Interview with Tim Gregory

Tim Gregory has enjoyed a 50-year IT career during which he has witnessed the evolution of computing from punch cards and mainframes to AI and quantum today.

Starting out in 1968 as a 15-year-old trainee computer operator, Tim went on to have a varied career managing complex IT operations for the likes of Sherwood Computer Services, Lloyd’s of London and BACS, before leading CGI’s operations in the UK and Europe.

At CGI, he was responsible for the £1.7bn acquisition of Logica and grew the business to 7,500 staff and £6.5 billion turnover.

Speaking to AIT, Tim reflects on his career, highlighting the importance of continuous learning and seeking new challenges.

Tim shares his early passion for technology, inspired by “2001: A Space Odyssey,” and his decision to pursue a career in computing at age 13 despite being advised against it by his careers master.

Tim talks to AIT about his early experiences with mainframes, transitioning to programming languages like COBOL and RPG, and managing large IT operations.

He is proud of his contributions to the IT industry throughout his career, including the development of Faster Payments and the growth of CGI, as well as his work to support young people in the tech sector through initiatives with The Prince’s Trust and instigating apprenticeships.

Throughout his interview, Tim emphasizes the importance of making a difference and leaving a positive impact on the organisations and people he worked with.

Post-retirement, he continues to mentor young professionals and invest in startups, sharing his experience and expertise to help others succeed.

Tim Gregory was interviewed by Tola Sargeant in February 2025 at the Worshipful Company of Information Technologists Livery Hall in Central London.

+ Early Life

Tim Gregory was born in the early 1950s in Kent. His love for technology started at a very young age, he explains: “I had a passion for technology. I loved things that buzzed and electronically moved. 2001 Space Odyssey was my favourite film at the time. At 13 I decided I wanted a career in computing. I spoke to my careers master at the time, and he advised me that there was really no future in computing. However, I don’t give up very easily and at the age of 15, I started applying for a role in a computer department at IBM and Lloyds Bank. They were very kind and wrote back to me saying ‘Come back when you’re 18 and you’ve got your A levels’.”

+ ITT Services

In 1968, instead of studying for A levels, Tim left school at the age of 15 and joined the ITT Services Bureau as a trainee computer operator. Tim says of the experience: “It was a really exciting time for somebody who was very passionate about technology; all my dreams had come true. I had a four week period of intensive training along with the other trainees, on all aspects of computing, understanding binary, hexadecimal, how to read the holes in the punch card – a very crucial part of the role. After four weeks, we were released onto a shift and we were part of a two or three person team.”

As a full services bureau, ITT ran two IBM first generation 360s (360/40 and 360/50). Tim adds: “Amazingly they could only run one job at a time and they took up the whole floor of the second floor.  The disc operating system (DOS) was just going out, and the OS operating system was just coming in. As a trainee operator, I had to learn job control language and managed the systems. It was a very interesting time, very fast learning, very pioneering. There were really very few rules; you made it up as you went along.

“We used to have potential clients come in during the day and they hadn’t seen computers before. They were amazed by all the facilities, the tape reader, the tape drives, the disk drives. In those days, you actually removed the disks in a plastic container, spun it off and pulled it off by hand. One group of visitors couldn’t believe the printers were printing so fast, so I had to take the box of paper out and show it was blank one side and printed the other side.”

After just three months, Tim ran the platforms on his own. He adds: “It demonstrates how fast things moved, I was actually running the platforms on my own. I’d work most weekends and you were on your own the weekend, running the systems. I loved it. Really enjoyed it.”

In the early 1970s, ITT acquired an IBM 360-65 which was capable of running three jobs at a time and had two fast printers, I don’t know how many tape drives there were, probably 20 or 30 tape drives. By this time, the disks were all solid state disk drives, still spinning but you couldn’t open the drawers and take the drives out.”

With the upgraded IBM machine, ITT launched a global time-sharing service which covered North America and Europe. In those days, the only way you could actually run multiple jobs, or multiple tasks, was to steal time from the CPU. So effectively, when the CPU issued a Get Data command, it went idle, so that idle time was sliced, and hence it was called time sharing.

+ Hatfield Polytechnic

Having spent three years at ITT Services, in the early 1970s, Tim moved to Hatfield Polytechnic (now known as part of the Hertfordshire University complex), as a shift leader. It was known for its engineering courses and was close to Hawker Siddele and Rolls Royce.

Tim says: “Hatfield Polytechnic had two student computer rooms which contained about 30 to 40 teletext type machines. Students could go in 24 hours a day if they wanted to, and some of them actually did go in 24 hours a day! It’s where I learnt my first programming language, Basic, which all the students used at that time. It was my first experience of a DEC. They had a PDP-8, which handled the communications and they had a PDP-10, which was the processor.”

+ Romeo Vickers

After a few years at Hatfield, Tim moved to Romeo Vickers, an office equipment manufacturer with  2000 employees based in Langford, Essex. Tim explains: “There was a large factory complex, and I applied for the role of a computer manager to manage the computer room. It was another step up in promotion.”

On the day he joined the company Tim was promoted to Head of Operations which saw him managing 30 to 40 people. He adds: “It included the computer room, the data control centre, data control and the Data Prep Room,which was both a day and evening shift, all female, which was a whole new experience of managing a group of female staff. It was a great learning opportunity to manage people the first time and helping them to grow gave me the most satisfaction. Building a professional computer operation department was really, in my mind, what I wanted to achieve, and I like to think I did that. It was a good time.”

Tim continues: “While I was there data input medium was punch card and we saw the demise of the punch card. The IBM floppy disk system had been created, so we switched from the very old fashioned punch card to magnetic media. It was a big change for them, they had to relearn all the new machines with the floppy disk and understand how they all worked. It was a big change and we implemented in stages, in order that we could train them through a series of training programmes. They were great to work with and we had a lot of fun.”

After a few years, Tim, having learned COBOL and done several projects alongside his day to day management role, requested a transfer to the systems programming department and became an analyst programmer. He adds: “I started to go down a completely different career path. I remember my first programme. I missed the full stop off on the first card of COBOL and of course it threw every single card out after that.”

He explains: “In the same way I worked out that operations was limiting, I also worked out at that time there really were only three programmes; one to get it in, one to process it, and one to get it out, because there were no monitors. It was just literally data being crunched and then reported on in payroll or whatever. So I decided to go somewhere completely different and left Romeo Vickers to join Honeywell GEOS.”

+ Honeywell GEOS

In 1980, Tim moved to Honeywell GEOS as part of their training programme for sales consultants based in Soho Square, London.

Over a period of four weeks, Tim underwent training to become a professional salesperson. He says of the training: “They also spent a lot of time helping us understand the capabilities of their platform.  Honeywell had acquired General Electric’s computing services and out of that was born a company called GEOS which was a global time-sharing service. It was a full-scale computer operation, had its own database management system, very powerful database management system, had its own spreadsheet system. And that in those days the technology was ahead of its time. They effectively had invented the cloud, but they didn’t know they had invented the cloud because that terminology just wasn’t around.

“I spent three years with them, really enjoyed the time and gained a lot of experience working with what I would call professional sales people, in the sense that I was still learning the ropes. It was also the opportunity to work with a lot of different industries. It was fascinating to understand their businesses and how they operated. I learned a lot about business as well as how to sell and the GEOS platform.”

+ Start up

Having spent three years with Honeywell and looking for his next challenge, Tim assessed his skills and decided it was time to start his own business. He explains: “I’m a fairly self reliant person, and I really thought I could make a success of running my own business, and it ticked all my boxes in terms of helping people grow themselves, helping them develop their careers. It’s something I get a lot of satisfaction out of and that’s been true throughout my career. I also wanted to make a success of something really, make it mine, and be able to look back and say, I did that.

“So that’s what I started looking for and Lady Fate took another hand. I was reading the FT and there was an advert: Entrepreneur Wanted. It as the advert for a new startup, software house, fully funded by an angel investor, and I was successful and joined this zero company with this angel investor.”

The business partnered with UNIVAC selling the software solution to accompany their newly launched BC/7 a mini computer.

Tim explains: “The mini computer was effectively a large desk plugged into your three pin plug on the wall. Didn’t require any air conditioning, it could sit in the corner quite happily, but it also lowered the price point. It meant a lot of smaller companies that could never afford their own computer suddenly could afford one and be proud they had a computer, so we sold with UNIVAC. They sold the hardware, and we went along and sold the solution to go on the hardware, including things like stock control systems, invoicing systems, property management systems, we built a travel application. We were very successful on the back of UNIVAC, effectively doing the selling for us. That’s what made it a success.”

The company grew and prospered. Tim recruited several graduates from diverse backgrounds, none from the UK, and gave them their opportunity to enter the UK IT industry. However, the success was short lived. Tim continues: “We were doing very well, being successful. Two years we were growing quite rapidly and then my next lesson in life came along.

“I’d never managed the finances of a business and I’d made the mistake of letting the angel investor manage the bank account. He had about five other businesses. It turns out he’d been moving money from one bank account to another to stay one step ahead of the tax man and the VAT man, and as always, they caught up with him. The bank closed everybody down, all five companies, including mine. It was a very upsetting time, because I hadn’t seen it coming. I was happily out there being successful.

So my top tip to anybody is make sure that you’re in control of the finance, which I did with CGI. My finance director was brilliant, but I always made sure that he and I were hand in glove running it.”

+ Sherwood Computer Services

Having a young family, Tim needed to find a role and joined Sherwood Computer Services based in Romford. The company was a lead supplier to the London insurance market. Tim says: “I knew absolutely nothing about the market and I’m not quite sure why they took me on, but perhaps they saw something in me. I became Head of their Managing Member Agency Systems.

“The managing of member agencies in the Lloyds insurance market look after the syndicates, which are insurance companies, of which there were hundreds, some very small, some large, and the people who put up the wealth are called names. The managing agents and member agents looked after the interests of the syndicates, doing the HR etc for them. They also looked after the members and recruited members as well. We sold package solutions to that market on the IBM AS400 and we also provided AS400 processing lBureau service.

“It was a whole new area of learning, of understanding how the market operated, meeting the heads of syndicates and managing agencies, and understanding how that all worked in the model.”

After a couple of years in the Managing Member Agency Systems operations, Sherwood started development of a product called Saber, an underwriting box system, which would give direct access to underwriters to see their data for the first time in the room and also record. Tim asked for a transfer to the join the development team.

He says: “It was effectively taking the Lloyds market out of the analogue world into the digital world, it was a stepping stone into the digital world. I asked for a transfer. It was a two people team at the time; a director was head of the development, and one other developer. I joined as the sales arm, or business development. It was extremely successful. The market quickly caught on to the fact that having direct access to their data from the underwriting box and to be able to analyse it and get information back, was just a whole new world for them, and it caught on very quickly and became quite competitive.”

Sherwood also introduced the first flat screen for insurance market. Tim adds: “It was about an inch thick. If you imagine a box (desk area) with 10 people on it, it was a very cramped space, and the big monitors were very deep in those days. So having the flat screen was a revolution and we sold hundreds of them into the market. Quite a pioneering time.”

Tim went on to become Client Services Director and eventually Deputy CEO at Sherwood.

+ Lloyd’s of London

The next move in his career, saw Tim headhunted by Lloyd’s of London to help them with their electronic placing system (EPS).

Tim explains: “The idea of the EPS was to unify the brokers and the underwriters so that data could be input from the broker. They could then walk over to the underwriter without carrying great bundles of paper as the underwriter would already have the data on their screen. That was the idea of it. It wasn’t going well. In fact, it was going very badly. They asked me to take over and try and rescue the project, and also then see through the rest of the E projects that they were building at the same time. So I joined the Lloyd’s market.”

The project was having difficulties for a number of reasons, including the fact that it involved not only new technology but also a culture change. He says: “Lloyd’s made a number of fundamental mistakes in the project itself. If you’re going to do a very large project, break it down so you deliver bits of it as you go. You show benefits, you prove it works. They’d gone for one big bang. They were going to go from zero to total data access across all the underwriters and all the brokers. They hadn’t mandated a single interface and so there was something like 17 software houses trying to integrate their platform into this EPS system.

“There were also a lot of anti EPSers, both brokers and underwriters, the truth of the matter is, they liked coming into the market with their paper. When they get to the box with a set of risks, it’s a negotiation, and that negotiation is easier on paper than a green screen if it’s got data on it. I think to be fair, that the ambition of the project was beyond the technology that was available at the time, they were trying to do something that you really couldn’t do in an easy way. Everybody understood it was the future of the market, but nobody quite wanted it to be them going first. It became clear that EPS was not going to be successful and with Board agreement the project was closed down. At the same time the market had invested in the London Market Network (Limnet), the single network for all of the insurance market brokers, underwriters.”

As Head of IT Services and Operations for the market, Tim was given the tasks of slimming down IT operations and proving to the market that the central services could deliver E projects successfully. In order to do this, he eventually turned to outsourcing as a potential option. Initially, he ran a bid process for infrastructure outsourcing which was won by Integris. After that proved to be successful, he ran a further bid process for systems programming, which was again won by Integris.

He concludes: “Effectively they took over the computer operations with Lloyd’s. It felt like job done. I didn’t really want to be the CIO of an outsourcing contract. It didn’t give me the sort of interest or challenge. I loved the market. … So I started looking for the next challenge.”

+ BACS

In the mid 1990s, Tim joined BACS as the Head of Services. BACS is the direct debit credit operation recognised as a critical infrastructure to the UK economy. At that time, BACS was owned by the banks, today is owned by Visa.

Tim says: “My role covered not only IT but all the service operations. BACS had a couple of fairly significant challenges that it was facing as an organisation. It had an ageing infrastructure, and it also had an ageing architecture that the platform had been built on which was some 10 years old by that time.

“I have to take my hat off for the people who designed it. It was a very clever design. It was built on a concept of non-stop processes that basically took the data in and then filled up the wells, as they were called. There was another set of computers that were emptying the wells as fast as they could processing the data. That created buffers between the two sets. So in fact, if this got slow for whatever reason, the data could still be coming in every hour, every minute, and going into the well and then back out again.”

With the potential upgrade to the aging infrastructure, one consideration was a shift from a three day turnaround for a payment to same day settlement. Tim explains: “BACS had actually presented to the Board, which was made up of all of the major banks, to enhance the infrastructure and the architecture of the platform, but also to create same day settlement. It had been turned down twice by the banks because the cost was just too high. When I joined, I looked at the project, it was a major piece of work for BACS, and I felt they’d made the mistake of presenting it as a technology upgrade rather than a cost-benefit solution.

“So we reworked it completely. There were three objectives; deliver a cost savings to the bank, deliver same day settlement, and deliver it in stages so there was early benefit in the cycle.

“We submitted the investment to the Board, and after much face to face lobbying, and pushing them through, it was approved. It was just over £100 million spend over three years with five stages of delivery. It actually took five years, but I’d long left by that time. Out of that faster payment was born. What is used today as faster payments, is, in fact, that same day settlement system that was built through that investment.”

In addition, the BACS system security was also increased to deal with the ever growing sophistication of threats and the computers were moved from North London to the Bank of England while the staff moved to a separate location.

+ Miller Insurance - e-commerce

Having settled BACS restructure plans, Tim realised he was missing the commercial side of business and decided to move on. He says: “I missed the commercial side, and I missed the Lloyd’s market a lot, it had become part of me. I really wanted to get back into the cut and thrust of the commercial world again, perhaps BACS was just a bit too laid back for me.”

His next challenge was as e-commerce director with an insurance company, building their business to business and business to customer internet capability. Unfortunately, despite very rapid growth, the company amassed too large a debt to survive the financial downturn and Tim found himself looking for a new role.

+ CGI

Tim next joined CGI, based in Stevenage, to build and lead their UK outsourcing capability. He explains: “I got a phone call from the sales director that I’d worked with on outsourcing the Lloyd’s insurance operations. By this time, Integris had been acquired by CGI, and they were looking for somebody to lead and build their outsourcing capability within the UK. CGI was predominantly a North American operation in America and Montreal. It was one of the major systems integrators and outsource companies and they were looking for someone to lead and build that UK capability. They hadn’t done any outsourcing at that time as CGI, Integris had.”

With a small team of around 50 people, Tim started to identify possible outsourcing opportunities. He adds: “When you’re outsourcing a contract it takes anything between 12 months and two years. It’s a marathon, not a sprint. We got lucky that we identified an opportunity, and we worked very hard as a team, and at the end of 12 months, we’d won our first major contract with an insurance company that had a link to Lloyd’s market. It was a £100 million 10-year tenure outsourcing contract. A major success. On the back of that, we then had a credibility that we could do these things.”

Tim was promoted to President of the CGI UK operation growing the business to between 130-150 people and continue to win contracts, large and small, across a number of sectors including property estate agency, the insurance sector and finance sector. The continued success saw Tim promoted to President of the Europe.

Logica acquisition

Part of Tim’s mandate as President of Europe was to find an acquisition which would allow CGI to build the European operation up to the same size as the American operation. Tim proposed Logica. He explains: “I identified Logica as a perfect target for a couple of reasons. They were clearly in some financial difficulties, and I remember saying to the board, if I was running Logica, I’d run to CGI. But they also fitted perfectly because they were big in Europe. It would have been a very nice fit of the US coming in from the CGI side and the European coming in from what was the Logica side. We first approached Logica at the beginning of 2012 and they basically said we were too small to take them over. Logica was bigger than we were at that time, headcount wise and turnover wise.

“We went away, CGI is a very patient organisation and in the middle of 2012, Logica approached us and said they’d like to have serious discussions about us acquiring them.” Tim and a team of 50 people spent months doing very intensive due diligence and a deal for £1.7 billion was finally agreed at the end of 2012. Tim was appointed President for the UK, managing 7,500 employees and with a turnover of around £650 million.

Integrating the acquisition

Tim explains some of the processes of uniting the two organisations. He says: “We were given the target of 90 days to realign the Logica structure into the CGI structure, to create the business units, appoint a head of each business unit. In the UK I had five business units. That’s an important lesson to learn; once you’ve created your structure, then it’s up to the managers of those structures to do whatever needs to be done to get them working the way it should operate.

“We had another 90-day target set to get the workforce down to a size that met CGI’s operating standards. This included implementing all the CGI systems that helped managed the business, Finance, HR, Time tracking.

At the end of the second 90 days, we had identified what needed to happen to the staff, clearly a very difficult and challenging time. It made me more compassionate about what people were going through, because I’d been through it, and we were very sensitive about the process. But it had to be done. The company could not survive if we didn’t slim it down to an effective operational business and a profitable business.”

During this transition period Tim spent a lot of time visiting every business unit under his jurisdiction to explain how CGI operated and to encourage employees to become shareholders and explain the need for reducing the workforce.

He explains: “I have been a firm believer that if you’re going to do a headcount reduction, do it once. Don’t do death by a thousand cuts. What you’re trying to do is to handle people sensitively. Be very professional about the approach. Help them as much as you can, but then you have to have responsibility for the staff that are left. You have to help them understand they have a secure role going forward, and it’s worth them investing their time, their energy, in staying with the company, you can’t just do one half of the story. We spent quite a lot of time making sure that staff understood what the business plan was for the UK once we settled it into its operational cycle.”

Red projects

With the restructure taking place, Tim also needed to concentrate on the ‘red projects’ he had inherited. He explains: “These were major contracts that Logica had which were bleeding money that was part of the profitability problem they were challenged with. I took personal control of managing those through the executive team, not doing it hands on, that wasn’t possible, so I ran the red reviews each month. I met with every single client that had a red project. Some of those were very uncomfortable meetings, probably the most uncomfortable I’ve ever had, but they needed to beat someone up first and then I needed to convince them that we would sort it and deliver it. I’m very proud of the exec team and the people who work on their projects. They turned them around. We retained every one of the clients.”

As well as slimming down the staff from 7500 to 6500, CGI’s turnover grew from £650 million to £750 million. In the UK, Tim oversaw the development of an open source digital lab in Scotland which created 200 new jobs, won three major outsourcing contracts in Scotland worth £350 million. Tim adds: “We went from almost zero in Scotland to running a very nice business. We also started working with the SMEs in Scotland and made them part of our solution when we were bidding on the outsourcing deal. We helped a number of small companies grow as well at the same time and they obviously created jobs as well. “That’s part of the cycle that CGI is very committed to, and I’m personally very committed to, working with the community, with other companies.

We also started the degree apprenticeship programme. We’re very proud of that. It’s very successful. I think a degree apprenticeship is a great way of people having that combination of academic and actual hands-on experience.”

In addition to this, the company added a further 200 new jobs to its centre in Wales with over 1000 employees.  We also created the first CGI cyber security centre. Tim adds: “CGI UK was a main supplier to GCHQ and MOD, so we had a great credibility in that space of security.”

+ Portfolio Career

Having spent 15 years with CGI, Tim, at the age of 65, decided it was time to hand over to the next generation.

He says: “I’ve kept busy as an angel investor, part of the ScaleUp Group for a couple of years, NED on a number of startup companies and in some cases, just as an advisor. Some have been paid for. Some I haven’t been paid. It’s not really for the money, I just want to keep busy, out of mischief, and it’s been fascinating.”

In choosing a potential company to invest in, Tim says: “It’s all about the person, the founder. Have they got that passion for their business, for their solution. Do they live and breathe it every day, every hour, every day. The old saying of when the going gets tough, the tough get going, is very true. People starting up a business have got to recognise that it’s not always going to be fine, you’ve got to stay with it.”

On the subject of angel investors in the UK, Tim comments: “There are a lot of angel investors out there, and I have to congratulate the government on the enterprise investment scheme. It’s highly successful and it’s been key for a number of companies to get off the ground. The UK is thriving in terms of young businesses. They really are at the forefront of that. I think there have been more businesses in the UK set up than the rest of Europe put together. So it’s been highly successful.”

+ Starting over

Asked what he would do if he were starting his career today, Tim says: “Looking back on my 50 years, I was privileged to start on the mainframes, go through the mini computers, PCs, the growth of the internet, cloud, and of course, now it’s AI. If you look back at the Industrial Revolution, AI is going to be the digital revolution. We have to accept it’s going to be a very significant impact on society as a whole, the impact on people’s jobs. That isn’t necessarily a threat. It isn’t saying that the Industrial Revolution was a threat. But what we don’t want is people smashing up the weaving machines. We don’t want them smashing up the AI computers, we have to manage it carefully. If I was starting out now, I would go into AI for sure. It’s going to be a digital revolution in all aspects of our personal lives, as well as our business lives.”

+ Doing things differently

Asked if he would do anything differently in his career, Tim says: “I think the choices I made were all part of having a much wider breadth of capability and experience and knowledge and learning, a thirst for learning, and also ensuring that I had multiple experiences and skills that could make me more attractive to a role. I like a challenge. I had a motto which I started fairly early on in my career, which covered two things. One was set out to make a difference and set out to leave something in a better condition than you found it. I always wanted to be able to look back at that role and say, I made a difference. I helped the company grow, I helped the individuals grow, I helped the organisation be a better organisation, and that was quite important to me.”

+ Proudest Achievements

Reflecting on his achievements, Tim highlights the help he has given people in developing their careers to become senior leaders in IT. He adds: “That’s been very satisfying, and they’ve also helped me. It’s been a two-way street.

“I’m also very proud of Faster Payments. I see it every time I use my bank account. Someone actually called me the father of Faster Payments! I’m not sure that’s wholly true, but certainly without getting that investment through, we wouldn’t have the Faster Payments that we have today.

“I was very proud of what we achieved at Sherwood, becoming the lead supplier of the underwriting systems. I wasn’t proud of closing EPS down, but I was proud, if you like, that the market didn’t throw me out for having closed it down. They could separate the two things between what I could deliver to the market and the fact that I hadn’t been responsible for creating EPS.

“I’ve always been very proud of helping other people develop their careers. I’m mentoring a couple of people at the moment whom I worked with years ago. They’ve gone off to set up their own businesses.  That probably sums it up; I can look back and say I made a difference.”

+ Advice

Asked what advice he would give a young person starting out today, Tim says: “Everything’s a learning experience. Never stop learning. Never stop going to look for that next experience and that next challenge. You never know where it will come in useful and it makes life more interesting.

“By the time I finished my technical part of my computing career, I could programme in four languages, COBOL, RPG, Fortran and Basic. If I’d been a programmer for life, I would never have been out of work. It’s important that if you are in the role, you learn the next role, you have to be able to do the next role before someone will promote you to that role. So if you want to be a senior programmer, the chances are you’re going to be a very good programmer before they make you a senior programmer and so on. So always have multiple skills at your fingertips so that you can look for the next challenge, but also be of interest to an employer. People are looking for skills all the time. With AI now, there’s going to be a huge increase in skills required, and at the moment there aren’t the people with those skills. It’s going to be an enormous investment over the next well, three to five years.”

+ Interview Data

Interviewed and transcribed by Tola Sargeant

Abstracted by Lynda Feeley