Webster received a full National Merit Scholarship to study computer science at Brigham Young University, graduating in 1978 with a bachelor's degree.
He then served as Chief Technical Officer at Object Systems Group (now OSG), reviewing troubled corporate IT projects, and subsequently worked as a Director at PricewaterhouseCoopers (ibid).
Since 2017 he has also served as an adjunct professor for the BYU Computer Science Department, teaching a senior-level class on real-world software engineering.
Webster was co-designer and principal programmer of the original Apple II version of SunDog: Frozen Legacy, a real-time space trading and combat game released in 1984.
In a 2008 article, Webster has coined the term "dead sea effect", a situation where tech organizations lose their best talents and as a result end up with a large number of less capable employees.