Grammarly vs Microsoft: Founders, CEOs and History
Grammarly was founded in 2009 by Max Lytvyn, Alex Shevchenko, Dmytro Lider and is led by Shishir Mehrotra. Microsoft was founded in 1975 by Bill Gates, Paul Allen and is led by Satya Nadella.
Company facts
Founders
Grammarly
Max Lytvyn
Max Lytvyn co-founded Grammarly in 2009 with Alex Shevchenko and Dmytro Lider. The idea came from their MyDropBox work: helping people write well rather than catching plagiarism afterwards.
Alex Shevchenko
Alex Shevchenko co-founded Grammarly in 2009 and helped shape it as a product-led company built around a free tier. That approach scaled through the 2015 Chrome extension.
Dmytro Lider
Dmytro Lider co-founded Grammarly in 2009 and led early work on its language technology from Kyiv, where the company kept a large engineering presence.
Microsoft
Bill Gates
Microsoft possesses arguably the most well-known, foundational founding story of the entire personal computing revolution, rooted in the intense, effective partnership of two teenage computer prodigies who recognized the software potential of the microcomputer…
Paul Allen
Paul Allen co-founded Microsoft and was crucial to its earliest technical and strategic decisions. He helped develop Altair BASIC, gave the company its original name, and participated in the operating-system opportunity that led to MS-DOS.
CEOs and their tenures
Grammarly
- Brad Hoover2011–2023
Former Chief Executive Officer
Led Grammarly through its bootstrapped years, the 2015 free-extension launch, and funding rounds in 2017, 2019 and 2021.
Source - Rahul Roy-Chowdhury2023–2025
Chief Executive Officer
Former Google Chrome product lead; head of product at Grammarly before becoming CEO in May 2023, overseeing the launch of GrammarlyGO generative features.
Source - Shishir Mehrotra2025–present
Chief Executive Officer
Co-founder of Coda and former YouTube product executive; became CEO when Grammarly acquired Coda, led the Superhuman Mail deal, the Superhuman rebrand and the GPTZero agreement.
Source
Microsoft
- Bill Gates1975–2000
Co-founder and CEO
Gates built Microsoft's licensing model: software sold to many hardware makers rather than tied to one.
Source - Steve Ballmer2000–2014
CEO
Ballmer grew revenue from about $23 billion in FY2000 to about $78 billion in FY2013 and built the enterprise server and sales business that Azure later scaled on.
Source - Satya Nadella2014–present
Chairman and CEO
Nadella made Azure and Microsoft 365 the company's core, opened Microsoft to Linux and open source, and positioned it early in generative AI through OpenAI.
Source
Timeline: Grammarly and Microsoft side by side
1975Microsoft
Microsoft Founded
Bill Gates and Paul Allen founded Microsoft after recognizing that the Altair 8800 needed usable programming software. Their first product, Altair BASIC, turned a hobbyist computer kit into a programmable platform.
1981Microsoft
MS-DOS Ships With IBM PC
IBM introduced its personal computer with MS-DOS 1.0 and other Microsoft products. The milestone mattered because Microsoft's operating-system work moved from a small software supplier's project into the emerging corporate PC standard.
1985Microsoft
Windows Launch
The release of Windows 1.0 began Microsoft's long move from command-line operating systems to graphical personal computing. The first version was not an instant blockbuster, but it gave Microsoft a user-interface path that could evolve with PC hardware.
1990Microsoft
Office Suite Release
The bundling of Word, Excel, and PowerPoint into Microsoft Office created a productivity suite that became central to business work. The bundle simplified enterprise purchasing and made file compatibility a competitive weapon.
1998Microsoft
U.S. Antitrust Case
The U.S. Department of Justice accused Microsoft of using Windows power to suppress browser competition. The case mattered because it placed Microsoft's platform tactics under public and legal scrutiny at the height of its PC strong position.
2009Grammarly
Grammarly Founded in Kyiv, Ukraine
Max Lytvyn, Alex Shevchenko, and Dmytro Lider founded Grammarly to help people communicate clearly in English.
2010Microsoft
Azure Commercial Launch
Azure gave Microsoft a way to compete in cloud infrastructure as enterprise customers began shifting workloads away from company-owned servers.
2011Grammarly
Brad Hoover Becomes CEO
Brad Hoover, a former General Catalyst investor, became CEO; the company later based its headquarters in San Francisco while engineering stayed in Kyiv.
2014Microsoft
Satya Nadella CEO
Satya Nadella became CEO and moved Microsoft away from a strategy that forced every product to serve Windows. He prioritized Azure, Microsoft 365, open source, Linux support, cross-platform software, and a more collaborative developer posture.
2015Grammarly
Launches Free Chrome Extension & Ignites Viral PLG Growth
Debuted the free Chrome browser extension, transforming Grammarly into an omnipresent consumer phenomenon.
2016Microsoft
LinkedIn Acquisition
Microsoft agreed to acquire LinkedIn in 2016 for $26.2 billion in cash. The deal mattered because it added a professional identity network to a company already strong in Office, Dynamics, cloud services, recruiting tools, advertising, and enterprise sales.
2017Grammarly
$110M First Outside Funding Round Led by General Catalyst
After eight years of profitable bootstrapping, raised $110 million led by Hemant Taneja at General Catalyst.
2018Grammarly
Grammarly Business Expands Enterprise Offering
Grew its paid offering for corporate teams with admin, billing and style controls.
2018Microsoft
GitHub Acquisition
Microsoft acquired GitHub for $7.5 billion in stock, reversing years of developer skepticism toward the company. The acquisition placed Microsoft inside the daily workflow of software developers across languages, clouds, and operating systems.
2019Grammarly
$90M Round at $1.0B+ Unicorn Valuation Led by General Catalyst
Achieved official unicorn status, debuting tone detection to evaluate emotional resonance in writing.
2021Grammarly
$200M Financing at $13.0B Valuation Led by Baillie Gifford
Raised $200 million at a $13 billion valuation in a round led by Baillie Gifford and BlackRock funds.
2023Grammarly
Rahul Roy-Chowdhury Appointed CEO & Launches Grammarly AI
Former Google executive Rahul Roy-Chowdhury became CEO, launching generative AI and contextual email rewrites.
2023Microsoft
AI Leadership
Microsoft's expanded OpenAI partnership and Copilot product rollout placed the company at the center of enterprise generative AI adoption.
2023Microsoft
Activision Blizzard Acquisition Closes
Microsoft completed the Activision Blizzard acquisition after intense regulatory review. The deal added Call of Duty, World of Warcraft, Diablo, Overwatch, Candy Crush, and other franchises to Microsoft Gaming.
2024Grammarly
Agreement to Acquire Coda
Grammarly agreed to acquire Coda in December 2024; Coda co-founder Shishir Mehrotra became Grammarly's CEO.
2025Grammarly
$1B Financing, Superhuman Mail Deal and Rebrand
Closed $1 billion from General Catalyst in May, completed the Superhuman Mail acquisition in July and renamed the company Superhuman on October 29.
2026Grammarly
Superhuman Docs Launch and GPTZero Deal
Rebuilt Coda as Superhuman Docs and agreed on June 23 to acquire GPTZero.
Acquisitions
Grammarly
- GPTZero2026Undisclosed
- Superhuman (Superhuman Mail)2025Undisclosed
- Coda2024Undisclosed
Microsoft
- Activision Blizzard2023$68.7B
- Nuance Communications2022$19.7B
- ZeniMax Media2021$7.5B
- GitHub2018$7.5B
- LinkedIn2016$26.2B
Questions about Grammarly vs Microsoft
Who is the CEO of Grammarly Inc. and Microsoft Corporation?
Grammarly Inc. is led by Shishir Mehrotra and Microsoft Corporation is led by Satya Nadella. Both serve as the top executive responsible for the company's strategy, operations, and financial performance.
When was Grammarly Inc. founded vs Microsoft Corporation?
Microsoft Corporation was founded in 1975 — 34 years before Grammarly Inc., which was founded in 2009. Microsoft Corporation's longer operating history gives it a deeper track record but also potentially more institutional inertia compared to the younger Grammarly Inc..
How many employees does Grammarly Inc. have compared to Microsoft Corporation?
Grammarly Inc. employs approximately 1,000 people, while Microsoft Corporation employs approximately 223,000. Microsoft Corporation has the larger workforce at 223,000 employees, compared to Grammarly Inc.'s 1,000. A higher headcount does not necessarily imply greater efficiency — it often reflects differences in business model (e.g., manufacturing vs. software).
Where are Grammarly Inc. and Microsoft Corporation headquartered?
Both Grammarly Inc. and Microsoft Corporation are headquartered in United States, meaning they operate under the same primary regulatory and tax environment.
Who founded Grammarly Inc. and Microsoft Corporation?
Grammarly Inc. was founded by Max Lytvyn, Alex Shevchenko, Dmytro Lider. Microsoft Corporation was founded by Bill Gates, Paul Allen.
Which company has a longer operating history — Grammarly Inc. or Microsoft Corporation?
Microsoft Corporation has been operating for approximately 51 years, making it the more established of the two companies. Grammarly Inc. has been in operation for around 17 years. A longer operating history often signals greater institutional resilience and brand recognition, though it can also mean slower adaptation to new market conditions.
Figures come from each company's filings and the sources linked beside them. Amounts reported in another currency are shown in US dollars at an approximate rate and marked with ~. Back to the Grammarly vs Microsoft overview