Charles Armitage’s early business had customers, stock and a fatal weakness in accounts receivable. He bought sweets in bulk and sold them at school, extending credit to his fellow pupils. The sweets disappeared. Some of the money failed to return. Even a promising confectionery concern can discover that goodwill is difficult to deposit.
Years later, as co-founder and CEO of Florence, he would have rather more demanding arrangements to think about: workers, employers, investors, software and colleagues in different countries. Yet the school business belongs in the story. Armitage’s public account of building things contains enough wrong turns to make the successful ones interesting. He has been willing to describe enthusiasm arriving before understanding, and the work of putting that order right.
Florence began with a question about how people find and organise work. It became a company through less glamorous activities: calling potential customers, reconsidering a product and persuading people to trust something new. Armitage had to learn how to make an idea useful to somebody else. A customer, after all, is permitted to have entirely different interests from a founder.
The sweets were popular. The invoices were less so.
Making things was part of his childhood. He grew up in a large household with sisters and animals, parents he remembered as hardworking and present, and limited access to television. Entertainment required some effort. There was the Encyclopaedia Britannica to read, or something to construct. An early gift of woodworking tools made an impression; money could be earned by working in the garden.
These are domestic details rather than an entrepreneurial prophecy. A child with tools need not become a chief executive. They do, however, help explain the range of interests Armitage later brought to work. His enjoyment of painting and sculpture sat alongside a preference for practical activity. He studied medicine and surgery at the University of Edinburgh from 2007 to 2013, then worked as an NHS doctor.
The eventual career change involved recognising an appetite for creative work and considered risks. Company building offered scope to make decisions about an uncertain future, then discover whether they held up. His childhood sweets trade had already supplied one warning: being interested in business and running a workable one are separate accomplishments. The latter tends to involve questions that the former would prefer to postpone.
A pub, two perspectives, one beginning
Late in 2016, Armitage met Dan Blake. Armitage had been working on another product idea. Blake brought experience of a housing charity associated with care homes, and a view of staffing from the organisation buying it. Armitage knew the worker’s side. They sat down in a South London pub and began discussing a marketplace for flexible staffing.
The pairing mattered because a marketplace has two sets of customers to disappoint. Giving a worker more choice is useful only if an employer can find the right person. Helping an employer book someone is useful only if the arrangement works for that worker. Each side can have a perfectly reasonable demand that complicates the other’s afternoon.
Armitage’s transition into entrepreneurship happened quickly. Within a few months of that conversation, he was concentrating on the business full time. Florence dates the founders’ meeting to October 2016 and its first completed marketplace shift to 2017. The distinction leaves room for the part of a startup’s history that a founding date often conceals: the stretch between deciding something ought to exist and getting it to function.
The app that sent him back to a spreadsheet
Florence’s first software attempt went wrong. Armitage has described spending money on an application that failed to address what users needed. The founders had moved into building before understanding enough. A more substantial product had given them a more substantial way to discover the mistake.
The recovery included Google Sheets. It also included the telephone. Armitage found a list of London care homes and called them individually. On the worker side, the team sought people through Facebook and existing connections. Early relationships required effort that could not simply be handed to software. When the product was imperfect, the person answering a call had to give customers a reason to remain patient.
There is an agreeable indignity in that sequence. A company formed to improve cumbersome arrangements first had to perform plenty of cumbersome work itself. But those calls supplied information a specification could miss: what a customer was trying to achieve, which obstacle mattered today and what could wait. An ambitious feature list has no special claim on another person’s priorities.
The story also complicates the idea that personal experience settles the product question. Armitage knew one part of the market well. Blake knew another. They still had to learn what people would actually use. Familiarity gave them somewhere to begin; customers retained the power to send them back to the beginning.
- 01Build the first appThe product misses users’ needs.
- 02Return to simple toolsGoogle Sheets and direct conversations.
- 03Learn through bookingsUnderstand the work before adding features.
When the team becomes the work
By June 2022, Florence was announcing a $35 million Series B round led by AXA Venture Partners, with Roo Capital and SEEK Investments participating. The intended uses included product development and international expansion. Funding bought room to attempt more things. It also increased the number of decisions that had to agree with one another.
The company launched in France in November 2022 and Canada in February 2023. Its range widened beyond individual shift bookings, including tools for scheduling and professional development, then agency management. An idea discussed by two people in a pub now had to travel through teams, products and markets.
Florence’s Series B funding round, announced for product expansion and international markets.
By early 2023, the company had grown from one person to more than 200 within five years. At that size, a founder’s job changes. A decision can no longer be explained separately to everyone who will act on it. The explanation has to survive being repeated, questioned and applied to situations its author has not personally seen.
Armitage’s leadership preferences are demanding without making unpleasantness a qualification. He describes himself as competitive, wants colleagues to challenge one another and values trust, humour and kindness. His chosen inspirations include explorers such as Shackleton and Captain Scott, along with Antoine de Saint-Exupéry: people whose attraction, for him, includes resourcefulness and a sense of duty under difficult conditions.
The practical side of that thinking appears in Florence’s office arrangements. In 2024, Armitage and people-operations leader Caroline Hayes described an approach with Monday to Thursday in the office and Friday flexible. Meetings without a collaborative purpose were directed towards video calls. Whatever one’s preferred working pattern, the distinction is useful: occupying the same room and doing something together are different activities.
Florence’s June 2023 placement at number 21 in the Sunday Times 100 supplied a public marker of progress. Armitage later wrote about attending the awards and acquiring a red trophy for his shelf. His daughter, he noted, seemed rather less impressed. Companies can rise rapidly through a ranking while remaining subject to a brisk domestic valuation.
Some decisions have no easy return ticket
In March 2026, Armitage appeared on Jesse RT Coleman’s Master Your Mistakes podcast. The discussion returned to the first product, choosing co-founders and the consequences of early ownership arrangements. These are useful subjects for someone whose company has lasted long enough to live with its initial decisions.
The episode’s emphasis on choices that are hard to reverse gives his enthusiasm for risk some necessary detail. A feature can be changed. A relationship between founders, or a badly considered allocation of ownership, may remain part of the company for years. Courage becomes more useful when it distinguishes between an experiment and a commitment that will be expensive to unwind.
Armitage also described the value of other chief executives facing similar problems at similar stages. Some of his most useful advice comes through small WhatsApp groups. The appeal is easy to understand. Someone close enough to the same decision can ask the question a more distant observer would never think to raise. Experience becomes practical when it arrives at the right moment.
The conversation ended with poetry, which prompted an amused response from Armitage afterwards about having been made to read it aloud. It is a fitting detail for a founder whose interests have never been confined to software. Even an interview devoted to mistakes can leave room for something that has no immediate place in a business plan.
The garden gets the last word
For a shorter piece of advice, Armitage has offered something refreshingly specific. No grand theory of leadership is required to understand what action to take.
“If you cycle in London, buy bike insurance.”Charles Armitage
Away from Florence, he gardens. His company biography mentions time outside with his dog, Rosie. In 2023, he described moving between vegetables and flowers, with ferns then enjoying his attention in a north-facing, shady garden. The conditions of the place helped determine what he grew.
There is no need to make the ferns responsible for Florence. They are an appealing ending because they belong to a person, with tastes, limits and other uses for a Saturday. The business has required ambition, money and repeated decisions about what to build. His account of it also leaves space for a failed app, an unpaid sweets bill and a daughter unmoved by an award. Those details make the work easier to picture. Somebody had to do it, learn from it, and come home.