Kristel Kruustük: Three of my biggest challenges scaling a startup

Kristel Kruustük, a co-founder of Testlio, a mobile app testing startup, writes that building companies is tough and entails making a lot of mistakes that are emotionally draining, but one’s got to keep fighting as long as you have yourself, your team and your customers who believe in what you’ve built.

It was a sunny summer morning in Burlingame when a colleague and I grabbed an early breakfast with one of our investors. We chatted about our opportunities and the mistakes we had made in the past and what we had learned from them.

As we were finishing up, I asked our investor: “If you knew this outcome would happen, why couldn’t you just force us make the right decision?” The answer was something I deep inside of me knew: “If we gave you all the answers you wouldn’t learn anything about building a company and that’s not scalable.”

Team offsite in Viljandi, June 2015

Building companies is tough, especially if you’re trying to grow at a rapid pace in just a few years. You will make a lot of mistakes that are emotionally draining, but you’ve got to keep fighting as long as you have yourself, your team and your customers who believe in what you’ve built.

My investor was right: there’s no-one out there who has ever built the same company twice. There will never be someone there to give you a perfect piece of advice every time there’s an issue. Every company has different variables and figuring out an equation for success will always be complex. Your company’s success can depend on people, markets, funding, speed, timing etc.

Today we are a team of 65 people with offices in Tallinn, Estonia, and San Francisco, CA. I have personally faced tremendous amounts of emotional stress building Testlio. Every setback or a challenge that we didn’t know a solution to was devastating for me. So over time I’ve learned to let things go, grow a thicker skin and face every challenge with positivity.

As we’ve grown our team from two to 65, we’ve faced some monumental challenges. Here are the three biggest hurdles we’ve faced to reaching scale.

1. Building a committed, responsive and spirited team

The team is everything. Until we were a team of 25, everyone in the company knew exactly what everyone was doing on a daily basis, but once we passed 25 we realised we couldn’t continue like that for one simple reason – it’s just not an efficient use of everyone’s time. That’s when we started a so-called leadership team: a group of people whose strengths were to elevate and lift everyone in their department to a higher level and think strategically about our long term goals and vision.

As much as I wanted to, I couldn’t expect myself to have 1–1 conversation with everyone each week. Having an organisation without any leaders in a team didn’t scale for us. I can still call it flat, as we are still equal. It’s just playing with people’s talents, experiences, ambition and goals.

After different types of transformations in the team and structure it also becomes clear on what’s your vision and what types of people are you actually looking for to build the dream with. You will make mistakes along the way, but isn’t that inevitable when you’re dealing with figuring out your organisation and its goals and you figure out who you are along the way with your strengths and weaknesses? Expectations set last year might not be the same a year later. You just have to believe and adjust to changes as the company grows. Thinking back, we didn’t hire enough people with experience to lead and develop people, which is crucial for any team’s success.

2. Recruiting and retaining talent

Once you assemble a great team, you need to keep them and motivate them toward your company’s goals. As you grow, communication between team members gets slower; people start to work in teams. As a founder I’ve realised how frustrating it was and that’s where we’ve had to implement changes. Things that worked yesterday will not work tomorrow and as a team you have to keep an open mind to experimenting. I constantly try sourcing the best solution and act on considering my full picture and insights into every department.

Therefore, while hiring talent we always talk about the upcoming unknown challenges to set that as an expectation for any future member of Testlio. The goal is to set them up for success from the beginning and we always want the best for everyone coming on board with us. And while we are just not looking for people ready for unexpected challenges, we also have to look for people that reflect the same values with us, not just people that have the technical skillset. Culture is very important for us and retaining talent in your team will be hugely influenced by it. Every company has its own face and personality, it’s important to find who you are and be confident that this is the right way to move forward. Over time I’ve matured myself and we are more clear in who we’re looking for – someone who is passionate, has a good heart and cares. In addition, from hiring perspective I value people to have the skillset that can take the company to the next level.

3. Constantly being self-critical about your strengths

While you’re part of building a high-growth company it’s important to constantly evaluate your skills and be aware of your strengths that make you happier and are valuable for the company’s growth. Over the past month, my co-founder and I realised how we have actually compensated and balanced each other throughout the years of building Testlio. We realised that I wasn’t productive and efficient in owning objectives and key results and managing the business day-to-day. Instead of bringing someone in to own this, we realised that this was what the other co-founder has been doing since the beginning of the company. We switched gears so I could focus on external facing opportunities and challenges and the other co-founder can work on internal operations. It’s important to leave your ego at the door – this is what makes your team more successful. Do you only care about yourself or are you putting your team members and company goals before you? Remember, there’s no ‘I’ in team.

Presenting at Startup Passion event, January 2017.

I still clearly remember some startup and leadership books back in 2013 like “Startup Boards” or “The Hard Thing About Hard Things”, when a lot of the things that I read didn’t make any sense to me. I was sure that I would be able to do things differently – eg skip mistakes on hiring talent or valuing skills over cultural fit. But if every founder knew every challenge they would face, who would found a startup?

Being part of any startup is a constant learning process. You should never stop learning and never think you know everything. Satya Nadella has said: “Don’t be a know-it-all; be a learn-it-all.”

Reading an article on Harvard Business Review nicely concludes what I’ve written about:

“Scaling challenges nearly always come down to the same problem: the difficulty of spreading something good from those who have it to those that don’t – or at least don’t yet. It is always, in other words, the problem of more.”

Finding the right fuel to replicate the success that you had when you were just a 10-person team is an exciting challenge and growing with the same energy and drive is something that’s possible, but it will always make you learn it the hard way. And by the hard way I mean parting ways with people that don’t scale with your team and company along the way. And that’s totally OK. That’s normal and part of life.

To succeed you have to focus and let other people around you focus on their strengths. Growing bigger is something that you will get to do when you have the drive, passion and don’t give up attitude. Just keep going, enjoy every challenge with lots of positivity and energy. You will get through this. I know this, because I’ve been through this and still going through this every day as our company grows.


This article was first published on Medium.

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