Steve Singh had a week to account for roughly $150,000. The money was sitting in unfiled business expenses, accumulated while he traveled to explain his software company to potential buyers. An acquisition was approaching. The finance chief gave him a deadline: submit the reports before the deal closed, or lose the reimbursement. For someone accustomed to writing software, the assignment involved an unreasonable amount of paper.
He spent the week working through receipts and copying details onto forms. He suspected he lost money anyway. The experience helped produce the idea behind Concur: surely this routine corporate chore could be handled better. Expense reports have a peculiar talent for making successful people feel defeated by a taxi receipt. Singh had acquired enough material for a serious grievance.
Concur would eventually sell to SAP for $8.3 billion. Yet the irritating problem that started the business would outlive that transaction. Singh kept returning to the larger question behind those forms: why does a business trip require so much work from the person taking it?
Before the corner office, the Macintosh
Born in India and raised in Michigan, Singh began his professional life in Silicon Valley. His route into management came through engineering. He wrote code for the Macintosh, and he and Mike Hilton were among the original developers of MacWrite II. They also worked on software that became ACT, the contact-management product. His early career included work connected with Apple, Contact Software, Oracle and Symantec.
The founding story has an interesting wrinkle. Concur, established in 1993, generally credits Singh, his brother Rajeev and Hilton as co-founders. In his own early account, Steve described a more specific division of labor: Rajeev and Hilton started the company; he supplied early investment and served as an active director. He still had a three-year employment commitment to Symantec. He became Concur’s CEO in February 1996.
That distinction gives the familiar startup photograph some depth. The idea could begin with his frustration while the work of turning it into a product belonged to his brother and their colleague. The company initially sold a retail version of expense software before pursuing enterprise customers. Over time, the question expanded from filling in a form to changing how a company bought and used software.
A honeymoon with management reports
In April 2000, Singh was on a flight for a much-delayed honeymoon, reading management reports. There are more romantic choices of in-flight entertainment. Distance from the office, though, gave him room to see the business more clearly. Concur’s expense-management work was going well. Its moves into human resources and procurement were struggling. He also saw limits in the future of licensed software.
After thinking it through, he gathered the team and proposed moving toward an on-demand model. Customers would consume a service, with economics closer to outsourced payroll, instead of taking on a conventional software installation. The change required decisions about products, personnel and revenue. A recurring service could be attractive to customers while creating an uncomfortable transition for a public company.
Concur had gone public in 1998. Its shares subsequently fell from around $60 to 28 cents during the period of upheaval. Years later, Singh called it a “character building moment.” The understatement did useful work. A stock price can turn a strategic debate into a daily public referendum, and the market was delivering its opinion in very small denominations.
His account of getting through that period centered on company culture and the willingness to make difficult decisions. He even joked that he had remained CEO because “nobody else wanted the job.” Behind the laugh was a practical problem: a leadership team had to keep working through a change whose benefits would arrive later than its costs.
An exit large enough to look like an ending
By 2014, the company was serving more than 23,000 customers. SAP’s agreement to acquire Concur valued the transaction at $8.3 billion. For a business that began with the administrative aftermath of travel, it was quite a distance from the original pile of receipts. The purchase placed Concur inside a much broader enterprise-software business.
Singh joined SAP’s executive board and ran its cloud business group. He left SAP in 2017 and became chairman and CEO of Docker that May. The assignment took him into software infrastructure and the work of turning developer adoption into an enterprise business. He stepped down as Docker CEO in 2019. In January 2020, he joined Madrona as a managing director.
His explanation for becoming an investor was personal: he wanted to pass along guidance and help founders avoid mistakes he had already made. Investing offered another way to work on products and companies. He brought the experience of an operator who had seen a business through a public offering, a painful change in its business model and an acquisition.
There was also unfinished travel business. The phrase he used at Concur, “The Perfect Trip,” described a connected experience from planning through the return home. By 2021, he was writing that the work remained incomplete. A successful sale had closed a transaction; it had left him with plenty of product questions.
“More than two decades later, I still feel like the work is unfinished.”
Steve Singh · On the Perfect Trip, 2021
The meeting that almost never happened
Sarosh Waghmar’s account of recruiting Singh into Spotnana begins with persistence. Before he could speak to Singh, Waghmar met former Concur executives who examined the idea. Then came a scheduled meeting in New York that Singh missed because of calendar confusion. Waghmar called rather than letting the opportunity disappear.
He offered to pick Singh up and use a car ride to the airport for a half-hour conversation. Eventually they met that day. The discussion ran for two hours. It is a pleasingly untidy beginning for a partnership concerned with making travel run smoothly: the calendar failed, a meeting nearly vanished, and a human being had to keep insisting.
Spotnana gave Singh a fresh route toward his old ambition. The company was building travel infrastructure that other businesses could use, with an emphasis on connecting systems and allowing partners to develop services on top. He became its CEO in June 2024, alongside his executive chairman role. His engineering background was again relevant to a problem travelers usually experience as waiting, retyping or calling for help.
In April that year, an investor group he led acquired Direct Travel, with former Concur executive Christal Bemont becoming CEO. The pairing mattered: a technology platform and an established travel-management company could work together on the software and the service. Bemont brought a long working relationship with Singh, as well as knowledge of the customers whose trips the software would have to support.
The trip keeps changing after you buy it
The arrangement also raised a reasonable question among travel companies: would Spotnana remain a platform for other agencies while Singh chaired Direct Travel? Its executives said it would continue to serve partners across the industry. That commitment matters to the strategy. An open platform needs other businesses to believe that building on it remains worthwhile.
The collection of businesses has continued to change. American Express completed its acquisition of Center, the expense-management company Singh had chaired, in April 2025. That September, Direct Travel acquired its longtime partner ATPI, announcing combined annual travel volume above $6 billion. That figure measures travel passing through the businesses, rather than their revenue. In August 2026, Spotnana completed its acquisition of TROOP, bringing meeting planning and group logistics further into its platform.
By September 2026, Singh’s public emphasis had moved toward service after a booking. He argued that automation and AI could cut servicing costs by 50% or more. That remains his stated expectation, rather than a universal measured result. He described Spotnana’s AI agents handling routine cancellations, unticketed flights and refunds, leaving people more time for interactions that benefit from personal attention.
The appeal is easy to understand. Buying a ticket occupies a moment; dealing with a change can occupy an afternoon. Singh’s ambition asks software to carry more of that burden. The useful test will be whether travelers spend less time explaining the same itinerary to different systems and whether the people helping them have the information they need.
Spotnana completes its acquisition of TROOP, extending its work in meeting planning and group travel logistics.
A school with no pupils - at first
There is another family story about building something and waiting for people to believe in it. Singh’s mother, Kamala, had attended school only through fourth grade. After raising her family in the United States, she wanted to use the retirement savings she and her husband, Gopal, had accumulated to establish a school for girls in their village in India.
In Steve’s account, his parents bought land, built the school and invited the girls to attend. Nobody came. Kamala went from door to door, explaining her own life and why an education might change theirs. Families gradually began sending their daughters. The school, Jangi Singh Girls College, became a lasting focus of the family’s giving.
The details of her plan mattered: meals, school clothes and an education without a charge to the children. Those choices addressed the practical obstacles around attendance, down to the possibility that one pupil might feel she had less than another. Steve’s family foundation supports girls’ education and conservation, alongside local charitable work.
Outside business, he enjoys skiing, exploring new places and meals with family and friends. The interests fit someone who keeps choosing an industry built around movement and encounters. His professional life has spanned code, expense software, cloud infrastructure and investing. The recurring pleasure appears to be working with people on something they believe can improve.
For Singh, business travel still supplies an unusually durable assignment. The receipts were an early symptom. The missed meeting, the changed flight and the unanswered service request offer fresh versions. After three decades and an $8.3 billion deal, he remains occupied with the time people lose between deciding to go somewhere and getting home.