Dean Benson and the habit of changing the game

Dean Benson’s sisters kept beating him at Pong. He dealt with this family inconvenience by changing the code: his bat grew, theirs shrank. The game became easier to win. Any objections from the other players have, regrettably, failed to enter the business record.

It is a small story with an unusually long afterlife. Benson went on to co-found Visualsoft, help retailers sell online and employ hundreds of people in a business rooted in Teesside. The young player’s intervention offers a useful place to start: he wanted to understand the machinery well enough to alter the outcome. The appeal of a system, for him, included the possibility of improving it.

His father introduced him to computers when he was seven. Much later, Benson described himself as “private by nature but curious by default.” The two qualities sit comfortably together. His career supplies plenty to examine without requiring a grand performance from its central character: a change of market, a buyout, a different approach to working hours, and money directed back towards the next generation of programmers.

A training venture finds the shop floor

Benson graduated in computer science from Teesside University in 1997. Visualsoft followed in 1998, initially as an online training venture. Ecommerce became its business. That shift matters because the company’s eventual identity can make the starting point look inevitable. It began with one proposition and found another use for its technical abilities.

The early financial backing included a £20,000 Barclays loan and £80,000 from Benson’s parents. Among the consequential customers was shoe retailer Charles Clinkard. Benson later described the company’s first ecommerce site as a pivotal moment, particularly in the move towards recurring monthly revenue. A website could become an ongoing commercial relationship, with fresh work to do long after its opening day.

That practical problem helped define Visualsoft: how could code and marketing help a retailer make more sales? A finished website was only part of the answer. The business developed its own ecommerce platform alongside services that helped customers attract and convert shoppers. There was always another adjustment available, provided it earned its place in the customer’s business.

Buying the business, loosening the clock

In July 2014, Benson led a management buyout. The new board brought together his role as managing director with Tim Johnson in business development, Matt Burton in technology and David Duke in online marketing. Visualsoft then employed 155 people. The announced ambitions included 50 more jobs over the following year and a threefold increase in turnover by 2017. Those were targets, with the work still ahead.

Benson was the remaining founder taking the company forward with a new management team. Sixteen years after its establishment, Visualsoft had both a history to preserve and decisions to revisit. Its original training proposition was already far behind it. The next changes would concern the people doing the work as well as the work itself.

During this period, he introduced flexible working and unlimited holidays. His stated premise was that people understood their responsibilities and deadlines; they could have more discretion over when they fulfilled them. It was an approach built around trust, with delivery still expected. These were policies Benson described during his leadership, rather than a description of employment terms today.

He gave flexibility an energetic demonstration. Getting up at three in the morning, he drove to the Lake District, climbed Scafell Pike and returned to his desk that afternoon. The point could probably have survived a less strenuous illustration. Still, a photograph at the desk after a mountain is harder to overlook than an internal memo.

The useful discipline of a five-year plan

For all the experimentation, Benson’s advice to his younger self was about focus. By January 2020, he wished he had adopted a clear five-year strategy earlier. Visualsoft had taken more than two decades to become the business people were congratulating him on. Looking back, he could see room for a more deliberate route through those years.

He also remembered a smaller rescue from the early days. Heading to London for a Visualsoft meeting, he realised at Darlington station that they needed business cards. Turning round revealed a machine that printed them. Sometimes preparation has to accept assistance from the station furniture. The anecdote makes a pleasant companion to the strategic advice: a plan does not remove the need to solve whatever is immediately in front of you.

Asked for a book recommendation, he chose Spencer Johnson’s Who Moved My Cheese?, a short account of responding to change. The choice fits the advice about planning: give yourself a direction while remaining willing to reconsider the route. His own company had already changed its market, its management structure and its way of charging customers. None of those decisions could be settled by technical skill alone.

By 2019, Benson was arguing publicly for a larger share of online retail. Visualsoft reported that £750 million of goods had passed through its sites in 2018, equivalent to 1.2% of UK business-to-consumer ecommerce sales. His ambition at an Entrepreneurs’ Forum event was to double market share over five years. The figures measured customer commerce flowing through the platform, a different measure from Visualsoft’s own turnover.

In November 2020, Livingbridge announced its investment. Its account described more than 1,000 customers, over 280 staff and £18.5 million in FY2020 revenue. The Shared Success model removed upfront build costs and linked the relationship to retailers’ growth. Investment gave another marker to a business that had started with training software and become deeply involved in the daily mechanics of selling things.

Room for other people’s ideas

A growing software business also changes its founder’s job. The code remains important, but useful observations can arrive from any desk. Benson argued for a culture in which even the most junior colleague could put forward an idea. One employee’s suggestion led to Visualsoft exploring Dubai. Its map expanded because someone inside the business saw an opportunity worth testing.

His own weekly diary in 2019 had a conspicuously human variety. There were leadership discussions, client meetings, university governance and conversations with fellow entrepreneurs. There was also the school run. He met friend and business partner Mark Leader to exchange ideas, and spoke with the High Tide Foundation about opportunities for young people. The calendar placed company decisions beside family obligations and local commitments.

His interests spread beyond Visualsoft. Through Northern Stable, he was involved in supporting developing software businesses, including Salesfire and Hive HR. In 2021, he talked about learning to take brand more seriously, after early years when the emphasis had been heavily technical. Colleagues, customers and partners were brought into that work. A company’s understanding of itself needed attention too.

The brand discussions acknowledged something easily missed in a business full of technical expertise. Benson said the early understanding of branding had amounted to a name, a logo and some colours. As the company developed, those choices came to represent its culture and promises. Asking other people what the business stood for gave its leaders a chance to compare their intentions with the experience they were actually creating.

The graduate comes back

Benson’s attachment to the Tees Valley has been a recurring part of his public ambitions. In 2019, he called for digital businesses to work more closely with universities, colleges and training providers. His argument joined two problems: businesses needed skills, and people needed a clearer route into the jobs being created. Growth would ask more of the region than additional office space.

“I want to make it a place where people move to, rather than from”

Dean Benson on the Tees Valley, 2019

In December 2021, he made that commitment financial. A personal gift of £50,000 established the Dean Benson Scholarship programme at Teesside University for computer science students from the Tees Valley. The first two scholarships were planned for autumn 2022. He had also contributed £20,000 to a local campaign providing computing equipment for children. Access to a device and access to a degree belong to different stages of the same journey.

The university relationship continued across roles. Benson served as a governor and received its Long Service Volunteer Award in 2024. In July 2025, he returned as an honorary Doctor of Science. The computer science graduate of 1997 had become an employer, supporter and donor, with opportunities to influence what came next for students following a related path.

Still looking for the next useful fix

His current work carries several strands. A Stockton-on-Tees council biography describes his continuing Visualsoft board role and his work as co-founder of Pulse Reviews, which brings reviews, analysis and business insight together. In December 2025, he described building that venture with business partner Kiya. The former Visualsoft CEO had another product to work on, while retaining a connection to the company he helped establish.

He has also turned his attention to practical AI and automation through Dean.id. In introducing the site on LinkedIn, he opened with a deliberately overblown burst of AI-generated promotional language, then punctured it himself. He went on to talk about websites, automated systems and taking tedious work away. A person who spends time with technology can still enjoy a joke at its expense.

At home, the appetite for connected systems persists: energy dashboards, automation and experiments in making things run more smoothly. There is a recognisable continuity here, even as the projects change. The boy who altered Pong wanted a different result from the machine in front of him. Decades later, Benson is still interested in what a useful adjustment might make possible. His sisters might reasonably have asked for a code review.