#65 - Dennis Woodside, CEO at Freshworks
Slice of Technology Team
05/14/2025
Join us on this week's episode of the Slice of Technology AI podcast, hosted by Jared S. Taylor!
Our Guest: Dennis Woodside, CEO at Freshworks.
What you’ll get out of this episode:
- Freshworks serves the mid-market with AI-enabled IT and customer support software, offering enterprise-grade features at a fraction of the cost.
- AI is central to Freshworks’ growth, with products like AI Agents, Copilots, and Insight tools driving productivity and efficiency.
- Real-world adoption metrics include 70% deflection of queries with AI agents and a 30% boost in support productivity with copilots.
- Dennis Woodside emphasizes a growth mindset, encouraging teams to embrace AI and upskill for future roles.
- The future of interaction is agentic, making company-customer engagement faster, smarter, and more human.
Watch
Listen
Read More
Understanding Freshworks’ Edge in the AI Software Space
Dennis Woodside, CEO of Freshworks, discusses his journey from Google and Dropbox to leading a billion-dollar software company. At Freshworks, the focus is laser-sharp: building intuitive, AI-enabled tools for IT and customer support teams, especially in mid-market businesses—those often left behind by complex legacy software from larger vendors.
Meeting Mid-Market Needs with Enterprise-Grade Tech
Woodside highlights that over 300,000 mid-sized U.S. businesses need sophisticated software, but lack the resources to deploy and maintain systems built for giants like FedEx or JP Morgan. Freshworks fills that gap with out-of-the-box, scalable solutions that are easy to implement and cost-effective—typically one-third the cost of legacy alternatives.
AI at the Core: Smart Tools, Real ROI
AI is not just a buzzword at Freshworks—it’s a product strategy. The company offers:
- AI Agent: A virtual assistant to automate routine support queries.
- Co-pilot: An assistant for human agents that increases response speed and accuracy.
- Insights: A conversational analytics tool for managers to extract real-time service data insights.
With rapid adoption across its 73,000 customers—including names like Bridgestone and Newcore Steel—Freshworks is seeing tangible outcomes: 70% query deflection and 30% agent productivity improvement.
Leadership in the Age of AI
Woodside’s leadership philosophy embraces a "growth mindset," urging employees to adapt and leverage AI tools daily. Internally, Freshworks has deployed over 70 AI applications, and team members—from engineers to designers—use tools like GitHub Copilot and Figma to enhance productivity.
The CEO stresses the importance of creating a culture where experimentation with AI is encouraged and securely managed, rather than restricted.
Future Outlook: From Reactive Support to Proactive Engagement
As AI capabilities evolve, Freshworks envisions a future where software not only answers queries but takes intelligent actions. The ease and speed of these AI interactions will reshape customer engagement—turning hesitant inquiries into seamless, meaningful exchanges that benefit both users and companies.
One Piece of Advice for Organizations
Woodside’s closing guidance is clear: embrace the grassroots AI innovation happening within your teams. Blocking access to generative tools out of fear only stifles progress. Instead, train your workforce, implement guardrails, and empower learning. The businesses that do will outpace those that don’t.
