DocuSign CEO Preps for an IPO, While Trying to Appease His 11 Bosses

Dan Springer inherited a lot when he became chief executive officer at DocuSign Inc. this year. The company’s electronic document software is an essential part of the real estate and insurance industries in the U.S. Investors value the business at $3 billion, making DocuSign one of America’s most valuable technology startups.

It’s also one of the oldest. Numerous suitors have come and gone since DocuSign was founded in 2003, including recent overtures from IBM, Microsoft Corp. and Oracle Corp. The San Francisco company has been discussing plans for an initial public offering since at least 2013 but remains private. Even Springer’s hiring took longer than usual. He was appointed in January after a CEO search that lasted 15 months, more than three times longer than the norm.

A half-dozen people familiar with DocuSign’s management blame the company’s sluggishness on an indecisive board. DocuSign has 12 directors. That’s more than most public companies and nearly double the size of the average board at a private firm, according to the National Association of Corporate Directors, a trade group.

While many companies fill the room with a handful of board observers, who offer counsel without a vote, that’s not the case at DocuSign. It has a separate board for that. DocuSign’s global advisory board meets four times a year and is composed of investors, partners and friends of the company. It has 120 members.

Bringing order to the boardroom may prove to be the biggest challenge facing Springer as CEO. Directors control a company’s most substantial decisions, and oversized boards can be paralyzing, said Betsy Atkins, a consultant who has served as director at 60 closely held companies. “Smaller is better,” she said.

Despite the overabundance of opinions, Springer has a few of his own. He said his priorities are to develop new features, like possibly offering discounts from Home Depot or other stores when someone purchases a home, and continuing to expand outside the U.S. He said the company expects to file for an IPO late this year or early next. But he acknowledged DocuSign’s board situation is unique. “The board, as a whole, has a lot of opinions,” Springer said. “It can be complicated.”

Keith Krach, the previous CEO, is an adept fundraiser, bringing in $450 million of venture capital during his six years on the job. But the company’s board grew with nearly every funding round as certain incoming investors expected a seat at the table. Venture capitalists make up half of the 12-person board.

For corporate boards, research shows big is usually bad. Companies with fewer directors tend to outperform their peers, according to a 2014 study of 400 public firms by GMI Ratings, a corporate governance researcher. Experts on board composition at private companies discourage having more than seven. “If you can’t make decisions quickly, it doesn’t matter how good your thinking is,” said Jay Millen, who specializes in board and CEO placements at executive search firm Caldwell Partners.

When there are too many people in the room, members are more prone to groupthink, less likely to ask penetrating questions and take too long to make decisions, said Bernie Tenenbaum, managing partner at Lodestone Global, who has served on more than five dozen boards in the past two decades. “You need to go out with a laser to find board directors, not a butterfly net,” he said.

Having an overcrowded board with many—and often contradictory—agendas made some decisions difficult at DocuSign, including the IPO plan and CEO search, according to people familiar with discussions. In 2015, DocuSign was preparing to go public but pulled back because there was no one to lead it. Krach, the CEO and board chairman, wanted out. “I said I’d do it for two years, and I’d been doing it for six,” he said.

Krach, who took Ariba public in 1999, announced his intention to resign in 2015 as soon as his replacement was found. This launched what would become one of the lengthiest CEO searches in startup history.

During the process, DocuSign was approached with several acquisition offers, including one from Microsoft, which is an investor, for more than $4 billion, people familiar with the discussions said. The board debated the offer and ultimately decided to hold out for a higher one or wait for a new CEO to take the company public, the people said. Visa Inc., another investor, proposed a similar deal around the same time, but it never reached a vote, the people said. Other offers came from International Business Machines Corp. and Oracle, a person with knowledge of the discussions said. “Everyone had a different opinion,” another person said.

DocuSign declined to comment. IBM, Microsoft, Oracle and Visa didn’t respond to requests for comment.

Early last year, the board decided to give the CEO job to Rick Osterloh, but the candidate backed out at the last minute to return to his former employer Google, Bloomberg reported at the time. The lack of a backup plan highlighted a key weakness at DocuSign. “Good boards create a pipeline of CEOs,” said Friso van der Oord, director of research for the trade association representing directors.

DocuSign has had more luck with parts of the business that aren’t determined by the board. The sales team has successfully expanded beyond real estate into banking, insurance, government, health care and life sciences in recent years. Developers have rolled out much-requested features, such as document tracking and archiving, and created a system for other apps to connect with DocuSign functions, a strategy that now accounts for 58 percent of transactions. And the company is beginning to grow globally, though North America represents about 85 percent of revenue. There are more than 2,000 employees worldwide.

In January, Krach finally relinquished the CEO post to Springer, who also received a board seat. Krach, 60, retains the role of chairman. Whether the board decides to eventually sell the company or list publicly, Springer has experience with both. The wiry, fast-talking, 54-year-old executive took email marketing company Responsys public in 2011 and sold it to Oracle two years later for about $1.5 billion.

The DocuSign advisory board got its first chance to meet Springer in February at a white linen and wine affair in San Francisco. The 120-member board has executives who hail from Chevron Corp., McDonald’s Corp., UBS Group AG, Xerox Corp. and other business giants. Krach has described the group as “one of the most strategic things we do.”

Dozens showed up to the winter event to give a piece of advice to Springer. The new CEO said his favorite suggestion came toward the end of the four-hour meal. Arjun Gupta, founder of venture firm TeleSoft Partners, which is not a DocuSign investor, told him to be aggressive and trust his gut, Springer said. “You don’t want to spend too much time navel-gazing and building consensus,” he recalled.