Monday Guest Anna Kainova-Y3-W13

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Get to know Anna Kainova

By: Mohammed Alqaq   |  March 25, 2024   |  Year 3  –  Week 13/2024

Greetings everyone! 

My name is Anna Kainova. I am a proud Ukrainian, Customer Success professional, mentor, and responsible living ambassador. 

I love exploring the world, making my specialty coffee in the morning, doing yoga, learning about the human brain, and making sure all businesses are customer-centric :). 

I have spent several years being a part of AIESEC – the world’s largest youth-run organization, and this experience has significantly impacted me and shaped my values. Even after joining the corporate world, I still try to ensure my work is purposeful and do some daily actions that are good for the planet. 


I have visited 34 countries and almost all continents, except Antarctica, just yet! I am also proud to know people from dozens of countries and nationalities and have worked with customers all over the globe.

In my free time, you can find me reading a book in a coffee place, planning my next trip, or spending time with my family and my dog, Maltipoo Percy. 

Although I am adopting a slow-living lifestyle now, I still seek growth and progress, so I am on my way to finding balance in self-development.

We asked Anna to take us through a journey telling us about her career path, how she spends her workday, what advice she can share with someone starting as a customer success manager, and many other questions.

Enjoy reading this interview  

Table of Contents

Tell us about your career path?

Before embarking on the corporate journey, I spent several years being a part of the largest youth-run organization AIESEC. It allowed me to significantly grow my professional and personal skills, meet people from all over the globe, live in and visit several countries. I had various roles, from communications to project management to talent management, but the special one was in customer experience, which set the stage for everything else to come.

I joined the tech industry in late 2016 as a Sales manager at a local outsourcing company. I quickly grew to the position of the Head of Sales, managing a small team. Later on, and I will describe this transition in more detail in the next question, I started doing account management, which led me to customer success. Currently, I am doing Customer Success at Grammarly, the world’s leading AI writing assistant. (Yes, Grammarly is up and running, making sure this text is compelling and error-free).

Besides my main job, I also mentor startups and professionals at StartupWideGuys B2B accelerator and Ukrainian Tech Institute Projector. This gives me an incredible sense of fulfillment, being able to share my knowledge and help other teams grow. At Projector, most of my sessions are donations-based, with all proceedings going to support Ukrainian people.

How did you join Customer Success?

In 2020, back at my first corporate job, I started taking on account management responsibilities, and this period of time grounded me in the idea that I am more inclined toward building long-term customer relationships, proving value, and helping customers succeed.

In September 2020, I started my first proper Customer Success Manager role in a US-based knowledge automation startup working mostly with enterprise customers. The product is very complex and technical, so we had to focus greatly on successful onboarding and implementation to guide customers to value quicker and ensure the solution stays relevant to them in the midst of the digital transformation many enterprises were going through back then.

This role allowed me to hone my CS skills, work with clients across industries and countries, and deepen my business acumen. It also led me to join Grammarly in 2022, where I am now working, focusing on nurturing our partnerships with higher educational institutions in EMEA and APAC.

How would you describe the ideal CSM candidate?

In my opinion, a CSM is a Value Master. The person taking on this role needs to have the business acumen to be able to understand customers across the industries, their unique pains, payoffs, decision-making, and hierarchy, and at the same time, be a customer advocate internally at their own company.

The ideal CSM would be strategic enough to know how to drive additional revenue for their organization while focusing on the customer’s desired outcome. To me, the greatest CSM is an expert in their product, an empathetic relationship builder, and a knowledgeable expansion driver.

What one piece of advice would you give to someone just starting out as a Customer Success Manager?

Get as much customer-facing time as possible. Schedule short 20-minute meetings with your clients and just ask questions. The sooner you can have a complete overview of their business, what they value in your product, and how they make decisions – the better equipped you are to handle all the operational and strategic work.

Another thing I’d recommend is to keep a running list of your achievements and strengths and list your accomplishments, however small they seem at first. Since we cannot rely on our memory, this list can help boost your self-confidence and always have what to present at an interview!


Get as much customer-facing time as possible.

Can you take us on a journey describing what your workday looks like?

I start my day at a different time, depending on whether I am meeting my customers from APAC today or not. If I don’t have anything scheduled for the morning, I would typically start by reading a few pages of a book because it always increases my mood and motivation.

I would then start reviewing my email and sorting out quick tasks and customer requests. This gives me a sense of accomplishment earlier in the day before moving to more complex activities. Yes, I don’t believe in the “Eat the Frog First” concept because, according to various research, our brains need something easier to start the day with and check off the list instead of a daunting, challenging task that could drag on for hours.

In the middle of the day, from around 12 pm until 4 pm, I usually have very few or no meetings and can dedicate it to focus work, like customer or market research, planning my expansion outreach, building out a playbook, etc.

The end of the day is usually occupied with internal meetings or team syncs since most of my colleagues are in the USA, and we have to align in our time zones.

Again, depending on the meetings and workload, I end my day at a different time. While it may look like a poor work-life balance at first, I always take breaks during the day to have lunch, go for a coffee, or walk my dog, so such increments of work and pauses are better for me than uninterrupted 9-5.

What makes you feel inspired or motivated?

The sense of meaning and bigger purpose. I feel a burst of energy and inspiration when I know that my work can contribute to something meaningful or valuable for this world. This was the main reason that led me to AIESEC and all the career changes that followed. Whatever step I make, I should absolutely know that I am doing something beneficial for others.

What’s one thing that people are generally surprised to find out about you?

What a question! It got me reminiscing about all my recent conversations with new acquaintances. I’d say people are usually surprised when they learn about all my interests and activities outside of my main job. For example, that I run a blog about personal finance and stock investment.

Who do you look up to the most? 

I am inspired by exceptional women who can do absolutely everything at once. There is no single personality I’d point out, but there are a few Ukrainian female entrepreneurs I follow who are my role models.

In terms of thought leadership, I love the works of Adam Grant, and Simon Sinek.

What are your top 3 priorities now?

Life-wise, I want to keep safe, ensure my family is safe, and try to live the best life possible. This means traveling, deepening my self-awareness, and prioritizing self-care.

Work-wise, my big rock is to be a valuable team member and the main source of knowledge about the international higher education market, which I am leading now. It also means growing my customers and driving more revenue.

My other priority is to be a good leader for the team and help others identify their vectors and grow towards them.

What advice would you give to Customer Success Managers to grow and develop their careers?

Besides spending more time with customers, as mentioned earlier, I’d also recommend that CSMs always understand two aspects: what matters to their organizations now and what matters to their customers.

Oftentimes, CS teams get so focused on the customer needs that they start neglecting their own business, why certain decisions are made, and why we don’t build some features to benefit the customers. Although this level of empathy is probably the unique skill of a CSM, it could also sometimes cloud their judgment, so I would advise aligning with the internal needs, too.

Another piece of advice I’d give is to always learn and seek knowledge from different areas: finance, product management, marketing, HR, etc., as it helps develop the overall understanding of the business and position yourself as an expert in front of your customers.

What’s your favorite book, and why?

I love reading, and many books impacted me in a certain way, but there is one book that I’d recommend everyone to read, regardless of age, occupation, status, or interests. This book is “The Power of Habit” by Charles Duhigg.

It is an in-depth, psychological, and engagingly written book on habit change for individuals, organizations, and societies. It perfectly balances real-life stories and science-based research, making it an exceptional manual for life and business.

Charles Duhigg provides a deep explanation of how habits are formed and how they work, making it easier to understand the mechanics and change or build new habits to improve one’s life.

I absolutely loved it and can name a few more popular or well-marketed books inspired by “The Power of Habit”, however, this one is the true original. 

» Check out the 10 Books a CSM should read to advance and improve their skills.

Have you had your “I’ve made it” moment yet?

In my life, such moments are usually related to travel and reaching the destination I’ve dreamed of as a child. For example, when I traveled to South Africa and was standing on top of a rock overseeing the Cape of Good Hope. Or presenting my global project at a conference in Argentina.

Work-wise, those were some significant milestones of winning over a tough customer, building out and implementing a customer journey map, and seeing the success of the startups I mentored!

I also feel very fulfilled after running a session or a workshop and receiving very positive feedback after 🙂

What should I have asked you but didn’t? 

I believe you nailed it with questions.

Where can people go to find out more about you?

Feel free to connect with me on LinkedIn, or follow me on Instagram. I do mentoring for startups and individuals and gladly welcome new people to my network.

Thank you, Anna, for sharing your knowledge and for the opportunity to know you more.

Do you have a Customer Success Leader, Expert, or Influencer you would like to know more about?