Oscar Giraldo and the work of being noticed

Oscar Giraldo was about twelve or thirteen when he first appeared in his hometown newspaper. He was going to Medellín for a roller-hockey tournament, representing Del Café Hockey Club. He had trained with his teammates for close to a year. There was a photograph with their coach, Carlos Alzate. For a child preparing to compete, a little space in the paper could make the whole enterprise feel rather official.

Years later, he remembered the feeling as recognition: somebody had decided that what he was doing deserved to be seen. When his software company attracted newspaper coverage in 2012, the sensation returned. The subject had changed from hockey to Silicon Valley. The pleasure of having the effort acknowledged was familiar.

That is an unusually useful place to begin the story of Playvox. Giraldo built a business around the people who answer other people’s questions for a living. Their work is easy to measure and surprisingly easy to overlook. A queue has a number. A conversation has a duration. The person having it has a much longer story.

The detour through Chile

Giraldo grew up in Manizales, Colombia, with a father whose curiosity about electronics rubbed off on his children. He and his brother Mauricio studied systems engineering at Universidad Autónoma de Manizales. Computers supplied one possible future. Roller hockey supplied another. Chile, where he went hoping to pursue the sport, offered both.

His early working life included banking and software development. A later role at Needish introduced him to building a startup from inside its engineering team. He also cofounded Medularis, a business connecting online customers with sales representatives by telephone. Before he was thinking about the quality of conversations, he was helping make the telephone ring.

There is a tidy engineering appeal to connecting a website visitor to an available salesperson. Then the connection succeeds and the difficult part begins: two people have to speak. In Giraldo’s account of the next turn, a customer wanted to cancel because the calls being generated were failing to become sales. He went to investigate. The agents were unmotivated. A visit to another operation showed him a different atmosphere and different results.

That contrast gave him something more interesting than another telephone feature. The working environment could change the outcome of the same basic task. He recognized something of his own frustration in an earlier bank job. Building software for that problem would mean paying attention to how work felt to the people doing it.

A game with a supervisor in it

By August 2011, Giraldo was running Arcaris in Santiago. Its team of seven represented five nationalities. The business was moving from click-to-call technology toward a product called Playcall, which brought game mechanics into contact centers. Giraldo and product manager Ariel Cordiviola were preparing for a Silicon Valley incubation program at Plug and Play, through Chile’s Global Connection initiative.

One detail of the early product deserves a pause. Achievements needed a supervisor to send them with praise. Recognition had a human sender. A digital reward could therefore become an occasion for a manager to notice somebody’s work. The software was arranging a small social encounter, with a score attached.

Gamification invites a certain amount of office comedy. Put a leaderboard beside a spreadsheet and someone will eventually call the spreadsheet a sport. The more serious question is whether the game changes the attention people receive. Giraldo’s early approach placed the supervisor inside the mechanism. An employee’s achievement gave another person something specific to acknowledge.

Learning to sell across a language barrier

Playvox dates its founding to 2012. Reaching American customers required Giraldo to learn a market while learning its language. He arrived in Silicon Valley with limited English and began seeking out people who understood contact centers. Carol Snell, a cofounder of Aspect Communications, became one of the consequential connections in that effort. An initial meeting eventually became a longer relationship with the company.

The difficulty was bigger than vocabulary. Selling business software requires a founder to explain a problem in terms a buyer recognizes, then show why it is worth changing an existing system. Every familiar objection has to be understood in an unfamiliar language. The product may live in the cloud; the sales conversation still happens between people.

Giraldo’s later discussion with Startupeable returned to those early American sales, international pricing, and communicating a vision. It also preserved a useful piece of chronology: the company’s rapid growth began in 2017, five years after its founding. Those years belong in the story. The eventual customer list can make the beginning look more straightforward than it felt while it was happening.

The agents got a vote

As Playvox expanded, its remit grew to include quality evaluation, coaching, learning, and performance management. Giraldo described a habit of talking directly to the agents as well as the people managing them. He wanted feedback from the people using the tools each day. A purchasing decision and a working day provide different views of the same software.

His argument for agent experience was practical. Companies expected staff to provide quick, knowledgeable service across more channels. Those expectations deserved a corresponding investment in the people delivering it. He took satisfaction in hearing that supervisors and quality analysts had more time to help agents improve. A useful tool could create room for a better conversation inside the company, too.

He also described a future in which automation handled simpler inquiries while people and bots worked together. That was his expectation in 2020, before the current wave of generative AI products. The ambition running through it was consistent: technology should leave people better equipped to do their jobs. Even in a business full of metrics, he kept returning to what a supervisor could do with the time saved.

“We listen to our customers,
but not just the managers.Oscar Giraldo · 2020

The company outgrows the first job

In January 2021, Playvox announced a $25 million investment led by Five Elms Capital. Its cumulative funding then stood at $34 million. The company had bought the corporate-learning business Trainbox and was adding Agyle Time, whose tools covered staffing schedules and demand forecasting. The original concern with motivation was becoming part of a wider collection of tools for running customer-service operations.

The geography had widened as well. By that January, Playvox had more than 200 customers across 34 countries. Its operations extended across the Americas and Europe. Names including Dropbox, Delivery Hero, and Electronic Arts made the distance from its Colombian origins easy to describe. The harder achievement was operating a business that could keep serving customers across those distances.

Expansion also brought people with experience Giraldo needed: product and strategy executive Kristyn Emenecker, sales leader Chuck Krogman, product-marketing executive Jennifer Waite, and finance executive Ana McCloud. His interest in attracting talent extended beyond recruiting engineers. Growing the business meant adding different kinds of judgment.

In August 2021, Louis Bucciarelli became CEO, after serving as chief operating officer. Giraldo moved to chief innovation officer and remained on the board. His new brief covered technologies, partnerships, and innovation. There is a revealing distinction between founding a company and occupying its top operating job forever. Giraldo’s career contains a specific moment when those responsibilities separated.

Trust takes a lunch break

In June 2022, Giraldo joined a Colombia-Spain leadership program alongside fellow founders Maite Muñiz of Truora and Sergio Pachón of Kiwibot. One engagement brought them together with representatives of fourteen Spanish startups over lunch in Madrid. The setting was less hurried than the cold approach to a potential customer.

This was not his first appearance in an entrepreneurial delegation. In May 2019, he was among fourteen Colombian entrepreneurs accompanying President Iván Duque on a Silicon Valley visit. By then, his own route between Colombia and California gave him a particular perspective on the trip. The engineer who had once sought introductions was taking part in a wider public conversation about Colombian technology.

Giraldo valued the informal conversations and the trust they allowed. Meeting the people inside large organizations made those institutions feel approachable. He saw opportunities in Spain’s talent and in relationships between entrepreneurs across countries. He also recognized that the introductions were only a beginning: the participants would have to maintain the relationships afterward.

For someone whose products organize communication at scale, this enthusiasm for sitting down together is pleasantly concrete. A message can start a relationship, as his early outreach demonstrated. Keeping it alive asks for more. Lunch, at least, has the advantage that neither party can accidentally mistake the other for a dashboard.

Another company, the same precious resource

Playvox became part of NICE in 2024. Giraldo’s subsequent work includes Oversai, where he is founder and CEO, and SOBERAN, which also identifies him as its founder. Oversai applies AI to reviewing customer interactions and understanding customer feedback. SOBERAN connects business operations such as inventory, orders, and customer conversations. The scope has broadened beyond the original contact-center scorecard.

His SOBERAN manifesto makes the personal ambition explicit. He wants room to create independently, to find purpose through building, and to make the business profitable enough to sustain that freedom. The resource he wants software to return to other people is time. It is a fitting concern for somebody who has spent years studying what work asks of people.

The hockey photograph belongs at the beginning because it gives the later business story a human scale. A boy trained, competed, and liked seeing the effort recognized. Years later, Giraldo was designing ways for managers to notice their teams. Across the changes in company, country, and technology, that small transaction keeps its value: someone did the work, and someone else paid attention.