people around me who lean in to help me succeed. Whether it’s offering advice, critical or positive feedback, or “rubber ducking” with me (which I’ve found not just to be useful when debugging code!), these connections continue to shape my development today.
When building your network, I recommend:
Being intentional: Aim to build relationships with people whose experiences and career paths you value, as opposed to trying to grow your network for the sake of it.
Engaging thoughtfully: Do the groundwork to understand someone’s background and ask specific, meaningful questions. Genuine curiosity often forms the foundation of strong professional relationships.
Following up: Maintaining relationships requires effort. A quick message to check in, a note on how their advice helped, or a casual coffee catch-up can strengthen these connections over time.”
Continuous Learning
“Learning happens in many forms—through formal programs or hands-on experiences—and is something we feel very passionately about at Rapid7, as it relates to our core value of ‘Never Done.’ Shortly after joining, I participated in the Manager Bootcamp, which laid the foundation for understanding Rapid7’s leadership expectations. Later, I joined the Amplify program, which provides 360-degree reviews and insights from senior leaders, including our CEO, Corey Thomas. As I went through the Amplify programme, I read ‘Scaling people: tactics for management and company building, by Claire Hughes Johnson. This book helped reinforce concepts I was learning and is one that I would recommend to anyone in a leadership role.
Outside of these formal programmes, learning is embedded into our everyday culture and how we operate as a global company. In the Cloud Security engineering teams, we have lunch and learn sessions, show and tells, and have recently launched cloud technology and cloud security training, which cover the various cloud providers and industry certifications. At Rapid7, we are open to giving people stretch assignments or leaning in on new projects that relate to an area or topic they are interested in and want to learn more about. If you want to do something different or specialise in another area of the business, you don’t need to leave the company to find those opportunities. Having learning be tied to our culture enables internal mobility and growth in a way that is really unique.”
Great insights Cathal!
Thank you to Cathal and Rapid7 for permission to repost this article.
