The CEOs You’ll be Working With

A man is buttoning his suit

The previous posts were somewhat ‘heavy’ so today I’d like to have a shorter and lighter post. Hence, today we’ll be discussing the various types of CEOs you might come across in your career, how they will affect your day-2-day and the ways to tackle it.

This post aims towards more senior PMs and will be highly relevant to product leaders. If you are a relatively junior in your product management career then I suggest you keep this post for future reference.

 

But, as always, first things first:

The impact of the CEO on your role

First, when I say CEO, I also include all the sorts of ‘general managers’ and ‘presidents’ out there, in case your company is big enough to contain several business units. 

If you’re working closely with the CEO (and it doesn’t mean you’re reporting directly to him) you’ll certainly feel the direct impact of this relationship on your day-2-day. 

Specifically, you’ll need to interact with the CEO when:

  1. You want to approve a new product strategy or a north star
  2. You want to enforce alignment between departments based on the strategy/north star (see here for more details)
  3. You want to make a leap-of-faith and experiment with a new product (which is not trivial to implement) that may open the company to new opportunities, but could also result in a waste of time, after all (this what happens with experiments from time to time).
  4. You want to promote a re-org or a fundamental change of processes and how things work
  5. You want to increase the budget to your department

 

If you are in a senior role, if it hasn’t happened already, then it’s just a matter of time before one or more of the scenarios from the list above will be relevant to your reality.

When it happens – you need to know how to approach and pitch the need/change you want to the CEO so you will get their blessing.

 

With that in mind – let’s see what are the various CEO stereotypes I mapped and what’s the right approach to their heart/ears.

CEO Stereotypes

The ‘Wonder boy/girl’

This CEO is usually a young but brilliant dude who managed to convince the investors community to put their money on his/her vision. They usually bring a disruptive vision and they can be quite charismatic.

Because everyone around you may believe that this person is probably the next ‘Steve Jobs’ – you are the one who needs to stay objective and judge their big words by their actions.

Yes, it could be that you are lucky enough to work with a genius who is going to change a whole industry. In that case – buckle up because it’s gonna be an amazing ride.

But it also could be just talks. This person was able to sell a very sexy story… which is totally not aligned with reality and where the market is going. In that case – you better identify it in time and leave the ship before it sinks.

 

But let’s be success oriented for a second and assume that this person really knows what they are talking about. In that case you are dealing with a CEO who is truly innovative in the way they think and see the world. It brings the following pros and cons:

Pros:

  • It should be very feasible to convince this person to experiment and try new features and approaches. 
  • This person will give the product a ‘place of honor’, and hence the product managers in the company will feel significant.
  • Processes will be flexible and nothing is written ‘in the stone’

 

Cons:

  • This stereotype usually lacks the experience of how to manage a company. They also don’t allow themselves to be bound within rules or policies. Therefore – expect chaos across the board.
  • They are probably very ‘opinionated’ and hence if your idea/suggestion is interpreted as not aligned with their vision – it probably doesn’t have a chance.
  • They may overlook the small details and focus purely on the big vision, which will make it harder for them to stay disciplined and enforce a new methodology or an approach, because they may find it unimportant or just a disturbance. 

 

Having such a CEO is not an easy journey.

This CEO isn’t afraid to rock the boat or change their mind often. Sometimes even too often.

As I noted above, it’s very possible that this CEO doesn’t care about the small details and the management of the company is just a nuisance for them. Therefore, if that’s indeed the case, you need to look for the person they trust and who whispers in their ears. It could be a person who was officially embraced as the ‘internal’ decision maker, but it could also be very unofficial. From your perspective – it doesn’t matter. 

This is the person you need to target and convince in all of your efforts to make a significant change. If such a person exists – start building a relationship with them right away, even if you don’t have an immediate need (it’s actually even better).

Such a person, again, if exists, is probably the one who is making the shots. They are also probably more pragmatic and deeper in the details. If your initiative is good for the company, there is a good chance they’ll hear you out and make it happen.

 

If such a person doesn’t exist, then you can either pitch your request via your boss (if you have someone between you and the executives) or directly to the CEO. Just make sure that your request is aligned with the big vision and directly contributes to it. Otherwise – there is a good chance it’s a lost cause or even worse – it will get approved, you start working on it, and the plug will be pulled out shortly after, because something more correlated came up.

The CFO

This stereotype describes a person who was born and raised in the finance department. They have a strong affinity to numbers and all the challenges they come across are translated to some sort of balance sheet.

Most likely, they weren’t part of the co-founding team and joined later down the road. Why do I say that? Because most CFOs are becoming relevant when the company is starting to have some meaningful revenues. Also, most CFOs I know are having a hard time with innovation and the time it needs to incubate. When they are asked to invest in a company which still doesn’t produce meaningful revenues they will focus on the projected revenues and how fast you can get to break-even. This is healthy thinking in some situations, but for some companies, which require a bigger leap of faith and time to grow – it can be devastating.

The pros and cons of such a CEO are:

Pros:

  • Will push towards making the company a real business as soon as possible instead of letting it search for purpose and product market fit indefinitely.
  • Will push you, the product manager, to be more business oriented and to look for the money.
  • Very down to earth and can help you build a solid revenue projection

 

Cons:

  • Will push towards making the company a real business as soon as possible. Yes, I wrote it in the pros as well. This fact can become a real problem if the company does need the time to reach a product market fit.
  • Very little tolerance for experimentation and initiatives
  • May push towards local optimizations on revenues and miss the long term optimizations on market share because of that.
  • Very tight budget that may not allow the grow the company needs

 

Having such a CEO stereotype is quite challenging, especially if you are not working in a corporation. If your company is still searching its way towards PMF, then it may never reach it.

If you do believe in the business and the vision, and you strongly believe all the company needs is just more time to prove itself – you should definitely fight for this. However, it’s not gonna be an easy fight. Whenever you pitch to such a CEO, your story must include a revenue model which is nailed down and verified by domain experts.

No matter how you look at it – your pitch must show the money eventually. Otherwise, your chances of getting what you want are quite small.

The sales person

If your CEO started their career and raised in the sales department then there are quite a lot of similarities to the CFO stereotype.

However, there should be a little less focus on the overall revenues and more focus on the deal size and the amount of deals closed. This stereotype just loves to close deals.

 

The pros:

  • Knows how to sell; Knows how to tell a story. You should definitely listen and learn.
  • Can probably help you frame the story of your product and its value proposition.

 

The cons:

  • May focus on the amount of closed deals rather than chasing the right customers.
  • May put too much energy into a specific prospect or customer even though the right thing to do could be to let go.
  • Vision and strategy may not appeal to them. They may favor pure opportunism and hence force you to release a bunch of useless features

 

Having sales leading a company is as worse as having a CFO lead a company as I see it. The priority on closing deals may put a lot of pressure on the product team to be purely tactical and give up on any strategy they will try to form.

Your product may become a bunch of features pasted together, based on the queue of requests from the customers or prospects. Any attempt to explain why this is bad may fall on deaf ears as the CEO refuses to give up on any existing customer/prospect.

 

That being said, as a senior product person in this company – you have no choice but to keep explaining the value of a proper product strategy and the need to stick to it with proper discipline.

Use whatever in your disposal to build your case:

  • Past features that were developed but never used (or served a single customer)
  • Customers whose hunger is never fulfilled even though you gave them everything they wanted to date
  • The customers who churned because your team never reached the roadmap items that should have cater to them (because they worked on a bunch of other useless features)
  • The lack of any meaningful progress on the roadmap and having the competition closing the gap much more quickly

 

If your CEO is not an idiot – he/she may actually see the devastating results of their short-sighted thinking. Sometimes it’s too late, but sometimes it’s not. Just don’t give up – unless it’s really too late.

The engineer

If your CEO was raised in the engineering department then they probably love technology and what it may accomplish. The main danger here is that they fall in love with technology, rather than the real pain they are trying to solve.

 

Pros:

  • Quite straightforward. No bullshit. Less politics.
  • If your product edge is indeed a technological one, then having such a leader is a huge plus.

 

Cons:

  • May lack proper business understanding, including marketing and sales
  • May focus on the engineering aspects of the solution rather than the value the product needs to deliver
  • May not possess great communication skills

 

Having an engineer as the CEO may not be as bad as having a CFO or sales in my humble opinion. However, things can still go south very quickly if the CEO is not humble enough to admit that they lack business & product understanding and need your help.

A lack of self awareness in the engineer stereotype can be devastating for the company.

Someone needs to therefore support the CEO by filling the gaps on the marketing, sales and product aspects. Your company may have an awesome, cutting edge technology, which is indeed far ahead of the market – still, this technology needs to be productized and marketed properly.

If you don’t think that these gaps are filled, try to step in and offer your help. Aside from helping with the productization of the technology, you can help by identifying true gaps in the marketing & sales efforts, and suggesting how to fill these gaps.

You can help educate the CEO about the importance of reaching PMF, and explain that the road to PMF goes through marketing and sales (see here).

If you are pitching this from a humble and true place – then good chances you will be heard and a proper action will be taken to bridge these gaps.

Such an education can also help in mitigating the risks of focusing too much on technology and ‘perfecting’ it at the expense of moving fast and releasing more features. You definitely need to introduce the KPIs and the north star that will help your company to stay focused and on the right path.

The product manager

That sounds awesome, right? A CEO who spent some time as a product manager.

Well, on the face of it – yes.

But there are risks here as well. 

 

Pros:

  • An holistic view of the business
  • Understanding the pain points and hence the value of the product
  • A potentially good balance between sales, marketing, engineering and product

Cons:

  • Too much focus on growth while forgetting to turn this into a business
  • Lack of knowledge in sales and marketing may not create enough awareness to the product

 

So yes, I definitely prefer to have a past product manager as a CEO. However, there are true risks here as well.

The main risk, as I see it, is having too much focus on growth. We’ve seen it all in 2021 and 2022 and what happened to companies who adopted the ‘product-led growth’ mentality and took it to the extreme.

I’m not saying by any way that I’m against a ‘growth’ state of mind, but I do believe you need to combine it wisely with revenue generation and definitely have a goal of becoming break-even at some point which is not too far in the future.

Product managers tend to forget it. Hence, if your CEO is product focused and he/she is all-in for growth, then you need to serve as the responsible adult and make sure the product is supported by a true business model that is sustainable and can generate great revenues 1-3 years from now.

The veteran

This stereotype has been to a startup or two before. They have been on the rollercoaster more than once. They have earned their scars from the battle, and they have learned some lessons the hard way.

This is my favorite type, because they understand that they are far from Kansas by now and they know that only by having the right balance between all the functions in the company will they reach success.

 

Pros:

  • A true understanding of PMF and why it’s important
  • A true understanding of the importance of the supporting units – marketing, support, sales and engineering, and how they should work together
  • A true understanding on how to run a company

 

Cons:

  • Trying to make it all ‘too perfect’ by trying to apply ALL lessons together

 

A true veteran has learned from past experience and past mistakes. And you have a lot to learn from such a CEO – so you want to stay as close as you can and watch how he/she works.

One pitfall such CEOs can fall into is to try making everything too perfect and hence spending too much time on perfecting each step and department (marketing, sales, engineering, etc..) at the expense of speed. They may get too involved with this because they are determined to fix past mistakes.

If you identify that this is happening just try to raise awareness to this. A veteran CEO can be snapped out of getting too deep or too involved with something which is not that important, because they already know the price they will pay for ignoring warning signs. Hence, they know when to listen to advice, and when to ignore it. So, they will definitely hear you out at the bare minimum.

Summary

In this post I tried to expose you to the various CEO stereotypes. Yes, in reality these stereotypes are not that black and white and you can definitely see an amazing first time CEO who grew up in sales (for example). And yes, I probably missed a type or two.

That being said, it’s important and beneficial to map your CEO to one of these stereotypes, if possible, so you can understand how you should approach and communicate with such a person. At the end of the day – the CEO, the president or the general manager can make or break some of the major initiatives you are trying to explore, so you better know how to speak her/his language.

 

That’s it for today.

If you found this post/series useful – please let me know in the comments. If you think others can benefit from it – feel free to share it with them.

 

Thank you, and until next time 🙂

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