Robert Petrie and the Case for Leaving at Two

At two in the afternoon, an employee at Origami Risk could leave for a school concert or a soccer game. The condition was straightforward: clients had to be happy and the work had to get done. Robert Petrie, the company’s co-founder and CEO, was willing to leave the scheduling to the people doing it. In 2019, he put the arrangement plainly: “We give them a job to do, and we trust them to do it.”

Insurance software makes an unlikely setting for a small rebellion against the office clock. Its daily concerns include records, deadlines, calculations and access controls. Yet the distinction between controlling information and controlling every hour of someone’s day is useful. Petrie’s company needed the first. He had found room to relax the second.

That choice is a good entry into a career spent building software businesses and the organizations around them. The software is only part of the story. Someone has to understand the customer, make the system work and remain available after the sale. A founder can put trust in a presentation. The harder task is deciding where to put it in the business.

Insurance, entered through a side door

Petrie’s route into insurance began with a software company he established as a college student. After selling it, he took a technology job at Johnson & Higgins, the insurance brokerage. He stayed through its acquisition by Marsh & McLennan. A student venture had brought him into an industry with a considerable appetite for organizing information.

At Marsh, his work ranged across technology and operations. He founded and led CS STARS, the risk management information systems business later known as Marsh ClearSight. He also became Head of Global Operations and Client Technology, with more than 3,000 employees across 11 countries. Along the way, he formed and led businesses including Whereiwork.com, BenefitSmart.com and STARS Audit.

Those responsibilities put two kinds of complexity on his desk: the information a customer needed and the organization required to deliver it. A software feature can be demonstrated in minutes. Changing how thousands of people work takes longer. His career had given him experience of both before he co-founded Origami Risk in 2009.

The initials RMIS stand for risk management information system. The name is accurate, if unlikely to sell cinema tickets. These systems help organizations bring risk information together and use it. Origami’s founding proposition was a single-version, cloud-based platform that could be configured for different customers. One underlying product, many sets of requirements.

The people behind the configuration

That last detail is where a business like Origami becomes interesting. A public entity and an insurance company may both need reliable records, but their processes and responsibilities differ. Configurability creates room to accommodate those differences. It also creates work for the people who must understand them.

In his contribution to a 2014 industry review, Petrie described a service model built around experienced risk technology professionals and continuing customer relationships. He said the company added features and enhancements six times a year, many suggested by customers, without an additional charge for those improvements. Buyers would receive updated capabilities without complicated upgrades.

That approach makes the customer relationship an ongoing part of product development. The first specification cannot anticipate every use. People discover requirements as they work, and their suggestions become material for the next version. A release schedule gives that exchange a practical rhythm. There is a reason to keep listening after the contract is signed.

“Support and service are just as important as the product.”

Robert Petrie, 2016 RMIS discussion

The staffing figures offer another view. Origami’s entry in the 2017 RMIS guide listed 129 employees in its RMIS division and reported that 84% of staff were client-facing. That is a historical snapshot, but a revealing one. A large share of the organization was situated where the software met the customer’s working life.

The distinction matters when judging a software company. Code can be distributed widely; understanding a customer’s process still requires attention. Petrie’s public emphasis on support places that effort inside the product’s value. The demonstration may win interest. The implementation has to earn continued use.

Five years before the check

Petrie also had views about the organization financing the work. In 2015, responding to acquisition rumors in an industry review, he said Origami was owned by its management and had no plans to sell. Independence was part of the argument he made for serving clients.

Three years later, the company accepted its first institutional capital. Spectrum Equity’s March 2018 investment was a minority position. The announcement described access to additional resources and the capacity to pursue acquisitions. Petrie’s stated priority remained client success, with technology and experienced people supporting customers’ business objectives.

The relationship had started well before the transaction. Spectrum first met Petrie in 2013 and describes meeting him several times a year over the following five years. By the time it invested, it had watched the company operate through a substantial stretch of its development. Five years gives a prospective partner plenty of opportunities to see what happens after a forecast.

There is a practical tension here. Additional capital brings opportunities; an owner’s timetable can influence how a business pursues them. In a 2021 industry discussion, Petrie welcomed private equity’s ability to direct capital to growing companies, while warning about repeated ownership cycles that could push mature businesses toward short-term profit improvement before a sale. His position allowed for both the usefulness of investment and the consequences of its structure.

The spreadsheet’s long goodbye

Origami’s opportunity also extended beyond replacing competitors. In that same 2021 discussion, Petrie said more than half of its recent RMIS buyers had previously had no such system. They were first-time buyers moving from spreadsheets. A market can expand because more people decide the old arrangement has become too cumbersome.

For those customers, buying software also means changing routines. Information that lived in separate files has to be organized in a shared system. Responsibilities need to be clear. People have to know which record to use. A new screen is easy to notice; a dependable handoff between colleagues is often the more consequential change.

In 2019, Petrie described a broader ambition for risk systems: insurers, brokers, third-party administrators and risk managers could use a common platform, with permissions governing what each participant could see or change. Sending a spreadsheet created a separate copy that could fall out of date. Shared access offered a way to keep people working from the same information.

He also described enterprise risk management as a communication problem across the management team. Some risks produced familiar historical records; others had few precedents. Collecting and updating information across departments could help make those different exposures visible together. The implication for a software builder is demanding. A system must accommodate both the familiar record and the unfamiliar question, while making it clear who is responsible for the next step.

A 2017 customer example gives the idea some weather. After Hurricanes Harvey and Irma, Compass Group USA used Origami’s audit and workflow tools to collect business interruption and property damage information. The company’s risk team adapted tools already available in the system to a pressing information problem. The usefulness lay in getting details collected and circulated while they mattered.

As the customer base grew, the business itself needed more room for different demands. In 2019, Origami established separate operating divisions for core insurance processing and risk solutions. Petrie said the core processing side had grown to about one-third of revenue. Giving each division its own leadership was a way to provide attention to two complicated markets.

Expansion brought another decision in September 2023, when Origami acquired Dais Technology. Dais supplied no-code insurance technology, storefront tools and rating capabilities. It would operate as a subsidiary led by co-founders Jason Kolb, Aaron Larson and Milos Dedovic. The transaction added capabilities alongside Origami’s existing insurance systems, as well as another team with its own experience of the industry.

The next version of the same question

By 2024, Origami had reached more than 1,000 clients. The number describes a company far removed from its founding days, but it leaves the individual implementation problem intact. Every new organization still brings its own records, decisions and expectations. Scale does not spare a vendor from those particulars.

In 2026, Petrie and product executive Ryan Cantor appeared in the program for an executive conversation about AI and enterprise technology. The proposed discussion emphasized adaptability, connected systems and AI embedded in governed business workflows. Those subjects extend a familiar line of inquiry in Petrie’s work: how information becomes useful inside an actual organization.

His name also appears on the speaker list for Origami’s October 2026 Elevate conference in New Orleans, as president, founder and CEO. The program includes user roundtables, product discussions and practical training. For a business built around configurable software, those conversations have a clear purpose. Customers can explain what happens when the product reaches their desks.

The early departure at two belongs in this story because it concerns the same working relationship. Responsibilities were clear enough for people to have discretion. Petrie had built software to help organizations coordinate their work, and he was prepared to let his own employees exercise judgment about theirs. The school concert could begin on time. The client still expected a working system.