Scott Scherr gave employees a card with “Trust” on one side and “Forever” on the other. It was a compact piece of management literature. No diagrams. No numbered principles. A person could read the whole thing while waiting for the lift. The difficult part, naturally, came after the printing.
At Ultimate Software, the company he founded in 1990, Scherr tried to turn that promise into an operating habit. Employees received stock awards. Colleagues stayed long enough to become senior leaders. The founder remained for nearly thirty years, through a public listing, a change in how software was sold, and an approximately $11 billion acquisition. His preferred language came from family businesses and sports teams, two institutions where everybody eventually learns who will show up.
A cubicle before the campus
The family business came first. Scherr grew up in the Bronx and spent summers working at his father’s data-processing firm. Reuben Scherr had founded Management Statistics in 1959. Scott later operated the business himself, before joining ADP in 1979. Over the next eleven years, his roles there included sales executive and vice president of operations. He knew the payroll business from inside an established provider before trying to build a competitor.
He also graduated from the University of Miami. His eventual company would put down roots in South Florida, a place where an enterprise-software career could come with palm trees outside the office. The geography is a useful correction to the familiar technology-founder itinerary. Scherr’s working life connected a New York family enterprise, a major payroll company, and a Florida startup.
For all its eventual scale, Ultimate began with four employees and very little space. Robert Manne, a friend who became the company’s lawyer, supplied its first office accommodation. He described the starting point as a small cubicle outside his own office. Before there was a campus, there was somebody willing to make room.
That detail suits the rest of the story. Scherr’s early advantage included people who already knew him and were prepared to help. A borrowed cubicle is a modest asset on a balance sheet. For a business still trying to become a business, it can be exactly the right size.
Ownership you could take home
Scherr’s reasoning was straightforward: take care of employees and they would take care of customers. In HR and payroll software, that chain had a particular relevance. Ultimate sold tools for managing other companies’ employees. Its own treatment of staff gave customers something to inspect beyond a product demonstration.
The policy with the clearest financial consequence was employee equity. Ultimate awarded stock to new hires, giving them a stake alongside their jobs. Scherr spoke of employees as partners. By January 2014, longtime people leader Vivian Maza was describing employees who told her they had bought an “Ulti house.” The phrase brought corporate ownership down to the level of front doors.
Scherr also reported that roughly half of new hires came through referrals. “When you get good people, they recruit good people,” he said. That is a recruitment strategy with a social obligation attached: the person recommending a friend expects to see that friend again on Monday.
Equity does not erase the ordinary difficulties of work. It does give a statement about shared success a mechanism. An employee can check an award, understand the stake, and decide what it means. Scherr’s version of belonging had an entry in the company’s records.
“Successful people are the foundation for successful business.”
Scott Scherr · 2012
A small card with a long promise
The trust cards made Scherr’s expectations portable. They also made them memorable, which is useful when a company grows past the point where everybody can hear the founder directly. A two-word message travels more easily than a management binder. Employees could keep the promise close enough to hold him to it.
The people carrying that message included Maza, one of Ultimate’s original four employees. She started as office manager in 1990 and became chief people officer in 2004. Her career put a familiar face behind the company’s culture as the headcount increased. Loyalty had to move through managers and colleagues, through introductions and decisions, long after the founding group stopped fitting around one desk.
Scherr’s approval among employees was measurable too. In 2016, he placed second in Glassdoor’s US CEO ranking, with 99 percent approval. Such a score records what responding employees thought at a particular moment. It cannot describe every working day. Still, it is a useful piece of evidence beside the founder’s own account of his intentions.
Loyalty still had to ship software
There was a product underneath all this. UltiPro brought together HR and payroll functions, and Ultimate moved into hosted subscription delivery in 2002. Selling a continuing service changes the relationship with a customer. The vendor has to keep earning the renewal. The customer has reason to pay attention to the people answering the next call.
The transition also changed the financial rhythm. In 2002, Ultimate reported a net loss of approximately $14.6 million. A business moving toward subscriptions cannot assume that the eventual attraction of recurring revenue will make the intervening years comfortable. Scherr’s loyalty philosophy operated inside those financial constraints.
By 2017, an analyst visit offered a view of both the culture and the unfinished work. Scherr discussed company history and his trust card. The product assessment was more demanding: the company was delivering against its roadmap, while parts of the user experience still needed improvement. That combination gives the portrait some texture. A friendly workplace still owed customers better screens.
Three years, one growing obligation
Annual revenue · US$ millions
Fiscal years ended December 31. Values rounded to one decimal.
By 2018, annual revenue had reached $1.14 billion, including about $997 million in recurring revenue. Those figures help explain how a four-person venture could become an acquisition target worth billions. They also show the scale of the obligation Scherr’s team had accumulated: a large base of customers expecting the service to continue.
The coach on the bookshelf
Scherr found a language for that work in Pat Riley’s The Winner Within. He received the book a few years after starting Ultimate and said he reread it almost annually. New employees received copies. His interest went beyond borrowing a sporting phrase for an occasional presentation. He kept returning to the same text.
He first encountered Riley as a reader. Later, Riley gave a keynote at Ultimate’s Connections customer conference in Las Vegas, and the relationship eventually became commercial. In September 2017, Riley and Scherr appeared together to announce Ultimate’s partnership with the Miami Heat. The company’s name would appear on the team’s jerseys.
There is something pleasingly literal about the sequence. A founder reads a coach, hands the book to his employees, meets the author, then gets his company onto the uniform. Most reading recommendations end with a book left on a bedside table. This one acquired a patch.
The basketball vocabulary also reveals something about Scherr’s idea of leadership. He talked about developing a bench and keeping players. In software, as on a team, experience has value only if people remain able to contribute. The metaphor asks the leader to coach, and gives colleagues a shared result to work toward.
Giving somebody else the whistle
In May 2019, an investor group led by Hellman & Friedman acquired Ultimate for approximately $11 billion. Scherr stayed through the transition. Adam Rogers became co-CEO in June; Scherr retired on December 31. Rogers took over as CEO the following day.
The succession had been prepared over several years. Rogers had joined Ultimate in 1997 and served as chief technology officer from 2007. He had helped lead the company’s cloud development. By the time he received the top job, he had spent twenty-two years inside the organization.
Family was also present in the formal organization chart. Rogers is Scherr’s son-in-law. Scott’s brother Marc served as vice chairman and chief operating officer. These relationships give the company’s family language a literal dimension, alongside the careers and responsibilities of the people involved.
At retirement, Scherr said he wanted more time with his family. The ambition was smaller in scale than the transaction that preceded it, and perfectly understandable after nearly thirty years. Ultimate merged with Kronos in April 2020; the combined business became UKG. The company continued into a chapter under other leadership.
Another team in South Florida
Scherr’s public activities after Ultimate kept a connection to sport and community. He was an honorary co-chair of the 2023 JCC Maccabi Games and Access in Broward County. In September 2025, Hyperspace Ventures named him among the limited partners of the Palm Beach Royals, a Major League Pickleball franchise.
The ownership group connected him with athletes including Aleksander Barkov and Bianca Andreescu. His place in that group marks a new investment rather than a return to running a payroll company. It also supplies a fitting continuation for somebody who spent years talking about teams.
Across these different settings, Scherr’s recurring interest is easy to recognize: people agreeing to build something together, then staying long enough to see what happens. The first cubicle has long since served its purpose. The question printed on that little trust card remains a useful one for any founder making promises to the people across the desk.