Jolliffe exhibited with artists including Jocelyn Robert, Thecla Schiphorst, Garnet Hertz, Ken Gregory and others and wrote about the work of Diana Burgoyne and Diane Landry.

[9] Jolliffe's 2014-15 kinetic installation, Nearest Costco, Monument or Satellite, deployed networked technology to humourously explore a contemporary sense of place.

[11] Jolliffe and collaborator, Thecla Schiphorst created Room for Walking in 1999 using interactive technologies that mimic human sight and speech, kinesthetics, and spatial awareness to investigate the meanings of communication.

Jolliffe's part in the collaboration involved a small wagon-like vehicle that operated like a computer mouse to control a projection of a topographical satellite image.

[14] Jolliffe's interactive public "speech sculpture", One Free Minute, was exhibited at La Biennale de Montréal in 2009, after being presented in 2006 at the World Urban Festival.

[15][16] Jolliffe's work Perfect View (2016), is held in the permanent collection of Zebrastraat Vaste Kunstcollectie, Stichting Liedts-Messen, Ghent, Belgium.