Anna Tsyupko of tomato pay: 5 Things I Wish Someone Told Me Before I Became a C-Suite Executive

…be conscious about where and when to cut corners: it’s easy to go all out perfectionist and hope for everything to be ideal, but one of the advantages of working in a startup/small business is that you can be lean and that you can experiment and put out a quick and dirty prototype. There are certain elements of the business where you don’t want to cut corners — you need to get these elements right straight from the beginning like your legal agreement — but you might want to put in the effort and cost into a better place like the initial website. Always put your effort into something that can support your business model, and don’t get caught up in the detail with certain things.

As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Anna Tsyupko.

Anna Tsyupko is the Chief Operating Officer at tomato pay. She is an entrepreneur and operational leader in the area of B2B SaaS companies with a passion for operational excellence that leads to well-organised, highly motivated teams and financial growth.

Anna is a multi-lingual tech professional with an established track record in evaluating the viability of strategies and ventures, and experience in investor relations and investment management.

Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Anna Tsyupko started her career in a family office working on early-stage investments. One of these investments happened to be in the payments/technology industry. Through this investment, Anna got her first taste of the world of fintech, and soon became the CEO of this investment.

Can you share the most interesting story that happened to you since you started your career?

I was supporting this investment, however, the investment was not doing as well as it could have been. That was when the investors asked if I wanted to lead the pivot of the business.

I felt that it was crazy I had been recognised and asked at the time, and at a very young age (23). At the time, I had no leadership experience, I knew little of the payments/technology space, and if I had understood the magnitude of what was being asked of me at the time, I may not have taken the opportunity to be CEO of the company. In hindsight, it was great that I knew so little about the expectations attached to the opportunity. The business had 15 employees, we pivoted from B2C to B2B, and I led the new business model. It was a crazy ride, and one I had a lot of fun and learnt a lot by going on.

Can you please give us your favourite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

“Do not spoil what you have by desiring what you have not; remember that what you now have was once amongst the things you only hoped for.” — Epicurus

This is relevant in a lot of ways, especially in a business context. You can keep wishing for double, or triple the revenue, but if you take a step back and take a look at what you have achieved, you realise you have a lot to be proud of. The larger lesson here is that gratitude is so important, and acknowledging that what you have now is so much more than what you had before. You cannot just focus on the future and not be present, as it is not helpful.

Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

Radical Candor is a book I got from a former team member. The main essence of the book is that it is very human to want to be nice especially in a work context, and we may not say something that doesn’t go super well or point it out because we’re afraid of hurting someone’s feelings. It’s the wrong approach. Ultimately the team is trying to push the business forward, so we need to right all wrongs quickly, fairly, with kindness and empathy yet in the frankest way possible. We should all be radically open about what can be done better, and adopt the framework in the book. The culture you operate in then improves because iteration can happen faster, and corrections can be made quicker. A culture where people can speak up, and no one is afraid of speaking up means you can make the best possible decisions for the business.

What do you think makes your company stand out? Can you share a story?

Our company, tomato pay (where I currently work as Chief Operating Officer) is supporting small-to-medium-sized businesses and sole traders with a payments and invoicing app.

tomato pay is a QR-code based payments app for businesses and sole traders to receive payments from their customers in a fairer, ethical way.

A more affordable way to collect payments, tomato pay allows businesses to receive payment almost immediately into their bank account, gets rid of card minimum fees at the till, and ensures that business owners receive no more chargebacks.

Customers can support their local communities by paying businesses in an ethical, cashless, hassle-free way whilst earning rewards and saving money in the process.

We strongly believe in empowering communities by allowing businesses to keep more of their revenue, and by giving customers a way to uplift their local businesses through a fairer way of paying for goods and services.

Payments are something everyone uses, but no one pays much attention to it unless there is a problem. A seamless payment experience means that you will barely notice it’s happening. Those who are really impacted by payments services are business owners who have to pay extortionate fees when receiving payment for their goods or services. These fees have been normalised, but actually there is a better way to support our local businesses.

The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?

Know your ‘why’, it is because of this that you’re doing what you’re doing. Ensure that you have a wider purpose attached to your ‘why’, as ultimately this will allow you to get you through the tough times. Ensure that you’re dedicated to this purpose, because when it gets really tough (because you will struggle at some point) you should go back to the ‘why’ and attached purpose to remind you of why you’re doing what you’re doing.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Women are very intuitive, and I struggled with this question because honestly, I have not got a story here. I feel that women might have this experience a lot less than men due to our intuition. We know when something doesn’t feel right, and we feel this strongly, even if several people are telling you otherwise. As women we research our ideas thoroughly, we don’t go into our work blindly. Plus, we work extremely hard to achieve any goal as the odds have been stacked against us so many times in our lives.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Perseverance: there are ups and downs to working in fintech as it is such a new industry, but the outcomes and benefits far outweigh the downsides, but you need to persevere at first.

Empathy: finding the right approach with every team member and every report. Empowering them in the right way is important. A good example of this is a report of mine in my previous role, where I helped them step up from an entry-level job to a c-suite role in one and a half years just by recognising their potential and steering them in the right way.

Seeing the bigger picture: There are different aspects of the business, take a step back and make sure that it’s aligned, and that your team is aligned.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

The vision: big vs the small. The constant zooming in and out.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

When you’re the CEO/Exec, everyone thinks they work for you and they do to an extent. Yet in reality, the CEO/Exec works for the team, as their main job is to unblock and empower the team to be in the best position possible to do incredible, moving work. You should be assisting the team as opposed to the team doing everything for you.

What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

It’s tough, yet being defensive, leading from fear, being extra authoritative and constantly feeling as if they need to justify their leadership position are common errors to make. It’s common to have imposter syndrome, so the best thing to do is be open about your flaws with yourself, acknowledge them and be authentic with the team.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

The people aspect. Your team is your biggest asset. How well aligned the team is and how empowered they feel will dictate the success of your business. There’s a huge wellness and mental health discussion happening right now, and this is so amazing, yet businesses still under-appreciate and under-invest in the people side constantly.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.

1. How important work/life balance is; doing less is more. I was working crazy hours at my previous role and suffered from burnout, and anxiety attacks. The cost to get out of that negative, mental hole was not worth the extra hours of work. Rather, I should have filled my life with more excitement and non-work elements to give me the energy to bring back to the workplace and prioritise myself.
2. You are not your business: you shouldn’t equate your success with the success of your business, do not base your self worth on how well things are going in the business, when someone criticises the business or doesn’t want to invest, ultimately you are not your business, so do not take the criticism so personally and let it affect you mentally.
3. Ask for help: ask your team for help, you don’t need to have it all figured out, you’re there to support your team, and it goes the other way around too. In terms of a personal example, every single time I’ve opened up to teammates, I have always been met with kindness and openness so the result was much better. We shouldn’t put that pressure on ourselves just because we’re leading a team, we should be vulnerable and open for help.
4. To be conscious about where and when to cut corners: it’s easy to go all out perfectionist and hope for everything to be ideal, but one of the advantages of working in a startup/small business is that you can be lean and that you can experiment and put out a quick and dirty prototype. There are certain elements of the business where you don’t want to cut corners — you need to get these elements right straight from the beginning like your legal agreement — but you might want to put in the effort and cost into a better place like the initial website. Always put your effort into something that can support your business model, and don’t get caught up in the detail with certain things.
5. Don’t get caught up with the wrong metrics. We realised in my previous role, that our Sales Qualified Lead (SQL) were going through the roof, and it gave us a lot of confidence, but in reality, the ratio in live clients and SQL was far from ideal, the really important metric would have been live paying clients. A vanity metric lulled us into false security. Really consider what the true metrics are that really correlate with the business’s success.

In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

Allowing each person to own a piece of the company is a great way to make people know and feel that they are building something for themselves, and not just for the business itself.

Also by championing people who are bringing difficult discussions to the table, especially when it comes to identity, we should be giving these people a platform to talk about something so personal openly because more often than not, there will be positive ramifications for it. Plus, you never know who might learn something new, change the way they approach situations, and support each other and different causes.

We also should recognise that people’s personal and professional life is more intertwined than ever, and because of that, we should practice more empathy and compassion when people might be having an off day, an off week or even an off month.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Authenticity and vulnerability — championing these traits within the workplace — to truly be ourselves and to be authentic as it makes us stronger as a whole. Whatever you would like to see more of in the whole world, there is no better place to start than within the business you’re leading and working for.

How can our readers further follow you online?

Your readers can further follow me on LinkedIn, and support tomato pay on LI, TW, IG, FB!

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!