Rev spends about 90% of its energy taking care of the people who do the work, not the people who pay for it. That inversion - workers first - is the whole idea, and it explains almost everything about the company Jason Chicola built.
Today Chicola runs Rev, the Austin speech-to-text company that turns spoken words into text you can search, cite, and trust. It is a two-sided marketplace: on one side, more than 100,000 clients - among them roughly 60% of the Fortune 500. On the other, some 50,000 freelance transcriptionists and captioners who log in from kitchens and spare bedrooms around the world. In the middle sits software, and increasingly, artificial intelligence.
What he is working on now is a turn most people did not see coming. Rev started as the quiet tool of journalists and researchers - the thing you used to get an interview off tape and onto the page. Chicola is steering it toward the courtroom. In 2025 Rev acquired SmartDepo, a maker of AI-powered deposition summaries, and was named the first-ever AI partner of the State Bar of Texas. The pitch is blunt: the American justice system is drowning in evidence, and AI can accelerate the search through it without replacing the human doing the judging.
That line is the thesis of the whole second act. In a market full of AI tools that guess confidently and wrongly, Chicola is betting that the boring virtues - accuracy, reliability, security - become the premium ones the moment the stakes are real. "We're not changing what Rev stands for," he wrote in a 2025 note to customers. "We're applying the same principles that earned your trust to solve one of the most pressing challenges in our justice system."
Employee number three
Before Rev, there was oDesk. In 2004 Chicola met the founder of the young online-labor marketplace and signed on as its third employee - and its first non-engineer. He would become Director of Marketing & Sales. oDesk later merged with its rival Elance and rebranded as Upwork, which now trades on the Nasdaq.
The lesson he took from those years was not about software. It was about people. He watched remote work rewrite lives in real time - programmers in Russia who started around $2 an hour climbing to $30 and beyond once a marketplace connected them to the world. Geography stopped being destiny. That image - talent everywhere, opportunity nowhere near it - never left him.
So when he founded Rev in 2010, he kept oDesk's belief that people everywhere want to work from home and added one twist. Open marketplaces make the customer do the sorting - post a job, sift the bids, gamble on a stranger. Chicola wanted the opposite. Rev would curate the talent, guarantee the quality, and hand the buyer a finished product at a transparent price. No "request a quote." No risk on quality. Just words, done right.
Why it's called Rev
The name is not an abbreviation. "The reason we call the company Rev," he has explained, "is because you rev an engine. Think speed, rev your engines." It is a small tell about how he thinks: the brand itself is a performance spec.
The origin was almost accidental. Chicola came across an interview with the writer Shane Snow, who credited a transcription service as essential to how he got his work done. A tedious, unglamorous task that people would happily pay to make disappear - and that could be done from anywhere. That was the opening.
He did not build it alone. Rev was founded with his MIT fraternity brothers from Kappa Sigma, and he still builds alongside cofounders David Abrameto, Mark Chen, Paul Huck, and Daniel Kokotov. The company that put tens of thousands of strangers to work remotely began, fittingly, with a handful of old friends.
The MIT triple threat
Chicola grew up in Miami and went to Miami Palmetto Senior High before heading north to MIT in 1996. There he did the improbable and majored in three things at once: electrical engineering, computer science, and economics. It is a useful shorthand for the founder he became - equally comfortable with the machine, the code, and the market it all has to survive in.
After MIT and before startups, he collected a resume that reads like a finance recruiter's wish list: consulting at McKinsey, venture capital at Globespan Capital Partners, private equity at H.I.G. Capital. He learned how money and companies actually work. Then he walked away from all of it to be the third person at an unproven marketplace - and, later, to sell transcription.
Human plus machine
Rev has never been purely one thing. It sells human-plus-AI transcription when accuracy is everything, and it also runs Temi, an AI-only service for people who want fast and cheap. In effect, Chicola built a company that competes with itself - which is one way to make sure no competitor gets to define where the human ends and the machine begins.
That balance is the harder version of the AI story everyone is telling right now. Rev employs a global human workforce and pours resources into models at the same time. The company's answer is not "humans or AI" but "humans and AI, aimed at accuracy." When the output is a caption, a mistake is annoying. When it is a deposition or a piece of evidence, a mistake is a problem with consequences. That is the ground Chicola has chosen to stand on.
Employees, for what it is worth, seem to like the arrangement. On Comparably, Chicola has carried a CEO approval rating around 82 out of 100 - putting him in the top tier of leaders at similarly sized companies. For a founder whose entire model depends on treating workers as the product's raw material and its beneficiaries at once, that is not a trivial number.
What comes next
The through-line from oDesk to Rev to the courtroom is consistency, not reinvention. Give people meaningful work they can do from anywhere. Make quality something the customer never has to worry about. Keep the technology honest. Chicola's newest chapter simply points those old principles at a system where getting the words wrong can cost someone their freedom.
It is a strange arc for a company that started by transcribing podcasts. But it is a coherent one. Chicola has spent two decades on a single question - how do you turn the human voice into something reliable, searchable, and fair? - and he keeps finding higher-stakes places to ask it.