Grammarly - Igor Karpets
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    Snovio Labs were lucky to sit down for a talk with Igor Karpets, the Head of Enterprise Sales at Grammarly to find out how Grammarly manages to close multimillion-dollar deals, how to make your first sale, and, of course, Grammarly’s plans for 2019. Read the interview below.

    Hey Igor! In this part of the interview we usually ask our interviewees to introduce themselves and their product, but I’m pretty sure everyone has used or at least heard of Grammarly at some point. So instead I want you to tell me about how it feels to join a company like Grammarly at the very start and see it grow so much and so fast?

    Igor Karpets: I feel fortunate. Fortunate to have the company that we have right now, and fortunate to have the pleasure to watch the company grow even bigger. I joined back in 2005, when we were still working on another project that dealt mostly with plagiarism detection. In 2008 we sold it to a learning management platform called Blackboard. After that, we decided to switch gears and create something that would help academia. That’s how the idea of Grammarly was born.

    Grammarly was initially focused on grammar and spelling correction for universities. But we soon saw its potential as a writing assistant that can help anyone communicate more clearly and effectively in English. So it’s been a journey, and I’m still enjoying it.

    As you’ve mentioned, you’ve been with the company since before it became Grammarly. Not many would have left a company [ed.note: MyDropbox] to follow their founders into another, new project. Did you have that strong a belief it was going to be a success?

    IK: When you’re just starting, you have to believe that something good is going to happen. And looking back at the leadership, even back in 2009, I saw that the mentality, the mindset our founders had… you could trust that they would do whatever it takes to get the job done, even if they had to bootstrap the project to success.

    Seeing as MyDropbox was sold to Blackboard, I have to ask – have there ever been offers for Grammarly from giants like Microsoft or Google?

    IK: I can’t disclose that information, but what I can say is that when a company starts to become successful, people notice.

    When you’re just starting, you have to believe something good is going to happen. [And] the mentality, the mindset our founders had… you could trust they would do whatever it takes to get the job done.

    Grammarly started in Ukraine, a country that has not yet produced a unicorn. You were named one of the Forbes’ Top 100 World’s Best Cloud Companies last year, so, realistically, do you feel like Grammarly might become one in the future?

    IK: I have high hopes that we will also make it. And we will not be the only ones in Ukraine.
    Right now we already have a few companies in Ukraine, like Competera and Readdle, who got a good start and could be on their way to becoming unicorns.

    Most of Grammarly’s operation is based in the U.S. right now. Do you live in Ukraine or the U.S.?

    IK: Most of our marketing team, executive team, and a part of the IT team are based in our San Francisco and New York offices. But right now we have more people in the Kyiv office than we do in the U.S. And me, well, my body is in Kyiv, but my mind lives in San Francisco. [Laughs]

    You speak at a lot of conferences in Ukraine, is the IT community there important to you?

    IK: Yeah! I don’t have plans to move anytime soon, and I’m interested in developing the IT community, especially the Sales and Business development communities in Ukraine.

    I’m seeing pretty positive signs of this happening right now. Just five to eight years ago the sales niche was almost non-existent. Everyone just lead gen-ed. They had SDRs in Ukraine, but the salespeople were all based in the US and Europe, and no one trusted that a salesperson in Ukraine could close a deal! But now things have changed – many product companies, and even outsource companies have salespeople in Ukraine. So I’m very optimistic that we’ll expand and scale, and the IT community, in general, will grow to an extent comparable to Silicon Valley or San Francisco.

    Huge business opportunities can take up to a year [to arrange].

    Which country uses Grammarly the most? Is there even a need for a spell checker extension in English-speaking countries?

    IK: Well, there’s no doubt that #1 is the U.S. And yes [there is a need] for better communication around the world.

    We communicate with more people around the world across more channels with less time. There are more opportunities for misunderstanding than ever before! Grammarly’s writing assistant aims to help people better understand and be understood by one another. This goes beyond just spelling and grammar correction into areas like clarity and conciseness.

    Grammarly began by selling to universities, so what made the company change their mind and shift to B2C?

    IK: After starting Grammarly, we soon found that it wasn’t just people from academia who were using it, but also authors, marketers, bloggers, and others as well. The need for effective communication is universal. Everyone who writes in English needs Grammarly to some extent because no one is 100% perfect or immune from making even small typos.

    Identify the pain points of the company and then package your solution in the best wrapping possible.

    When reading your stats, it doesn’t seem like client acquisition was ever a problem for Grammarly. What usually stops people? The price? The feature set?

    IK: Various reasons. Sometimes things just don’t seem to be working out. Price can be one of the factors, since our prices are pretty much U.S.-based, so others may not be able to get on this as fast as they’d like.

    How long is your average sales cycle?

    IK: On average, three weeks to a month. However, huge business opportunities can take up to a year.

    You’re the Head of Enterprise Sales, you must’ve mastered the art of convincing. What’s your #1 trick to convince?

    IK: The secret is in detecting different pain points for different verticals.

    For example, for academia, Grammarly helps students graduate with confidence by helping them write their essays and reports better. And it works because a huge number of companies see that students struggle with poor writing habits, even after college or university.

    For any client-facing department in a business, Grammarly is essential because you know that if you make a writing mistake or are unclear in your sales pitch or communication with a potential customer, it could cost you a sale. It makes Grammarly a no-brainer for anyone who wants to stay competitive.

    Call your current clients or give out your product for free to potential clients, and ask for feedback. The feedback is critical. 

    If it’s not a secret, what’s the average worth of sales you close now?

    IK: Unfortunately, we can’t disclose that, but it’s multimillion for the enterprise department.

    What deal are you most proud of?

    IK: For now, one of the best deals I’ve ever closed was with one of the largest universities in the world. It was a complex deal because it involved a huge amount of negotiations and custom requests. It lasted 9 months and the deal was large enough to make me happy! [Laughs]

    How many people are there in your department currently?

    IK: In enterprise sales, we have 11 people: two lead gens, two SDRs, five sales reps, and one enterprise customer support rep.

    It’s not a small team, what do you use for project management?

    IK: We use Jira for devs, we use Asana for the non-tech side. For communication we use Slack and, of course, Grammarly.

    Find the person who will be your brand advocate at the company. This person may not have the money to buy your product but they can recommend it to the decision maker.

    We’ve met at IT Arena where you were giving a talk on Grammarly’s cold email strategy. What, in your experience, is the key ingredient to a perfect cold email that often goes ignored?

    IK: Before sending any cold email, do extensive research on your client’s pain points and the ways in which your or any other product can help. Here’s what I mean by research — talk to your clients! Either call your current clients and talk to them or give out your product for free to potential clients and ask for feedback.

    The feedback is critical. Unless you know what pain points your product addresses, the cold email system will not be successful to the extent that it can be.

    You’ve now almost answered my next question, but what’s your advice for young entrepreneurs trying to sell their product for the first time?

    IK: If you’re a beginner, define your niche, define your vertical in the market, and do the necessary research to define what pain points your company can help with. Once you define the pain points, define the personas who would be interested in buying your product. Define your buyer persona and also find the person who will be your brand advocate at this company. This person may not have the money to buy your product but they can recommend it to the decision maker.

    Do you have a motto when it comes to sales?

    IK: If you have a great product, if you offer a great service, you don’t have to aggressively push it. Identify the pain points of the company and then package your solution in the best wrapping possible.

    It’s important to embrace challenge because it brings in new knowledge and new experiences.

    Do you make most of your deals via phone, email or face-to-face? Is real life contact overrated or underrated?

    IK: It depends. If you are closing a multimillion-dollar deal, it makes sense to travel for that real life contact, because the emotions, the handshaking, the time spent together – those are priceless. But for smaller deals, screen sharing and a conference call in a meeting room will suffice.

    If you could give advice to the 2009 version of you, what would it be?

    IK: [Pauses] That’s a good question because to be really honest, I feel like everything happened pretty organically. Everything that happened I’m pretty happy with — the way the processes were built, the way I was feeling about my job, and Grammarly.

    The need to learn and optimize is ongoing, and that hasn’t changed over my career. It’s important to embrace challenge because it brings in new knowledge and new experiences.

    If you are closing a multi-million deal, it makes sense to travel for that real life contact, because the emotions, the handshaking, the time spent together – those are priceless.

    How do you wind down? Do you have any hobbies?

    IK: To wind down I go to the gym two or three times a week to keep my body and mind in tune. I love traveling, I travel a lot with my family. Spending time with my wife and my son is always a highlight. Other than that, I really enjoy skiing!

    Obviously, all future projects for Grammarly would be secured under NDAs, so I’ll just ask one simple yes or no question – do you have anything big cooking for 2019?

    IK: Yes. We’re constantly improving our algorithms and introducing new capabilities. In 2019, we’ll be introducing a few new checks and focusing on helping people better achieve their communication goals.

    Big grammar question for you: Oxford comma – yes or no?

    IK: [Sighs] There will always be a debate about this. Some of my clients say it’s absolutely critical to have an Oxford comma, others say you can drop it. And that’s because English, like any other language, is not homogenous – you have dialects, variations, slang, and more. English is too universal and widespread to have any single opinion on what’s right and what’s wrong.

    And the rules are constantly evolving. A hundred years ago, no one could imagine we’d have the idioms we have today, so who knows what will happen in a hundred more!

    This interview has been edited and condensed for clarity.

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    Dana Rudenko is the chief editor at Snovio Labs, bringing you the freshest marketing content and exclusive insights from the world's most successful startups. In her free time you can find her creating playlists, gardening, or googling dogs in cowboy costumes.

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