Jobe was a litigator for top law firms and the US government before becoming General Counsel and C-suite executive to startups backed by Andreessen Horowitz, Menlo Ventures, and others. He graduated magna cum laude from Harvard (AB), Princeton (MPA), and UC Berkeley (JD), where he was a member of the Law Review. Jobe began his career as a judicial clerk for the US Court of Appeals for the First Circuit.