I consider myself a jack of all trades. I run a small biz on the size. I’m quite disheartened by the lack of generalist leadership roles in companies.
There is no natural career progression for a chief of staff. Plus, salaries for chief of staffs are not at par with CXOs.
Is there no other way to rise up the ranks in a generalist role?
All titles with Chief in them aren't CXO roles. Chief of Staff is definitely not one and never will be.
It depends on where your inclinations are - I'd suggest a detour into Biz Ops / Strat Ops / Rev Ops of your firm is big enough to sustain those kind of roles.
You could then get into a COO type role, assuming you are looking at a progression from CoS.
My inclination is towards product mgmt, where I have past experience. I’d ideally like to move at a director/principal level but all PM roles ask for years of “relevant experience” where I’d fall short.
Try and Head - Customer Success.
Thats where the real product management needs to happen.
Most orgs look at it as "support" but it needs to be oriented to "customer value delivered". Also sets up a solid feedback loop into Engineering.
A generalist is a breadth based person who can coordinate and collaborate in daily operations and strategy but cannot add value beyond a point as they lack strategic know-how or depth. Since it is a coordinator-collaborator (Program Management+Sounding Board) role, it is more of a will and less of a skill game. Hence, the endless supply of junior folks can always end up doing the generalist roles.
This essentially means that your role would never be valued as there will always be a cheaper/inexpensive alternative to you.
Hence generalist roles won't be able to succeed unless they specialise in something and become T-Skilled.
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