
Josh Gillespie
SaaS Sales Leader, Founder, AI Sales Expert, and Mentor
San Francisco Bay Area, California, United States
Joined January 2025
Network
16.2K connectionsSWSBMM
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Summary
Josh Gillespie is an accomplished SaaS sales professional with a strong background in building and scaling sales organizations. As a founding Account Executive at PandaDoc, he was instrumental in growing the company from $0 to over $90M ARR, developing its sales culture and strategies, and helping numerous companies transition from DocuSign. His experience extends to leadership roles at Yelp, Pinchit, Glassbox, and currently as Head of Growth at Aomni. losingbydesign+3
With a philosophy background, Josh has transitioned into a sales leader specializing in the AI space. He is currently Head of Growth at Aomni, an AI-powered account-based research platform, and actively discusses the opportunities and challenges of AI in sales. aomni+1
Committed to mentoring and supporting the tech community, Josh provides pro bono training as a Sales Trainer at AlwaysHired Sales Bootcamp for first-time tech and sales applicants. He is also the Founder and CEO of Losing by Design, a venture focusing on AI coaching for sales professionals. losingbydesign+2
Work
Education
Hobbies
Josh is an avid basketball fan and enjoys playing basketball. losingbydesign+2
He enjoys Bay Area adventures with his two dogs. losingbydesign+1
He enjoys baking deliciously complex desserts. losingbydesign
He enjoys salsa dancing with his wife. pandadoc
Notes
Mar 28, 2026
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