Sebastián Valin and the trouble with a simple question

Sebastián Valin was trying to do his younger brother a favor. Find insurance for a new car. Compare the options. Choose one. A small errand, of the kind that ought to fit between lunch and whatever happens next. Instead, he found himself making calls, gathering quotations and assembling a spreadsheet. The customer was expected to become the comparison engine. An engineer could do that, of course. The more interesting question was why anybody should have to.

He had studied civil engineering at Universidad de los Andes in Chile and finished his thesis in 2008. He liked mathematics, physics and large structures. He also wanted a business of his own. The qualifications had arrived before the idea, an awkward sequence if you are waiting for inspiration to supply a job description. For a while, he went to an office lent by a family acquaintance and tried to think of something worth building.

The insurance search gave his working day a purpose. Different prices were only part of the difficulty. Different descriptions and conditions made the products hard to set beside one another. A screen displaying several numbers would help, but it would leave a buyer with another question: what, exactly, am I buying? That question would follow Valin through the creation of ComparaOnline and into its later experiments with artificial intelligence.

An apprenticeship in other people’s ideas

His first commercial experiments had been rather more tangible. At university, he persuaded friends to let him convert their old VHS recordings to DVD. He also worked as a DJ and took engineering internships. Before insurance policies came family recordings and music. Both are useful reminders that a founder’s early career can look less like a strategy and more like several ways of making himself useful.

Once the comparison idea took hold, Valin spent his savings on a trip to Europe. He met five companies in London and Madrid to understand how their businesses worked. Discovering that someone else had already built a version of his idea encouraged him. There was a market to study. There were mistakes he might avoid. Originality could wait while he asked practical questions.

He later described those meetings as an education that helped him persuade both investors and insurers. Back in Chile, he spent nearly three months preparing a business plan. This was the unphotogenic portion of starting a technology company: learning the economics, writing them down and putting the proposal in front of people who could say no. Several did. Eventually, a group of angel investors backed the project.

ComparaOnline launched in 2009. Its attraction was easy to explain: bring choices together so a customer could compare them without repeating the same search across separate providers. Making that explanation into a working business proved less tidy. A comparison could produce interest without producing a purchase. The gap between those two events became an education of its own.

The telephone earns its place

The early model relied on insurers to follow up with people who requested quotations. Sales stalled. Valin’s response was to bring that work inside the company and establish a call center. A business built to simplify an online transaction needed people on the telephone to help complete it. Anyone who has tried to interpret a policy might consider this an unusually sensible use of a telephone.

The adjustment matters because it shows how he treated the model he had travelled to study. He could borrow the comparison mechanism; he still had to learn how to serve its customers in Chile. Bringing information together addressed one part of the purchase. Answering questions addressed another. His later accounts repeatedly return to that second task, the conversation that makes a complicated choice possible.

By 2013, he was describing the company as a sales channel, with insurers paying for completed business and, in some cases, online marketing. He compared its display of other companies’ products to a supermarket. The analogy takes some glamour out of financial technology, which is helpful. A well-arranged shelf earns its keep by making the contents easier to understand.

The engineering runs through the idea even though he did not go on to build the structures he studied. Assemble the inputs. Put comparable things alongside one another. Find the point where the system fails. Then change that part. In Valin’s case, the unexpected component was a conversation. The customer had been in the design all along; the operating model needed to catch up.

The introductions that became a map

In 2012, Valin was selected as an Endeavor Entrepreneur. The network gave him access to advice and to people building companies elsewhere in the region. Expansion was already on his mind. His early ambition included a future Nasdaq listing, an aspiration that says something about the scale he imagined for a company born from a family errand.

The relationships had practical consequences. Kaszek, founded by MercadoLibre veterans Hernán Kazah and Nicolás Szekasy, became an investor. In 2013 came a strategic alliance with Brazil’s Buscapé. Then, in September 2018, ComparaOnline announced its acquisition of Colombian insurance marketplace ComparaMejor. Through Endeavor, Valin had met its founders, Fernando Sucre and Omar Ynzenga. An introduction had become a route into a closer business relationship.

He was also willing to take the other chair at the table. Speaking about helping younger entrepreneurs, he resisted presenting himself as a formal mentor. He received people who asked, remembered the time others had given him and wanted to return the favor. He said he enjoyed being in a position to help.

In October 2019, Valin made a public commitment about pay at ComparaOnline. From November, he said, no team member would earn less than 22 UF gross, with the same floor to apply to employees of recurring contractors from January. The announcement included people whose work supported the company from outside its own payroll. It was a specific promise, with a number and a date attached, alongside the broader language of building a business.

There is a useful modesty in that description. Advice can be an appointment between two people before it becomes a role on a biography. Valin’s account keeps the transaction small enough to recognize: someone is starting, someone else has already made a few mistakes, and an hour together may save some trouble. The expanding company had also made its founder a person other founders could call.

“Ahora estoy en posición de poder ayudar a otros y me encanta hacerlo.”

Sebastián Valin, on helping new entrepreneurs · 2015

Brazil refused to follow the plan

Geography did not become obedient simply because the introductions were good. Brazil was difficult. ComparaOnline’s first effort there failed to reproduce the business it had built in Chile. A small operation remained, while the larger ambition waited. This is the part of an expansion story that a map, with its reassuring colored territories, tends to leave out.

By June 2024, Valin was discussing a renewed attempt using AI. He described the work as a second experience of being in a startup, years after the first launch. The appeal lay in applying new technology to the consultative work that insurance sales required. The problem that had once brought a call center into the company was now a candidate for another redesign.

There was a business behind the experiment. ComparaOnline finished 2023 with sales above US$60 million, a figure Valin discussed in March 2024. Its significance here is more practical: he was revisiting an old difficulty after years of operating a substantial business, with customers and experience to bring to the attempt.

His stated ambition in 2024 was to keep growing organically and independently, with a stock-market opening something to consider eventually. He framed the purpose as giving people information and transparency so they could make informed financial decisions. Those are goals that have to survive contact with the purchase itself. A comparison earns the customer’s attention; the usefulness of the answer determines what follows.

A founder still interested in the next version

The later public conversations suggest how closely Valin connects the technology to the daily work. In April 2025, his discussion with Nico Orellana ranged from AI to intuition and the value of writing to think. Writing is an apt interest for someone whose business began by turning scattered information into something that could be examined. A thought, like a quotation, becomes easier to question when it is in front of you.

That July, he shared a conversation with broadcaster Marcelo Comparini, describing their meeting as the fulfillment of a wish. The subjects included organizational culture, lessons from the previous year and leading a company through continuing change. He spoke enthusiastically about the technological possibilities ahead. The pleasure of meeting Comparini gives the public portrait a welcome human detail: a chief executive can still be delighted to meet someone.

His connection to the team also appears in smaller public dispatches. In July 2024, he wrote about travelling to Chile to meet 30 members of Compara’s leadership group and coordinate the plan for the second half of the year. The company now describes itself as fully remote. Even a distributed business has moments when people need to gather and agree on what they are trying to do.

A useful way to read Valin’s career is as a succession of revisions to a clear ambition. Make the purchase easier. Learn from companies abroad. Put people into the process when the process needs them. Return to an uncomfortable market when there is a reason to try again. Each revision carries work that the original idea could not settle. His brother’s insurance search was a small problem with a surprisingly long afterlife. Valin is still working on the answer.