How do you turn AI investment into measurable outcomes, not just inflated expectations? In this episode, I’m joined by Dennis Woodside, CEO of Freshworks, to unpack how mid-sized businesses can move fast with AI, show results quickly, and stay competitive without enterprise-level complexity or pricing.

Dennis shares how Freshworks is helping companies achieve real productivity gains and customer support improvements through accessible, enterprise-grade AI tools. With solutions that boost agent performance, reduce repetitive tickets, and deliver useful insights to managers, Freshworks is proving that you don’t need to be a tech giant to see value from AI.

We also explore the challenges that hold mid-market businesses back from adopting AI, and how Freshworks is helping them overcome barriers with tools that are fast to implement, easy to evaluate, and flexible enough to grow with the business. Dennis also reflects on what the industry can learn from customer case studies, including how one company achieved over 250 percent ROI and saved $100,000 annually by streamlining support with AI.

If your business is exploring how to make AI work without long timelines or runaway budgets, this conversation offers a grounded view into what’s working—and why. Are you measuring real return on AI in your organization, or just chasing the trend?