The baton changes hands at the Chennai/the US based Freshworks, the SaaS ‘baby’ founded by Chennai-based entrepreneur Girish Mathrubootham 14 years ago. He handed over the reins to President Dennis Woodside, who joined the company 18 months ago. Mathrubootham’s decision to hand over the post of CEO to Woodside has evoked mixed reactions.

While it came as a surprise for employees and his close friends, analysts raised eyebrows on the timing.

Sources said Mathrubootham is likely to spend more time with the Chennai R&D team on developing various AI-based products. There was no pressure from the company’s board on the transition. It was his own decision, they added.

Mathrubootham currently holds about 4.3 per cent stake in the company compared to 6.5 per cent at the time of the IPO.

His decision left the stock price dive by 21 per cent in the extended trading on Monday, and also sent shock waves among many of his fans and young entrepreneurs, who see him as a ‘mentor.’

“I’m committed and excited to continue our journey of growth toward becoming a $1b revenue company and beyond,” Woodside said in a social media post.

‘Mixed Emotions’

“Freshworks is my baby, and over the years I have seen her grow—as a toddler trying to walk, a child growing really fast, and a teenager growing stronger. The emotions running through my mind are similar to a father experiencing his beloved daughter’s marriage, happy and sad at the same time, knowing fully well that she has found the right one and is going to accomplish greater things in life,” Mathrubootham wrote to his employees.

“As I write to you today, I’m filled with many emotions. The past 14 years have been an incredible journey, one that has seen Freshworks grow from a fledgling startup in Chennai into the global SaaS company that we are today. I’m incredibly proud that we are the first Indian SaaS company listed on Nasdaq. We’re a true friend to more than 67,000 customers worldwide, and our global Kudumba now has over 4,900 talented members. This journey, however, would not have been possible without each of you—coming in and making Freshworks a little bit better every day,” Mathrubootham wrote.

“As I pass the baton to Dennis and move into my new seat as Executive Chairman, I look forward to continuing to serve Freshworks, focusing on our long-term product vision and AI, spending more time with our teams in India, and being a trusted advisor to Dennis. Our mission remains unchanged, and our future is bright. The road ahead is filled with limitless possibilities, and I am excited to see where Dennis’ leadership takes us,” he said.

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When an analyst questioned the timing of the transition, Mathrubootham said, “It was something planned as part of my succession. When we hired Dennis 18 months ago, our expectation was that he would eventually be my successor. And so we have been working in a similar fashion where Dennis was helping Freshworks get the operational rigour, put in place a world class team, and focus on go-to-market excellence.”

“I was actually focusing on all the Artificial Intelligence that you are seeing right now with Freddy and the product strategy. I think the short answer is playing to our strengths. I think I have always been a believer in playing to strength, and we feel that what’s right for Freshworks is for me to focus on long term product strategy and AI,” he said.

At Dropbox, Dennis scaled the company from $200 million to north of $1 billion in like four years or so. He brings the right expertise. “So this was the plan, and I feel comfortable that this is the right time to do it,” Mathrubootham said.

“This is the second shock that I got when I joined the company a decade back. The first was when I got a sizable amount of ESOPs. However, as I got up today and saw my inbox, I got my second and irrecoverable shock of Mathrubootham’s message,” said an employee of Freshworks.

Entrepreneurs and industry watchers say that letting go of control could not have been easy for Mathrubootham, but his leadership and entrepreneurial skills are needed to take Freshworks into the AI era.

“It will be an emotional moment for him for sure, and I can’t wait to see what is coming next,” Arvind Parthiban, co-founder and CEO,, said. Parthiban is among the ‘Freshworks mafia’ who was inspired by Mathrubootham to start his own entrepreneurial journey.

‘Not Easy’

Another SaaS executive noted that AI is emerging as “an existential question” for every tech enterprise and Mathrubootham is “the best person” to navigate it at Freshworks.

“It’s not easy to do that while being a CEO of a public company,” the person said.

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“He (Mathrubootham) is a brilliant product and marketing mind,” another SaaS CEO said.

While questions remain as to whether the move was dictated by stock price movements, the mood at Freshworks’ India office is upbeat as employees are excited about seeing “G” (as Girish Mathrubootham is fondly called by employees) more frequently at the Chennai office.