I have been working in the same business for around 10 years. Much of this has been fulfilling. I support the aims of the business, and have been repeatedly promoted and am now (on paper) a senior employee / decision maker in a strategic development role.

However, it suffers from chronic internal problems. I want to leave, but don’t want to “give up on them”. The below (all IMHO of course) is an attempt to give context, not list grievances:

  • Senior management are biased towards “making the next big sale”; we focus on elephants over deer - which in turn has led to a reactive, sales-target-based mindset with little direction or forward planning. Many products / features exist to meet sales contracts rather than part of a coherent vision or offering.
  • As a business “we” ignore good practice and are not interested in improving - and it shows. We repeatedly over-commit, under-prioritize, and under-deliver; we cargo-cult badly; important technical decisions are made by people managers or interns because relevant staff are too overloaded or too busy fire-fighting; site monitoring services are “not worth paying for” because customers phone us up when things are broken for free; we are “too busy” for luxuries like regression testing or documentation; and so on.
  • Due to mismanagement many key staff and locations have been lost. We pretend to be a global company, but in practice it’s the East Coast with the rest of the world as an afterthought at best. About 90% of staff are in the main office with a handful of remote work-at-home, including me.

So in the last few years the business has changed from a successful first-mover to getting beat up by newer, more agile competitors who have a game plan and think in terms of a platform / service instead of a yard sale.

Now for me: what used to be a fun and interesting place to work has become frustrating and boring. As a remote employee, I have little visibility to the rest of the business and am frequently sidelined. Due to all the chaos and short-termism, my time is spent in heroics, fire-fighting, pinch-hitting, and dysfunctional meetings. I am very busy, but feel highly underutilized given my skills and experience; I cannot fulfill my current role, never mind consider career progression.

Of course, these problems are common. I’ve tried the usual countermeasures (express concerns with senior management, convince them of the value of good practice, increase your visibility, improve the company from within, etc.) But to be blunt, these haven’t worked. At most I get the “you’re doing a great job, and yeah, this quarter is real crazy; things will calm down and then you can start on the roadmap” pep talk, but of course the next quarter is just as crazy.

So the scale of this problem seems outside my ability to influence it. I also don’t want to move to the main office; I doubt it would solve the root cause anyway.

In addition, as a senior employee myself, I know that I am part of the problem, and have attempted to lead by example and “do the right thing”. I got shouted down by the project manager, even though I was the tech lead on the project and executing my own job description. My own line manager backed him up.

Again, I support the aims of the business - it is basically the only reason I’m still there. But I’ve also had enough of banging my head against the wall. I feel I have outgrown the opportunities within the business and it’s time to be have more impact / value somewhere else.

(EDIT: question put on hold; tried to clarify "why and how to make a decision".)

How can someone determine, and evaluate, further countermeasures or interpretations in this or a similar situation?

Alternatively, what sanity-checks are available that signal all reasonable options have been exhausted and it's effectively time to quit?

Possibles include:

  • Re-attempt sane man countermeasures above (communicate issues to the business, take ownership and "do the right thing" yourself)
  • Decide this is a minor issue ("I am being a diva; should stop trying to improve things and take the paychecks")
  • interpret this that my job role is no longer needed, and this is a method of edging me out the door
  • rationalizing jumping from a failing business
  • accept that I have been over-promoted into a role that I can’t fulfil
  • While it's useful to write out your thought like this when making a decision, this is the wrong site to post it. Scanning your post and reading @JoeStrazzere's comment I get the impression that you want us to tell you what your best next step is in your career and that's a very personal choice that you have to make. – Lilienthal Sep 10 '16 at 19:49
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    This isn't something anyone can really answer because we don't know how much you'll put up with in order to not give up on them. I would say that even though you haven't given up on them yet they seem to have given up on you. It should be a two-way street; you give them your hard work and they give you good experience and career growth. It sounds like in the beginning they did help you grow but may now be holding you back. Start thinking about what you want out of your career and if you aren't going to get it where you're at then leave. – Ray M Sep 10 '16 at 20:46
  • Thanks, I'd +1 these but don't have enough karma. – vektisbrack Sep 14 '16 at 12:05

what criteria can I use to validate I have effectively run out of options and it's time to quit?

Getting shouted down for doing your job and having your line manager not back you up is a pretty clear validation criteria. Your idea of the businesses aims are not based in reality anymore. Sales has taken over the company.

I have seen many businesses with this model, you either ride with it and take on that same aim which as a tech person means a LOT of disaster management and damage control or you move on. Usually they tend to chew through techs. But the model allows for that.

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  • I'd +1 this, but not enough karma. That does sound like a clear criteria... – vektisbrack Sep 14 '16 at 12:05

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