Jessiman was born in Wellwood, Manitoba, and has lived in Brandon for all of his adult life.
He worked as a Western Regional Manager for the provincial government's Driver and Vehicle Licensing, and is now retired.
He filed his nomination papers minutes before the deadline, saying that none of the parties were sufficiently focused on seniors or housing for young people.
[5] Juba ran for Mayor of Winnipeg in 1986 and finished third in a field of ten candidates, behind frontrunners William Norrie and Russell Doern.
Juba later contested the Mynarski ward in the 2002 Winnipeg municipal elections and placed third against Harry Lazarenko with 1,138 votes.