Kevin O’Connor
Engineering Leadership Coach
Self-Advocacy, High-Impact
Location: Westchester County, NY (Eastern)
Experience/Qualifications: With two decades of experience in the tech industry, my journey has taken me through many different roles - everything from racking servers in data centers and networking, to leading 60-person teams in rapidly growing startups, to engineering extremely large scale distributed systems. I've had the privilege of working in diverse environments, spanning non-profits to venture-backed companies, with a focus on data platforms, cloud infrastructure, security, and both infrastructure and platform teams across industries like e-commerce, social media, and fintech. Notable stops in my career include Internet Archive, Reddit, Kickstarter, and Memorial Sloan Kettering.
Area of Expertise: I specialize in helping organizations tackle complex organizational challenges, refine recruitment processes, plan for growth in engineering teams and in their systems, and excel in vendor and contract negotiations. For individuals, I offer guidance in career development, whether you aspire to excel as a high-impact individual contributor or aim for leadership roles. I also have extensive experience supporting employees with salary negotiations, advocating for themselves at work, and clearly communicating their impact and value.
Coaching Philosophy: My coaching philosophy is centered on helping people learn how to solve their own problems. I’m not here to fix things for you or tell you exactly what to do. Instead, I focus on helping you increase your impact at work and grow your career in the direction you want—whether that means continuing as a strong individual contributor or stepping into leadership.
How I Measure Success: I measure the success of a coaching engagement by whether we set clear, ambitious goals early on and whether those goals are achieved. In our first conversation, we spend time talking about where you are in your career, how you’re feeling about it, and where you want to go next. From there, we establish clear, ambitious goals early on and by the end of our work together, you should see real progress and tangible outcomes. Coaching is not therapy—I’m not here for venting or complaints. My role is to help you take action, improve performance, and move forward.
What I’m Known For As a Coach: I like to help people create lasting change in their careers. The work doesn’t stop when the coaching engagement ends. The goal is for you to carry the lessons forward and apply them across roles, jobs, and future challenges. Rather than giving quick answers or prescriptions, I help clients think differently about problems so they can approach new situations with more clarity and confidence.
Hobbies/Interests: Outside of work, I enjoy spending time with my family and working on hands-on projects. I like building things around the house. Shoveling snow, shoveling mulch…just shoveling in general.

