Harry Franks did not have a desk. Deliveroo was growing so quickly that he found himself standing at something resembling a bar, wondering why prospective couriers were disappearing during sign-up. The company had people willing to work and customers willing to order. Somewhere between the two sat an insurance policy. It was proving surprisingly good at stopping a delivery before it began.
Franks was Deliveroo’s global head of procurement. The question bothering him was practical: why should someone hoping to work a few hours have to arrange insurance on terms built around a much longer commitment? A phone could summon a job almost immediately. The paperwork behind that job seemed to inhabit a more leisurely century.
He asked whether it could be done differently. The answer he remembered receiving was that this was simply how things were done. That explanation has a useful quality for an entrepreneur: it sounds final while explaining very little. Franks took the problem home. Walking with his wife, he described an idea for using data to make insurance adapt to the person buying it.
In 2016, he left Deliveroo and put his own savings into Zego. Sten Saar and technical co-founder Stuart Kelly helped turn the observation into a business. Franks became its founding chief executive. The starting point was small enough to explain without a slide deck: a courier’s insurance ought to bear some relationship to the hours the courier actually worked.
An operator, before he was a founder
Before Zego, Franks had worked at onefinestay, the business arranging stays in private homes, and then at Deliveroo. He and Saar had worked together at both companies. Their partnership therefore arrived with a history of operating businesses where a digital transaction had to produce something dependable in the physical world. A booking needed a home; an order needed a rider.
That background mattered to early backers. LocalGlobe’s account of its investment pointed to the pair’s experience at sharing economy platforms. They had seen how people earned through these services and how conventional financial products could fit awkwardly around them. The opportunity was visible from inside the daily work, where an abandoned application was a concrete problem rather than a market forecast.
Zego’s original model connected cover to a delivery shift. Workers registered, funded an account, and benefited from integrations with the platforms through which they found work. Insurance could start and stop around their activity, with the cost taken from their account. Reducing the number of things a busy courier had to remember was part of the product.
The underlying coordination was more demanding than the customer’s experience suggested. Work platforms, insurance partners and Zego’s own technology had to agree on what was happening and when. Franks’s operational experience belonged in that gap between a convenient promise and the machinery needed to keep it. An app could make the purchase look easy. Someone still had to make the arrangement work.
A business built with the incumbents
In July 2017, Zego announced £1.23 million in seed funding led by LocalGlobe. Franks was already arguing that insurance had failed to keep pace with flexible work. The early offering covered scooter couriers, and car cover underwritten by Aviva widened the scope. The investment would support more staff, particularly in software development. The company needed engineering capacity as well as an attractive explanation.
By November, Balderton was leading a £6 million Series A. Its announcement recorded a team that had grown from seven to 33 during 2017, with further specialists needed in engineering and business functions. Rob Moffat would join the board. The numbers describe a familiar change in a young company: the founders’ immediate circle becoming an organisation with functions, hiring plans and obligations to investors.
Franks’s language about the established insurance industry was unusually conciliatory for a technology founder. “I really don’t see us as a disrupter at all,” he said in 2018. Zego could help insurers reach customers and activities their existing distribution had struggled to serve. Collaboration offered a way to create something useful without pretending that underwriting expertise was an unfortunate relic.
That view suited the business he was building. In its early form, Zego brought the technology and customer connection while insurance partners supplied cover. A convenient interface still depended on an insurer willing to stand behind the policy. Franks treated those relationships as part of the work. The business required cooperation across the insurance market, however unfashionable cooperation might sound in a pitch.
The diary is doing some of the work
Franks’s own account of leadership was less theatrical than the founding anecdote. By 2019, he described organising his day in blocks of half an hour to an hour. He worked within four priority areas and tried to avoid being pulled into everything else. “Being a leader is about delegation of work and saying no,” he said. His calendar appears to have had a firmer editorial policy than many newspapers.
He also talked about giving colleagues room to develop the business, letting ideas be challenged, and setting objectives every 60 days. Weekly celebrations gave the targets a social counterpart. These details make his interest in company culture more tangible: there were intervals, decisions and routines attached to it. A supportive workplace still had to decide what it was trying to achieve.
In a separate discussion of purpose, he described changing the way Zego reported progress internally. Attention moved from premium and sales totals towards the customers the business had satisfied. The commercial activity remained, but the wording brought people closer to the work’s intended beneficiary. Franks wanted employees to connect what they did each day with the person who needed the policy.
He linked that sense of purpose to recruitment, too. Developers had other employers available to them. Zego had to offer work they cared about and colleagues with whom they wanted to build. His interest in the human arrangements behind a company was consistent with his interest in insurance: the terms of participation affect whether people can do their work.
“Being a leader is about delegation of work and saying no”
Harry Franks / 2019
From a shift to a larger insurance business
In 2018, Franks was speaking about customers whose working lives crossed several occupations. Zego said 30% of its customers were using the app to insure themselves for multiple jobs. That observation widened the original question. Someone could be a delivery worker during one part of the week and do something quite different during another. Their insurance had to accommodate a person with a changing schedule.
His ambitions reached beyond a single kind of courier. By then, the business had added public liability cover and was developing products with established insurance partners. Franks argued that customers should be able to manage what they needed simply, even when their work resisted a single occupational label. The flexibility was meant to carry through from employment into the financial service supporting it.
A $42 million Series B followed in 2019. Target Global led the round, which also brought support from backers including Balderton, LocalGlobe’s Latitude fund and Wise co-founder Taavet Hinrikus. Franks was then chief commercial officer. In November that year, Zego secured its own insurance licence, giving it more freedom to develop policies while continuing to work with insurance and reinsurance partners.
By early 2021, Franks held the chief business development officer title. Partnerships involving Voi, TIER and Ginger placed Zego inside the emerging e-scooter market. The company was applying its approach to other ways of hiring and using vehicles. Each relationship extended the task he had first encountered at Deliveroo: making the supporting insurance fit the way the service actually operated.
The valuation and the person are different stories
In March 2021, Zego raised $150 million at a $1.1 billion valuation. DST Global led the round, with General Catalyst joining and existing investors participating. The business had reached the valuation threshold associated with the word unicorn. A company that began with a courier’s insurance problem now had an international expansion plan and a considerably more elaborate cap table.
Saar was chief executive by this stage, having succeeded Franks in 2018. Franks remained a co-founder with commercial and business development responsibilities. Keeping those roles straight gives the achievement its proper shape. Several people built Zego, and its leadership changed as it grew. The founding chief executive’s contribution sits alongside the work of the colleagues who took the business into its next phase.
The 2021 investment announcement described more than 17 million policies issued and over 200,000 vehicles covered across five countries. Those are measures of the company’s activity at that time. The original unit of attention, however, was still recognisable beneath them: a person needed to use a vehicle to earn money, and insurance could either help that happen or stand in the way.
Franks’s approach offers a useful way to read those figures. His operational experience, attention to partners and interest in customer-focused reporting all concerned the arrangements beneath growth. A funding announcement could mark progress. The continuing test was whether the service worked when someone needed to start a shift.
Making room for another chapter
Franks’s departure from Zego became public in February 2024. The company said he wanted more time with his growing family and the opportunity to explore other challenges. It also said he continued to support Saar and the business. The explanation made room for a founder to leave an active role without turning the departure into a quarrel.
The formal record gives the transition more than one date. He resigned as a director of Extracover Holdings on 2 March 2023 and of Extracover Limited on 28 September 2023. The distinction matters because a company’s public story often compresses several legal and personal steps into a single announcement. His working chapter at Zego had an ending spread across that period.
His later public profile connects him with Safe365. In April 2025, speaking as an investor associated with the company, he returned to a familiar subject: culture. He praised its emphasis on delivering the work in an industry susceptible to excitement about itself. Years after his early Zego interviews, the interest in how a company behaved remained visible.
There is a pleasing detail in the route from the original question to this later chapter. Franks helped build insurance that respected the way people wanted to allocate their working time. Eventually, he made a decision about his own. The courier’s hour, the founder’s half-hour diary slot, the time a family gets together: his story keeps finding its way back to the calendar.