A buy button is an unassuming piece of real estate. It sits below a price, waits for a finger and promises that wanting something can turn into owning it. In 1994, William S. McKiernan was working on the less decorative part of that promise: how to sell software over the internet, collect the money and deliver the product. His business began as an online shop. The checkout would acquire a life of its own.
The shop was software.net. To operate it, McKiernan’s company developed payment processing and fraud capabilities, then began licensing those capabilities to other businesses. The machinery beneath the sale became CyberSource. The software retail operation eventually went its separate way. There is a pleasing reversal in this origin: the thing built to support the business became the business worth following.
A shop discovers another business
Software could be sold and delivered electronically. That was the original proposition. But an online merchant also needed a customer’s payment to reach the right place, and a way to judge the transaction’s risk. Other shops faced the same problems. CyberSource offered them an alternative to building and maintaining that infrastructure themselves.
This is the useful distinction in McKiernan’s beginnings. He was working inside commerce, encountering its practical requirements. The opportunity emerged from operating a store, rather than from an abstract prediction about how big the internet might become. A customer clicking a button was only the visible end of a much longer process.
The dates tell two parts of that development. CyberSource traces its origins to 1994. Its separate corporate inception was in December 1997, while McKiernan’s software retail business became known as Beyond.com. By 1999, CyberSource was publicly traded. Within five years of the initial venture, he had moved from selling software online to running a listed company that helped others sell online.
software.net→02Build checkout
Payments + fraud→03Serve merchants
CyberSource
An operator before the internet checkout
McKiernan arrived at this experiment with experience in companies where the operational work was already substantial. He had held management positions at Price Waterhouse and IBM/ROLM, then served as vice president of Princeton Venture Research from 1990 to 1992. The latter combined investment banking and venture consulting. His next role put him inside another software business at a consequential moment.
From 1992 to 1994, he worked at McAfee Associates as president and chief operating officer. He was there for its initial public offering in October 1992. Two years later came the online software venture. His early career therefore included both advising businesses and helping run a software company through a public listing.
His education had taken him through Boston College, where he earned a bachelor of science, and Harvard Business School, where he earned an MBA. Much later, when asked to name his best investments, he chose getting the MBA. The answer is brief, but it gives those credentials a personal weight: he still regards the education as money and effort well spent.
That background makes the CyberSource story more interesting than a lucky discovery in a new market. McKiernan was a founder with an operator’s experience, entering a medium whose commercial routines were still being worked out. The opportunity was new. Running a business was already familiar territory.
Small merchants, larger ambitions
CyberSource’s next important expansion brought it closer to sellers with fewer resources. In 2007, it acquired Authorize.Net, which focused on smaller online businesses. CyberSource had built its position serving medium and large merchants. The combination widened the range of businesses it could reach, from modest operations to international brands.
By early 2009, its customers included Avis, Facebook and Fandango. McKiernan was watching the recession through the behavior of merchants and shoppers. Bargain-conscious consumers were looking online for prices. People were opening niche businesses to supplement their income. Larger sellers were considering the economics of online stores alongside physical premises.
He described these developments as long-term forces favoring ecommerce. His account was grounded in changes to the customer base: more shops, more products and more shoppers. Even during the recession, he said CyberSource had signed up more than 106,000 new merchants in 2008. That was a particular year’s figure, but it conveys the pace at which internet commerce was becoming ordinary business.
Those figures explain why the company had become interesting to Visa. Its services occupied the point where a merchant’s website met the payments system. As online commerce grew, that position became valuable to the network as well as to the shops.
The buyer changes the conversation
The path to the Visa acquisition contains a twist worthy of a meeting agenda with insufficient room in the margins. CyberSource was considering buying another company. It approached Visa about a possible investment to help finance that purchase. The companies already knew one another: they had partnered since 1999.
On March 1, 2010, McKiernan and CyberSource CEO Michael Walsh met Visa CEO Joseph Saunders to continue the investment discussion. Saunders said Visa was interested in acquiring CyberSource outright. McKiernan and Walsh had come to discuss financing their own acquisition. They told him they were unprepared to discuss selling and asked him to reconsider participating in their bid.
The following day, McKiernan convened a special board meeting. The board saw strategic reasons for a combination. Negotiations followed, including his request for a price of $28 per share before proceeding exclusively. The eventual agreement was $26 per share. A conversation about supporting one transaction had opened the door to an entirely different one.
Visa announced the deal in April and completed it on July 21, 2010, for approximately $2 billion. McKiernan was executive chairman by then; Walsh was president and CEO and continued to oversee operations. McKiernan joined Visa as an executive adviser, spending two years there before establishing WSM Capital in 2012. The sale changed his role, while keeping him close to payments.
The Irish connection had an engineering address
McKiernan’s connection to Ireland reaches further back than a technology investment. His paternal grandparents left Mohill in County Leitrim for New York in 1906. He grew up in Stuyvesant Town in lower Manhattan, with Irish aunts and uncles living nearby. Irish culture was part of the neighborhood and the family, rather than an affiliation acquired later in his career.
In 2008, CyberSource opened a development center in Belfast in partnership with Invest Northern Ireland. The center became one of the company’s engineering hubs. When the Irish Technology Leadership Group recognized McKiernan in March 2010, he emphasized what CyberSource had gained from the relationship: engineering talent and progress on demanding research and development goals.
That answer gave the connection a practical dimension. Belfast was a place where work was being done for the company. The recognition took place at Stanford, connecting his Silicon Valley career with an operating relationship across the Atlantic.
He also began attending Ireland Funds events in San Francisco. Those encounters led to greater involvement in the organization during a difficult period for Ireland’s economy. His proposed contribution drew on the work he knew: encourage people to build businesses that could create employment.
A prize for learning to begin
In 2012, he established The Ireland Funds Business Plan Competition. It was modeled on a Harvard Business School initiative and aimed at developing entrepreneurial skills. A competition gave young founders a reason to write down their ideas, explain their markets and put a plan before people who had built companies themselves.
“Every job starts with an entrepreneur.”Bill McKiernan, 2013
He wanted participants to grow more comfortable with taking risks and learning from failure. His stated aim included confidence: encountering successful entrepreneurs could make starting a company feel more possible. The ambition was long-term job creation, with education as part of the route there.
By 2018, the programme included pre-acceleration workshops and mentoring before the final pitch. Ten shortlisted ideas received help moving from concept to presentation. The winner could receive €10,000 and an opportunity to pitch for an NDRC investment programme; further prizes went to the runners-up. Preparation was built into the competition, rather than left to happen somewhere offstage.
The next founder gets a turn
WSM Capital gave McKiernan a vehicle for investing in payments and other technology companies. His involvement in entrepreneurship education continued alongside it. IDEATE Ireland lists him among its founding team, with entrepreneurs including Options Technology’s Danny Moore and Safecility’s Cian O’Flaherty. O’Flaherty had himself participated in the 2018 business-plan competition.
That connection makes the later chapter tangible: a participant in one programme became part of the team supporting others. In 2022, McKiernan appeared at an IDEATE open evening to share lessons from starting and growing a company. He was bringing operating experience into a setting where people were deciding how to begin.
The broader Irish connection remains active. Bill and Betsy McKiernan were listed among sponsors of The Ireland Funds’ San Francisco Gala in March 2026 and on the committee for its Nantucket Celebration that July. The relationship has continued well beyond the founding of a single competition.
Cereal, a charger and a list
For all the transactions in his biography, McKiernan’s public questionnaire leaves room for domestic scale. A useful purchase under €100? A three-device charger for his phone, tablet and watch. An unusual thing he loves? Cereal. The breakfast industry may take quiet satisfaction in surviving an investor’s scrutiny.
When overwhelmed or unfocused, his answer is equally compact: “Make a list.” It is an agreeable final detail for a career involving public companies, payment infrastructure and negotiations that changed direction in the room. Some tasks still benefit from being written down.
The arc begins with a shop needing to complete a sale and continues with other people needing help to start a business. Across those settings, McKiernan’s work has concerned the practical conditions that let commerce happen. The buy button was small. Building the business behind it took years. Helping the next founder begin gives that experience somewhere else to go.