Former Pompey forward Svetoslav Todorov is set to link up with Kevin Bond at Southend.
The Bulgarian, who made 88 appearances and scored 33 goals during his time with the Blues, is poised to take on a coaching role at the Shrimpers.
The 40-year-old will be reunited with former Pompey coach Bond at Roots Hall.
He was assistant manager to Harry Redknapp when the Blues, including Todorov, secured the old 2002-03 Division One title.
That season Todorov netted 26 goals in 48 appearances for Pompey.
Since leaving Fratton Park in 2007, Toddy played for Charlton, Litex Lovech and Hoverla before retiring in 2013.
He leaves behind an academy coaching role at Crystal Palace to take up his new job at Southend.