In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Dennis Woodside, CEO of Freshworks, the $2.5B public software company helping IT and customer support teams use AI to work faster, smarter, and more efficiently. Dennis shares how Freshworks serves more than 75,000 companies around the world, including major names across technology, sports, education, entertainment, manufacturing, and enterprise software.
Dennis breaks down how AI is transforming the way companies operate, from freeing creative teams from administrative work to helping IT departments automate repetitive requests and focus on higher-value projects. He explains why the next wave of enterprise software will be defined by speed, simplicity, and the ability to help teams adapt without needing months of custom implementation.
Jess and Dennis also dive into what it takes to lead a founder-built company through major transitions. Dennis shares lessons from his time at Google, Motorola, Dropbox, Impossible Foods, and Freshworks, including how founders can successfully hand off the CEO role, how public companies can maintain long-term ambition, and why profitability, focus, and discipline matter more than ever in today’s SaaS market.
This conversation is a practical look at AI, enterprise software, founder transitions, public company leadership, and how Freshworks is building AI-powered service software for the agile enterprise. If you care about SaaS, scaling, leadership, AI adoption, or the future of IT, this episode is one to watch.
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