Facing Challenges and Winning the Race: Olga Grynenko shares her journey of breaking into Silicon Valley as a Software Engineer

Olga Grynenko is a software engineer for Grammarly, a Silicon Valley company known for its AI-powered writing tool. Grammarly announced that it reached unicorn status this past October. Here we catch up with Olga — who’s a Ukrainian expat as well as a passionate runner and cyclist — to find out how she made it in the industry and where she finds her inspiration.

Grammarly is now considered a unicorn. Congrats on the very exciting news! How do you feel being a part of such a successful and useful product?

Thank you! There is something magical about writing colorful lines of instructions (aka code) that help millions of people around the world communicate better. I am proud to be a part of the Grammarly team and feel fulfilled knowing that my work and effort matter and have a sizable impact.

What are you currently learning? How do you see your growth and development?

I have been working as a backend engineer at Grammarly for the last 2.5 years and recently transitioned to our Data Platform team, which builds our internal data analytics tool. Their codebase is mostly Scala, and I am looking forward to this new challenge. One of the projects I am actively working on is our internal experiment framework. Over the next few years, I plan to get more experience working on distributed systems and big data. More and more product ideas are being realized, and it’s necessary to have a solid toolset to ensure stability and make rapid growth possible. I think building platforms and tools is going to become an even more fruitful area in tech.

It’s your first full-time job as a software engineer. Can you please share your job search and the challenges you faced along the way?

My job search started in the fall of 2016. It took me roughly six months to get my first full-time job as a software engineer. I had just finished a full-time master’s degree in Ukraine at Taras Shevchenko National University of Kyiv. The “work” experience I had at that point was limited to volunteering. I was a math tutor for high school students for two years and a computer science teaching assistant for one year. I was also actively working on my pet project, Commute Marker — which is still running by the way.

The biggest challenge for me was to get through to tech recruiters.

There were no internships or related work experience on my resume. My school was not on the list of the top US schools, either. The response from 80 percent of the places I applied to was something like “not enough experience, come back in a year.” The job search was a rather frustrating and stressful process for me.

All of my on-site interviews were at the companies I was referred to by friends or friends of friends. Referrals proved to be the most productive channel. And that’s exactly how I eventually ended up at Grammarly.

Did you attend any meetups and what do you think was useful or a waste of time?

Many of the meetups I have attended were organized by Women Who Code (WWC). I’ve found some others via the Meetup app. There were three meetup series that were most productive for me.

My favorite one by far was the Interview Prep series by WWC. Each meetup covered a specific chapter from the book Cracking the Coding Interview by Gayle Laakmann McDowell, including sessions on linked lists, dynamic programming, stacks and queues, etc. Each meeting’s topic was announced in advance, and people were expected to come prepared. Attendees were split into small groups and were assigned a mentor who acted as an interviewer. Each person got to have a mock on-site interview and solved a coding problem on the whiteboard. This was extremely helpful for me — both to practice solving problems on the whiteboard in front of strangers while getting instant feedback, as well as to see how the process looks to an observer.

Another favorite was the hands-on Ruby on Rails meetup series (where my pet project was born). Students had to come to sessions prepared with what they tried to build and questions about what hadn’t worked. The meetup mentors would help to figure out the issue and think through a solution. This series required doing “homework” and was mostly oriented around active learning. So the attendee group was quite small, which allowed some one-on-one attention and help from the mentors in every session. Such hands-on meetups proved to be a good place to get a solid recommendation or a referral based on the actual in-person experience of working together.

The last meetup I found extremely helpful was dedicated to writing a good resume. From there I learned how recruiters read resumes, how they use LinkedIn and other platforms to find matching candidates, what types of offers and positions we could be offered (contract, contract-to-hire, full-time), and the differences between them. I showed my resume to a recruiter after one of the sessions, and she advised on how to restructure the contents so that the most important and worthy things would catch one’s eye.

What soft skills are required of an Engineer to work in a Silicon Valley startup?

1. Providing Feedback. Giving direct and candid feedback in a timely manner really helps build sustainable relationships and a nurturing work environment around you. If you are comfortable giving and receiving feedback, you are opening up a very solid channel for your own growth.

2. Adaptability. With rapid product growth, needs and priorities change fast too. This means that sometimes you need to pivot and start working on something completely new. It is important to be adaptable and look out for opportunities that both match the business needs and your career aspirations.

3. Communication. You need to be able to communicate ideas clearly based on facts and support them with appropriate data.

4. Listening. Try to fully understand what someone is trying to convey. If it’s not clear from their words, ask follow-up questions so you’re on the same page.

You mentioned your own project, can you share more?

Sure! It’s called Commute Marker and is an add-on web app for Strava. It analyzes athletes’ workout activities (biking, running, etc.), detects commutes, and marks them on Strava automatically.

The project started because I was volunteering at two places every day, which meant four commute rides per day. I was opening the Strava app at least four additional times to manually mark my commutes after I’d completed them. So I decided to figure out how to tag commutes on Strava for me automatically. I started with a simple Python script, which I ran daily from my computer. Then I shared it with my husband, and soon some of my friends expressed interest.

In October 2016, Commute Marker placed fourth in Strava Developer Challenge and quickly became a popular add-on service among Strava athletes. It was my first serious non-academic project and the process of building a product on my own with no prior relevant experience required a lot of reading and learning for me as a “newbie” in software engineering at that time.

So, you have a very active life — family, a full-time job, a pet project, sports, and travel. What’s your secret, how do you balance?

The answer is simple: planning and adaptability. Having a full-time job and a long commute from the South Bay to SF brought a tight schedule to my routine. Amazingly, I’ve noticed that the less time one has, the more things one gets done. I do my sports activities before or after work, leaving the fun long bike rides and runs for the weekends. We try to plan all the races and vacations a few months ahead and form a high-level plan for each weekend during the preceding week. Such an approach might sound boring, but in reality, it means we have time for some spontaneous fun and decisions while minimizing the stress from dealing with uncertainty all the time.

AI is considered one of the underrepresented areas in tech in terms of diversity. Do you agree?

My guess would be that the AI workforce has the same distribution of diversity as the tech workforce in general. There are challenges related to diversity in the tech industry in terms of underrepresented minorities (women, people of color). Tech giants and startups are working toward improving their diversity stats. But I am not aware of any company at the moment that has found a perfect solution to overcome these complex challenges. It’s important to recognize that there is always room for progress and to continue to make strides to improve.

Grammarly is in the AI space, and our most recent stats say that about 43 percent of the Grammarly team identify as women (higher than the industry average of 30 percent). For our tech teams, women make up 18 percent (higher than the industry average of 15 percent), while 42 percent of Grammarly management identifies as women. We want to increase representation across all our functions and roles and are making investments to make that happen.

Have you ever been the only woman on a team? What challenges do you see?

Yes, there was a time when I was the only woman engineer on the Growth team at Grammarly. The good news is that I did not feel restricted or underrepresented at all. I felt treated fairly, like every other software engineer on the team, and had access to the same resources, opportunities, and mentorship. I believe that gender should not be the only defining factor when it comes to hiring for any positions. First and foremost, people should be evaluated based on their skills for the job and for having a personality to be a great cultural fit.

But until recently, I did not fully internalize what an impact having a woman in company leadership could have. Several months ago, our VP of Legal, Virginia, started on our exec team. Grammarly has a pretty flat structure, and our exec team consists of very open and approachable people. When Virginia started, it struck me what was missing — the ability to relate to someone like her on our exec team. Virginia has a cheerful and easygoing personality, believes in leading by example, and advocates for transparency and openness across the board. I think she is a great role model. If I ever end up in a leadership position, I want to be like this woman. So I do feel more empowered and inspired by seeing this personality and gender role being a leader at my company.

I believe that gender should not be the defining factor when it comes to hiring for any positions.

What’s your idea of an inclusive culture/climate in a tech company?

This is another challenge, like diversity, that many tech companies are actively trying to solve right now. To me, an inclusive environment is one where people are comfortable talking about their problems and feelings because they know their ideas matter. It is also an environment where people know how to listen to what others are saying and genuinely care about their peers.

You were a tutor at Girls Who Code, how do you like this experience? Why is it important to empower girls in the tech industry specifically?

I was a tutor at Girls Who Code as a part of College Track and a teaching assistant for a CS class in the TEALS (Technology Education and Literacy in Schools) program. At College Track, volunteer tutors help high school students prepare for tests to get into college. There were not many kids interested in CS at College Track, so the Girls Who Code program was open to everyone, not just girls. The TEALS program, on the other hand, is designed as a full academic year at a high school with CS classes happening every other day. I was a teaching assistant for two classes, and both of them were open to all students. Even though the ratio of girls and boys in these CS classes was 1:3, I noticed that the girls were usually more diligent and goal-oriented and studied harder. If I were to write down the top 10 students in these classes, I think half of them would be girls.

At the end of that academic year, I got a letter from one of the female students in the TEALS program I taught. After reading it, I realized that it is not the actual CS knowledge I gave them that mattered most. The most impactful thing was my being present for them, showing by example what is possible and being open to sharing my successes and my struggles. I think this is true for all humans, not just girls in CS classes.

What’s your advice on how to prepare for and crack the interview?

Hard to say. Everyone’s background and gaps are different and I am not sure that there is a universal recipe to follow. Aside from solving problems and brushing up on CS, I would suggest that you know your story. By this I mean that you should prepare to have examples to popular broad questions like “What is your favorite bug/feature?” or “What would you do differently if you were to build this project again?” Think about how you’d respond if someone asked you to describe a situation where you disagreed with your team.

Preparing a draft of your answers can help you consider the situations again with some distance and become more conscious of your own actions at the time. It also helps you to sound more confident and concise when answering behavioral questions in an interview.

Do you interview candidates yourself now? If yes, what’s important for you and what advice can you give to recruiters and hiring managers?

I am on a few interview panels now, and I see how the skills I acquired while working with students help me interview people. There are many approaches to solving any problem. The hardest part for the interviewer, in my opinion, is to grasp the direction the candidate has picked, stay one step ahead, and help them succeed with their solution. Sometimes it is easy to be biased toward a solution you expect to see and therefore nudge the candidate toward it. But I prefer to have a dialogue during the interview. Aside from solving problems, it is important for me to see that the person is willing to explain themselves and is up for a challenge. I also look for how the person is reacting to suggestions and questions and whether they are open to feedback. By the way, we’re hiring at Grammarly right now!

What advice can you give to girls who are just starting their careers in Software Engineering or are looking for a new job?

I think the hardest part for me was to figure out which field I wanted to go into as a software engineer. It’s OK if you don’t know and can’t decide right at the start; many people can’t. In reality, you just need to get your hands dirty and stay adaptive as your career progresses. There are many things I learned along the way that could be applied in any tech field. The most useful and important things are to learn fast and provide actionable feedback. At the same time, there are things specific to the field. I think this is the beauty of the rapidly developing tech industry — one can keep learning forever, either going deeper into one field or expanding their breadth of knowledge to other areas.

The truth is, there are ups and downs in the job search process. There were times when I thought I was done and too tired of all the rejected applications. During such moments, I pushed myself a little further and took a couple more extra steps, solved just one more problem, added one more extra feature, submitted one more application — and my efforts paid off!

Everyone’s story is different, and you have to find your own path; don’t try to follow someone else’s steps. Get inspiration from women around you to whom you can relate. Find someone who makes you think, “She did it and I can too!” Work hard and remember to advocate for yourself. No one else is more interested in your success than you are.

What is your advice for expats who have come to the United States to follow their dreams to work in Silicon Valley?

While I was growing up, both at school and at home, I was taught to “do everything right.” Maybe it was some sort of cultural norm in post-USSR countries. I’m not sure. Eventually, I ended up being a straight-A student with great test scores and got into one of the top colleges in Ukraine. I rarely made mistakes, or so it seemed to me.

Once I moved to the US and started volunteering at the high school, I noticed a big difference in the mindset of the students and the structure of the curriculum. It was encouraging students to do things instead of just to do things right. I was awestruck seeing how these kids think of the challenges ahead. Turns out, of course, the more times one attempts something, the better their skill gets, and the more confidence they acquire, regardless of whether the outcome is a success or a failure. While talent itself should not be discounted, I believe it is mostly the number of trials and errors you go through that truly make up the total score of your success.

What would be my advice? Moving across the globe puts expats in a unique position of getting the best out of both cultures. I would encourage everyone to stay open to new things and find your own sweet spot in this culturally diverse area.

Edited by Kory Tran and Grammarly :)