UPDATED 16:40 EST / NOVEMBER 17 2025

Dennis Woodside, chief executive officer and president of Freshworks, discusses AI for ITSM and modern service operations with theCUBE at Refresh North America 2025. AI

From help desk to growth engine: Freshworks’ AI bets big on the midmarket

Information technology service management is a crucial arena for the adoption of artificial intelligence in mid-sized enterprises. But while AI offers efficiency gains, most mid-market organizations continue to face challenges in realizing measurable value from their investments — including in strategically leveraging AI for ITSM.

Freshworks Inc. is addressing this gap by integrating AI capabilities directly into its IT service management platform instead of offering them as separate add-ons. Service teams are being repositioned as revenue centers, rather than cost centers, through AI’s ability to handle routine queries, according to Dennis Woodside (pictured), chief executive officer and president of Freshworks.

Dennis Woodside, chief executive officer and president of Freshworks, talks with theCUBE about AI in ITSM and service desk automation at Refresh North America 2025.

Freshworks’ Dennis Woodside talks with theCUBE about using AI in ITSM to automate routine service tasks and improve employee experience.

“Our customers want their employees who are in service roles to be doing higher-value work,” he told theCUBE. “They don’t want them answering the same question or taking the same actions. ‘How do I return my order? How do I reset my password?’ That’s not interesting work for the agent.”

Woodside spoke with Bob Laliberte, principal analyst at theCUBE Research, at the Refresh North America 2025 event, for an exclusive interview on theCUBE, SiliconANGLE Media’s livestreaming studio. They discussed the deployment of AI for ITSM and what it means for the future of the sector as companies seek to secure measurable return on investment. (* Disclosure below.) 

AI for ITSM meets the support landscape at a crucial moment

Adoption patterns have changed significantly in the last year. By late 2024, all participants on Freshwork’s customer advisory board reported active AI deployments, up from less than a quarter, according to Woodside. This reflects a marked change in C-suite expectations for IT and support leaders to serve as AI champions within their organizations — regardless of prior expertise.

“The IT leader or the customer support leader is perceived as the AI leader now, whether they intend so or not,” Woodside noted. “If we can arm them with knowledge and information, then that becomes a way that we support them beyond just providing a product.”

This pressure places new demands on software providers beyond product delivery, and Freshworks is leaning into the opportunity. The company now positions itself as an insights partner, helping customers navigate AI terminology, quantify business impact and build compelling internal narratives around value creation. This approach is already translating into larger, higher-value relationships as customers increasingly adopt its AI capabilities across the portfolio, according to Woodside.

“In Q3, we saw a more than 40% year-over-year increase in the number of new and expansion deals with greater than $50,000 in [annual accruing revenue],” he noted during Freshwork’s Q3 earnings call. “Our strategy has focused on three key growth drivers: investing in employee experience, delivering AI capabilities across our products and accelerating adoption, and driving continued expansion in customer experience.”

Looking ahead, Freshworks sees growing demand for software that delivers tangible outcomes rather than experimentation for its own sake.

“Around the world, businesses are choosing software that delivers real outcomes: speed, simplicity and measurable ROI,” Woodside said. “That’s exactly where we stand out.”

Here’s the complete video interview, part of SiliconANGLE’s and theCUBE’s coverage of the Refresh North America 2025 event:

(* Disclosure: TheCUBE is a paid media partner for the Refresh North America 2025 event. Neither Freshworks, the sponsor of theCUBE’s event coverage, nor other sponsors have editorial control over content on theCUBE or SiliconANGLE.)

Photo: SiliconANGLE

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