How to help a 40-year-old with a stalled career?

Hi Penelope,

My fiance (40m) has been fired from his last two tech sales jobs in the past 2-3 years. Both times for not meeting his quota. He has been insanely stressed (and taking it out on me/bringing it home) and wants to switch to a less quota-based role with a different kind of stress. He had been doing quite well in sales up until that point (well, actually until he was PIPed in early 2020). But the company he worked for and the general tech working environment was a lot easier at that point in time.

He tried to apply for channel management roles (where you are managing the relationship with the channel partner that sells for you) and even almost got in by being an internal hire at his last company, but they ended up going with an external hire with 5 years of experience. The hiring manager told him he wowed them in the interview and that there wasn’t anything he could’ve done differently, just that they needed someone with more experience for how the company is doing at this time. His former coworker who he worked with at two jobs has vouched that she thinks he’d be much better suited to channel management than to tech sales. But he can’t seem to get a foot in anywhere (he’s applied elsewhere too).

He hates personality tests, but he is extremely extroverted and everyone’s best friend at the office. A “personality hire”, if you will. Not only that, but he’s extremely tech savvy. Coming from a family of teachers, I feel like he has that rare gift of being able to explain and clarify complex tech to people in a way that isn’t patronizing or insulting. He also knows quite a bit about personal finance.

Part of his issue is also that he never finished his college degree and left after two years, so some of the temporary jobs that might be available to someone else (i.e. substitute teaching) aren’t available to him.

So my question is, what should he do next? What type of job should he look for? Or should he start doing something on his own? Are there any certificates he should try to get?

Thank you in advance,

E

1 reply
  1. Penelope
    Penelope says:

    His issue is definitely not the college degree. And he does not need certificates. I’m sure he’s great at interviewing. I also think he can do fine in a sales quota job. This is what I think probably needs to happen:

    1. Rewrite resume to make him look like someone who always hits quotas so he can get a job with manageable quotas. 
    2. Learn to recognize companies that hire disposable sales people to test product viability. I have a feeling he has been in one or two of those positions and they will almost always be impossible. I think something in his resume signals to people that he can be pushed around on quotas.
    3. A/B test a second resume that gives him the opportunity for career change. The biggest hurdle for career change isn’t the resume – I can always rewrite a resume to get an interview. The hurdle is getting through the interview process mainly aiming high confidence. Your husband sounds like he could do that. 

    If he’d like to have a coaching session with me, I can get most of this done with him in a one-hour session. Here’s the link to sign up for a coaching session. https://app.paperbell.com/checkout/packages/59688

    A word to you: you can already see that when he’s under stress he takes it out on you. That will never change, and the workforce gets more and more difficult as people get older. Be careful letting yourself believe you can fix him.  Even if I can fix the current resume/job problem, how he handles frustration isn’t something you can change.

    Since you’re probably not leaving your fiance, take responsibility now for setting boundaries so he cannot relive his frustration by directing it at you.  

    Best wishes,
    Penelope

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