Ollie has started off his professional career with a string of back injuries which have led to back surgery in 2015. Contracted with Somerset, Ollie made his county debut against Hampshire at Southampton in 2016 in a T20. Since then, Ollie has taken consistent wickets in second XI for Somerset in his quest to break into the first side in 2020. In 2020, Ollie was included in the T20 Blast side for Somerset where he took 11 wickets in 8 games.

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Ollie spent the 2020 summer in Sydney to work on his game before heading back into an English summer.