Know your founder CEO

Entrepreneurship is the lifeline of the technology industry, and it starts with founders with an idea who attract investors and employees to their passion.

The first few years are truly lean. Capital and resources are limited, and the goal is to prove product market fit.

Founders at this stage are wearing multiple hats: attracting investors, selling the product, defining the product, and building, testing, and finally supporting the product. They might be the sole employee or have a couple of other employees or consultants in their journey to next stage.

Being a founder is a lonely life. Founders are captaining a ship alone in a wide ocean without any land in sight.

Eventually, founders have enough momentum to attract institutional money, giving them the resources to scale the company. They start hiring professional management and team members.

This is when the founder makes the difficult transition to CEO, running a real company whose employees and customers rely on them.

This stage is critical for the founder. Their management skills come into play. They are no longer charting a course alone; now they have other people on the ship. All founders have to make this difficult transition to being a CEO.

When joining a company at this stage, employees need to understand the CEO’s personality because the transition that the founder makes to CEO is correlated to the culture that the company ends up with — which contributes to the success or failure of the company.

You need to understand the kind of CEO you work for

In the past 20 years, I have worked for half a dozen startups. I have joined companies after series A, when the founders have the resources to build a real engineering stack. In many of the companies, I have been head of engineering and/or the first engineering hire. This has allowed me to work with founder CEOs very closely.

Here are the traits I have observed.

The Founder
This is the CEO that never makes the transition. They continue to be the sole decision maker in the company. Their direct reports rarely talk to each other, and all cross-functional initiatives need the CEO in the room.

The Tinkerer
This is the CEO that believes that they know best what to build because they are the only ones who understand the market and customers. The voices in the product team are usually muted in this organization.

The Parachuter
This is usually the CEO who has been a programmer in a past life. This CEO focuses on the details of the technology stack. They hamper engineering morale if they are not careful, since they parachute once in a while, but leave the details to the engineers.

The Seller 
This is the natural state of a CEO. They have been pitching investors for a long time. Their pitch was successful, since the company now has institutional investors. This CEO can never stop the pitch. They look at the end of journey but forget the steps needed to make that journey.

The Roadie
This CEO enjoyed the rush of winning the institutional advisors, which involved a large amount of time on the road, so they continue to spend time outside the office and miss the realities within the company.

The Biggie
This CEO is often from a big company. They continue to cultivate their network from the past. They are trying to make strategist deals using the same skill sets that worked for them in the past. They forget the leverage they have on the table when in a large company they no longer have when in a smaller company.

The Showoff 
This CEO loves showing off technology. They will agree to demos to showcase the product vision they have while forgetting to account for the resources needed to build the demo — resources not spent building a sustainable product.

The Buddy
This CEO wants to be liked by everyone. They want to hang out with the employees. While their intention is good, they forget they are CEO and employees will always treat them differently. A CEO who wants to be a buddy is not ready to make hard decisions like firing an employee.

The Know-it-all
This CEO has all the answers. This is a trait that not only a CEO can have but could be a co-worker. The difference with the CEO is the dynamics end up being different. The employees do not end up not challenging the CEO. Better approaches to a problem are silently muted.

The Nostalgic 
This CEO has worked with a startup that had a big exit. In many cases, the CEO has joined the startup much later. They forget that how the processes within their previous company evolved over the years. Additionally the world has changed and same rules might not apply.

The Jock
This CEO is extremely motivated for success. They themselves are workaholics and expect their team to be the same. They forget that the jackpot they will make is vastly different than what their employees can expect.


All founder CEOs have their quirks. Each will bring parts of their personality when they transition from being a founder to a CEO. The path to a great company is understanding those quirks.

As an employee, you should take steps to understand the founder CEO during the interview process. If you are going to spend a large part of your life executing their vision, spending time observing and understanding the founder you work for will be instrumental in your personal success.

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