Ambarish Gupta and the business of answering the next call

Before Knowlarity had a finished service, Ambarish Gupta had a question for prospective customers. Would they want a system that handled their business calls automatically? He spoke to eleven companies. Nine wanted it. For someone whose first business had ended without finding its market, those conversations mattered more than a handsome prototype.

A ringing telephone is an oddly modest place to begin a technology story. It has none of the theatre of a rocket launch. Yet a business that misses a call may lose a sale, and a business receiving hundreds needs something better than hoping the right person is beside the handset. Gupta saw a commercial problem inside an everyday irritation.

He now leads Basis Vectors Capital in New York, acquiring and working on established software businesses. The distance from a property-listing startup in India to a private equity firm in Manhattan looks large on a map. Follow the decisions along the way, though, and a smaller, more interesting story emerges: an engineer learning to ask what customers will pay for, then learning how to help other companies deliver it.

An engineer comes home with an idea

Gupta grew up in a business family in Kanpur. The family traded jute bags; he was drawn to science. He studied computer science at IIT Kanpur, graduating in 2000. In his later recollections, intellectual excitement and the desire to see the effects of his work sit side by side. The attraction was to making something that mattered beyond the code itself.

His early working life took him through Germany, Australia and the United States. By 2003 he was back in India, trying to build an online property-listing business, Inventica Solutions. A rental search on the internet sounds straightforward now. Being able to describe a useful product, however, does not mean its customers are ready to use it.

At a 2013 startup panel, Gupta recalled spending two years on the business without generating revenue. He said he had misread the market. That admission gives the episode its weight. The failure was more specific than the usual inspirational fog surrounding entrepreneurial setbacks: a product existed, effort continued, and the commercial response did not arrive.

He went to Carnegie Mellon for an MBA, completing it in 2007, and worked at McKinsey. Strategy, operations and finance became part of his vocabulary alongside engineering. His public career history also includes Microsoft and Booz Allen Hamilton. The route was already a series of changes of direction, rather than a single idea carried triumphantly from university to market.

The telephone after the telephone revolution

The idea behind Knowlarity followed a sequence. India’s consumers had acquired mobile phones. Those consumers would call businesses. Businesses would need systems to receive, route and understand the calls. Gupta was looking for the commercial demand that followed a much larger consumer change, rather than trying to create a new consumer habit himself.

Knowlarity was founded in 2009 with Pallav Pandey. Its early experiments included electronic fax and outbound voice messages. An election campaign in Odisha gave the team an early practical use for mass calling. Over time, the focus moved toward inbound calls and the virtual receptionist: software handling the unglamorous business of getting a caller to the right place.

A company phone number could sit above several people and locations. Calls could be greeted, recorded and routed; customer information could be connected to other software. For a smaller business, the appeal was access to capabilities that otherwise required a more elaborate telephone setup. A caller did not need to know how small the office was.

Gupta’s own short verdict on the opportunity was “Enterprise telephony is less sexy but more safe.” There is some pleasure in hearing a founder endorse a business on grounds that would make a poor nightclub invitation. Paying customers have a way of improving an idea’s social standing.

The founder learns to let go

In a 2014 account of his journey, Gupta described himself as a childhood tinkerer. He also acknowledged a less convenient habit: having built a startup by doing everything himself, he found delegating difficult. The transition from making a product to running a company required him to change how he worked.

His explanation of the first failure was blunt: “My first startup failed because I was not flexible.” He credited greater willingness to change direction in the second venture. That is a useful distinction in a culture fond of praising perseverance. Staying at work and staying attached to the original plan are different decisions, and sometimes they pull against each other.

He brought people with failed startups into Knowlarity, hiring former founders from different fields. The appeal was their experience and willingness to act without waiting for an instruction. It gave entrepreneurial disappointment a practical afterlife: knowledge that another business could use, rather than a blemish to be quietly removed from a résumé.

He also helped employees Sanny Chaudhary and Daman Singh Kohli as they developed a ready-to-cook food venture. Their boss became someone to test ideas with. These episodes show a founder making room for initiative beyond his own product. They also complicate the image of the entrepreneur as a solitary author. A company’s accumulated experience can travel out through its people.

“Before you become a Founder... you have to know who you are.”

Ambarish Gupta, Founder Thesis

A number is only useful when it works

Knowlarity raised $6.5 million from Sequoia in 2012 and $16 million from investors including Sequoia and Mayfield in 2014. The holding company moved to Singapore in 2013 as the business expanded internationally. Funding and geography changed; the customer’s expectation remained simple. Someone, or something, had to answer.

In June 2016, Gupta and colleagues spent a night working through a disruption after telecommunications authorities suspended lines over compliance concerns. They dealt with customers and sought to resolve the issue with the authorities. It was an uncomfortable demonstration of how much a cloud service still depends on institutions and infrastructure outside its own software.

By February 2022, when Gupshup announced its acquisition of Knowlarity, the company served more than 6,000 customers in 65 countries. The announcement described a business spanning cloud telephony, contact-centre automation, voice assistants and speech analytics. The original problem had grown into a broader communications offering.

The acquisition joined Knowlarity’s voice capabilities with Gupshup’s messaging business. It also gives Gupta’s first successful company an ending more concrete than a flattering valuation anecdote: another communications company saw a reason to put the businesses together. The product had become part of how customers operated.

Private equity, with the sleeves rolled up

Basis Vectors announced its first $50 million fund in May 2020. Gupta and co-founder Upmanyu Misra were targeting vertically focused business software. The attraction lay in companies already serving identifiable customers, with room to improve how the business ran. Capital would arrive alongside operating help.

The early model grouped that help into engineering, finance, sales and support, and marketing. It was called SaaSMachine. The premise was that a software founder should not have to invent every business function from scratch. A recurring subscription does not, by itself, assemble a reliable sales process or an efficient engineering team.

That brought Gupta back to an interest he had held before Knowlarity: private equity. His description of the move in a founder interview emphasized the opportunity to affect several businesses. He had acquired the experience of running a software company; the next step was to apply it across a portfolio.

In July 2022, Basis Vectors acquired CommerceV3, a subscription software and services business serving food and gift merchants. The announcement said co-founders Blake Ellis and Nathan Focht would continue running daily operations. The deal joined an existing customer base and experienced managers with an investor offering help for the next stage.

Another acquisition, Cadient, was announced in April 2024. Its software supports high-volume hourly hiring. Ecommerce and recruitment are different markets, but both involve repeatable work that customers need done consistently. The connection is practical: established software, a defined business task, and the possibility of improving execution.

The danger of getting comfortable

Gupta’s writing reaches beyond deals. His 2022 essay, “Why Companies Die,” considers how organizations lose their ability to change. Processes and standardization help a company grow, he argues, but can also make it rigid. The habits that make scale manageable can leave people poorly prepared for a shifting market.

He takes particular aim at office politics that rewards loyalty over performance. His proposed responses include fresh perspectives, movement between management roles, new product launches and willingness to close failed products. These are his arguments about organizational behaviour, rather than a claim that any one remedy guarantees survival.

The essay makes an interesting companion to his investment work. Buying an established company means buying useful systems and habits, including some that may need changing. The investor has to preserve enough continuity to serve customers while making room for unfamiliar decisions. An organization can have an excellent memory and still need to learn something.

Gupta’s public essays also wander into philosophy and perception. “Layers of reality” opens with Interstellar; other pieces consider leadership and the way people understand one another. The engineer from a trading family has retained an appetite for questions whose answers cannot be put neatly into a quarterly report.

What the next call might ask

Today, Basis Vectors describes its investment focus as established B2B software companies, typically with $10 million to $50 million in revenue. Its operating approach brings technology, product, finance, people and customer retention into the same conversation. Artificial intelligence is one of the capabilities it deploys, with priorities adapted to each company.

The firm describes a sequence of optimizing, growing and scaling. That puts the emphasis on diagnosis before intervention. A company may need better infrastructure; another may need help selling or retaining customers. The language is more systematic than Gupta’s early startup experiments, but the underlying question remains recognizable: where is the business getting stuck?

There is a temptation to read the career backward and make every detour look intended. Gupta’s accounts resist that neatness. There were ventures that failed, jobs that changed his interests, and opportunities that depended on timing. His progress came through altering the plan as well as working on it.

The nine interested companies at the beginning of Knowlarity did not settle every question. They gave him something to work with. Years later, the same respect for a concrete business need connects the telephone company to the investment firm. For Gupta, another call still offers the possibility of discovering what should happen next.