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The 33-year-old shotstopper is to combine a player-coaching role at Conference side Tamworth with coaching duties at Bournemouth and Colchester.
Based in Oxford, Whitehead looks set to rack up hundreds of miles every week as he travels to each of his clubs.
With his playing career approaching it's conclusion, the veteran took the decision to embark on coaching courses last season and is now half way to achieving his UEFA B License.
Whitehead today confirmed that he will coach Bournemouth's keepers twice a week. Speaking to the Bournemouth Daily Echo, he explained how his new role with the Cherries came about.
"I heard Bournemouth were looking for a goalkeeping coach and somebody put a good word in for me. I went down there for a couple of days and they decided they wanted to take me on.
"Goalkeepers need specialised coaching to ensure they are kept at the top of their form and I am really looking forward to working with the lads at Bournemouth."
Whitehead was released by Reading at the end of last season after four seasons with the club. Having held the number one shirt as his own for three consecutive years, the signing of Marcus Hahnemann bumped 'Big Phil' down the pecking order.
Whitehead's subsequent moans, combined with injury, ensured that the former fans favourite was allowed to leave the Madejski on a free without anyone batting an eyelid.
His coaching deal with Colchester United is yet to be confirmed, although boss Phil Parkinson, another former Royals, is expected to announce the shotstopper's appointment as his new coach shortly.