Grammarly: The Story of How Three Ukrainians Created The Most Popular Online Grammar Checker

Grammarly, the online English grammar checker, is known and used by millions of users. Only for Google Chrome, the service is being used regularly by 10 million people. In 2014, the Managing Partner of Aventures Capital, Yevgen Sysoyev, valued Grammarly at USD 100 million. Grammarly was founded by three Ukrainians: Oleksiy Shevchenko, Maksym Lytvyn, and Dmytro Lider.

Galyna Bozhok
9 min readJul 3, 2020


The Beginning

Oleksiy Shevchenko and Maksym Lytvyn met each other at the end of the 1990s, during their student years at International Christian University in Kyiv, Ukraine. International Christian University was one of the first universities in Ukraine with degree programs entirely held in English.

Kyiv, Ukraine. Source: Unsplash; Elena Mozhvila

At the university, they first came up with an idea for their first mutual business — the service for checking student works for plagiarism, MyDropBox. At that time, many students were downloading ready term papers and homework from the Internet. This was a big problem for Ukrainian and foreign universities: professors were not able to properly check texts, and, as a result, they were giving high grades for stolen texts. Unfortunately, there was no service to check written works for plagiarism. By the way, besides Ukrainians, Americans were also targeting this problem, but their company TurnItIn appeared on the market later than MyDropBox.

Maksym Lytven and Oleksiy Shevchenko. Source: AIN

The first team of MyDropBox included 3 members — the already mentioned friends, Oleksiy and Maksym, and the system administrator. Maksym wrote the programming code for the system, and after the creation of the working product, friends started thinking about its monetization.

Maksym and Oleksiy tested the service with a few pilot clients in Singapore and the USA, and started selling licenses for the use of technology to the US universities. However, they faced a problem — it was very difficult to sell a product to American clients from Ukraine. As a result, the young entrepreneurs decided to move closer to the target market and continue their education in Western universities. Maksym got accepted into the MBA program at Vanderbilt University in Tennessee, and Oleksiy started his MBA program in Toronto two years later.

Toronto, Canada. Source: Unsplash; Zia Syed

After his MBA program, Maksym moved to Canada, and partners started to actively sell their products. They were searching for new clients at the technology conferences for higher education institutions. At the events, they were gathering reviews on their project, meeting with university representatives, and proposing to them to try their product. At that time, the name of the product — MyDropBox — wasn’t associated with the famous file sharing service Dropbox because Dropbox appeared on the market a few years later — in 2007.

Together with the universities, publishers of educational literature became interested in MyDropBox — they started to supply MyDropBox in the sets with textbooks to increase the latter's value. After the sale of the first licenses, the size of the company rose to 12–15 developers in Ukraine and 5–6 sales managers in North America. By 2007, the product was used by 800 universities and around 2 million students. Today, similar services are being used by 95% of North American universities.

After the start of sales, MyDropBox joined the Blackboard Developer Network. MyDropBox developed a plug-in SafeAssignment for the largest US educational platform, Blackboard, which allowed Blackboard to check its users for plagiarism. The plug-in was integrated with Blackboard and easy to work with.

The popularity of SafeAssignment was increasing, and clients started to recommend it to each other. Blackboard made an acquisition proposal to MyDropBox. The amount of the transaction isn’t announced. However, Oleksiy Shevchenko states that the amount was relatively small. One of the acquisition conditions was the 2-year lock-in for Maksym Lytvyn. During this time, he needed to teach the colleagues at Blackboard, transfer all the information, and develop multi-lingual support systems.

Around that time, the future co-founder of Grammarly, Dmytro Lider, joined the team. At first, he was a developer at MyDropBox. After the acquisition, he managed the adaptation of products per Blackboard’s requirements. And, after Maksym and Oleksiy founded Grammarly, they offered him the role of a Technical Partner.

Source: Unsplash; Samuel Bourke

Whilst Maksym was in Washington, Oleksiy and Dmytro started working on a new project. From the previous experience in the US, they knew that even Native-speaking students had a problem with grammar. That is why they decided to create a product, which would help students to improve their writing.

At the beginning of 2008, a new version of such a product was created — EssayRater. A few days before the launch, Ukrainians tested the integration with AdWords, spent a few dollars on advertisement… and, received the first customer, which bought a subscription that was 10 times costlier than the advertisement.

Throughout the following year, the team understood that the service was useful not only for school or work but for casual life too: many people were interested in checking their grammar before sending an email or posting on social media, etc. Thus, the product would have success in the mass market too.

Grammarly was founded in 2009. In 2010, Brad Hoover, the former Partner of the investment fund General Catalyst, joined Grammarly as a CEO.

How Does Grammarly Work?

Grammarly helps users to create mistake-free, understandable, and effective texts. The service immediately detects mistakes and stylistic errors and also explains how to avoid the repetition of those. The algorithm recommends the changes, which the users may accept or deny. For each recommendation, an explanation is added.

Today, Grammarly is available for three browsers (Google Chrome, Firefox, and Safari), desktop applications for Microfost Windows and Mac OS, and Microsoft Office. The users may also check the text by pasting it into the online editor on the website.

At Google and Microsoft, the teams have been trying to improve their algorithms for checking grammar for many years. In comparison to Grammarly, these companies have almost unlimited financial capabilities and qualified staff. However, the products of Microsoft and Google suggest wrong corrections or miss more mistakes than Grammarly’s products do.

The program code of Grammarly is a complex hybrid system, which combines the grammar rules of the English language and machine learning.

How to Attract Such Clients as Cisco, Boeing, and US Universities

Even though Grammarly is very popular in the mass market, the team continues to target corporate sales. At the moment, Grammarly has over 700 corporate clients, including Cisco, Boeing, Dow Jones, Dell, Expedia, Salesforce, and the leading US universities.

Source: Unsplash; Ethan McArthur

Within a few years of MyDropBox’s operations, the team studied the academic market and built multiple relationships with potential clients. The first corporate sales of Grammarly took place because of these experiences and loyal clients of MyDropBox. Also, the acquisition of lists with possible clients and participation in conferences contributed to the sales process.

Grammarly defines three key drivers of success in sales:

  1. Treat clients as partners, focus on long-term relationships. First — build relationships, later — start selling. It is especially important to teach this driver to the teammates who participate in the decision-making process.
  2. Be ready to change the product per the client’s requirement. The majority of clients (on the level of Bank of America) ask for multiple legal requirements and technical changes in the company’s product itself. The security concern may be above the functionality or speed of the provided product.
  3. Hire “therapists,” not wolves of Wall Street. Aggressive sales bring fast sales, which only results in one-time revenue. But sales “therapists” develop long-term relationships with clients because they work as consultants, not as salesmen.

From experience, the Head of Sales Department of Grammarly, Igor Karpets, states that business relationships are built on trust. Many clients may send payment information or give access to their databases without any additional questions or legal documents. However, one mistake or broken promise may lead to a company being crossed out of the contact list for years.

The sale of licenses to corporate clients brings Grammarly over 20% of its total profit. In addition, corporate clients provide exposure to Grammarly and contribute to its reputation.

However, sometimes Grammarly uses little tricks in order to bring in new clients. Grammarly has a special team, Lead Generation Team, which searches for quality leads, and finds e-mails of large companies' executives. Grammarly generates detailed profiles of each potential client. Instead of sending out cold-emails, they write personalized letters to each company representative.

Promotion of the Service Through Social Networks

Like the majority of IT-companies, Grammarly sells its products online. Therefore, the company doesn’t have offices in all countries in which it conducts sales. Grammarly finds new clients with the standard promotion methods:

  • banner ads
  • SEO
  • content marketing
  • e-mails
  • SMM
Source: unsplash; Kon Karampelas

The best advertising methods for Grammarly are social networks. Today, over 7 million people are subscribed to the company’s Facebook page. The first subscribers were friends of Grammarly’s staff — at that time, Facebook wasn’t overloaded with information, and users were actively subscribing to pages with interesting content. To gain more subscribers, Grammarly decided not to post advertisements on its page but to provide interesting articles for people who were curious about life and wanted to become more well-rounded. Now, the majority of Grammarly’s subscribers on Facebook are loyal customers of Grammarly.

To convince a person to pay for the product is not easy, but possible. For example, a Facebook user may click on the infographics with the 10 most common mistakes and get transferred to Grammarly’s website. On Grammarly’s website, there will be a more detailed article with the proposal to subscribe to the service. Such methods often work because a person understands the value of the product.

According to the SMM representatives of Grammarly, it is essential to understand the change in Facebook designs, algorithms, and preferences of users in order to quickly adapt and not miss out on any opportunities.

Also, entertainment posts attract new subscribers — GIFs, short videos, and broadcasts. Therefore, understanding of interests of the audience results in success.

Source: Unsplash; Mimi Thian

At Grammarly, only a few people are responsible for the content, which is viewed and read by the multi-million audience. Two employees are responsible for writing articles and coming up with other posts, and a designer is responsible for a virtual picture, and developers with executive managers are offering ideas for posts on social networks.

Kyiv, Ukraine. Source: Unsplash; Vitaliy Zamedyanskiy

Employee Motivation and Teamwork

It is very hard to find any bad reviews on the work environment at Grammarly. Grammarly is ranked as one of the top employers in Ukraine. That comes as no surprise as Grammarly pays close attention to the development of healthy and productive work culture. The ideal corporate culture has to correspond with the values of its team and help the company to achieve its goals.

Kyiv, Ukraine. Source: Unsplash; Vitaliy Zamedyanskiy

For many people, Grammarly is associated with the service for grammar correction. However, the company aims for a more ambitious goal: to improve communication between people with the use of technologies; and, in the future, to help machines to communicate with each other.


  1. How Ukrainian Grammarly Changed the Culture of Writing in the USA and Attracted Such Clients as Cisco, Boeing, and Leading Universities. AIN. October 2015.

2. Timur Vorona. A Million-Dollar Startup. Vivat. 2017.



Galyna Bozhok

Exploring art, photography, entrepreneurship, and investments