A native of Washington State, Webb grew up in Tacoma and graduated from Bethel High School. He earned an educational doctorate from Seattle University, a master of arts in teaching from Lewis and Clark College, and a bachelor of arts in politics and government from the University of Puget Sound.

Webb, age 46, has been a teacher and administrator for public school districts in Washington and California. In 2006 he left his position as superintendent of Apple Valley Unified School District in California (a district of 15,000 preK-12 students) to take the job with Vancouver Public Schools. Previously, Webb served as deputy superintendent at Lake Stevens School District in Washington. He also was assistant superintendent for secondary learning and technology and principal of Lake Stevens Middle School. Webb was an assistant principal at Gig Harbor High School and Key Peninsula Middle School in the Peninsula School District, and he was an assistant principal at Port Townsend High School. He taught social studies and English at both Camas High School and Sedro Woolley High School.

Webb has been an adjunct professor for City University, teaching in the Educational Leadership and Principal Certification program. As an assessment and school improvement planning (SIP) specialist, he has provided staff training for several school districts in Washington State.

Since moving to Vancouver, Webb has become actively involved in the community through civic organizations and his church. He serves on the boards for Share House, the Rotary Foundation, Boys and Girls Club, and the Washington State University Vancouver Advisory Council.