Richard Burke once described an unusual feature of the Envoy Global office: large portraits of people whose immigration cases the company had helped handle. They were reminders that an application belonged to someone with a life beyond the application. An employer might see a position to fill. An attorney might see a file. The pictures gave everyone another way to look at the work.
It is a useful place to begin with Burke, a Chicago executive whose career has moved through corporate law, apartment listings and work visas. There are acquisition prices and investment rounds along the way. But the portraits suggest a question that survives each change of business: how does somebody get from where they are to where they have a chance?
Burke spent a decade leading Envoy, then stepped out of the chief executive’s job in July 2025. His next chapter includes chairing The Rise Foundation by Envoy, which provides free immigration legal help. The route to that work began with a different sort of paperwork.
A lawyer finds the operating side
Burke earned a bachelor’s degree from the College of the Holy Cross and a law degree from Georgetown. He practiced at Skadden, Arps, Slate, Meagher & Flom and at Burke, Warren, MacKay & Serritella. Corporate law put him close to companies at the moments when an agreement could turn an intention into something that actually existed.
In 1997, he signed the papers forming Classified Ventures. That year, he also represented the business in its purchase of Visual Properties, the predecessor of Apartments.com. He joined Classified Ventures as chief legal officer in October 1998. A company he had helped assemble on paper became the place where his own responsibilities would expand.
As senior vice president of administration and corporate development, he oversaw HomeGain.com and a collection of functions that rarely appear together in a glamorous job description: technology, legal work, human resources, communications, facilities and corporate development. It was a good vantage point for seeing how one department’s elegant decision could become another department’s Tuesday afternoon.
At Apartments.com, where he became president in 2012, his remit included sales, marketing, product development, production, customer service and technology. The work required attention to the entire business around the website. A renter needed useful information. A property manager needed prospective tenants. The marketplace had to make those interests meet often enough to sustain a company.
CoStar bought the Apartments.com business in April 2014 in a transaction announced at $585 million, subject to working capital adjustments. Burke had led it through the sale. For a lawyer who had signed the founding documents of its parent years earlier, the transaction offered a particularly long view of how a business develops.
An apartment marketplace and an immigration business do not look especially similar on a balance sheet. Viewed from the customer’s side, the connection becomes easier to understand. Both concern a move, and both require people to navigate information they cannot afford to misunderstand. That parallel helps make sense of Burke’s next professional choice.
Chicago, with a wider map
Burke joined VISANOW in January 2015. The company, founded in 1998, would become Envoy Global in 2016. He had reasons to like the opportunity that were thoroughly commercial: its market, its competitive position and its financial backing. There was also the location.
“I love Chicago. I’m from here and wanted to stay,” he said in 2019. The role let him combine his background in law with the experience he had accumulated running technology businesses. He could remain rooted in one city while working on a problem that crossed national boundaries.
The company’s model brought software and legal representation into the same customer experience. Technology could organize the work, while attorneys supplied professional judgment. For an employer managing international employees, the two needs arrive together. Knowing that a document has been uploaded is useful; understanding what that document means is useful in another way.
That division of labor is central to the business Burke chose. A technology company can make a process easier to follow. It cannot make every difficult legal question disappear. A professional service can supply expertise. Its customers still need a manageable way to keep track of work. Envoy’s offering put those capabilities alongside one another.
Burke had arrived after running a consumer marketplace, but he was now serving employers and the people they sponsored. The consequences of the work reached past the hiring department. Permission to work could shape where someone lived, where a family settled and whether a professional opportunity could be taken up.
The arithmetic of crossing borders
In October 2017, Envoy raised a $21 million Series C led by Catalyst Investors, with General Catalyst participating. The company said the money would support its commercial expansion and further development of its immigration services and software. Susan Bihler of Catalyst joined its board.
Palladium Equity Partners invested in September 2021, alongside existing shareholders. Catalyst and General Catalyst retained minority stakes. Those successive investments accompanied the expansion of a business combining a technology platform with services that employers needed to manage international hiring.
By the time of the July 2025 leadership handoff, Envoy reported more than 1,000 customers and a presence in over 15 countries. Its board credited Burke’s tenure with taking annual revenue from seven figures to nine. Those are broad revenue bands rather than a year-by-year account, but they describe a substantial change in the company he had joined.
The demand for help crossed borders in both directions. In March 2023, Burke discussed employers moving work abroad when U.S. immigration obstacles prevented them from keeping employees in the country. Envoy’s survey reported that 81 percent of responding companies had transferred foreign national employees to an overseas office because of visa-related issues in the previous year.
The number described those surveyed employers, rather than every American company. Even so, it made Burke’s concern concrete. A business unable to retain a person in one country could try to retain that person somewhere else. The job and the worker did not necessarily part company when a visa problem arose; the location could change instead.
Burke also hosted conversations that reflected that wider map. In 2021, he spoke with Canada’s then immigration minister, Marco Mendicino, about the country’s approach to attracting talent and employers. His work placed him between a company’s immediate staffing needs and the broader decisions that influence where work happens.
Dignity is an operating principle
Burke’s interest in people’s potential had an earlier influence. While in college, he got to know Sargent Shriver. He later described being struck by Shriver’s belief in what people could accomplish and by his insistence that they be treated with dignity and respect. Burke said he tried to carry those lessons into the workplace.
There is a management problem tucked inside that aspiration. Respect has to survive the occasions when interests diverge. Employees, customers, investors and board members can want different things from the same decision. A chief executive’s manner matters because the decision comes with authority attached.
Burke has spoken candidly about the loneliness of that authority. He said he had initially been skeptical of the familiar claim that the CEO job was lonely, then came to understand it. Accessibility, candor and transparency were his stated ways of addressing it with colleagues and the board.
“I was hired to scale the business.”Richard Burke, 2018
Scaling also changes what the leader has to learn. Burke repeatedly described the company as unfinished work: the methods that carry it to one stage need to evolve for the next. It is an unromantic view of growth. Yesterday’s useful habit may become tomorrow’s constraint, however fondly everyone remembers it.
That makes the office portraits more than decoration. In a business measured through cases and customers, they supplied a visible reminder of the person at the other end. A photograph cannot solve an operating problem. It can help keep the purpose of solving it in the room.
A different kind of access
RISE was founded in 2022. Its work focuses on low-income clients and humanitarian cases, providing free immigration legal services to people with valid legal claims. Burke serves as chairman of its board; Nancy Sandifer Barillaro is its executive director. The organization turns attention toward people who may have a route through the legal system but lack the resources to pursue it.
The distinction between an available legal pathway and the ability to use it is the foundation’s concern. Preparing an application, understanding a case and finding professional help require time and expertise. Eligibility alone does not supply either. Here, the customer’s budget is a different kind of obstacle from the ones Burke encountered serving corporate clients.
When Jason Brennan succeeded him as Envoy CEO in July 2025, Burke remained a shareholder and board advisor. In his own account of the handoff, he thanked colleagues, clients, investors, advisors, friends and family, along with the people who had trusted the company to help them live and work where they hoped to go.
He said he would take some time to think about his next chapter. Growing RISE and advising other businesses were already part of the plan. After years of responsibility for a company’s daily operations, he had chosen to keep working on the question that connected so much of his career.
First, a place to live. Then, permission to work. Now, access to legal help. The settings have changed, as have the people able to pay for the service. Burke’s work keeps returning to the distance between an opportunity and the practical means of reaching it. Somewhere behind the paperwork, there is still a person who would like to get somewhere.