Tim Cuckow

Tim Cuckow is an experienced sales professional currently serving as the VP of Sales at Klear.ai since March 2025. Prior to this role, Cuckow held positions as a Senior Sales Executive at Origami Risk and as Director of US/Canada Technology Sales at Aon. Cuckow’s extensive background includes serving as a Senior Sales Executive at Origami Risk, V.P. of Sales and Marketing at JW Software, Inc., and Regional Sales Manager at both Valley Oak Systems and At Global, Inc. Additionally, Cuckow was a Sales Manager at Progressive Insurance, where responsibilities encompassed direct sales, operations training, and software sales. Tim Cuckow holds a BA in Communications from John Carroll University.