Nov 18, 2025
In this episode, Tim Wilbur sits down with Canadian entrepreneur Jody Glidden, founder and CEO of Postilize, to discuss how artificial intelligence is changing client engagement in the legal sector. Glidden talks about the evolution from traditional CRM to proactive relationship management, the challenges law firms face with data, and how AI can help lawyers anticipate client needs and manage business development more efficiently. Postilize is used by major law firms in the US.
Jun 16, 2026
Litigator Allison Speigel joins host Tim Wilbur to talk through how a small firm uses flat-fee billing, quick decisions, and plain talk with clients to take on the country's largest firms
Jun 02, 2026
Flex Legal's Erin Cowling joins CL Talk on AI billing fights, the shiny-object trap, and why freelance counsel are senior strategists
May 26, 2026
A candid conversation with one of Canada's leading legal innovators on what AI looks like inside a major firm
May 19, 2026
The retired judge’s memoir lays bare the failures of family and criminal courts
May 05, 2026
A coach, speaker and former Bay Street lawyer on why it is not just about knowing the law
