Lott Caskey
Senior Technical Account Manager at Cloudflare
Orlando, Florida, United States
Summary
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Senior🎓
Top SchoolLott Caskey is a Senior Technical Account Manager with 17 years of hands-on experience and a 25-year career arc spanning technical support, cloud operations, program and service delivery leadership. He has repeatedly built and scaled support systems—co-founding the OSDial call‑center project and later architecting automated case communications and generative-AI summarization workflows at ServiceNow that reduced engineer load across hundreds of thousands of cases. Known for calm incident leadership and a “working manager” approach, he blends SRE-level technical depth (networking, middleware, integrations) with strategic roadmapping, KPIs, and continuous improvement. Now at Cloudflare in Orlando, he continues to translate complex backend cloud operations into better customer outcomes while mentoring cross-functional teams. An early adopter of automation and proactive monitoring, he brings a rare mix of product-minded ops, developer pedigree, and operational discipline.
17 years of coding experience
25 years of employment as a software developer
Programming Certification, Computer Programming, Programming Certification, Computer Programming at Orange Technical College Mid Florida CampusValencia College
Github Skills (5)
tkinter1
macos1
python1
mime-message1
outlook1
Programming languages (1)
Github contributions (5)
southskies/osdial
Feb 2009 - Nov 2014
Contributions:2597 commits in 5 years 9 months
ndrober/convert-outlook-msg-file-MacOS
Jun 2023 - Jun 2023
Python library to convert Microsoft Outlook .msg files to .eml/MIME message files. Includes a TKinter GUI as a Universal 2 Ventura MacOS application
Contributions:2 releases, 4 PRs, 4 pushes in 1 day
macosmime-messageoutlookpythontkinter
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