• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Exclusive

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

TechDocuSign

DocuSign and Smartsheet Boomed on First Day Trading After Their IPOs

By
Jonathan Vanian
Jonathan Vanian
Down Arrow Button Icon
By
Jonathan Vanian
Jonathan Vanian
Down Arrow Button Icon
April 27, 2018, 5:47 PM ET

Shares in DocuSign and Smartsheet soared after the two business software companies went public on Friday.

DocuSign, which specializes in software for signing documents digitally, was up 37% in its first day of trading to $39.73. Meanwhile, Smartsheet, which sells software to manage business tasks, rose 30% to $19.55.

The two IPOs are part of a recent trend of enterprise software companies going public after drought of several years.

Just last Friday, the Dell Technologies subsidiary company Pivotal went public, while workplace software and online storage company Dropbox held its IPO in late March. Zuora, which sells software for companies to manage their own subscription services and payment plans, also went public in April.

DocuSign CEO Dan Springer said that more enterprise companies are going public now because several took big funding rounds over the past few years to help them grow their businesses to the point where they would be ready to IPO. It’s also likely that startups’ venture capitalists and other investors were urging them to go public so they could generate returns.

Indeed, DocuSign landed $233 million in 2015 while Dropbox raised $350 million in 2014. Pivotal raised $253 million in 2016, while Smartsheet raised a more modest $52 million in 2017.

This new wave of enterprise companies, although they focus on different types of software and services, all have one thing in common: they are unprofitable.

DocuSign, for example, lost $115.4 million on sales of $381.5 million during the year ending Jan. 31. Likewise, Smartsheet’s revenue for its latest year was $111 million, while it lost $49.1 million.

Wall Street investors, however, appear to be unphased by unprofitable technology companies as long as their finances indicate that they are rapidly growing. DocuSign’s overall sales jumped 52% year-over-year while Smartsheet’s sales skyrocketed 66%.

Smartsheet CEO Mark Mader believes that cloud software companies like Salesforce (CRM) and Workday that have built businesses that sell recurring subscriptions instead of collecting one-time payments have paved the way for businesses like his. These types of companies require years of investment and big customer rolls before they eventually make money through recurring payments.

Wall Street investors “are really understanding the dynamics of building a subscription businesses,” Mader said. “The ‘smart money’ understands that model.”

That said, enterprise software companies face a huge challenge in retaining customers that can cancel after they pay their last monthly or yearly bill, which Smartsheet acknowledges in its regulatory filing. Additionally, both Smartsheet and DocuSign face fast-growing competitors like Adobe, Microsoft, and Google.

DocuSign’s Springer conceded that Adobe’s competing electronic signature business is a challenge, but he believes that DocuSign’s biggest test is convincing companies to forgo paper documents in favor of their digital counterparts.

“Instead of thinking who we are looking at attacking, we look at attacking paper,” Springer said.

For Mader, going public and the publicity it brings will help improve the company’s ability to win more customers. Also, an IPO gives the company more legitimacy.

It's been a great day for our Smartsheet team. A big thank you to all of our customers and partners for joining us on this journey. #SmartsheetLife #SMAR pic.twitter.com/DvvA2pVl0G

— Smartsheet (@Smartsheet) April 27, 2018

“Do you want to be a real company or do you want to keep plodding along as a private company?” Mader said about Smartsheet’s IPO decision.

Will Mader miss being a privately held startup that doesn’t have to deal with demanding Wall Street investors and extra public scrutiny each quarter?

“Two words—hell no,” Mader said. The executive acknowledged the fact that most startups fail and that it took years of hard work and luck to finally go public.

Get Data Sheet, Fortune’s technology newsletter.

“Do you know how low the odds are?” Mader said about the chances of a startup surviving. “You really have to have an appreciation for the present day.”

About the Author
By Jonathan Vanian
LinkedIn iconTwitter icon

Jonathan Vanian is a former Fortune reporter. He covered business technology, cybersecurity, artificial intelligence, data privacy, and other topics.

See full bioRight Arrow Button Icon

Latest in Tech

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Tech

Environmental advocates and progressive lawmakers hold a rally in support of legislation that would put a moratorium on new data centers in the state on Wednesday, May 13, 2026, at the Capitol in Albany, N.Y.
AIData centers
Americans’ AI hate wave might just be gathering steam: Data centers could hike power costs in some states over 50% by 2030
By Tristan BoveMay 19, 2026
22 minutes ago
How a book convinced Arundhati Bhattacharya, one of India’s most powerful bankers, to try working for a U.S. tech company
AsiaMost Powerful Women
How a book convinced Arundhati Bhattacharya, one of India’s most powerful bankers, to try working for a U.S. tech company
By Angelica AngMay 19, 2026
24 minutes ago
altman
CommentarySam Altman
Musk vs. Altman: AI safety cannot be one man’s job
By Stavros GadinisMay 18, 2026
10 hours ago
Pope Leo launches an AI commission days before he releases a papal letter alongside Anthropic cofounder Christopher Olah
AIPope
Pope Leo launches an AI commission days before he releases a papal letter alongside Anthropic cofounder Christopher Olah
By Catherina GioinoMay 18, 2026
10 hours ago
John Ketchum, CEO of NextEra Energy, speaks during BlackRock's 2026 Infrastructure Summit in Washington, DC, on March 11, 2026. Photographer: Daniel Heuer/Bloomberg via Getty Images
EnergyNextEra Energy
NextEra’s $67 billion Dominion takeover creates the world’s largest utility—just in time to win the AI data-center power surge
By Jordan BlumMay 18, 2026
11 hours ago
Harvard University banners hang in front of a building
CryptoCryptocurrency
Harvard sold off its entire $87 million Ethereum stake just one quarter after buying it
By Jack KubinecMay 18, 2026
11 hours ago

Most Popular

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
6 days ago
While Trump insisted the Iran war would end ‘soon,’ an account in his name was buying millions in oil, defense and gold
Economy
While Trump insisted the Iran war would end ‘soon,’ an account in his name was buying millions in oil, defense and gold
By Eva RoytburgMay 18, 2026
13 hours ago
Current price of oil as of May 18, 2026
Personal Finance
Current price of oil as of May 18, 2026
By Joseph HostetlerMay 18, 2026
18 hours ago
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
3 days ago
EXCLUSIVE: An hour in the Oval Office with the CEO-in-Chief, President Trump
Politics
EXCLUSIVE: An hour in the Oval Office with the CEO-in-Chief, President Trump
By Alyson ShontellMay 18, 2026
1 day ago
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
Economy
The top foreign holders of U.S. debt may soon dump Treasury bonds and bring their money back home, potentially spiking borrowing costs
By Jason MaMay 17, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.