The numbers in Surga Thilakan’s working life once made a rather abrupt change of scale. At Goldman Sachs, one assignment involved an $8 billion structured loan. At Ujjivan, back in India, she worked on lending that included an Rs 8,000 loan to a group of women. Keep the currencies separate; the contrast is striking enough without a conversion. The second sum brought her closer to a question that would occupy the next stretch of her career: how does someone acquire a dependable livelihood?
She had trained for a different sort of success. A chartered accountant, then a management graduate, she had entered a profession where complicated transactions were the work. She could do that work. The difficulty was finding enough meaning in it. Looking back, she put the distinction plainly: “My job was intellectually challenging but not meaningful.”
That dissatisfaction eventually produced two ventures with Sreeraman Vaidyanathan, her IIM Ahmedabad batchmate: iSTAR, focused on skills and employment, and Salesken, which brings AI assistance into sales conversations. Across the changing business descriptions, a practical interest persists. People need to perform a skill under pressure. How close can the help get to the moment they need it?
The smaller loan
Thilakan grew up in suburban Mumbai in a South Indian family. Both parents worked in government. Her early professional life included tax advisory at Ernst & Young, followed by private equity and structured finance work at Goldman Sachs. Her assignments took her into the machinery of investments and infrastructure, a considerable distance from the circumstances of someone seeking an entry-level job.
IIM Ahmedabad supplied a lasting connection as well as a qualification. Thilakan attended its 2003-2005 postgraduate programme. After graduating, she went to Goldman Sachs in London; Vaidyanathan joined Microsoft in Hyderabad. Their paths would come together around education and employment. The partnership preceded the sales software, the investor presentations and the category descriptions.
At Ujjivan, Thilakan worked on products intended to support livelihoods and led marketing. Lending brought her into contact with the economics of households whose next step depended on regular income. A loan and a job address different parts of that problem. Her attention moved towards what it took to obtain the job, and towards the gap between finishing an education and being ready for work.
That gap can sound abstract until a person has to cross it. An employer wants somebody who can deal with a customer. A candidate needs the opportunity to learn how. Qualifications do not automatically provide practice, confidence or the right words in a difficult conversation. This was a problem with enough daily consequences to become a business.
An extra room on the terrace
The early iSTAR workplace was an extra room on a terrace. An IIM Ahmedabad alumnus later provided a room. It is a pleasingly literal version of starting at the top, although the founders had rather more immediate things to worry about than the view. Money was uncertain. Contracts were uncertain. An earlier corporate career did not furnish a map for every new decision.
There was learning on both sides of the classroom. Vaidyanathan learned Kannada to communicate with people in the communities where they worked. The founders remembered the first cohort’s graduation, when almost all the students had secured jobs, and the pride their families brought to the occasion. For an employability venture, that was a result with faces attached.
By June 2015, iSTAR’s work had reached 150 colleges across three states and 17 districts. Around 17,000 students had received training over five years, with more than 150 trainers involved. A further investment from Unitus Seed Fund was intended to support expansion and a technology system for managing learning. The effort was acquiring an infrastructure of its own.
Training also moved onto the smartphone. Talentify, developed by iSTAR, let people practise conversational skills with a virtual trainer. The intended destinations included customer service, banking and automobile sales. The appeal was practical: someone preparing for a customer-facing role could rehearse on a relatively inexpensive device. A skill that demanded conversation could be practised through interaction.
Help before the call is over
The next problem appeared after the lesson. Preparing someone for a conversation left a difficult question about what happened when they actually spoke to a customer. Salesken took that question into the workplace. Its premise was to provide useful guidance while the exchange was still happening, alongside analysis of the conversation.
The timing matters. A customer raises an objection. The salesperson has to interpret it, recall what might help and answer without letting the exchange collapse. A manager listening later can identify a missed opening with splendid accuracy. The opening itself has already gone. Salesken’s product ambition was to shorten that distance between noticing a problem and helping with it.
One early lesson concerned the person who would use the software. Sales managers wanted information, but the representative needed a reason to welcome another tool into the working day. The team’s answer was immediate assistance with the sale. That made the product useful to the employee whose actions would determine whether it was adopted at all.
There is a small workplace comedy inside that lesson. A company can buy a tool for an employee with the confidence of someone choosing a gift for a relative they barely know. The recipient still has opinions. Thilakan’s approach took those opinions seriously: the representative’s own incentives had to matter in the design.
Learn the product. Rehearse the conversation.
Use live cues while the exchange continues.
Examine the call. Identify what needs work.
A phone, a headset, a different workplace
Product development also had to contend with the equipment people actually owned. Salesken’s mobile telephony app launched in June 2020. A desktop setup in a contact centre offered one set of assumptions; an employee making calls elsewhere from a phone offered another. Network quality, the device and the absence of a nearby team leader all affected the experience.
The app allowed representatives to speak through a Bluetooth headset while viewing guidance. Calls could use telephone or internet modes, depending on what worked in a particular location. Cues could offer responses to concerns about price, including available payment options or discounts. These were concrete design choices about how to keep assistance accessible during an ordinary call.
Such details rarely make a glamorous company origin story. They do explain the distance between a demonstration and a usable product. Advice has to be readable. The audio has to arrive. The connection has to hold. A sophisticated system still meets its user through a screen small enough to fit in a pocket.
For Thilakan, the recurring training problem had acquired an engineering dimension. The software needed to listen and assist while a person was already busy listening and speaking. A helpful cue also competes for attention. The ambition depended on fitting guidance into a working conversation without asking the representative to stop having it.
“I think fundamentally I'm a creator at heart.”
Surga Thilakan, 2022
The apprenticeship behind the investment
In March 2020, Salesken announced an $8 million Series A led by Sequoia India. In November 2021, it announced a $22 million Series B led by M12, Microsoft’s venture fund, with Sequoia India participating. Plans for the later round included North American expansion and further product development. These were substantial company milestones after years spent working on skills.
By the second round, Thilakan described a customer base extending across education, banking, financial services, construction, logistics and consumer businesses. Different industries brought different products and customer concerns, but the person on the call still had to connect a response to what had just been said. The company was pursuing that recurring moment across markets.
Recognition had arrived through more than one part of her career. Business Today included her in its 2018 Most Powerful Women in Business coverage during the iSTAR years. Crunchbase included her in its 2023 Influential Women in Sales list. The dates trace a move from employability work into enterprise software without erasing the earlier effort.
Her stated ambition for Salesken has been international, centred on assistance that augments what people can do. It is an ambition grounded in a familiar task: help a person get better at their work. The funding allows the company to attempt that at greater scale. It does not remove the need for the individual employee to find the help useful.
Another kind of canvas
There is more to Thilakan’s public life than the executive biography. Her personal website collects visual art, poems and film reviews. The presence of that work is a useful invitation to step outside the language of funding rounds. A person who builds a company can also spend time making things that do not require a customer acquisition strategy.
The interest is longstanding. A 2018 alumni profile recorded painting, travel, poetry, board games and movies among her pursuits, alongside a wish to produce an animated feature film. That last ambition is easy to enjoy without turning it into a prediction. It leaves room in the biography for a project whose shape differs from the companies she has already built.
One can draw a connection between the creative work and her description of herself as a creator, while leaving the paintings and poems their own space. They need no supporting role in a business parable. They show another way she chooses to spend attention, and another reason a job title provides an incomplete introduction.
The professional story returns to a modest interval: a person hears a question and has to answer. Thilakan has approached it through education, practice and software, following the problem closer to the working day. A large ambition can begin there, in the search for a useful word before the moment to say it has passed.