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Justin Sky

Co-founder, Rose Rocket

Logistics

Justin Sky co-founded Rose Rocket, the Toronto transportation management software company, in 2015 with Justin Bailie and Alexander Luksidadi. FreightWaves identified him as co-founder and CEO in September 2025, when Rose Rocket bought Centro, its first acquisition, to add email-reading automation. Rose Rocket raised a $38-million Series B in 2023.

Justin hasn’t spoken on a TechTO, TechVancouver or TechWaterloo stage. This profile is here because Justin co-founded Rose Rocket, which appears in 1 talk in the archive.

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Quick answers

Who is Justin Sky?

The Globe and Mail reported on 2023-06-20 that Sky co-founded Rose Rocket in 2015 with Justin Bailie and chief technology officer Alexander Luksidadi, and described him as the chief executive of the Toronto company.

Is he still Rose Rocket's CEO?

FreightWaves identified him as co-founder and CEO at Rose Rocket on 2025-09-29, and Apple Podcasts' listing for The Hard Part with Evan McCann, episode dated 2025-10-29, describes him the same way. No 2026 source confirming the title was found, so only the co-founder title is published here.

What does Rose Rocket do?

Y Combinator's company page, checked 2026-09-19, describes Rose Rocket as a modern transportation management system founded in 2015, in the Summer 2016 batch.

What has Rose Rocket raised?

Freight Caviar reported on 2023-06-23 that Rose Rocket raised a $38M Series B, and The Globe and Mail reported on 2023-06-20 that the company had raised US$25-million in mid-2021.

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Maintained by TechTO · facts sourced and dated · last reviewed Sep 19, 2026