Chapter seven

Going Digital

Forty Years of Bentley Systems

In September 2011, Greg traveled to London with Malcolm Walter to open Bentley Systems’ new U.K. headquarters. The company’s U.K. footprint had grown eightfold over the previous decade to approximately 200 colleagues dispersed across the country. Now, they had a center of gravity at 20 Gracechurch Street, roughly equidistant from Saint Paul’s Cathedral and the Tower of London.¹

They also had an incredible view over a skyline bristling with contemporary marvels—many of which had been created using Bentley Systems software. To the east lay Norman Foster’s neo-futurist London City Hall. To the west, the towering cantilevered observation wheel known as the London Eye. Just a few blocks to the northeast rose 30 St Mary Axe: 41 stories of shaded blue glass within a steel diagrid exoskeleton whose elegant taper suggested an elongated Easter egg—or, as the energy-efficient skyscraper came to be popularly known, The Gherkin.

Bentley moved into the former Barclays Bank headquarters in 2011

“We etched on the windows the name of the user who had created each thing you could see from the building,” said Greg. “It was magnetic.”

Yet as Walter pointed out at the opening ceremony, some of the most impressive work was largely hidden from view, in the form of two massive—and massively ambitious—underground initiatives then taking shape as digital models.

One was the Thames Tideway Tunnel, an environmental sustainability megaproject to resolve the problem of wastewater discharges into the river from the city’s 150-year-old sewer system. London’s 8 million residents had overwhelmed Joseph Bazalgette’s feat of Victorian-era civil engineering, causing tens of millions of tons of untreated sewage to slosh into the Thames every year. The proposed solution involved digging 21 cylindrical shafts, roughly 30 meters wide and twice as deep, in strategic locations throughout the city to intercept and re-route sewage overflow into a gargantuan 25-kilometer-long tunnel to be burrowed mostly beneath the riverbed.

This artery, large enough to contain three of the city’s iconic double-decker buses side by side, would start in the west London community of Acton and traverse the full width of inner London, falling one meter for every 790 meters it ran east, until reaching a pumping station at Abbey Mills at a depth equivalent to 20 stories below ground. In addition to London’s highly variable soils, which range from clay to sandy gravel to flint-studded chalk, the giant bowel would have to navigate a subterranean maze complicated by 1,300 building foundations and 43 other tunnels, including ones used by the London Tube mass transit system.²

Construction on this £4.5 billion undertaking, whose anticipated completion in 2025 was expected to reduce pollution discharges by roughly 95 percent, began in 2016 and involved a sprawling constellation of contractors. In 2017, Mott MacDonald, a U.K. engineering consultancy acting as lead designer for the 10-kilometer eastern portion, won a Be Inspired Award for its contribution. Creating a single 3D model with AECOsim Building Designer, and using ProjectWise to facilitate collaboration across 12 design disciplines and a varied set of contractors and stakeholders, the firm improved efficiency by 30 percent and shortened design delivery time by six months.

The second project Malcolm Walter named was even more complex and far-reaching: Crossrail, a £15.8 billion bid to increase London’s passenger rail capacity by 10 percent via a new line that would be named after Queen Elizabeth II. With 118 kilometers of track, including 21 kilometers of twin-bore tunnels linking eight new subsurface stations, Crossrail would connect Heathrow Airport with the commercial heart of London in Oxford Street and the business hubs of the City of London and Canary Wharf. Bringing an extra 1.5 million people to within 45 minutes of central London and enabling upwards of 200 million passenger trips per year, it was expected to generate £42 billion in net benefits over a 60-year period and designed to last at least twice that long.³

Bentley’s Connected Data Environment helped improve collaboration on the Thames Tideway project

Crossrail, Europe’s largest infrastructure project, won multiple Be Inspired Awards

The scale of what would become Europe’s largest active infrastructure project strained even the most capacious imagination.

The scale of what would become Europe’s largest active infrastructure project strained even the most capacious imagination. A fleet of eight 150-meter-long tunnel-boring machines, operated by 20-person crews for 24 hours a day, would each burrow about 100 meters per week beneath the streets of London.⁴ The excavations would produce over 7 million tons of material, nearly half of which would be shipped 75 kilometers to Wallasea Island to create a 165-hectare intertidal nature reserve on the Essex coast.⁵ Construction processes would use water at a rate touching 275,000 cubic meters per year—enough to fill 110 Olympic swimming pools.⁶ The tunnels would be lined with 200,000 concrete segments, some 15,000 kilometers of electrical and communications cable would be laid, and the total labor bill for construction was estimated to be 70 million working hours.⁷

Managing the design and construction meant wrangling a mind-boggling amount and variety of information. As a pair of Harvard professors noted in a 2019 case study: “With 23 design contracts, 34 enabling works contracts, and 56 construction and logistic contracts, packaging the information and creating relationships between different types of data was a complex challenge.” That was an understatement, considering that Crossrail would ultimately involve some 5 million documents, 450,000 drawings, and 660,000 assets of varying relevance to the nearly 10,000 contributors permitted to access different data sets.⁸

It so happened that Greg and Malcolm traveled to London just as Crossrail was installing a new chief executive.⁹ His name was Andrew Wolstenholme, and he soon decided that he wanted a single technology partner to help coordinate the activities of scores of contractors spanning virtually every engineering discipline. That decision and its timing could hardly have been more serendipitous for Bentley Systems. Freshly energized by their new headquarters, U.K. colleagues found themselves in a position to capitalize on an opportunity that the company had literally spent years practicing for.

Malcolm Walter hosting the Year in Infrastructure conference in London

“Let’s do a project ourselves— let’s organize ourselves as if we were an engineering company and take on a project.”

BOPS priorities for 2012, Working Smarter Together

As part of its mid-2000s commitment to comprehensiveness, Bentley had begun test-driving its own software via “managed environment benchmark” exercises. The idea, as Greg sketched it, was straightforward: “Let’s do a project ourselves—let’s organize ourselves as if we were an engineering company and take on a project.” In addition to their normal day jobs, willing colleagues would don hats as engineering contractors tasked with imaginary scenarios that mirrored the kinds of real-world endeavors Bentley’s software aimed to support. “We are going to be the users,” Greg explained, “and the most important thing we’re going to be doing is making a list of things that could have been better, and should have been better, that may not have occurred to one or another of the product teams independently.”

A new oil reservoir has been found in Northern Canada/Alaska, went one of these set-ups. This oil looks like it is economically viable to extract and due to the environmental protections in Alaska, the production facilities will have to be in Canada. NCP (Northern Canada Petroleum) has land leases that might be suitable. The workflow will cover how this oil will be extracted, transported to an existing oil refinery that must be modified to accept this quality crude oil and then move into the operations and maintenance of this refinery.¹⁰

“I joined Bentley in 2004 and participated in one that very year,” recalled Bob Mankowski. The projects simulated “a team environment within a fixed timeframe” of just the sort that Bentley’s users operated within. Designed to “validate interoperability across platform and vertical product lines,” the benchmark exercises served to “identify obstacles and opportunities” that arose. A benchmark exercise focusing on an urban development scenario in Toronto, for example, deemed ProjectWise a “real advantage” in terms of secure document management and data tracking, but revealed slow performance in the program’s “detailed Raster view” and “strange problems” where nodes and pipes met in Bentley Water.¹¹

“The result in every case,” said Greg, “was a big step forward in the quality of the integrated portfolio.” All that preparation paved the way for Bentley to play a role in meeting the demands of the London 2012 Summer Olympics, whose yearslong planning process made use of ProjectWise.

Shortly after joining in 2004, Bob Mankowski participated in an internal project designed to validate product line interoperability

“You could be located anywhere around the world, yet be able to collaborate in a way that’s really unique to this industry.”

ProjectWise was implemented by many delivery partners of the London 2012 Olympics

The London Olympiad was announced in 2005, well before platforms like Dropbox and Microsoft Teams changed the face of collaborative file management. ProjectWise was “competing against the D drive,” said Harry Vitelli, who started managing the product in 2007. He credited sales colleagues like Mike Sedgwick, Tom Gergel, “and, of course, Malcolm himself” with communicating the value proposition to engineering firms that had become accustomed to a more restrictive status quo. “You could be located anywhere around the world, yet be able to collaborate in a way that’s really unique to this industry. Because we’re dealing with these complex CAD files—which have layers on top of layers and reference files—it’s really complex.”

Longtime colleague Neville Glanville, a U.K. sales director at the time, helped to catalyze its uptake by firms involved with the London Olympiad. The campaign began at a sales meeting he hosted on the very day the International Olympic Committee announced which city would host the 2012 games. “We plotted out our strategy at that meeting to engage with as many of the consortiums bidding for the games as possible,” he said, “and we successfully implemented ProjectWise across many of the delivery partners on the project. This project consumed a good part of my life between 2005 and 2013.”

Crossrail chose ProjectWise as its platform for multidisciplinary collaboration across the many firms involved in the project.

“London 2012 really galvanized the Brits,” Greg reflected. “They had to do it right and it had to be done on a certain schedule and so forth. That was an infrastructure challenge for which we provided some good stuff that has long since melded into the whole of our product range—and it got us qualified to be selected for Crossrail.”

Crossrail chose ProjectWise as its platform for multidisciplinary collaboration across the many firms involved in the project. A new Bentley initiative, AssetWise, played a complementary role. It was built around a software package called eB Insight, developed by Enterprise Informatics, which Bentley acquired along with its CEO Alan Kiraly in 2010.

Alan Kiraly, who joined via the 2010 acquisition of Enterprise Informatics, led the expansion of Bentley’s product portfolio to the operations phase of the infrastructure lifecycle with AssetWise

A central plank in what Greg called the “Enterprise Aspiration” phase of Bentley’s 21st-century evolution, AssetWise aimed to create value beyond infrastructure design and construction by supporting the operation of infrastructure assets across their entire lifecycles. For Crossrail, it would supply all participants with a common data environment (CDE) that would ultimately be handed over to the owner—Transport for London, in this case—for use in operations, maintenance, regulatory compliance, and so forth. This advancement in Building Information Modeling (BIM) was likened by many in the industry to a “digital railway” that could drive efficient operation in the physical one.

Crossrail began implementing eB Insight in October 2011. “Our users have quickly taken to the new software,” said Malcolm Taylor, Crossrail’s head of technical support services, adding that project contractors were “impressed not only by its ease of use, but also the significant improvement we have seen against our old transmittal processes, cutting the time taken to complete these from hours to minutes.”¹²

In 2012 Bentley partnered with Crossrail to take it a step further, launching the Crossrail/Bentley Information Academy to provide technical training in collaborative BIM technologies to users across the project’s supply chain. Over 2,500 participants from more than 60 organizations visited Bentley’s UK headquarters to attend sessions at the academy,¹³ learning how Crossrail was managing information across multiple linked technology platforms to create a “single source of truth” within the project’s CDE. Taylor would ultimately credit the CDE and related technology and management systems with saving Crossrail approximately £120 million.¹⁴

We had the company pre-Crossrail, and then post-Crossrail,” Greg declared. “It just reinforced our own commitment to be qualified for such endeavors— to be the infrastructure engineering software company.

“Infrastructure projects of the scale and complexity of Crossrail do not come around very frequently,” explained Wolstenholme at the time. “I want to use the Crossrail opportunity to move the whole industry forward in a number of areas, which include the use of Building Information Modelling through the delivery and lifecycle phases of major projects. Many of our project contractors are already developing their own capabilities in this important area. BIM is not simply about the application of new software—it’s about a different way of working.”¹⁵

The construction of the Elizabeth Line, which was officially opened by the Queen in May 2022 during her Platinum Jubilee year, represented what Greg called an “enterprise inflection” for Bentley Systems. “It was a comprehensive environment where everything had to work together—and that’s what we accomplished,” he reflected. “It was run exactly the way you would want a construction project to be run.”

It also furnished invaluable lessons and experience that positioned Bentley Systems on the cusp of a new digital frontier in infrastructure engineering and management.

“We had the company pre-Crossrail, and then post-Crossrail,” Greg declared. “It just reinforced our own commitment to be qualified for such endeavors—to be the infrastructure engineering software company.”

Crossrail’s Malcolm Taylor receiving a Be Inspired Award from (left to right) David Huie, Harry Vitelli, and Rob Whitesell

Crossrail proved to be the inflection point that reinforced Bentley’s commitment to be the infrastructure engineering software company; Greg presenting Bentley’s mission statement, 2012

If the path to Bentley’s Crossrail inflection point was paved with technical advancements, there’s little doubt that a non-technical contributor played an important supporting role. David Hollister joined the company as CFO in 2007. Having held the same position for a Bain Capital group of portfolio companies, he was lured to Bentley by Malcolm Walter and David Nation, who, along with Greg, gave him the sense that big opportunities lay ahead.

“It felt like a company on the cusp of really being ready to explode, in a good way,” Hollister recalled. “Plus,” he added with a good-natured chuckle, “they needed me.”

“Bentley Systems had always had technology as its core priority,” he explained, “but they had gotten big, and some of the financial and administrative matters needed to catch up. So, there was a great opportunity for me to step in and add some real value.”

It felt like a company on the cusp of really being ready to explode.

Hollister made an impact straight away. Barry fondly recalled him as “one of these guys who’s irritatingly good at everything: He’s a great negotiator. He was a threat to win the golf tournament every year—even against the sales guys. He was a great bike rider. Irritatingly enough, he became a better pilot than me... and he was a great CFO. Whenever there was anything wrong, we put David Hollister on it and he’d figure out a way to fix it.”

For example, billing and collections were “a shambles,” in Barry’s telling. Hollister formed a team that straightened them out within a year. “There was some low-hanging fruit,” Hollister said. “We had to fix the capital structure of the business, and get a proper bank credit facility in place to support our growth trajectory and the investments we wanted to make.”

Greg credited Hollister with bringing focus, discipline, and rationality to Bentley’s portfolio development through acquisitions and internal investment.

David Hollister joined as CFO in 2007 and made an impact straight away

To some degree, Hollister oriented his approach around Keith’s perspective as CTO. “His vision of where he wanted the technology to go was always at the forefront—always interesting and motivating,” Hollister said. “So the question became: How do we help him?”

Over time, Hollister implemented a budgetary methodology known as the “head cost model.” It aimed to “calibrate our investment in people with our opportunities”—without overconcentrating decision-making power in the chief executive. Any budgetary mechanism that sets spending boundaries inevitably spurs a certain amount of grumbling, but the growth of Bentley’s workforce and the dozens of acquisitions during Hollister’s tenure showed that it could also stimulate investment.

“I got a lot of freedom to try new things within the head cost model—which we smile about,” said Bhupinder Singh, whose remit grew in the 21st century until he became Chief Product Officer. “There was a lot of freedom to explore different ways of doing things.”

Greg viewed it as a “terrific management innovation” that empowered Bentley’s senior leadership to exercise authority with confidence. Hollister emphasized another aspect: “Very rarely did we ever have to cut costs and eliminate positions—including during the 2008 financial crisis. That was important to the Bentleys, so we prioritized it.”

The company had a culture of respect—for ideas, differences, mistakes. There wasn’t this massive fear of failing.

“The company had a culture of respect—for ideas, differences, mistakes,” Hollister continued. “There wasn’t this massive fear of failing. There was just accountability: It was our company. We owned it. We weren’t going anywhere. We weren’t afraid to invest in what was best for the long term … What was really unique was walking this tightrope between embracing a family culture, while also providing everything that’s interesting and stimulating and challenging about a large and complex global business. Usually you don’t see both of those in the same place.”

Harry Vitelli, who joined the development team in 2007 after stints at Apple and Adobe, was struck by the same dynamic. Bentley Systems was a 2,500-person company when he started—yet it didn’t necessarily feel that way in Exton.

“The brothers were freaking great,” he said, hastening to add, “and Bhupinder—it was a family, and he was part of the family. You’d talk to them, and it was like talking to your buddies in South Philly. They’re Eagles fans, they’re Phillies fans, they’re down to earth. I used to call them blue-collar millionaires. You know, they owned hot-rod Mustangs, that sort of stuff. You could tell that the values they were brought up with were just down-home.”

Harry Vitelli, who joined in 2007, turned ProjectWise, the workhorse for work sharing, into the gold standard for project delivery

iModel became the currency for information exchange and iModelHub became the ledger of change

At the same time, “You really felt like you could make a difference,” he added. Vitelli found appreciation for the rigorous approach to software development and product management he’d honed at Apple and Adobe. “That was the other beauty of it—they just welcomed you with open arms, and if you had ideas about doing things slightly differently than they may have been done before, they were all ears. I felt like I could have an impact, and people were listening.”

Bentley’s growth—in product lines, workforce size, geographic reach—was counterbalanced by an important continuity. Keith, Barry, and Ray remained the beating hearts of software development. Their roles remained remarkably consistent over the years.

“Keith was always working on the future,” said Gino Cortesi. A prime example in this era was his development of the iModel, which Bentley first introduced in 2007. Keith described it as a sort of hinge between CAD and BIM. The CAD mindset was to “solve the problem of an individual’s task,” he explained. “Like if you’re designing the support structure of a bridge, you create data. Where do you put that data? You put it into a file—because every computer has a disk and you store it in your file.”

Bentley’s growth—in product lines, workforce size, geographic reach—was counterbalanced by an important continuity.

“ProjectWise’s mission was to try to manage each of those files,” he continued, “each of which has, internal to it, a small part of the big picture.” But there was huge value to be realized by truly integrating them into a coherent whole.

“So we said: Look, we need a place to store this data that isn’t constrained by the source application that built it—by the file format,” Keith said. “The concept with iModels is you don’t store that data in individual files—you amalgamate it together into a relational database that stores all that data in one place. So the structural analysis data, the subsurface data, the electrical design data, and so forth can all be held in an iModel.” The upshot would be “a container for data that can span not only disciplines within a design process, but also survive the construction process and become the operating manual.”

Bentley introduced iModels at a particularly opportune moment. The 2007-2008 financial crisis, which smashed construction budgets across the globe, helped to catalyze interest and uptake of BIM technologies, which enabled firms to design complete, virtual models of buildings and infrastructure assets long before ground was broken. The 2008 acquisition of Common Point, a pioneer in software products for construction simulation (ConstructSim) and operations simulation (OpSim), further positioned Bentley to accelerate integrated project delivery for infrastructure projects by closing gaps between design, construction, and operations.

“Ray,” Cortesi reflected, “was almost the inverse” of Keith. “He was focused on production—working on new features, but more in the trenches. Ray was always the guy that, if we told him, ‘We can’t get through this door, it’s impossible,’ he would break through that door … and there’d be splinters all over the floor after he got done.

“Barry was like a larger-scale architect,” Cortesi continued, “developing bigger, broader features—and absolutely meticulous in the way that he would research things.”

In other words, the founding brothers hit and passed their quarter-century marks without downshifting gears. “Ray in particular was just always there—he came in the earliest and just worked, worked, worked,” Cortesi said. “And that really drove a lot of other people to catch the bug.”

It may have helped that Ray had a knack for making play contagious, too. As Bentley Systems steamed into the 2010s, the enduring example was an intramural jam session that had gotten started in the late 1990s. “A bunch of guys at the office and I were looking for something to do,” Ray recalled. “It turned out that one guy played drums, another was a pretty good guitarist, and then we found a really good harmonica player.” Ray decided to try his hand at the double bass. “I figured it had to be the easiest instrument to learn to play, with four strings,” he said. “So, we just started fooling around in my barn.”

Ray was always the guy that, if we told him, ‘We can’t get through this door, it’s impossible,’ he would break through that door ... and there’d be splinters all over the floor after he got done.

By 2001, they were being written up in the local newspaper. “By day, Buddy Cleveland, Ray Bentley, John Gooding, Steve Cocchi, George Dulchinos and Cliff Stackonis work in software design at Bentley Systems, a developer of civil engineering software,” went an item in Chester County’s Daily Local News.

“After the sun goes down, they become the fearsome Voodoo DeVille Blues Band—two harmonicas, a bass, drums, keyboard and guitar. They practice at Bentley’s farm in Warwick and get paid in fried chicken and beer. They appear just about any place that will have them, from pig roasts to the flatbed trailer hitched to a pickup in the Birchrunville 4th of July parade.”¹⁶

Regulars at the St. Peter’s Inn, they also became a fixture at the annual Bentley Car and Motorcycle Show, laying down 12-bar blues in a festival atmosphere that grew over the years to include food trucks, monster 4x4’s, and—in what Tom Anderson called “the pinnacle”—a Pinewood Derby in collaboration with a local Cub Scout pack that drew 31 entrants, including Greg and several other father-kid teams.

The Voodoo DeVille crew weren’t the only music makers in Exton. Chris Barron, who joined the company in 2008 as VP of corporate communications, made sure of that. At the 2009 Be Inspired Awards ceremony in Charlotte, North Carolina, he decided to “lighten up the proceedings” with a surprise performance that melded the mellow tones of a cabaret act with the screwball subversion of “Weird Al” Yankovic. “He gets up there,” recalled Harry Vitelli, “and he’s got a baritone voice like Frank Sinatra.” But Barron hadn’t dressed to the nines to croon songs for young lovers.

“Aqueducts for irrigation,” he sang, as the bopping bassline of Peggy Lee’s 1958 rendition of “Fever” bounced in the background. “Airports to land a flight / Skyscrapers and transportation / You know I fell in love at first sight… of infrastructure!”

“It was a risky proposition,” Barron recalled. “But as I began, I looked down and saw both Greg and Keith clapping along with smiles on their respective faces, and I knew it was going to be okay.”

By the time he reached the end—becoming perhaps the first lounge singer in history to rhyme palatial with geospatial—Barron had all but booked himself a dozen years’ worth of follow-up gigs. Often decked out in a signature tuxedo jacket, he wove refineries and DOTs into Cole Porter’s “Let’s Do It, Let’s Fall in Love,” used a James Bond theme to exalt renewable electricity projects and reliable tap water, and rewrote Gilbert & Sullivan’s “I am the Very Model of a Modern Major-General” to reference BS1192 building standards. When he became Bentley’s Chief Communications Officer in 2016, Barron was presumably the only executive in southeast Pennsylvania with both a Harvard master’s degree in architecture and a job description that extended to pop-music parody.

The Oscars of Infrastructure themselves reflected Bentley’s increasingly global reach. Among the 320 nominations attracted by the 2010 edition, held in Amsterdam, was Pritzker Prize-winning British-Iraqi architect Zaha Hadid, who won a Be Inspired award for her proposed Stone Towers development in Cairo. London hosted the 2013 conference, where Crossrail CEO Andrew Wolstenholme detailed how mobile BIM apps on devices like the iPad—which hadn’t existed when construction began—had enabled 14,000 construction workers to access different data sets to improve their productivity. Award winners that year included Henan Water & Power Engineering Consulting for China’s Shahe Aqueduct—a 12-kilometer-long, four-channel, elevated waterworks ranking among the largest in the world, which was realized with Bentley products including MicroStation, AECOsim Building Designer, GEOPAK Civil Engineering Suite, Bentley Navigator, and ProjectWise; Italy’s TECON S.r.l. for the safe, environmentally sensitive removal—in a single piece—of the 114,137-ton Costa Concordia cruise ship wreck from its resting place in the Tuscan archipelago using Bentley’s SACS offshore structural analysis software; and the Philippines’ Maynilad Water Services for a remote leak-detection project using WaterGEMs hydraulic modeling that turned an estimated $1.7 million outlay for pipe replacement into a $1,160, three-day fix.¹⁷

The future as Bentley envisioned it entailed “Going Digital”— pivoting from merely digitizing paper to comprehensively digitizing workflows.

In 2017, Bentley held its first Year In Infrastructure conference in Asia at Singapore’s iconic Marina Bay Sands hotel, for which Arup had won an Innovation in Structural Engineering prize in 2010. Fourteen awards went to projects in Asia, including eight in mainland China—a fitting legacy for JB Monnier and Florence Zheng’s hard-won feats of business development there. In a visionary technology keynote address, Keith introduced the next generation of iModel and described a new cloud service called iModelHub that would store the history of time-stamped changes made to project or asset data stored in a cloud-based relational database. The future as Bentley envisioned it entailed “Going Digital”—pivoting from merely digitizing paper to comprehensively digitizing workflows. iModel Hub would be a major step toward the advent of infrastructure digital twins, making data accessible to users to analyze and manage change, and repurpose information for untold future applications.

Bentley’s 21st-century organizational footprint reflected the global reach of its software. In 2011, for instance, when Gino Cortesi shifted from product design for MicroStation to spearhead a new User Experience group, he recruited his first team member in Vilnius, Lithuania, where Bentley had opened a development center in 2005. The night before interviewing with Cortesi, a design buff named Kate Romanovskaja dipped into a pub near her house, hoping a beer might settle her self-doubts about going into the meeting with “zero infrastructure knowledge.” By happenstance, a structural engineer was lifting pints at the same place—“a power-user of MicroStation,” she recalled, who “spoke about MicroStation and Bentley with such passion that somewhere around midnight I made my solid decision to join Bentley.”¹⁸ For Cortesi, it was quite a first hire. Romanovskaja worked for five years in Vilnius, progressed to a senior role while working in the Amsterdam area, and took over as Director of User Experience in 2020, working out of Bentley’s office in Hoofddorp.

The establishment of development centers in Islamabad, Pakistan and Pune, India in the mid-2000s reproduced this dynamic countless times across the company. And in 2010 Bentley established a new shared services, sales, and marketing center in Dublin, Ireland, forming its new Europe, Middle East, and Africa headquarters.

Victorious cricket team, BSW visit to Pune, 2009

Back in Exton, meanwhile, one colleague remained rooted to the point of utter immovability—and in 2013, when plans were hatched to renovate Building 1, his home turf devotion sparked a comical battle of wills.

“When we moved in there, we all had an office and we all had a cube,” recalled Jim Bartlett, evoking Building 1’s half-empty days. “You would go into your office when you had to be on the phone or when you had to do a management conversation or something,” he continued, “but everyone preferred to work in the cubes—because you were constantly talking to people, yelling back and forth across the dividers.” Over the next two decades, as Bentley’s growth crammed that original space to the gills and the TPB Building opened to provide an outlet, just about everyone shifted their desk at one point or another. Except one.

“Ray is the only developer who never moved,” Bartlett said. “He stayed in the same cube for like his entire history. From the time we built the first half of the first building in Exton, Ray was in one cube.” He kept an office too, but it functioned primarily as a glorified shoe locker.

In the 1990s, Ray took up running, starting with 5k races and working his way up. He ran his first marathon in 3 hours 40 minutes, his second in 3 hours flat, and notched his personal record of 2 hours 41 minutes at the age of 49. Apart from long-distance races, he almost always jogged during the lunch hour. The exertion refreshed his energy and shook ideas loose, effectively turning one day into two. So, his office was handy as a changing room. But his cube, where a panoply of keyboards and monitors jostled for space with a fish tank containing his beloved Oscars, was his true home at Bentley. By his own admission it was an “ugly, cloth-covered” domain. But it sat in the heart of “the original development room—and I kept it from changing for all that time,” he proudly recalled.

So, when Bartlett, whose role as CIO encompassed facilities as well as IT, commissioned renovation plans from an architect, the contest began.

“It was a dungeon compared to every other place else we had,” Bartlett said. So, he’d been given “a relatively small budget” to upgrade it. “But Ray didn’t like the plan. He didn’t want to spend any money on it, and he didn’t want to push the project.”

“They started saying, ‘We’ve got to redo this office,’” Ray remembered. “And I’d say, ‘Eff that, everything is fine.’ I was the last of the Mohicans. I sat in that same cubicle for 20-some years.”

Bartlett, perhaps inspired by Sun Tzu’s counsel that the wise warrior avoids the battle—or his sage observation that all warfare is based on deception—threw his adversary off balance by surrendering at once. “I didn’t really want to have a debate with him about it,” Bartlett said. “So, I said, ‘Okay, Ray, what we’re going to do is redesign the rest of the building—but I’m going to have the architects draw a boundary around this old development room, and we’re going to call it the Historical District.”

Within the Historical District, nothing would change—not a single nub of tired carpet or inch of tattered cubicle cloth. “The architect,” Bartlett chuckled, “was disgusted with this idea. But I was like, ‘Please play along.’ So, we went through a few iterations, and the rest of the building starts looking gorgeous in the renderings … and then we have the Historical District, which was like six cubes around Ray. And eventually—eventually!—Ray said, ‘Okay, this doesn’t look like the Historical District anymore, it looks like the ghetto.’ And he acquiesced, so that we could just rebuild everything.” Or as Ray preferred to put it: “They steamrolled me.”

Ray is the only developer who never moved. He stayed in the same cube for like his entire history.

But Bartlett’s most inspired maneuver was yet to come. One day in 2014, after the renovation work had irrevocably been carried out, Ray’s wife Terry sent her husband out to their barn on a flimsy pretext. Ray dutifully tromped over, only to be met with an unexpected sight. It had been orchestrated by Geoff Bartlett, Jim’s brother, who’d run point on the renovation.

“He had talked to Ray’s wife secretly,” Jim recalled, “and he got Ray’s cube—with its carpet and the 20 years of dust bunnies and trash under the desk—and moved it to Ray’s garage … right next to his beautiful Cadillac. So there, among all these classic cars that were perfectly restored, Ray had his Bentley cube of his entire life—with all of the trash and carpet fuzz and everything else that was in there. We thought that was hilarious.”

Ray took it all in stride. “I almost walked right by it,” he said, “because I was so used to seeing it.”

Ray had his Bentley cube of his entire life

If the Great Cubicle Caper of 2014 had been carried out a year later, perhaps the plotters would have turned Ray’s workstation into a digital twin. In 2015, Bentley Systems acquired Acute3D, a French company that made software capable of stitching together digital photography to create 3D representations. Along with software like Pointools, acquired in 2011 from a U.K.-based company of the same name, which processed and edited point clouds—3D models of existing conditions captured with laser scanners—this paved the way for a major technological advance. In 2015 Bentley introduced ContextCapture, which allowed users to produce high-resolution 3D models from photos taken with any digital camera. The software generated a detailed reality mesh incorporating the referenced photography, creating a navigable 3D model with fine and photorealistic detail, sharp edges, and precise geometric accuracy. The same year saw the release of MicroStation CONNECT Edition, the first version of MicroStation connected to a growing list of cloud services from Bentley. It featured an intuitive ribbon-based interface, introduced parametric solids and surfaces, and supported ContextCapture reality meshes.

Autumn of 2015 also presented an incredible opportunity to test-drive the new technology—in an historic event that combined massive scale and immense public interest right in Bentley’s backyard. “We became aware that the Pope was coming,” Greg recalled. Philadelphia had been chosen to host the Roman Catholic Church’s triennial World Meeting of Families in September. The gathering would bring an estimated 20,000 pilgrims from 100 countries—and Pope Francis had chosen the occasion to make his first apostolic visit to the United States. Organizers envisioned a weeklong event without precedent in the city’s history. The Italian tenor Andrea Bocelli would perform a rendition of “The Lord’s Prayer” accompanied by the Philadelphia Orchestra and the Philadelphia Heritage Chorale. Aretha Franklin would sing “Amazing Grace” for His Holiness, followed by Puccini’s iconic aria “Nessun Dorma.” Pope Francis would culminate the proceedings by conducting a Sunday mass anticipated to draw upwards of one million congregants to the Benjamin Franklin Parkway.

The logistical demands of such an undertaking verged on the unfathomable. City officials proposed to close 25 miles of highways in the Philadelphia area and convert a 4.7-square-mile area of the city into a vast vehicle-free pedestrian zone. Nothing like it had ever been attempted before. Between baseline public safety measures and special US Secret Service requirements, the event would involve 33 miles of security barricades, 10 first-aid stations, 100 ambulances, 1,000 emergency medical personnel, and more than 6,000 National Guard peacekeepers, police officers, firefighters, and other support staff drawn from 71 local, state, and federal agencies.¹⁹

“We had just done that acquisition of Acute3D, which made us the leader in resolving overlapping imagery into a reality mesh model,” Greg said. “And we were really convinced of its virtue and applicability. It hadn’t been applied to an event before, but we really wanted to make the point that it could scale up to city scale.”

“We wanted to do something for Philadelphia, and especially for the Pope’s visit.”

“The other thing is that I really wanted us to do something pro bono,” he continued. “We wanted to do something for Philadelphia, and especially for the Pope’s visit. Philadelphia has so many Polish and Italian people and so forth. It was just the right thing to do.”

Greg beckoned Buddy Cleveland from his recent retirement to lead a wide-ranging team of Bentley Systems volunteers. The event production company ESM brought in AEROmetrix, an Australian digital aerial mapping company, to capture overhead images from helicopter flights. Meanwhile Bentley colleagues snapped thousands of digital pictures at ground level, taking in facades, street views, and the interior of the Cathedral Basilica of Saints Peter and Paul, where the pontiff would conduct a private mass. Some 28,000 photographs were fed into ContextCapture, which wove them into a single reality mesh from which one square mile was refined—a digital twin of Center City Philadelphia.²⁰

The ability to leverage this 3D reality modeling was absolutely a gamechanger for us.

“This was a very large-scale event,” said ESM co-founder and executive producer Scott Mirkin. “What we’ve typically done in the past is utilize 2D CAD drawings and do lots and lots of site surveys. But the ability to leverage this 3D reality modeling was absolutely a gamechanger for us.”

ESM’s production team imported the reality mesh into MicroStation, which Ray had lifted heaven and earth to fortify on an extremely tight timetable. That allowed designers to add 56,400 temporary facilities—the event’s infrastructure—directly into the virtual model. Bentley’s LumenRT software (acquired with the French company e-on the same year) was used to simulate the movement of vast crowds within the pedestrian zone and vehicle flows outside it, to ensure mobility within the city and smooth traffic around the road closures.²¹

An uncertain public mood shadowed all this advance work. Philadelphia’s underwhelming 1976 Bicentennial celebration had left a trail of sour memories. Would the city disappoint again, or might it just possibly redeem itself?

Reality mesh of the Philadelphia Museum of Art and Benjamin Franklin Parkway

Digital twin of Center City Philadelphia

Keith’s second once-in-a-lifetime opportunity

“This was a highly public and complex project, with many stakeholders and an impossible timeline,” reflected Buddy Cleveland. “We got involved right in the middle of it.”²²

“To capture a 3D model of the city of Philadelphia,” said Greg, “in a format that can be used by every engineer of infrastructure in the city, had never been accomplished at all let alone to accomplish it from scratch in such a short timeframe.”

“It had to integrate seamlessly with MicroStation and all the associated modeling tools,” Cleveland elaborated, “so that we could then begin to model all these temporary facilities directly within the model without having to go through a lot of translation and imports and exports. … With the integration work that Ray Bentley and his team did, it worked seamlessly.”

Three days before the Pope’s giant outdoor mass, a video representing a simulated flyover of the city, made possible via a digital twin, captivated Internet onlookers. Philadelphia magazine described it as “a tried and true version of Philadelphia so life-like, that you might have to squint to make sure it isn’t the real deal.”²³

For the hundreds of thousands of city dwellers and visitors who poured into downtown Philadelphia on Sunday, September 27, 2015, the experience was something close to transcendent. The streets and sidewalks between City Hall and the Philadelphia Museum of Art swelled with pilgrims who flowed from place to place in a state of beatific gladness and anticipatory joy. Car horns and combustion engines fell silent across the breadth of Center City. From river to river, men and women and children of all ages strolled and cycled through cityscapes that occasionally resonated with outbursts of spontaneous song. Even for nonbelievers—perhaps especially for nonbelievers—the spirit coursing through Philadelphia that day stirred enchantment and wonder.

The Papal visit transpired so smoothly that the plans behind it could have been mistaken for blessings. But of course the truth lay in the other direction. “In the end,” reflected ESM’s Scott Mirkin, “we experienced dramatic risk reduction, better decision making, exceptional timeliness, and greater efficiency. The goal we set with Bentley to test the applicability of reality modeling as a mission-critical event planning technology was completely validated, and we are now planning to offer this new value to our clients going forward.”

Ray offered another perspective. “Five years ago,” he said after the Pope had completed his visit, “if someone had told me this was possible—to produce a model of this accuracy from pictures—I would not have believed it. I still have a hard time believing that it works as well as it does now.”

He was not the only one to sense that a new era was dawning. As Keith later put it, the advent of digital twins gave him an eerily familiar feeling—that he was on the cusp of “my second once-in-a-lifetime opportunity.”

An infrastructure digital twin is a digital representation of a physical asset as well as the engineering information that allows users to understand and model its performance

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