Comrade Boss

That's the problem, Marxists attempt to apply an analysis of 19th century conditions to the 21st century, as if we still live in an age of family businesses where the owner is the manager - and that the rise of multinational entities and more importantly shareholding has created a glaring distinction between ownership and management

Unless of course you want to pretend that some old granny with a few thousand dollars in a mining company partially "owns" the means of production, while said mining company's new CEO who has no stock in the company doesn't, and is as divorced from the "means of production" as the shareless bastards at the bottom working the machines

hasn't* created a glaring distinction

CEOs do exchange labor power for a wage. Sure, they engage mostly in glorified paper-pushing — but so does the secretary down at the reception desk.

I actually wonder about this.

If a CEO isn't getting shares and is basically managing capital on behalf of someone else, particularly if they're essentially just the "first manager" and paid similarly to a middle manager (thinking in terms of nationalised industry here, for example) would they be considered technical proletariat? (i.e. wage only no stock options, but directs the business.)

To actually extrapolate on this, one thing I considered was that with this hypothetical CEO/manager, if outside conditions were imposed from above, he would generally encourage employees to strike if it could improve the situation. (i.e. if the government wants to privatise the industry.)

Shares existed back then too.
Also a number of other employees are often given shares in the company they work at.

Strictly speaking the basic analysis of capital would seem to be correct, if just slightly more diffuse. (Assume a 100% employee-owned-stock company. The workers exploit themselves on capital's behalf.)

But management was much more intimately tied with ownership that it is now, the current system being difficult to fit into the traditional Marxist definition of ownership of the means of production.

Indeed, and ownership of the means of production in the form of shares and stock portfolios, is actually being systematically used to transfer wealth from the workers to the economic elite.

At the same time, in the case of labor exploitation, the CEO is exploited by the owners, but also a part of a hierarchy of exploitation that benefits him more than any economic system where he would not be exploited.
The issue shows why speaking of exploitation and class consciousness in the classic sense, is increasingly futile when talking to western worker and middle class, as they more and more are part of the global economic strata that will not have any economic benefit of communism, because they today benefit from the exploitation of poorer workers, often in other countries.
Both the CEO and the "middle class" worker therefore will rightly find the idea of they being part of a exploited class ridiculous.

To clarify, by this I meant that they have a net benefit from the exploitation in the current system.

you have to analyze what he does with said wage. if he uses that money to reinvest in portions of the means of production then he is not part of the proletariat. Just that as capitalism has grown it has become better able to spread out risk which means that instead of one person owning one factory it will turn into thousands owning a hundred

CEOs don't own the business that is true, but remember, private propery is a spook anyway.
They might not own the business but they still have an arbitrarily defined role where they make a lot of money from other people's labour. Executive status is no more or less arbitrary and materially baseless than ownership.

In theory, yes, in practice, no. The problem with modern CEOs is that they are not there to actually make anything with their labor. In fact, most of the time, they are in cahoots with the people that are going to raid the company, gut it, and keep the value. They're economic vultures. So why do CEOs have such high wages? Simple, because they enable the legal gutting of many companies. The company is there as their own personal piggy bank. When shit goes tits up, they'll simply fire a bunch of employees, maximize shares, and the shareholders will sell to make a profit, all off the suffering of the people that actually made things and actually worked.