In a recent fireside chat, Girish Mathrubootham shared the story of his roller-coaster ride from a small Chennai office to ringing the NASDAQ bell. Here’s the journey of the man behind Freshworks and his $4 billion SaaS success.
Learning the Hard Way
Back in the late 90s, Girish Mathrubootham was just a guy teaching Java classes in Chennai. “Business was booming,” he recalled with a smile. “If you could spell Java on your resume, you got hired!”
But the dot-com crash changed everything. His training company shut down, and he joined regular employment. This whiplash taught him something crucial: “When everybody wants something, growing a business is easy. When the tide turns, even being good doesn’t matter.”
Years later at AdventNet (now Zoho), frustration with marketing led to a career-defining conversation. “My boss Kumar took me for chai and said, ‘Your problem is you’re an authoritative person. Marketing is consultative. Why not become a product manager?'” Girish Mathrubootham laughed at the memory. “I had no clue what that meant. I literally went home and Googled it.”
The TV That Launched a Billion-Dollar Company
Two random events sparked Freshworks. First, a shipping company broke Girish Mathrubootham’s TV in 2010. After getting nowhere with phone calls and emails, he vented in an online forum.
“The next day, the company president apologized, and money was in my bank,” he recalled. “That’s when I realized customer service was changing fundamentally. When complaints go online, power shifts to customers.”
Then came a casual Hacker News read after lunch. Zendesk had hiked prices 300%, and customers were revolting. “Someone commented that this created an opening for a better product,” Girish Mathrubootham said. “That was my slap in the face to actually do something.”
His honesty about starting up is refreshing: “Look, I wasn’t dreaming of a unicorn. My plan B if this failed? Join a bigger company so I could finally travel business class!”
Global From Day One
The magic of Girish Mathrubootham’s approach was rejecting conventional wisdom about Indian startups.
“Most companies start locally, then expand. We were global from our first week,” he explained, leaning forward. “With seven customers across four continents, we never tried selling face-to-face.”
This wasn’t just lucky—it was strategic. “Traditional enterprise software means meeting customers, talking about baseball and weather. That’s hard from India. But what if customers experience your product before ever talking to you?”
That insight powered their growth. While other founders chased meetings, Girish Mathrubootham built an online engine that attracted global SMBs to try their product first.
The $2,000 Revenue Bet
Freshworks might never have happened without one blog post. After writing about quitting his job based on a Hacker News comment, Girish Mathrubootham’s post went viral. Naval Ravikant noticed, making Freshworks the first Indian startup on AngelList.
The real turning point came meeting Shekhar Kirani from Accel. “He visited our garage office and noticed something funny,” Girish Mathrubootham recalled. “Our furniture was cheap, but every developer had a Mac.”
Later, he asked Shekhar why he’d invested when they had just $2,000 monthly revenue while passing on startups with $500,000. Shekhar’s answer was illuminating: “Your $2,000 comes from 70 different customers globally. Product-market fit is proven—there’s only execution risk.”
Then came Tiger Global’s Lee Fixel, making his first-ever SaaS investment. “Lee rarely came to Chennai but happened to be there for another deal,” Girish Mathrubootham said. “I pitched him at his hotel with just my iPad. Next evening, he called: ‘The numbers don’t make sense—you’re very early—but I’m betting on you.'”
The speed floored him. “Other VCs were asking for five-year cash flow projections. We were barely three months old! Lee said, ‘Skip the term sheet, let’s start due diligence.’ That’s when I knew he was our investor.”
Three Big Calls That Changed Everything
When asked about his most consequential decisions, Girish Mathrubootham named three without hesitation:
“First, going inbound and global immediately. We opened up a huge market instead of fighting for scraps locally.”
“Second, becoming multi-product early. Most companies wait till $100-200 million revenue. We didn’t. The secret? Start your second product when the first is doing well. During tough times, experimental projects get axed first.”
“Third, adding enterprise sales atop our SMB motion. Wall Street loves enterprise software. This completed our IPO story: multiple markets, multiple products, and success with both SMBs and enterprises.”
Finding Diamonds in Engineering Colleges
Building in Chennai meant talent challenges, but Girish Mathrubootham turned this into an advantage.
“In India, everyone studies computer science because their parents say so, but they’re not all built for it,” he observed. “We stopped caring about degrees and started looking for natural talents.”
For support roles, they hunted for empathy. For pre-sales, the ability to think on your feet. For sales, shamelessness—”I’d actually ask candidates to sing or dance in interviews!”
Girish Mathrubootham credits Marcus Buckingham’s book “First Break All the Rules” for this approach. “You can teach skills but not talent. We found people with raw talent and molded them into SaaS professionals.”
From Bachelor to Married Life: The Public Company
When Freshworks hit NASDAQ in 2021, Girish Mathrubootham felt the shift immediately.
“Being VC-funded is like bachelor life—you party, have fun, make mistakes. Going public means getting married. You become responsible, start thinking long-term.”
He laughed at the wedding analogy: “Everyone comes for the party, but I’m the one married to the company for the next 15 years!”
The discipline has been valuable though. “Every quarter, we learn from investors’ outside perspective. As CEO, my job became capital allocation—asking where money gets the best returns.”
When questioned if he regretted the public route, he responded: “Look at who’s created massive wealth over decades—Microsoft, Amazon, Google. There’s a reason smart people keep doing this despite the hardships.”
Surfing the AI Wave
Recently, Girish Mathrubootham moved from CEO to executive chairman to focus on AI.
“Back in 2016, we asked what could kill Freshworks. We answered: AI. That’s why we started investing in our Freddy AI platform,” he explained. “After ChatGPT, everything changed. The AI wave isn’t just another wave—it’s a monster wave. I had to grab my surfboard.”
His eyes lit up discussing AI’s impact on customer service. “If this gets automated by AI, someone has to build that technology. We’ve been preparing five years for this moment.”
Building India as a Product Nation
Beyond Freshworks, Girish Mathrubootham pours energy into making India a product powerhouse through SaaSBOOMi, a community that began with just 40 entrepreneurs in a Chennai “unconference.”
“We started as an experiment in 2015. Freshworks had hit $5 million revenue—the biggest Indian SaaS company then,” he remembered. “Now we’re seeing the SaaSBOOMi community explode across tier-2 and tier-3 cities.”
His passion extends beyond tech. At FC Madras, his youth football academy, he’s addressing another gap. “I once saw 80 kids playing on a dusty field while parents waited in the heat. The contrast with empty, perfect fields I’d seen abroad was striking. Someone needed to fix this.”
The Freshworks Family
Today, over 450 Freshworks alumni stay connected through a WhatsApp group. “They’ve changed jobs multiple times but still identify with our culture,” Girish Mathrubootham noted proudly. “We’re planning an ‘Extra Fresh’ reunion soon.”
His advice to founders balances ambition with humanity: “Be aggressive in work but not abrasive in relationships. That distinction is critical.”
When asked which role was hardest—being a founder, franchise owner, or investor—Girish Mathrubootham laughed loudly. “Founder, without question! Especially early on when you have no money. With the other two, you already have money and just wait to make more.”
Looking ahead, Girish Mathrubootham envisions India creating $500 billion to $1 trillion in product company value by 2030. “The second-largest pool of AI developers is in India. This will be the decade India becomes a product nation.”
And knowing Girish Mathrubootham, he’ll be riding that wave too.