US-Based entrepreneur and investor Giorgos Zacharia on scaling ideas and fixing Cyprus’ innovation pipeline

Giorgos Zacharia was one of the earliest investors in some of Cyprus’ most successful startups. In the US, he’s been instrumental in two of the most prominent digital marketplaces – in travel services and insurance. Now, a member of Cyprus’ new National AI Task Force, he hopes to bring quick, tangible success to Cyprus.

We were discussing the nuances of the co-CEO model, particularly one involving a married couple, so the conversation naturally veered toward the fine art of not talking shop at the dinner table, of leaving work at work. For Giorgos Zacharia, though, that’s never quite been the case. “We’ve discussed our kids’ homework and Insurify at the table for a dozen years now,” he said, smiling broadly. In 2013, alongside his wife, Snejina, and Tod Kiryazov, he co-founded Insurify in Boston, Massachusetts to become the Kayak.com of insurance. “Our children are actually very well-versed in digital insurance, raising money, what a term sheet is and all the struggles of a company,” he went on.

I chimed in. “So, you have a couple of entrepreneurs in the making at home?”

He laughed. “Well, one of my kids is convinced that she will never form a startup. She actually decided that it would be too much stress for her!”

From the lab to business and back

When Zacharia left Cyprus in the mid-1990s to study Maths and Computer Science at MIT, the plan was straightforward: academic research, a professorship, tenure and, presumably a towering h-index. But MIT had a way of rewriting plans. By then, its graduates and faculty had spun off nearly 4,000 companies and the university’s entrepreneurial culture was more a defining feature than a side-effect. That rubbed off. By his third year, Zacharia was already launching ventures, the most successful being Open Ratings during his master’s at the MIT Media Lab. It used machine learning to assess the likelihood of bankruptcy among SME suppliers in complex manufacturing industries – think Honeywell and United Technologies (now Raytheon Technologies). The Lab was funded by corporate sponsors, who enjoyed front-row seats to potentially multimillion-dollar ideas. Twice a year, researchers would showcase their projects during “Hell Week”, a caffeine-soaked time of demos, pitches and all-nighters.

Open Ratings made it out of the Lab and into the real world. The value proposition was sharp, especially in a post-9/11 and post-dotcom landscape, where bankruptcies were on the rise. “It was probably the most stressful decision of my life, much harder than even deciding to get married!” Zacharia quipped. The fork in the road: give up his PhD aspirations or double down on entrepreneurship. Funnily enough, he ended up doing both; Zacharia has four degrees from MIT.

The Kayak.com ride

In 2006, Dun & Bradstreet acquired Open Ratings’ risk analytics engine for US$8 million. Fresh from the acquisition, he found himself involved with two quant hedge funds – one in Boston, the other in Cyprus – in part to hedge the uncertainty of his visa status. As a Fulbright scholar, he faced a potential two-year residency requirement back in Cyprus.

In the end, he avoided it. But while navigating hedge funds and immigration law, one of his former engineers came calling with a machine learning problem from a fast-growing travel metasearch engine, Kayak.com. The company wasn’t receiving the freshest fare data from Northwest Airlines. The carrier was aware of the issue but had little incentive to fix it. “It was kind of acting as a bait and switch,” Zacharia recalled. “You will see a cheaper price, click on it, you will be upset it was inaccurate but, in the end, you booked the flight anyway.” So, he did what any good MIT-trained engineer would do: he trained an algorithm. By analysing the observed accuracy of users’ clicks, he managed to clean up the inconsistency. “And then, the founders made me an offer I couldn’t refuse,” he said, not making it clear whether he was referencing The Godfather or just stating a fact.

Zacharia went on to spend 17 years at Kayak on what he now calls “a fun ride” from Chief Scientist to Chief Product Officer, CTO and then President. The company saw dramatic growth, culminating in an IPO in 2012 and a US$1.8 billion acquisition by Priceline.com (now Booking Holdings Inc., the parent company of the eponymous online travel giant). The parent company continued its acquisition mode, snapping up rivals such as Momondo Group in a US$550 million deal in 2017 and HotelsCombined the following year for roughly US$140 million. A fun ride, indeed!

How Insurify came about

Rewind to 2012. Zacharia was in Cyprus, spending his summer holiday with the kids when, back in the US, his wife was involved in a minor car accident and given a speeding ticket for good measure. “So,” he recollected, “we received the new insurance bill for our car and it was dramatically more expensive. Thinking I was smart, I gave the bill to Snejina and told her, ‘OK, you caused this problem, now you should solve it!’”

She did. An MIT Executive MBA in her own right, Snejina Zacharia spotted a gap in the market. Several had tried and failed to build a true insurance marketplace but she made a strategic call and both she and Insurify became licensed agents. In the US, insurance is a regulatory quagmire with each state functioning like a separate country, complete with its own commissioner. But crucially, by becoming an agent, Insurify didn’t feel like a disruptor. “It was just the same kind of relationship they had with brick-and-mortar shops down the street,” Giorgos Zacharia explained.

After a slow start, the company found its footing. Since 2018, Insurify has achieved a blistering 98% year-on-year revenue growth and now employs 260 people, including agents. One of its core strengths is the platform’s conversion rate: users tend to choose the price they see when redirected to a partner’s site. Since launching, Insurify has helped over 10.4 million Americans save on insurance, with savings of US$300 million in 2024 alone. Amid this rapid ascent, Zacharia transitioned from advisor to co-CEO last year. “We are now the largest insurance comparison shopping platform in the United States. And we are very profitable,” he stated. So profitable, in fact, that they’ve closed the fundraising chapter altogether. It's worth mentioning that Insurify has raised US$128 million. Auto insurance still represents the lion’s share of revenue but home has surged in recent months, a response, in part, to high inflation and rising interest rates prompting consumers to shop harder for savings.

Rewriting the rules of insurance

To manage the growing volume of calls and texts, Insurify has deployed AI in its call centre to collect basic information – like names, birth dates, car registration numbers and models – from SMS. The team is also investing in how the platform presents quotes to users. “In baby steps,” Zacharia clarified. The long-term goal is to have an AI Insurance Agent that can both explain the algorithm’s decision-making process and offer more tailored advice. “A consumer may enter the same data they have on their current policy, asking for the same level of coverage,” he noted. “But their car now is older. Do they really need the same level of coverage? Probably not.”

The company has also launched its first proprietary insurance product, which is currently being tested in Texas and Florida. It tackles a common consumer pain point: the down payment, which is often structured as a six-month upfront cost. Insurify’s version offers flexible payments, allowing customers to pay weekly instead of making a large down payment or even monthly instalments. The plan is to roll out the service gradually, adding one state per month and hopefully speeding up to two by year’s end. Mileage-based insurance is also in the works – think per mile instead of per day – alongside expansions in home, travel and pet insurance. “It’s about providing flexibility to the consumer to help them realise savings,” Zacharia said. “And it’s about providing the right type of comparison experience, so they realise that value.”

What about the co-CEO model? Doesn’t that slow things down?

Zacharia shook his head. “It’s not that rare a model,” he said, pointing at successful examples like Netflix. “Our employees do try and play the mum against dad sometimes. If they don’t like Snejina’s answer, they come to me just in case. But we have some experience with that; we have two teenagers at home!” he said in jest.

Staying close to Cyprus’ startup scene

Despite his adventures in the US, Zacharia has stayed closely connected to Cyprus’ startup scene. He was one of the earliest angel investors in Hellas Direct, a digital auto insurance company that’s been scaling rapidly across Southeast Europe. More recently, he backed Keragon, a workflow automation platform for e-health companies founded by four Cypriot friends who met during their military service. It’s their second venture. The first – Avocarrot – also backed by Zacharia, exited in 2016 for US$20 million.

Last year, a group of fellow founders introduced him to Cyprus’ Chief Scientist and the Deputy Minister of Research, Innovation and Digital Policy. The meeting led to Zacharia joining the country’s newly formed National AI Task Force. His motivation is clear: “Cyprus has fallen behind in government digitalisation,” he said, pointing to smaller peers like Malta, Estonia and even Greece. To catch up, he argued, Cyprus needs faster processes, a better civil service and the integration of AI into the public sector and the economy.

He shared an example of a fellow Cypriot founder in Massachusetts who recently raised US$15 million for an AI-powered water infrastructure platform, which helps cities predict and prevent future problems in their water networks. When trying to hire Cypriot data scientists, he hit a wall: The Know Your Customer (KYC) process stalled because investment funds had just landed in his account. “So, he was unable to hire people from Cyprus to work on this fascinating, global problem. That’s a problem,” Zacharia said. “We make it too hard for our diaspora to invest in Cyprus and be competitive.”

Fixing Cyprus’ innovation pipeline

When it comes to the local startup ecosystem, he’s clear-eyed: the commercialisation conveyor belt is stuck. One key issue is that Cyprus’ public universities typically keep hold of patents resulting from lab-grown technologies. “Researchers only get a share of future income – this is anti-entrepreneurial and needs to be reversed,” he highlighted. The current system drags out negotiations, as every prospective partner must first bargain with the university, which mainly benefits lawyers’ pockets. And with researchers ending up with a small cut, many opt to publish their findings instead of launching a company. “Bottom line, it does not work. There are no notable spinoffs to speak of,” he noted. He suggested the 1980 US Bayh-Dole Act as a far better model. It lets universities retain ownership of patents but mandates quick, automatic, low-cost licensing – often for up to 6%-9% equity or revenue share – to the inventors or their startups. Typically, the researcher also retains around one-third of that share. Before 1980, fewer than 5% of patents were licensed. After Bayh-Dole, US universities began spinning out nearly one startup per working day and patenting activity rose more than tenfold.

Change is on the way

Encouragingly, change may finally be coming. A proposed reform of Cyprus’ national innovation strategy – Action 21 – is currently under review by the Legal Service, which aims to modernise spinoff rules. For faster wins, he proposed three tweaks: publish a one-page “fast track” licence that startups can sign in a week, not months; allow professors to hold meaningful equity so they stay motivated; and if a university can’t find a commercial partner within 12 months, let the inventors take full control. “These small changes would create real incentives and get Cyprus’ lab discoveries to market much faster,” he said. This is the same kind of high-impact thinking he wants to bring to the Task Force. “Not some vague, long-term vision,” he added. “I'd like to have some early, tangible success.”

• This article was first published in the June issue of GOLD magazine. To view it click here