Jason Diller
Editor Author at Chaotic-Good Engineering Managment
Old Toronto, Ontario, Canada
Summary
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SeniorJason Diller is a software product engineering leader with over 25 years in the industry and a 16-year record of senior technical leadership, known for turning product development teams into high-functioning, business-aligned engines. He has led engineering organizations at scale across startups and established companies—most recently in VP and director roles at Arteria AI, Gorgias, and PagerDuty—where he focused on cross-functional agility, developer advocacy, and measurable business outcomes. Jason pairs hands-on transformation experience (from legacy desktop rewrites to modern API-driven platforms) with a pragmatic people-first management style that prioritizes clear processes developers don't hate. He also teaches and authors, bringing an educator’s clarity to mentoring and documentation, and has contributed to widely used open-source tooling earlier in his career. Based in Old Toronto, he excels at bridging product, engineering, and business priorities to deliver reliable systems and grow engineering talent.
16 years of coding experience
23 years of employment as a software developer
Stackoverflow
3,358reputation
401kreached
41answers
7questions
twitter
top-5%
Github Skills (39)
twitter9
logging8
profiling8
stackdriver7
pmm7
otel7
datadog7
oauth6
agent6
api6
visual-studio6
apm-agent6
ansible6
open-source6
distributed-tracing6
Programming languages (2)
Github contributions (5)
minhajuddin/dotnetmerchant
Mar 2010 - Jun 2010
Contributions:36 commits in 3 months
jdiller/ansible_playbooks
Jan 2015 - Dec 2020
Contributions:71 pushes, 1 branch in 5 years 11 months
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