Is Microsoft Positioning LinkedIn to Challenge DocuSign?

DocuSign’s recent earnings report proves that the demand for digital signatures is booming. With remote work and digital transformation driving business operations, DocuSign has solidified itself as the industry leader. But as DocuSign thrives, another major player could be positioning itself for an entry into the space: Microsoft—through LinkedIn.

It wouldn’t be the first time Microsoft has partnered with a company, only to later compete with them. Looking at Microsoft’s history, this move would fit their playbook.

Microsoft’s History of Turning Partnerships into Competition

Microsoft has a well-documented history of working alongside companies before launching competing products. Consider these examples:

IBM and MS-DOS/PC-DOS

• Collaboration: In the early 1980s, Microsoft worked closely with IBM to develop the operating system for the IBM PC. Microsoft licensed and adapted a system called 86-DOS (from Seattle Computer Products) into MS-DOS, which IBM branded as PC-DOS. This partnership made Microsoft a key player in the PC ecosystem.
• Competition: As the PC market grew, Microsoft expanded MS-DOS independently, selling it to other hardware makers (e.g., Compaq) for "IBM PC-compatible" machines. This diluted IBM’s control over the PC market, and by the late 1980s, Microsoft’s Windows—built atop MS-DOS—further eroded IBM’s dominance. IBM tried to counter with OS/2 (initially co-developed with Microsoft), but Microsoft abandoned that effort to focus on Windows, effectively turning a partner into a rival.

Apple and the Macintosh GUI

• Collaboration: In the early 1980s, Microsoft developed applications like Word and Excel for Apple’s Macintosh, launched in 1984. This gave Microsoft’s team, including Bill Gates, deep exposure to Apple’s graphical user interface (GUI), inspired by Xerox PARC. Microsoft was a key software partner for Apple during this period.
• Competition: Microsoft used that experience to build Windows, first released in 1985 as a GUI layer over MS-DOS. While crude initially, Windows evolved into a direct competitor to the Mac OS by the early 1990s, sparking a bitter rivalry (and lawsuits from Apple over "look and feel"). The collaboration gave Microsoft a window (pun intended) into GUI design before they became Apple’s chief adversary.

Netscape and Internet Explorer

• Collaboration: In the mid-1990s, Microsoft didn’t directly partner with Netscape, but it licensed technology from Spyglass, Inc. (which built on Mosaic, a precursor to Netscape Navigator) to create Internet Explorer. Microsoft also relied on the broader internet ecosystem—where Netscape dominated—to understand browser demand.
• Competition: By 1995, Microsoft bundled Internet Explorer with Windows 95, launching the "Browser Wars." They aggressively undercut Netscape’s paid Navigator with a free browser, integrating it into the OS. This led to Netscape’s decline and a landmark antitrust case against Microsoft in 1998. The early reliance on industry players like Spyglass morphed into a strategy to dominate the market.

Novell and Networking

• Collaboration: In the late 1980s and early 1990s, Microsoft worked with Novell, a leader in network operating systems with NetWare. Microsoft even bundled NetWare-compatible protocols in early Windows releases to support enterprise customers. The two companies coexisted in the networking space for a time.
• Competition: With Windows NT (launched in 1993), Microsoft integrated robust networking features, directly targeting Novell’s NetWare market. NT Server gained traction, and by the late 1990s, Microsoft had overtaken Novell in enterprise networking, contributing to Novell’s decline.

Sun Microsystems and Java

• Collaboration: In the mid-1990s, Microsoft licensed Java from Sun Microsystems to integrate it into Windows, aiming to support the growing demand for platform-independent apps. This was a cooperative move to bolster Windows’ appeal to developers.
• Competition: Microsoft then created its own version, "J++," and tweaked Java’s implementation to tie it more closely to Windows, breaking Sun’s cross-platform vision. This led to a lawsuit from Sun in 1997, settled in 2001, but not before Microsoft shifted focus to its own .NET framework, a direct competitor to Java’s ecosystem.

Borland and Development Tools

• Collaboration: In the 1980s and early 1990s, Microsoft and Borland coexisted in the developer tools market. Borland’s Turbo Pascal and later C++ compilers were popular, and Microsoft even bundled Borland’s tools with some early Windows SDKs. The two companies indirectly supported each other’s ecosystems—Borland’s tools helped developers build for Windows.
• Competition: Microsoft ramped up its own developer offerings with Visual Basic (1991) and Visual C++ (early 1990s), directly targeting Borland’s dominance. By integrating these tools into the Windows ecosystem and offering aggressive pricing, Microsoft eroded Borland’s market share. Borland struggled to keep up, eventually fading as a major player by the late 1990s.

Lotus and Spreadsheets

• Collaboration: Before Excel, Microsoft had a loose relationship with Lotus, the leader in spreadsheets with Lotus 1-2-3. Microsoft didn’t partner directly but built Multiplan (an early spreadsheet) in the 1980s, which ran on platforms like MS-DOS alongside Lotus. They observed Lotus’s success closely, especially as Windows emerged.
• Competition: With Excel’s launch in 1985 (initially for Mac, then Windows in 1987), Microsoft pivoted to challenge Lotus head-on. Excel’s GUI and Windows integration gave it an edge over the DOS-based Lotus 1-2-3. By the early 1990s, Excel overtook Lotus, and Microsoft’s Office suite cemented its dominance, contributing to Lotus’s decline (later acquired by IBM).

WordPerfect and Word Processing

• Collaboration: In the late 1980s, WordPerfect dominated word processing on DOS. Microsoft worked with WordPerfect Corp. indirectly by ensuring Windows supported their software, fostering a period of coexistence as Windows gained traction. Microsoft’s early Word (1983) was a minor player compared to WordPerfect.
• Competition: With Microsoft Word for Windows (1989), the company leveraged the GUI advantage and Office bundling to challenge WordPerfect. WordPerfect was slow to adapt to Windows, and by the mid-1990s, Microsoft Word had eclipsed it. WordPerfect’s market share collapsed, and its parent company was sold off (eventually to Corel).

RealNetworks and Windows Media Player

• Collaboration: In the mid-1990s, RealNetworks (then RealAudio) pioneered streaming media. Microsoft initially supported Real’s formats in Windows and even invested in the company in 1997, taking a minority stake. RealPlayer was a popular add-on for Windows users.
• Competition: Microsoft soon developed Windows Media Player, integrating it into Windows by the late 1990s. With Windows Media formats (e.g., WMA, WMV) and aggressive promotion, Microsoft squeezed RealNetworks out of the mainstream. Real sued Microsoft in 2003 over anticompetitive practices, settling for $761 million in 2005, but by then, Real’s market lead was gone.

Slack and Microsoft Teams

• Collaboration: Before Teams, Microsoft didn’t directly partner with Slack, but Slack integrated with Microsoft’s Office 365 ecosystem in the mid-2010s, enhancing its appeal to Office users. Microsoft even reportedly considered acquiring Slack in 2016 but opted against it.
• Competition: In 2017, Microsoft launched Teams as part of Office 365, positioning it as a direct competitor to Slack. Teams leveraged Microsoft’s existing enterprise footprint and aggressive bundling (often free with Office subscriptions) to challenge Slack’s dominance in team collaboration. By 2020, Teams had surpassed Slack in daily active users, intensifying the rivalry.

(Have I missed any? Somebody let me know.)

Seeing this pattern, DocuSign’s current partnership with Microsoft may not be permanent—it could be a stepping stone for Microsoft to develop its own competing solution, likely via LinkedIn.

Why LinkedIn Could Be a Strong DocuSign Competitor

1?? Leveraging HR Data & Verification

Unlike DocuSign, which focuses on signing documents, LinkedIn has a massive database of professional credentials. A LinkedIn-based e-signature tool could do more than collect signatures—it could verify employment history, certifications, and professional credentials on the spot. Imagine signing an employment contract and having LinkedIn instantly validate credentials via blockchain-backed authentication. That’s a game-changer!!!

2?? Seamless HR & Hiring Integration

LinkedIn dominates the talent acquisition space, making it the ideal platform to integrate e-signatures directly into hiring workflows. Imagine sending an offer letter, collecting a signature, and automatically updating an employee’s LinkedIn profile—all in one system. HR professionals wouldn’t need to jump between platforms, making the process more efficient than DocuSign’s standalone product.

3?? Microsoft’s Ecosystem Advantage

If Microsoft decides to integrate a LinkedIn e-signature tool into Microsoft 365, Teams, and Dynamics 365, it could create a frictionless document signing experience without the need for DocuSign. Given Microsoft’s massive user base, they could instantly scale adoption, potentially pushing DocuSign out of key enterprise deals.

Why Microsoft Hasn’t Made the Move Yet?

For now, Microsoft and DocuSign have a strong business relationship. DocuSign’s e-signature technology is integrated into Microsoft products, including Word, Outlook, and Teams, streamlining document workflows.

However, Microsoft does not own DocuSign, and history suggests this partnership could be temporary. If Microsoft sees an opportunity to capture more market share, it might leverage LinkedIn’s ecosystem to launch a competitive product—just like it did with Internet Explorer, Office, Azure, and Teams.

The Big Question: Will Microsoft Make the Move?

Microsoft has the resources, infrastructure, and track record to enter the e-signature market through LinkedIn. The question isn’t just if they will do it—but when. (Dun, dun, dunnn...)

But hey, that's just my two cents worth of analysis. What do you think? Will Microsoft use LinkedIn to challenge DocuSign, or will it stick with its current partnership? Drop a comment—I’d love to hear your take!