[1] Prior to entering politics, Skelly worked as a journalist with CHCH-TV in Hamilton, anchoring and producing local and regional television newscasts.

"[8] The internet venture later stopped publishing and, after holding a contract teaching position at Mohawk College, Skelly returned to CHCH in 2002 following the station's purchase by Global TV parent company Canwest.

The plan, backed by the station's employees, would have sought an independent licence to operate and secure support from local businesses, media workers, and advertisers to stay on the air.

[14] After the death of Hamilton East MPP Dominic Agostino in 2004, Skelly was one of two local journalists rumoured to have been approached by the provincial Liberals to run in the electoral district's by-election.

After her former CHCH colleague Jennifer Mossop was elected in the electoral district of Stoney Creek in 2003, both Skelly and then-radio broadcaster Bob Bratina were both rumoured to be possible candidates in Hamilton East.

[20] In the lead-up to the campaign, Skelly hosted a fundraiser with prominent NHL players Darcy Tucker, Wendel Clark, and Dennis Hull.

[22] After long-time Ward 7 Hamilton city councillor Scott Duvall was elected to parliament in 2015, a by-election was held to fill the vacant seat.

Speaking to local reporters after she won, Skelly indicated she wanted to bring artists to Concession Street, cut red tape at city hall, and champion taxpayers.

[29] Following Skelly's remarks about the Hamilton Public Library, she made comments about the new Kitchener-Waterloo LRT line, calling the municipality's rapid transit project "not attractive", further generating controversy and leading Waterloo Region Record columnist Luisa D'Amato to write that Hamilton was "an industrial wasteland" filled with "angry and sketchy" people.

[30] In August 2017, rumours circulated that Skelly was the Progressive Conservative Party's preferred candidate in the newly created electoral district of Flamborough-Glanbrook.

Three contestants for the seat - Dan Sadler, 2014 Hamilton Mountain PC candidate Albert Marshall, and Skelly's previous nomination opponent Nick Lauwers - were all informed by the party that their candidacies would not be approved by then-leader Patrick Brown.

[34] Skelly was the centre of controversy during the 2018 election campaign when PressProgress, the media wing of the Broadbent Institute, reported that Skelly had attended a Christmas event in 2017 organized by McMaster University and Mohawk College campus conservative groups and spoke about "Free Bird Media", an alt-right website that featured videos and interviews with far-right Canadian political figures such as Paul Fromm, James Sears, and Kevin J. Johnson.

[37] During the COVID-19 pandemic in Ontario, Skelly launched a website called Relief Within Reach to connect local small businesses with available provincial and federal support programs.

[39] In March 2023, Skelly announced that Carmeuse Lime Limited would not proceed with its controversial application to burn alternative low-carbon fuels at its Dundas operations.