A legacy built on 40 years of trust - learnings from Greg Bentley as he steps down as CEO of Bentley Systems

George Lawton Profile picture for user George Lawton March 25, 2024
Bentley Systems CEO Greg Bentley discusses the lessons he learned from growing a scrappy startup in the 1980s with his four brothers into one of the world’s largest engineering tools vendors. A key ingredient was growing trust across the company, partners, and the community.

Greg Bentley

Greg Bentley and his brothers pioneered what became known as digital twin tools for physical infrastructure in 1984. They grew their company, Bentley Systems, into a $15 billion market cap with $1.2 billion annual revenues. At 69, he is the oldest of the Bentley brothers and the last to retire, a decision that was announced last week. He is leaving the company behind in the capable hands of current COO Nicholas Cumins as of 1 July. 

Although the company is headquartered in Exton, Pennsylvania, Bentley has spent much of his career in the UK, citing its unique strengths and opportunities. In a general session on the opening of their new UK headquarters, he said:

Can you imagine another place in the world that would be such a crossroads as we are here and now for thought leadership in the world in infrastructure? That's why we chose this venue for the announcement.

In particular, the UK has pioneered digital twins in the construction industry. Its engineering community has played a seminal role in BIM standards for connecting a golden thread across the lifecycle of building and infrastructure projects. Bentley recounted the most memorable description of the purpose of a digital twin from a Helsinki team who said it was to save each resident a half hour a day. Later, he was struck by proposals for the new Bank Station terminal that were assessed based on the value of the time savings for the residents commuting and working in London. 

Another thing that impressed Bentley about the UK is the willingness of large customers to work with small ones, developing innovative new tools. For example, his first company of three people could sell their derivatives tools to big banks. This would not have been possible in the US. He explained:

In the US, a big organization will not buy from a tiny company. They can't be bothered to. But in the UK, the small companies succeed. For example, Synchro, which was a cadre of a few people, could become the 4D modeling supplier for Crossrail, a £25 billion project. In the UK, enterprises have a greater receptivity to risk and reward trade-offs and are willing to give small companies a chance. And the result is thirteen companies that have gotten big enough one way or another to come to our attention and be acquired, representing now the bulk of the 450 people we have in the UK today.

Merchant engineers

Early in his career, Bentley was attracted to the UK owing to the greater receptivity of large firms to try out new things. Additionally, much of his success was inspired by a thriving ‘engineering merchant’ industry in which UK engineering firms grew by cultivating new talent as they expanded into new markets worldwide. These teams were tasked with building infrastructure that helped create the physical foundation for the UK’s global empire. He cited the example of Mott Macdonald, whose predecessors were building railroads and water systems across the world since 1888: 

What they invested as merchant engineers was not capital necessarily; it was their talent that led the way to infrastructure advancement in the world, which still results in British standards everywhere, even beyond the Commonwealth.”

Over the years, Bentley Systems has made over a hundred acquisitions as it expanded its portfolio to take advantage of new engineering technologies. I asked him how this idea inspired the company's growth. With each acquisition, they have invited the team onboard as well as tools, and the vast majority of its UK team came from the thirteen acquisitions here. 

A defining characteristic of weaving the new technologies and teams into Bentley Systems is that four of the five founders were software engineers. He said: 

The fact that our technical decisions have been made by the Bentleys has caused us to really insist on a platform approach. We try to write code only once and use it many times. And that has enabled them to build an ecosystem that takes advantage of our platform. They don't have to start from scratch if they want to do something specific to a discipline. They can build on our platform. So, most of these one-hundred acquisitions that we've done are among this ecosystem who have started with our platform. They had something in common to start with, so the integration was not as burdensome as it would otherwise be if it were a hundred random acquisitions.

Cultivating talent

The string of acquisitions also helped Bentley build out its talent pipeline: 

In some other fields, acquisitions are done for synergies, which means you don't need all the people. In the case of infrastructure and engineering software, we need all the talent we can find, and we have a very good record of keeping it. The founders are generally generalists and rainmakers who have sold, have done their own business development, and have made a payroll. It is just a great formula for someone who can be successful in our company. The bulk of our senior management have come from such acquisitions.

Another thing Bentley Systems has done is assimilate the team immediately rather than keeping the company intact as a separate team. The salespeople go into the sales group and marketing people into the marketing group, and the developers move to the developer group. They also have people who work to help assimilate the new team into the company. 

Bentley could be very persuasive in influencing people to join the company. Before joining his brothers, he started a company selling financial analysis tools in the UK, which had grown to 18 people after three years. They sold the firm to a larger company, which grew the team to a hundred people in three months. Bentley left after three years to work with his brothers, but his co-founder became Sungard's CEO and had 10,000 people working for him:

So, I say to the principals of firms, we might acquire you, and you will have a bigger opportunity in a bigger firm, and you might be my successor. Now, we know only as of today that my successor will be Nicolas, but most of the other people who report to him came to us through acquisitions.

He also learned that developing consensus and trust about acquiring new talent was important. Bentley explained:

We at Bentley Systems won't hire from our accounts. They might look around and say, ‘Greg, there are lots of people at Bentley Systems who did come from our accounts.’ Well, if one of our people wants to hire somebody from an account, they have, because that does happen. But, it won't be without the consent from the account. Someone has to show a letter that the account has consented to allow that person to be hired. We have pretty good arguments. 

We say, ‘We didn't go looking for that person. That person responded to an opportunity; they're probably going to leave you anyway. Wouldn't you like it better if they went to your software supplier so we would fully understand what you need? By the way, often, we make the person available to you in turn to help.’ That's just an example of needing to establish ground rules that are long-term oriented. And that has worked for us at Bentley Systems.

Words shape relationships

Bentley also believes strongly that the words we use to describe our relationships shape the way we think about them:

I flinch if I hear the word ‘customer.’ I don't allow people to say customer because customer connotes a transaction.  I say account or user, which connotes the person working with the software. I think the word customer is not a compliment. But user or account is someone we have a longitudinal relationship with over the long term.

He also uses the term colleague rather than employee. But here he is a bit more lenient in what each person says because he wants them to feel like the company has earned this trust:

I say I can't have a rule about this. That's not fair. Our colleagues have to feel that they are our colleagues, and if they do, they'll use the term. Hopefully, they don't feel like employees and don't use that term, but it's not because I mandate it. But customer, I feel when people say customer, they mean customer, and it doesn't have the right connotation.

Bentley also reshaped his view of his company’s role when Crossrail’s CEO, Andrew Wolstenholme, said he needed a partner, not a vendor:

I believe he meant people who tell us what's going to work and what's not going to work, don't hide from us what the challenges are, and so forth. I think that does pertain to colleagues and accounts as well. In forty years, I've come to believe you have to be forthright if you want somebody's trust.

Building trust in data

Wolstenholme had said that they knew things would change a lot throughout the Crossrail project and he could not be selecting software at the start that he would be using at the end. Rather, they were looking for an organization that would continue to adapt, invent, and be honest. So, Bentley set up a Crossrail Construction Academy to train all new contractors across its supply chain on its data infrastructure. Bentley explained:

The whole point of Crossrail’s strategy was to show them how important the data is by where it's going to go and how it's going to be useful in the whole construction progress, the whole project delivery, and then the operations of what became the Elizabeth line so that they will sit up straighter and see how important it is that they give us clean data of high quality. Not because the contract says to do it, but here is why. I didn't use the term digital twins at the time, but we would say today, ‘You're creating a digital twin for a brand new railway and here's why your data is important.’

Bentley was also very thoughtful in how the company brought teams in for training:

We would have people from the front line, in their boots, hard hats, and so forth, come through. Crossrail didn't want them to go to Crossrail for that because that would just seem like mandatory training. And we learned not to bring two organizations in at once because they would try to impress each other. Whereas if they come in on their own, they're really interested in learning and understanding. It was a lesson in change management. It helped create trust. And I think it helped make Crossrail successful.

The actual training program was a set of workstations that showed the process that led to the next workstation with the next process, demonstrating how Crossrail used that data across its lifecycle. Bentley said this helped everyone understand the importance of a digital thread linking people like them across the project:

The single distinguishing characteristic of Crossrail as a project from anything we had worked on before was that they understood that nothing they might do could substitute for the quality of their data that they got from their supply chain.


I asked Bentley what he was proudest of leaving behind in his legacy after forty years. He told me: 

The highlight is the team that succeeds me now because I'm the oldest of the five brothers, but I am the last to retire. And the standard I've had for myself is to get the whole succession completed, and then I can retire. As I mentioned, Nicholas and those who report to him are all in their forties. It's a cadre twenty years younger, which is a big advantage. The average tenure of a CEO in a public company in the US is five years. We don't want to look like just any company. What has benefited us is to have continuity in our management.

We have worked hard to ensure continuity in our products. If you open any file created by Bentley Systems software over its lifetime going back forty years, you could open that file today. You would be using completely different software. It's been remade from the inside out three or four times. But you could go on to renovate that building, bridge, water treatment plant or whatever.  It opens seamlessly. And that level of continuity has been possible because the Bently brothers have been in charge of who does what on the technical side all the way along. And we have avoided the temptation for engineers wanting to start from scratch every time. 

It isn't so bad for a building where the project only lasts a couple of years. You couldn't do it on a Crossrail project. And it's generally not a good idea for infrastructure, which has to live for generations. It wouldn't have mattered if we had been making software for games or something like that. However, software for infrastructure has helped meet the need and hit the spot for us to have this technical continuity for a long time. Now we have a new generation, and they're young enough to repeat that lengthy continuity.

My take

Bentley only told a small inner circle about his retirement before the presentation, which we all thought was about the new HQ. I could see many of the team visibly shaken and sad that their trusted leader was moving on from active leadership after so many years at the helm. 

‘Move fast and break things’ seems all the rage hyped by a few questionable Silicon Valley success stories. Bentley’s experience growing a business that cultivates trust across colleagues, accounts, and communities is an inspiring example of how we might create a greater legacy built on continuity and shared understanding. 

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