20 years in Information Technology | 16 years in Software Development
Email: jason @ this domain
LinkedIn: linkedin.com/in/jconroy/
I have led software engineering teams that delivered products used by millions of customers worldwide. Throughout my career, I’ve worked with diverse teams, launched impactful features, and built high-performing, collaborative teams that deliver real value to customers and achieve organisational goals.
In early April (2025) I was made redundant as part of a sudden and extensive company restructure and am now seeking a position with a company closer to home (Adelaide) that has local roots and a desire to improve things for the community.
Automattic Inc.
Prospress Inc.
Finding Simple
stratsec
Senior Director of Engineering
I’ve had the opportunity to work closely with Jason Conroy over the years on many complex team and org-level challenges, and he’s one of those leaders who brings stability, clarity, and a strong sense of ownership to everything he does.
Most recently, when Jason returned from his sabbatical, he quickly jumped into a situation with a team that needed direction. He connected with the people involved, understood the root issues, and helped the team reset by improving feedback cycles, raising quality standards, and helping the lead of the team regain confidence. His ability to step in and make an impact without missing a beat is something I’ve seen from him time and again.
Jason’s strength is in how he balances the big picture with the details. He’s thoughtful about how teams are structured, how work aligns to priorities, and how to support his leads and engineers to grow into their roles. He’s excellent at creating space for others to lead, while still offering the guidance and support they need.
He’s also a strong technical leader where he was helping to drive projects like our API consolidation, improving internal release tools, and working with our partnership focused products. He’s focused on building scalable, maintainable systems and ensuring teams have what they need to deliver at a high level.
Above all, Jason is consistent. If you’re looking for someone who can lead with a steady hand, support high-performing teams, and bring thoughtful engineering and technical leadership to your org, Jason is someone I’d highly recommend. I’d jump at the chance to work with him again.
Artistic Director WooCommerce
I am writing to recommend Jason Conroy, who served as an Engineering Director at WooCommerce / Automattic. During his time with the company, Jason consistently demonstrated solid technical expertise, effective leadership, and a professional approach to his work.
Jason’s role involved extensive partner collaboration and management, security and vendor audits, and ongoing product delivery. He brought strong technical skills to the table as a capable PHP developer with sound architectural knowledge. He was adept at defining solutions and resolving competing priorities, ensuring that projects were delivered effectively and aligned with organizational goals.
In addition to his technical contributions, Jason provided thoughtful leadership to his team. He worked to foster collaboration and psychological safety within the group and across teams. For example, he mentored a team member on improving their communication skills, which had a positive impact on team dynamics and overall collaboration. His approachable and transparent style made him an effective leader in building trust among colleagues.
Jason’s departure was a result of a company-wide restructuring and reduction in force (RIF). He had previously responded well to performance feedback and consistently contributed to the success of his team and projects.
I believe Jason would be a valuable addition to any organization seeking an experienced engineering leader with both technical expertise and a steady, collaborative leadership style.
Design Lead at WooCommerce
A user-centric developer, empathetic leader, and collaborative design partner.
Jason is a rare combination: a user-centric developer, an empathetic team lead, a collaborative design partner, and a kind and thoughtful person.
He brings insightful questions and observations to product discussions. When conflicts or uncertainties arise, he navigates them with care and humility.
Head of Product at WooCommerce
I got to work with Jason on a time sensitive project with Google that I still consider one of the best features we have at WooCommerce. He was able to work with minimal guidance from me and his team produced high quality work. He was also able to work cross functionality where his command of the technical requirements and collaborative attitude made the project such a success we modeled the approach to future projects.
He’s a strong engineering leader that will bring tons of value to any organization.
Product Lead at WooCommerce Analytics
I had the privilege of working with Jason during several high-impact projects at Automattic, including Google, Facebook, and Pinterest for WooCommerce. Jason is a remarkable leader who excels at balancing technical expertise with a deep commitment to his team's growth and well-being. Even as he moved into a Director role overseeing multiple teams, he made it a priority to maintain regular one-on-one check-ins, ensuring that each team member felt heard and valued.
Jason's leadership style is a perfect blend of empathy and effectiveness. He has an extraordinary ability to guide teams through complex projects while maintaining a collaborative, positive work environment. His calm and thoughtful approach to problem-solving, paired with his exceptional ability to manage cross-functional work, makes him a key asset to any organization.
What truly sets Jason apart is his genuine care for his colleagues, both professionally and personally. He fosters a work culture where collaboration thrives, and his support allows his teams to excel even in the most challenging circumstances. Jason is not just a leader but a mentor who encourages his team members to grow and take on new challenges with confidence.
Jason is the kind of leader people are eager to follow and the kind of colleague everyone is fortunate to work with. I wholeheartedly recommend him for any leadership role that requires not only technical acumen but also the ability to inspire and nurture talent.
Senior Software Engineer
I had the privilege of working directly with Jason during the initial development of the Google for WooCommerce marketing extension, and later as a team lead under his guidance for another two and a half years. Jason’s leadership style is defined by his calm presence, kindness, and genuine care for his team. He always led with empathy and patience, creating an environment where everyone felt supported and valued. It was truly a pleasure to work with Jason, his steady approach and thoughtful guidance made even the most challenging projects enjoyable and productive.
As I moved into my own lead role, I strived to lead my team with the same empathy, patience, and support that Jason demonstrated, aiming to create an environment where everyone could thrive. I'm grateful for the opportunity to have learned from him and highly recommend him as a leader and mentor.
Storyteller, Design Thinker
I hired Jason to help us redevelop the Stanford d.school website (dschool.stanford.edu.) We absolutely loved working with him, and he continues to maintain the site for us. He's a rare back-end developer who has a deep understanding of both user needs and the needs of content development/graphic design collaborators. I've never heard "this can't be done" from Jason, even when we've thrown our wildest ideas at him, he always comes up with an inventive solution.