21 SaaS CEOs Reveal How To Be Successful at Their Job

What is the most important quality a good SaaS CEO should have? 

The easiest answer would be: an ability to inspire people with her/his vision.

This is a quality though that differentiates CEOs from all the other founders. It doesn't necessarily make anybody a great CEO on its own. The quality that makes CEOs amazing is the discipline.

Keeping your word, applying highest quality of work ethics to yourself and holding yourself to a right level of thought discipline is necessary to achieve greatness as a leader.

What was (or is) the biggest challenge you were facing and what you have learned from it?

At "the growth stage" of the company the biggest challenge of CEOs is hiring and building an efficient culture. If I'm not spending time with customers and our product, I'm obsessing over the structure of our leadership and the overall efficiency of UXPin's team.

How do you measure the value you and your company provide?

UXPin's value is measured by a very careful and constant analysis of crucial metrics on the level of users' behavior (engagement), emotions (satisfaction) and unit economics (MRR, churn, LTV, CAC/LTV…).

When it comes to myself, as every person on UXPin's leadership I'm periodically assessed by the team in an anonymous survey (360 performance review). The report with my improvement plan is available to every person on the team.

I'm also sharing my weekly priorities with the team and every week we're checking together whether I'm achieving my goals. 

What is the most important quality a good SaaS CEO should have?

The ability to teach and educate their team on how they would like things done. Many times you see a CEO just tell people what to do and then criticize the work. We all need to be effective in training our team to create the outcomes we want.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Much of my focus has been on how we create an amazing culture while making sure we are all aligned with the company goals. Many times, having a great culture does not mean you are hitting the highest goals. Sometimes fun distracts people from creating a worldwide brand.

How do you measure the value you and your company provide?

I assume you say measure for our clients? We are very data driven and are experienced in most of the major analytics tools. The first month or two of working with a client we simply set up analytics and dashboards. This way everyone is on the same page with measurement. We tend to only track a few metrics to remain focused, but many times we are tracking a visitor to revenue conversion, LTV, and increased MRR.

What is the most important quality a good SaaS CEO should have?

Humbleness. Each stage of a company is different, it requires different skills. Our stage of minimal viable product and hustling is over and Convert.com is now a stable A/B testing software and a stable SaaS company that enters to the eight year.

We are converting into a conscious business with focus on strengthening the team and give awesome service to clients. It's a stage of growth and expansion and needs different skills than a small startup. It's been a wonderful but hard journey to make the mental switch so I like to stay humble and surround myself with a great team and mentors to grow into this and future stages.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Combining the incredible growth spurts a startup should have with a family life and children is hard. I think both my family and the company suffered much at stages of turmoil. I would recommend focus on one or the other, mixing them requires super human abilities.

How do you measure the value you and your company provide?

Great LTV and MRR are indicators that things are going well for our A/B testing tool. Our Lifetime Value metrics are our signal that clients love us. We have a Customer Success Program implemented and we do tons of life-chat with sales and support to keep the experience near to a level of excellence that is how our clients rate us now.

It's a difficult market with recently lots of changes and with competitors moving towards enterprise only and others just adding whatever weird feature, it seems we are just one of the most stable providers that take on billions of new tested visitors and growing.

What is the most important quality a good SaaS CEO should have?

Well, why the hell you think I have any idea about a good CEO?

But if I have to answer, it’s first talking and listening to other people – clients, employees, opinion leaders, mentors, investors, even family, who will be affected by your job in many ways.

Then, ability of doing, coordinating and delegating many parallel tasks and projects, while finding also some time to invest in activities which will pay off only in long term. 

There is of course a number of other very helpful qualities, like: learning new areas quickly; having a big vision and passing it down the organisation; representing company and doing PR; balancing interests of various stakeholders, including clients, employees, the other founders and, last but not least, investors.

What was (or is) the biggest challenge you were facing and what you have learned from it?

I love travelling and endurance sports, so my biggest challenges and best lessons taken were related to my shoestring travels, mountain hikes, ski runs and long distance cycling trips.

In terms of management, I benefited a lot from student activities and especially from being a captain of an amateur football team. We were not the most skillfull players, and me personally I was definitely not the best in my team, but strategy, team spirit and motivation lead us to some small successes, including winning a league we were playing in.

If I need to talk about my startup experience, the challenges evolve as long as the company grows. At the current stage it’s organising processes and optimising them as well as using our know-how and experience from domestic market to the foreign ones. 

How do you measure the value you and your company provide?

By loyalty of our clients and the growth of their businesses, which often is later reflected in upsells of our services. 

What is the most important quality a good SaaS CEO should have?

Be practical. 

What was (or is) the biggest challenge you were facing and what you have learned from it?

For SaaS companies, the biggest Challenges we faced, was the different cultures between countries and their tax complexity.

For example in Brazil, each state has a different tax for each service, product or component, high worries with geografic issues, what makes the companies spend a lot of time in how to adequate better to the fiscal law, instead of think about how to produce, operate or sell better. So, in this case we had to create a consulting product coupled to the platform to make a full diagnostic of the company, understanding the business, and than helping then to use the Saas tools.

It is a completely different way to see the usability of SaaS companies, once that this kind of country is not so early adopter as the world think. 

How do you measure the value you and your company provide?

We make the customer to increase the margin, profitability, we reduce costs (not necessarily changing the operation) and we make the customer perform better in marketing and sales taking action over the data we provide. And about me, I´m from one of those countries with complex laws and market, so I´m able to manage those guys to have a good way to perform and understand better how these countries works. 

What is the most important quality a good SaaS CEO should have?

There’s no such thing as the one, top CEO quality. There’re many different managerial styles. From my personal experience I would emphasize the following three features: persistence, integrity/high ethics and trust in the abilities of others. 

What was (or is) the biggest challenge you were facing and what you have learned from it?

My personal biggest challenge as CEO was tied to our success story. Once our company started to grow rapidly, I had to shift my focus from 'doing things on my own’ into 'managing people’. In the beginning I've had a strong internal belief that I do things best, which of course has proven to be wrong. I had to start trusting in my people’s abilities and stop micromanaging things.

How do you measure the value you and your company provide?

The best measurement for our company’s value are: references, word-of-mouth recommendations of our services and client retention rate.

Chief Executive Officer at PressPad

What is the most important quality a good SaaS CEO should have?

Good predictions and thoughtfulness, which leads to right decisions. For me that matters the most, especially in the new businesses in which you have to move fast forward and every single decision of where you and your company are going may lead to success or failure. There is no place for a mistake

What was (or is) the biggest challenge you were facing and what you have learned from it?

We faced a lot of challenges throughout the years and the hardest was when we ran out of money and had to make a lot of cuts to survive. We needed to change our product, the way we sell it and business model to get to the point we’re in. I wish we had made this changes sooner.

If something isn’t working as good as you need, it's very unlikely that it will miraculously change. You need to take a risk and try something else.

How do you measure the value you and your company provide?

For me it’s simply the number of paying customers. Surprisingly, you can get the nicest feedback about your idea, have thousands of followers on your brand's Facebook page and still struggle with selling your product to anyone. But when you see that people are actually willing to pay for it (and how much), you know that you made something valuable.

What is the most important quality a good SaaS CEO should have? 

Being a good manager but at the same time a visionary team leader who will be followed by a team. A good CEO needs to have strong vision and be confident enough to follow his intuition.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Lack of tech co-founders.If you think about having a SaaS startup and you want to hire a software house just don't do it. Find co-founders ASAP. Without them your company can work for few months but after MVP stage it's just necessary to build your own team. Co-founders are a must-have!

How do you measure the value you and your company provide?

Number of satisfied customers = number of paying customers. Referrals.

What is the most important quality a good SaaS CEO should have? 

A good CEO has to be patient, determined and ready for anything. Impressive results don't come in a week or two. It has to take time. Business is like a marathon. Don't give up, run, mile by mile and everything will be fine.

What was (or is) the biggest challenge you were facing and what you have learned from it?

In the payment industry everything is based on partnerships. The biggest challenge I'm facing since I have been working at PayLane is building relationships with the right business partners. The bigger the number of really good partners you have on your side, the more options you have. The more possibilities come with them. The more interesting the solutions for your customers. If you are small and unknown, noone wants to talk to you. Noone treats you seriously. But after some time, if you're determined enough, you might be able to build great relationships with the right business partners and everything will change since then.

How do you measure the value you and your company provide?

By talking. With anyone who wants to talk with me. Especially with customers, but also with business partners, website visitors, our content readers etc. No one tells you more about you and your company than people who pay you for your services.

What is the most important quality a good SaaS CEO should have? 

I believe that being a startup CEO differs from working as corporate CEO – there’s a huge difference of the scale you operate at. From my point of view, personal energy is the key.

A good CEO needs to be able to influence others and spread his/her ideas effectively. On the other hand, startups should value though leaders. For example, one of Facebook’s claims is “be bold!” – in such a dynamic community it’s often crucial to make tough decisions and take risk, otherwise you won’t grow and others will take your place (and funds!).

Still, a CEO needs to think of employees, as those people are the backbone of each company and build their story altogether. You not only need to know how to listen to them, but you should also be able to admit to your failures. This is how strong, effective teams are being built.

Last but not least, every CEO should motivate his/her team members for constant development. Those people have their own responsibilities and will eventually become leaders, too, especially in the holacracy model that is getting more and more popular.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Me and the Prowly.com team, we faced the very same challenge that every startup has to face – the struggle for getting our first fund.

Finding an investor that likes your idea and is ready to support you financially is an extremely demanding yet rewarding challenge. Having an investor is crucial at every phase of startup life, but the key factor is that once you receive it, you gain more confidence, and so does your team. 

How do you measure the value you and your company provide?

Once you have an idea that serves the foundation for your company – in other words, once you find a market need that is verified by customer demand – there is no other metric for a startup than sales. Plus, since our aim is to help PR people take their PR to the next level, we value when they actually succeed – this is the kind of feedback we’d like to hear every single day!

What is the most important quality a good SaaS CEO should have? 

There are many crucial qualities a good CEO should have so you can't list only one. A good CEO is defined by a mix of several features. In my observation, important traits are persistence, clear and consistent communication as well as a clearly defined goal (but at the same time you need to be constantly ready for significant changes).

In addition to this, the hierarchy of qualities a good CEO needs to have varies depending on whether you are a CEO of a large Fortune500 company, a mid-size company of 100 employees or a small company consisting of 10 people.

In other words, traits required for a CEO of a small company are different than for a CEO who leads a big enterprise (this also emphasizes the fact that being able to successfully shift from being a CEO of a small company to leading a much bigger one is also an important quality of a good CEO).

What was (or is) the biggest challenge you were facing and what you have learned from it?

There is no clear answer to the question about which challenges were the biggest ones. As our company changes, challenges evolve too.

As a startup founder and CEO, your challenges are different – you try to get to Market-Product fit, assemble your core team and if needed, look for financing your venture. After getting to Market-Product fit, your challenges shift to recruiting the right people, scaling your company (revenue, team, product, technology, etc.) and growing your business. 

Personally, some of my constant challenges are scaling my company and recruiting the best possible team.

How do you measure the value you and your company provide?

Our first and foremost KPI consist of two variables: a) number of candidate applications we deliver to our customers and b) number of jobs and companies that recruit young, talented people.

What is the most important quality a good SaaS CEO should have? 

The one that she or he is missing. Some of us are great developers, others are great salesmen, designers etc. Rarely (never?) we have all the skills and qualities required to succeed and rarely we start our companies with resources needed to hire people who possess them. Startup CEOs job is to deal with that quality-gap. Maybe that makes a quality itself? 

What was (or is) the biggest challenge you were facing and what you have learned from it?

The toughest part is always to deal with people around you. How to hire them, motivate them and fire them if needed. Like all startup founders I'm persistent and don't give up easily, neither on ideas nor people. So when I had to part ways with some employees I was positively surprised that people (unlike ideas?) can do great without you as sometimes you're slowing them down as much as they are slowing you down. So maybe we should be much quicker in saying a good bye. 

How do you measure the value you and your company provide?

I know we do something right for our customers because our retention is very high.

I know we do well for shareholders too because… I, as one of the largest shareholders, am still enjoying my work.

I also know that if we would disappear tomorrow the world wouldn't notice but we're working hard on changing that  

What is the most important quality a good SaaS CEO should have? 

 There are four things great CEOs do:

• Build a great vision for the company
• Hire exceptional people to execute on it 
• Provide capital for the company – investment in the early days, overlooking sales later 
• Remove obstacles preventing team members from doing their job

Over the years I found persistence to be the most important quality to maintain these 4 tasks. There are hundreds more but persistence is the key. 

What was (or is) the biggest challenge you were facing and what you have learned from it?

Two things: people and culture. At that point it must sound like a cliché but we don't work in a vacuum. People must love showing up in the morning and company's culture determine how well the organization scales and deal with tough situations. 

How do you measure the value you and your company provide?

In retention. If our customers keep coming back it means we deliver an exceptional value to them. At Contellio this makes me grin every day as we have close to 0% churn with a product, that is definitely not an impulse buy. 

What is the most important quality a good SaaS CEO should have? 

Should be able to listen to people and understand what they really mean. It goes both for the employees as well as clients/customers.

This helps him build better products/services that provide real added value and build better organization, a place where employees spend one third of their lives. 

What was (or is) the biggest challenge you were facing and what you have learned from it?

The biggest challenge I face every day is saying "no", mostly to users asking new features in our SaaS products. It's hard to resist temptation of diving into developing new features, especially when you hear "we'll buy from you when you add A and B". But this usually means getting distracted from the plan and loosing focus.

How do you measure the value you and your company provide?

Since we provide subscription based SaaS products, we see we provide value to our users when they renew paid subscription every month. For us the fact that they're willing to keep paying for what we give them is the most obvious indication it has value to them.

What is the most important quality a good SaaS CEO should have? 

I think that the most important thing is to have a clearly defined strategy for your company. It is obviously changing because of the dynamically developing market, but the CEO must know what his or her goals are and how he or she wants to achieve them. Contrary to what it may seem, many people do not know that. 

Another important element is to respect people and their work, analyse the problem from every point of view (not only his or her own) and make decisions quickly.

Finally, I would like to add one more feature – CEO should be able to make everyone he/she talks to enthusiastic about his/her idea.

What was (or is) the biggest challenge you were facing and what you have learned from it?

An interesting challenge was my previous project named useSelly, where problems (i.e. challenges) were happening on everyday basis.

The entire team was working online, and two of them were employed full-time in a corporation, which caused many problems with communication. In addition, we were not able to talk with the investors, which was a new experience for me.

The project taught me humility above all. This was the most valuable lesson I got so far. I would add one more piece of advice here: all planned expenses are to be multiplied, by a minimum of two times. They are always bigger than planned.

How do you measure the value you and your company provide?

The answer is really simple – REVENUE.

What is the most important quality a good SaaS CEO should have? 

Its complex question as I can't pick out a single one. I'd say a good CEO have to be the founder or co-founder of the project.

Only in this situation can he and will he work as hard as possible to bring the company to success. Also he has to have managing skills and ability to convince everyone that his product is the best. Great CEO is ready to change the way that his company goes if it's needed. And the last one is to hear his team, customers and market to make the best decision.

What was (or is) the biggest challenge you were facing and what you have learned from it?

I'd say its the feeling that your potentials don't need the product. It's hard to admit for many CEO and sometime its happend.

To decrease the risks that it can happend before developing every team member have to spend as much as possible time for customer development and finding first customers that will be ready to pay after your launch (or at least they say it).

All I want to say is you need to know whether your product have a real value for potentials or not.

How do you measure the value you and your company provide?

Deadline? Well, the most valuable metric is new customers to do that we spend a lot of time providing different hacks.

But I can say if potential don't need your product he never buy it. Deadline is important metric for development new features.

To not cross this line you have to have a dream team or devoted employees who believe to success.

What is the most important quality a good SaaS CEO should have? 

I think that the most important quality is ability to get right people to the company and keep them motivated enough to stay around.

Though at the beginning it seems like CEO is a one man army that handles most important tasks, in time the people you will get to you your company will be the ones that creates them.

They should be much smarter when it comes to their field than you and they will be the ones that will make your company a success or a failure.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Hard to say as there are biggest challenges every week/month. I think that generally the most important challenge I have is to keep the company focused and oriented on right goal despite the strong growth and new people.

When you are 5 people it's no brainer, but in time it's getting tougher and the role of CEO implies great communication all over the company to all people and departments. It's really tough to do it right while keep growing in a fast pace.

How do you measure the value you and your company provide?

Each team has their own "output metrics" that says how good job they our doing, but in the end it goes to two most important metrics: how many customers you are able to use your product and how many of those will stay around. 

What is the most important quality a good SaaS CEO should have? 

It is hard to pick one quality that is most important. For a CEO, your job is never finished and there are an endless amount of problems to solve and opportunities to take advantage of.

Some of those things you have to do amazing well, some things you have to do "good enough" and some things you don't need to do at all.

Knowing what needs to be done, when and how compete of a solution is needed is big but it's only the first part – the second part is being honest on where your own strengths and weaknesses are and then surrounding yourself with great people.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Biggest challenge I have faced so far was solving a circular problem. I needed investors, I needed a team, and I needed paying customers.

But I needed investors to convince the team to join, I needed the team to build the product, and I needed the product to have paying customers, but investors wanted to see paying customers!

Starting from nothing is an incredible challenge to overcome. Perhaps I should write about how we solved this sometime.

How do you measure the value you and your company provide?

I actually don't lose much sleep about measuring either of these. I feel like when you are really plugged into your own company and your customers, you KNOW when there is value being created and when there isn't.

The tricky part is knowing if you see the whole story or not, but that's hard to measure. I suppose the ultimate measure is if your company is "successful" or not, however you define success.

What is the most important quality a good SaaS CEO should have? 

Every CEO works with people and he can be only as good as his team, so of course the most important issues are: good communication skills, empathy and ability to motivate.

However, there is one important virtue that is rarely mentioned, and in my opinion essential for modern business – courage.

What was (or is) the biggest challenge you were facing and what you have learned from it?

The big challenge was IPO of my first company – SARE SA. Besides, it required a lot of work, suddenly we faced a need to communicate with a completely different audiences than ever before.

Previously, these were customers who had a good understanding of what we do, now we have to describe our value to investors, lawyers, advisers. It seems to me that that was the time I learned to listen to others more often.

How do you measure the value you and your company provide?

On the one hand, income is crucial, because people pay for things that are valuable to them. On the other hand, I pay attention on number of complaints and comments.

I think that every CEO is hurt the most with unflattering opinions about the service or product his business provides. However, you always have to face them, for example through satisfaction surveys.

What is the most important quality a good SaaS CEO should have? 

Two words – people skills. Being CEO (in my opinion) is all about the people. People you hire, people you partner with and most important, people you are selling to. You need to be able to create long-term relationships. Without them, you will get nowhere. If I were to point the second quality it would be something about learning from mistakes and not being discouraged by them.

What was (or is) the biggest challenge you were facing and what you have learned from it?

Actually for me the most difficult part was to recruit people in fields I did not have experience before. I was running a development house, Visuality and I knew how to hire good programmers or designers. But had absolutely no experience in sales or marketing – and it turns out – those are totally different recruitment processes. I made mistakes, paid for them but learned a lot since than.

How do you measure the value you and your company provide?

Right now Magello is at the beginning of our road but we already have some great customers. I believe that fantastic customer support and great relationships are the key. Of course we measure it and write down the results in Trello or PipeDrive, but the most important part of it is talking to our customers. We deal with problems, suggestions and we do everything we can to make them happy.