Jake started his League of Ireland career at Bray Wanderers in 2008 and made his debut as a substitute in an away defeat to Drogheda United on 1st August. He then scored his first goal in a 3-1 away win over Dundalk in an FAI Cup replay on 18 August. He made a total of 13 league and cup appearances in his debut season. In 2009 Jake cemented his place in the Bray Wanderers side and over the next three seasons he added 84 league appearances and scored 26 league goals.
In January 2012 Jake signed for Liam Buckley at St Patrick's Athletic. He made his Pats debut against his former club, Bray, on the opening night of the 2012 season and made 24 league appearances that year, also playing in the club's FAI Cup final defeat to Derry City. Jake made just 4 league starts in 2013 but totaled 16 league appearances thanks to 12 appearances from the bench. He also scored four league goals as Pats won their seventh League title.
In January 2014, Jake returned to Bray Wanderers. He was mainstay of the side, apart from when an injury in April ruled him out for nine games, as he scored five goals in twenty-two games for the club. The Seagulls finished tenth in the table and just avoided the relegation play-offs. In December 2014, Jake signed for Stephen Kenny at Dundalk.
Jake made 6 substitute league appearances for Dundalk, scoring once in a 3-0 win over Bohemians, and was on the bench for their European matches against BATE Borisov. In July 2015, Jake moved to Bohemians, managed by former Bray assistant Keith Long, and went on to be an influential signing as he scored five goals in 10 league appearances as Bohs finished fifth in the Premier Division. In 2016 Jake made 23 league appearances, scoring three times but left Dalymount Park at the end of the season to sign for Alan Mathews at Longford Town.