Why You Should Start Taking Startup Positions with Less Than Twenty People Seriously

Startups are all the rage. Competition for leadership positions in these companies grew at the same rate. Top-notch talent is giving up large cos, bank and consultancy positions to go and see what it’s like to work in startups.

For you who are considering taking the leap: choosing the stage to enter is important. A close look at these companies shows us an animal that undergoes a giant metamorphosis every year and a half. In this article, I argue that small ones, with less than 20 people, can be the entrance you are looking for in this universe, especially in the beginning of your career.

This is counterintuitive advice: when people see themselves working at a startup, they usually think of scale ups, with teams of more than a hundred people. They already have a nice office, they’re in the media, HR is ready with a great ‘employer branding’ effort. Like any scale up, they hire by the liters and need quick talent.

You have now applied and entered a scale up with an analyst role. You want to progress quickly, after all this is one of the reasons that brought you to this world, isn’t it? Because you are smart, you look to the organization’s leaders to understand what they did to be there.

Some will be people who joined the company way back when it still had less than twenty people. The guys who made the whole thing happen. For you to be one of these, you have to follow my advice :-) and get into a brand new startup.

But there are also the leaders who came later. People who came to assume leadership with the already large company. Then you think: I’m going to be one of these. Then you wait for an opportunity at the cafeteria ro ask the founder how he chooses these guys and you say a word: ‘track record’.

This means, in general terms, that the person has already fought in other battles with a relevant position and won. The founder needs people with ‘track record’ because the company, at this point, is hiring in large volumes and will not give more time to develop talent internally for leadership positions. At this stage, leaders have to hit the ground running. Doubt? So look at the job descriptions for leadership positions in scale ups, you’ll find the little word ‘track record’ there.

If you agree that you need such a ‘track record’, then how do you get it? Well, you’re going to need to be in an organization that gives you the lead on an important project, taking the risk that you’ve never done anything this complex before. This is the chicken-egg problem. In theory, no one will want to put you in the lead of a critical challenge until you’ve shown success in a critical challenge.

You can hold on tight, giving your best, for a few years. Someone will end up giving you an opportunity to take a leading role. It will take luck and time. You may need to switch companies once or twice until your time comes. But nobody promised it would be easy, did they? And good people (righteous, disciplined and talented) end up always finding their way to success.

But there is another easier place to create a ‘track record’: the small ones. In these companies, you simply have more challenges than experienced people to solve them. On the first day, they will give you a good ‘track record’ opportunity. That’s simple.

There’s only one problem, the company won’t be ready. Everything will be missing: processes, resources, access. It will be more difficult. The shortcut is always a bumpier road. And you have to succeed, failure doesn’t prove anything. But if it works, you’ll be ready to take the lead in this company when it grows or another.

The skeptic will say that we have, at the very least, a balanced choice between risk versus time. Fair.

But there is a tie-breaker: in the little one you will have time with the founders. You can work closely with these guys. People who have been doing this for a long time, with other cycles on their backs. And they’re going to need to invest a lot of their time in you. They have given you challenges that you are not prepared to overcome and they need you to win for their company to succeed. This same guy, who in 2 or 3 years will be super busy, available to newbies only in rare moments, will be there with you battling along for months. That makes a big difference.

Of course, for this to work, it is important to choose a strong team, with experienced founders and with good chances of success. Making this judgment is less difficult than it sounds, looking at the team working together it’s possible to get a good idea.

Finally, we are not in a game of right and wrong. There are several possible successful journeys. I thought it was important, however, to raise the bar for an option that ends up being somewhat forgotten by those who want to start a career in this type of company.

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