Charles Hipps and the problem of the perfect CV

Charles Hipps has an awkward customer problem. The people applying for jobs have acquired some very helpful software of their own. Their CVs can be fluent, orderly and persuasive. Their covering letters can strike precisely the right note. For the employer reading the pile, everyone’s sudden literary improvement creates a difficulty: which of these people can actually do the work?

Hipps has been building recruitment technology since 1995. He founded the business that became Oleeo when online hiring was still a young proposition, took it onto the stock market, and stayed through successive changes in how employers and candidates find each other. Now the application itself has become easier to manufacture. A handsome paragraph has acquired a suspiciously modest production cost.

His response is to put more emphasis on evidence, with a recruiter responsible for the final decision. This gives his current work an interesting tension. Here is a software founder making the case for more capable machines while insisting on a place for the person who can question them.

A business older than its name

Before recruitment came Oxford, where Hipps studied Engineering, Economics and Business Management. He then worked at Booz Allen Hamilton, advising organisations on strategy in Europe, Asia and the United States. The combination is suggestive: systems, incentives and the messy business of getting organisations to do something differently.

There was also a recycling company before there was a recruitment company. Hipps mentioned that earlier venture in a 2020 interview. It is a useful wrinkle in a career otherwise so closely associated with one business. He had tried building something before he began the enterprise that would occupy the next three decades.

World Careers Network, usually shortened to WCN, began in 1995. Hipps took the company public on the London Stock Exchange in 2000. Five years separated the founding from the flotation; a much longer stretch followed in which he remained involved in the work of running it.

The change to Oleeo arrived in June 2018, alongside expanded machine-learning and analytics capabilities. Its new name drew on “olio”, a varied collection. By then the company’s customer history included Morgan Stanley, Marks & Spencer, the UK Civil Service and NBCUniversal. The work had to accommodate employers with rather different ideas about what a promising candidate looked like.

Those dates give the career its proportions. The flotation was an early milestone, followed by decades of operating a recruitment business. The work continued after the announcement, through customer requirements, product changes and the next question about how hiring should function. A founder’s biography can fit a company launch into a line. Staying with that company produces a much longer story, with fewer neat stopping points. Hipps’s continued role makes the operating years central to understanding him.

A rebrand offers the pleasure of a fresh introduction. In Hipps’s case, it also risks concealing the age of the conversation. Oleeo sounds like a new arrival; its founder had already spent more than twenty years thinking about recruitment before the name appeared.

The small indignities of applying

His earlier writing is often concerned with practical obstacles. In 2013 he was discussing social networks as places where employers could meet people, including people who were employed and not actively searching. He encouraged companies to connect their career sites to the places where candidates already spent time.

That is a more demanding proposition than posting a vacancy and waiting. It asks the employer to sustain a relationship before there is an application to process. In that account, recruiting includes the patient work of becoming familiar to someone who may eventually want to join.

By 2018, his advice about job fairs was delightfully specific. Text candidates before and after the event. Let them enter their details on mobile devices. Connect that information with the recruitment system. Follow up while the conversation is still fresh. A stack of business cards, however satisfyingly tangible, has limited powers of recall.

The same article recommended understanding the candidate groups attending an event and the barriers they faced. Technology supplied the means to remember and respond. The recruiter still had to decide what would be useful to say. You can hear an enduring preoccupation in this: an encounter should survive the administrative process that comes after it.

Who gets seen?

Hipps’s writing about blind recruitment tackles a different obstacle: information that distracts an employer from someone’s qualifications. In a 2022 article, he explained the practice of withholding personal details that might prompt a prejudiced response. His recommendations included anonymising applications, training staff about bias and checking recruitment metrics.

He also advocated consistent interview questions focused on candidates’ abilities, alongside changes to job descriptions and the wider hiring process. Blind recruitment, in his account, belonged inside a broader effort. Concealing a name would achieve little if every subsequent stage restored the same old preferences.

There is an appealing discomfort in that argument. Employers generally want to believe they recognise talent when they see it. A consistent process asks them to explain what, exactly, they recognised. It moves some of the authority from instinct to criteria that can be examined.

“Human judgement stays at the centre of the process.”

Charles Hipps · October 2026

The question also reaches beyond software. What does an employer ask? What counts as a useful answer? Which details are allowed to influence the next step? His work keeps returning to the design of those encounters, where a candidate’s future can turn on a surprisingly small assumption.

When everyone writes beautifully

Generative AI has made this old selection problem newly awkward. Hipps has described recruiters receiving applications whose polished language makes them harder to distinguish. The writing can be accomplished while the underlying evidence of suitability still requires investigation. A CV has always been a sales document. Now more applicants have an editor.

Oleeo’s current response includes Select, its candidate-screening technology. The company describes a process in which employers set role criteria, the software identifies relevant evidence, and recruiters review the resulting recommendations. In October 2026, it announced that Select had received Bronze at the IHR London Live Innovation Showcase, held the previous month.

Hipps put the difficulty succinctly: “polish isn’t necessarily the same thing as capability.” The system’s intended role is to make the supporting evidence easier to inspect. Recruiters should be able to interrogate a recommendation and agree or disagree with it. That responsibility remains with the employer.

The distinction sets a practical test for the product. A recommendation needs to be understandable enough to challenge. Otherwise the human reviewer has a title and a button, but little basis on which to exercise discretion. Hipps’s position requires the recruiter to remain an active participant in the reasoning.

A different kind of job description

His December 2025 reflections on recruiters’ future work imagined more time spent designing AI processes, shaping candidate experiences and specifying how selection should operate. These were predictions about emerging responsibilities. His proposed job titles were ways of thinking through the work that automation might leave with people.

The recruiter who once carried out a repetitive task could increasingly have to explain how that task should be done. Instructions become more consequential when software follows them repeatedly. Deciding what to ask, what evidence to accept and when a person should intervene requires detailed knowledge of recruitment.

Hipps also sees continuing work in communicating an employer’s culture and persuading candidates to join. His vision gives people a role in designing the process as well as making its final decisions. It is an optimistic account, expressed as a direction he wants recruitment to take.

That emphasis on collaboration appears in how he describes his own motivation. He enjoys innovation and teamwork, and points to customers’ success and his people’s development as reasons to keep going. The founder’s ambition is expressed through other people getting somewhere.

Fishy, on dry land

Outside work, Hipps’s biography becomes noticeably wetter. Some people call him Fishy or The Wave. He swims, enjoys the sea and has a history of scuba adventures that includes following a whale shark and swimming with dolphins. His preferred extracurricular setting appears to offer fewer application forms.

On land, there is cycling. His travels have included South America, North America, China, New Zealand, Vietnam and a route along the Nile. The 2020 account also mentions the Atacama. This is a substantial itinerary for an interest that could have been satisfied with a spin around the neighbourhood.

His public posts carry that enthusiasm into business conversation. Inviting customers to a summit, he used cycling comparisons about climbs and tailwinds and cheerfully acknowledged the habit. Elsewhere, he has joked about a cat café advertising vacancies. Recruitment, apparently, can follow a founder even into a room full of sleeping cats.

These details give Hipps a life beyond the software, while his career shows the persistence of one professional interest. From getting applications online to making sense of machine-assisted prose, he has stayed with the question of how people get a chance. The next generation of tools will have to answer it one hiring decision at a time.