He Sold A Company To Zoom.info And Has Now Raised $20M To Built An AI Sales Engineer To Maximize Go-To-Market Efficiency

Arjun Pillai’s journey from a small village in Kerala, India, to becoming a successful serial entrepreneur in Silicon Valley is nothing short of remarkable.

With a deep passion for problem-solving and an unyielding entrepreneurial spirit, Arjun has built and sold multiple companies, navigating the challenges of bootstrapping, fundraising, and acquisitions along the way.

His story is a testament to the power of resilience, adaptability, and the belief in building something truly valuable.

Listen to the full podcast episode and review the transcript here.

Early Life: A Humble Beginning in Kerala

Arjun Pillai was born and raised in a small village in Kerala, a region known for its lush landscapes and agricultural roots. Growing up in a middle-class Indian family, Arjun’s childhood was filled with happy memories, cricket games, and a solid yet unremarkable academic record.

Like many Indian families, his parents encouraged him to pursue a stable career in engineering. Attending a technical school during his 8th to 10th grades, Arjun was introduced to electronics, computer science, and electrical engineering, igniting a passion for engineering.

He remembers being excited about physics and electronics. With his older brother as a role model, who had also become an engineer, Arjun set his sights on a career in this field. He started by going to college nearby to get his degree.

The First Foray into Entrepreneurship: A Rollercoaster Ride

At just 23, Arjun took his first step into the world of entrepreneurship after a short stint at Infosys. Armed with little more than youthful enthusiasm and a desire to create something of his own, he and three of his college friends founded their first company, Profoundis, in 2012.

However, the road to success was far from smooth. Over two years, they built four different products, all of which failed. Despite these setbacks, Arjun and his team remained undeterred, treating each failure as a learning experience.

“We were young and stupid,” Arjun recalls. “We didn’t know what we were getting into, but we didn’t see it as failure. It was just ‘next one, next one.'” The foursome bootstrapped the company by taking and outsourcing projects and then using the money to build a project.

As Arjun remarks wryly, the concept of investors was unheard of at the time. He simply got by on his small salary and living out of a men’s hostel.

Developing the First Successful Product at Profoundis

The co-founders’ perseverance paid off when their fifth product, a sales intelligence tool, finally gained traction. This tool, developed before the likes of Clearbit and Zoominfo, became their first real success. However, the launch of this product was as accidental as it was serendipitous.

One evening, the team noticed an unexpected spike in traffic to their website. Unbeknownst to them, their unconventional pricing strategy—a slider allowing users to choose their price between $2 and $30—had caught the attention of Dave Ambrose, a Silicon Valley investor, who tweeted about it.

Rand Hoover, co-creator of Product Hunt, noticed this tweet and subsequently featured their product on the platform. Within 36 hours, they had onboarded 2,000 users and garnered significant media coverage, propelling their company to new heights.

Arjun remembers manually onboarding users using chat. Of these, around 800 were PR people and writers. They wrote about the product in CNET, GigaWomb, LifeHacker, and LifeHacker Russia. As a result, they were up from 800 to 4,000 users over the next two to three weeks.

Seeing the organic pill, the co-founders realized they were onto something here.

The Challenges of Fundraising: Lessons Learned

Despite their product’s success, fundraising proved to be a daunting task for Arjun. He made several rookie mistakes during his first fundraising round, starting at an inopportune time and failing to secure firm commitments from investors.

After 65 rejections, he finally secured a $380K investment, but not without significant challenges along the way. Arjun remembers not making his investors sign a SAFE or convertible note. As a result, they only had interested people but no commits or actual investors.

Arjun’s experiences taught him valuable lessons about the fundraising process. He emphasizes the importance of understanding the investor’s mindset, securing commitments on paper, and synchronizing conversations with potential investors to create a competitive environment.

Arjun also learned the importance of asking the right questions about their product’s rationale, theses, and their thoughts about the ownership percentage. These lessons would prove invaluable in his future projects.

Profoundis started out with four people and scaled to 39 people when it became profitable. This time, Arjun got a fully committed pre-series term sheet for the company from FullContact, an existing strategic partner buying data from Profoundis.

The First Exit: A Milestone for Kerala

In 2016, after four and a half years of growth, FullContact acquired Arjun’s first company. This acquisition was not only a milestone for Arjun but also for the startup ecosystem in Kerala, as it marked the first product exit in the state’s history–which indicated its nascent ecosystem.

At the time, FullContact had raised around $30M and was about to close its seed round for about $25M, which in 2016 was a lot of money. The company was also doubling its revenue almost annually and was confident that the acquisition would generate much value.

Although the financial details remain undisclosed, the acquisition was life-changing for Arjun and his co-founders and served as a significant moment for the local entrepreneurial community.

After his exit, Arjun spent nine months consulting with tech companies, learning everything he could about the sales process.

The Birth of Insent.ai: A New Chapter

After a brief stint in consulting, Arjun was ready to dive back into entrepreneurship. His next venture, Insent.ai, was born out of his realization that real-time B2B conversations were becoming increasingly important.

Insent.ai aimed to create an account-based buyer-centric conversational experience for B2B companies, allowing potential customers to access information quickly and easily.

The product allowed buyers to eliminate the need to fill out a form and then wait five days for the information they needed. At the time, Arjun remembers there was Drift.com, a chatbot-oriented conversational platform, and Qualified.com.

The three companies developed an account-based marketing advanced B2B chat application sometime at the end of 2018. It was a B2B SaaS model with platform pricing for the underlying conversational platform, which included the integrations, setting up of the process, onboarding, and all of that.

Insent.ai offered a per-seat pricing with 10 seats baked into the basic platform fee. Users needing more seats could pay for them. Insent.ai was a SaaS model but without any pro services.

This time, fundraising was much smoother. Having built a successful track record with his previous company, Arjun found that investors were more willing to back him. He secured initial funding from previous investors and additional support from Techstars, raising a total of $2.7M.

The Second Exit: A Strategic Acquisition by ZoomInfo

The acquisition of Insent.ai by ZoomInfo in 2021 was another significant milestone in Arjun’s entrepreneurial journey. Unlike his first exit, which came as a surprise, this time, Arjun had built strong relationships within the industry, including with ZoomInfo’s CEO, Henry Schuck.

A simple email from Arjun to Henry, sharing relevant industry news, led to a conversation that eventually resulted in the acquisition.

Advice for Aspiring Entrepreneurs

Reflecting on his experiences, Arjun offers valuable advice to fellow entrepreneurs: “Don’t build a company to exit. Build a strong business as if you want to build for the long term and the best deals will come to you—whether from investors or acquirers.”

Arjun suggests getting the right support on the legal, tax, and other aspects when going through the process of fundraising and acquisitions. Professional advice can help them avoid paying substantial taxes.

Arjun also observed that once a company is sold, founders have a difficult time internalizing the fact that the company is not theirs anymore. They must break the emotional and mental attachment to the company and start looking at things objectively.

Regarding building companies, Arjun advises founders to learn customer-market validation and validate their products meticulously and thoroughly. He also recommends taking feedback from everyone they meet, particularly those smarter than them.

Building Docket

Arjun remained with Zoom.info for a while and then went on to build Docket. The concept of Docket emerged from Arjun’s belief that AI is the biggest paradigm shift and presents a huge opportunity. He identified a problem statement that resonated with him and wanted to solve it.

Docket is a SaaS product with platform-based pricing. Users can choose from a platform price or per-seat price. In Arjun’s opinion, AI will eventually enable the pricing to become more outcome-based.

Talking about the fundraising journey, Arjun reveals how he approached his previous investors. Four days after incorporation, Docket had around $3M in soft commits. Among the many entities that invested were Ashu Garg and Jaya Gupta at Foundation Capital.

The total round was $5.3M in which investors like Founder’s co-op in Seattle, Henry Shaq, a CEO, Jeff Lunsford, CEO of Telium, Anu Parathwaj, and Viral Bajaria, CTO of 6Sense, participated. Next, Arjun found a few pilots and design partners and started building and delivering the product.

Arjun also leveraged his long-term relationship with Rajiv Batra, Navin Chaddha, and Patrick Salyer at Mayfield to raise another $15M, which Foundation also joined.

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As he reveals, Docket is now an AI sales engineer in organizations where it assists existing sales engineers and account executors to a point where the go-to-market efficiency in those companies is enhanced.

Docket joins calls, answers questions, takes demos and serves as a full teammate in the B2B companies to ensure that they operate at super high efficiency. The goal is to create a vertically fully integrated AI sales engineer.

Conclusion: Building for the Long Term

Arjun Pillai’s story is one of resilience, learning, and growth. From his humble beginnings in Kerala to becoming a successful serial entrepreneur in Silicon Valley, Arjun has shown that success will follow with the right mindset and a relentless focus on building value.

His journey inspires aspiring entrepreneurs everywhere, reminding them that the path to success is rarely straightforward but always worth the effort.

Listen to the full podcast episode to know more, including:

• Arjun Pillai’s entrepreneurial journey began at 23, with multiple failed products leading to eventual success.
• Arjun’s first venture thrived on a lean budget, with a $200 monthly salary in India sustaining his early efforts.
• Arjun’s first successful product launch happened by chance, demonstrating the power of organic growth and unexpected opportunities.
• Arjun learned the hard way that securing investor commitments requires written agreements and strategic timing.
• Knowing how investors think can significantly improve your fundraising process.
• Arjun advises entrepreneurs to prioritize long-term business growth over planning for an exit.
• Both of Arjun’s successful company exits were driven by organic interest rather than a deliberate process.

 

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