More than a decade of grousing about product management

So, you want to be an executive …

cheerful senior businessman shaking hands with partner on street
Photo by Andrea Piacquadio on

Becoming an executive: what it takes, who it’s reserved for, and the stacked deck against disadvantaged individuals.

The Dude has had the idea behind this post for a loooooooong time. In his career, he has worked at large, medium, small and ginormous organizations, had the opportunity to talk to many levels in the executive ranks, and – naturally – has observations of who and what makes an executive.

Buckle up this is going to be a long, and likely very controversial post.

What is an executive?

It is probably easier to identify who is not an executive. A team lead, just starting as a people manager? Not an executive. A manager, or senior manager? Nope, not an executive.

Director? Now we get to the “it depends” category. By definition, the title of Director is the steppingstone in the executive ranks. However, the gravity of the title Director has been diluted, with it being essentially a perk of working for a small company (seriously, the Dude one worked at a company that had about 50 directors of product management, most of them managing teams of less than 3 people, and more than a few with no direct reports.)

However, at larger companies, the org structure is usually more rigorous, and director is the first position that has multiple managers (or senior managers) reporting to them, and compensation begins to shift from bulk in the base salary, with small tidbits of variable comp, to a larger component of variable comp tied to measurable objectives. But still, in the spectrum of the “Executive Class”, directors are the minnows or pilot fish.

The Vice President is a hard delineation of mere mortals and executives. At this level, you typically have P&L responsibility, and are often what is called a “General Manager” as well, of a business, business unit, or division. You usually get a LOT of RSUs (if you are a public company) and your variable comp is often targeted to be equivalent to your salary, with many accelerators that can blow your base salary away should you greatly exceed targets.

More importantly though, at this level your focus changes. You become a very different person. Your language changes, how you interact with people and teams also changes. Suddenly, you are part of the company, not just a cog in the wheel.

For many on the progression, the VP role is a make or break test. If you can transition into executive speak, the politics, the power struggles, you can progress. Alas, many people who crack into this, it is the apex of their career. They just don’t fully make the transition.

The Dude’s thoughts on why this is: If you have empathy for the common employee, it will put a hard brake on your upward progression. At the VP level and above, you must be able to completely fuck over the rank and file if you are asked to. You need to be a cold hearted motherfucker. You need to be able to walk into a room filled with your staff, and tell them their jobs are being eliminated, and then be able to go for a run, and sleep well afterwards.

Above VP, depending on the size of the organization, you will have a cloud of sharks with titles like VP, Executive VP, Senior VP and the like. These are all chum, all waiting for the opportunity to fuck over one another to get that next rung on the ladder. The ultimate goal is to get to the Executive Vice President role that is the rung from which people are elevated into the CxO role. The holy grail, the c-suite.

Now that we have defined the executive ranks, how does one get there?

In America, there is this belief that we are operating in a meritocracy. That anyone, as long as they work hard enough, put in the time, and catch a few breaks, can become the CEO of a Fortune 500 company.

This is complete and utter bullshit. A gifted kid from Watts is not ever going to get there. Sure, they might be able to make it to a Director role. The Dude has worked with several people who fit this category. But a chance at the corner office? No fucking way. Not gonna happen.

Why is that?

The deck is stacked against them. The pipeline of people for these roles begins in kindergarten. Parents of privilege working hard to shepherd their kids lives, structuring the right activities, the right studies, getting them in to the schools that build that pipeline (elite college prep schools, extra tutoring, one of the main universities (UPENN, Michigan, U of Chicago, Yale, Northwestern, Harvard, Stanford, … you get the idea). Their majors? Business, marketing, finance. Not physics, chemistry, or computer science.

For the budding executive, College is to build a network, not to build knowledge. Build a pedigree, not build skills. Oh sure, skills are useful, but for the career progression and potential, in the executive ranks, where you went to school, and who you went with is the goal.

If you ask an executive how they got to their position, they will universally tell you that they worked their ass off for it. That they hung it all out, took risks, bet and won. But that is largely bullshit. It is like Ivanka Trump, born on 3rd base, with a gold spoon in her mouth, and A-rod at bat to bring her home.

The truth is one of two possibilities:

  • Those who were groomed for their future by their executive parents, every step of the way mapped, analyzed, dissected, and planned. School, extra curricular activities, the right hobbies (golf, skiing, sailing/yachting), country club memberships, well, you get it. This provides a self awareness and an entitled mentality that reeks in that executive class.
  • Those who were tapped on the shoulder by an executive early in their career. Perhaps they showed a flair, or had an early success that attracted attention. This “hi-pot” or high potential selection, mostly occurs at mega corporations, where someone comfortably ensconced in the executive team looks for a mentee, and lifts someone from the rank and file into the executive track.

Of course, there are exceptions, as they say, the exceptions prove the rule. Someone with entrepreneurial instinct, and amazingly deep dedication (think the level of focus of John Wick) builds something of moderate success, and their company is bought by a mega firm, instant elevation to the Executive ranks. But how many of them go on to long trajectory executive roles at large organizations?

Very few. They cash in and play VC, betting on people like themselves, or they return to the entrepreneurial engine that made them great. But funny thing is, most of the latter folks never repeat the same level of success. Sure, they may build things that get bought, adding to their wealth, but the big score is difficult to reproduce.


Executives are not like you and me. They are different. Wired different, born different, developed differently. It is virtually impossible to make the jump or transition mid career. Senior executives (talking c-suite at major corps here) were prepped for that track from the moment of conception. They are not like us. At all.

In many ways, the Dude is glad that the shoulder tap that seemed inevitable early in his career never happened (a leader did talk to him about it, but then a humongous amount of turmoil at the mid-cap company he worked at shelved that path) and he enjoys plugging away at what he is good at doing. He doesn’t envy the executives. That ability to walk in and fire a whole organization and then be able to go for a run, and eat a nice meal just isn’t in the Dude’s DNA.

Thank God.

The Dude is reading a great book that discusses the environment that gave rise to Silicon Valley, “The Code” by Margaret O’mara. Highly recommended. While the Dude knew much of the things that happened, he was definitely surprised by how much the sloshing of Defense dollars were the seed corn that germinated the growth of Silicon Valley.

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A crusty veteran from the product management trenches. Plenty of salty language, references to cannabis, and a connoisseur of White Russian cocktails

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Written by pmdude