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Wellness Wednesday for November 23, 2022

The Wednesday Wellness threads are meant to encourage users to ask for and provide advice and motivation to improve their lives. It isn't intended as a 'containment thread' and any content which could go here could instead be posted in its own thread. You could post:

  • Requests for advice and / or encouragement. On basically any topic and for any scale of problem.

  • Updates to let us know how you are doing. This provides valuable feedback on past advice / encouragement and will hopefully make people feel a little more motivated to follow through. If you want to be reminded to post your update, see the post titled 'update reminders', below.

  • Advice. This can be in response to a request for advice or just something that you think could be generally useful for many people here.

  • Encouragement. Probably best directed at specific users, but if you feel like just encouraging people in general I don't think anyone is going to object. I don't think I really need to say this, but just to be clear; encouragement should have a generally positive tone and not shame people (if people feel that shame might be an effective tool for motivating people, please discuss this so we can form a group consensus on how to use it rather than just trying it).

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looking for career device.

i am a midlevel professional in my mid 30s, my work is essentially in business operations type roles in midsized organization. In addition to inflation kicking my butt this year, I have small children and will likely have more, whom I intend to send to private school. So I simply need to make more money. Right now, with school budgeted we're deep in the red. We spend more than we earn.

My goal has been to move up (or parallel with a reset inflation adjusted salary) in mid-level manager type roles within business /sales operations functions. (I have some management experience on my resume. I am technically a 'manager' now, but have no direct reports at the moment).

So i've recently been applying around (internally and externally) and gotten no luck. I realize that in business / sales roles, I am outcompeted by folks with field sales and sales management experience or MBAs. (I have a master's degree in something that gets me through initial hiring process gates, but isn't particularly an impressive competitive advantage).

In product or development management roles, I am not competitive because i don't have any technical experience on my resume.

So I basically have four options:

  1. Keep grinding through interviews until I get lucky

  2. Go get an MBA, take on a lot of debt, and hope to come out in a place to rapidly make it up.

  3. Jump down to field sales and climb back up through there back into business side/ management. My fear with this one is that I won't be competitive for any except pretty much entry level account executive roles. I'd essentially be starting over, but might see a big momentum gain /jump when I got back to the middle.

  4. Move into software dev. In school I was originally a CS major, I held a few programming internships, etc. before switching to a pipedream (long dead). Recently I've developed some React apps on my own, but I am not at a college grad level in terms of skill. I know both that I am capable of programming job, but also not a prodigy, and to invest back into this without a degree and with small kids to raise might be a barrier. Once again, I would have to start at the bottom, salary and level and work back up. But the upside here is better salary bands. (at a manager level, I currently make what devs from state U are coming in at).

Right now, I am just trying to maximize earning potential in the near, mid, and long term to take care of my family. Every single one of these seems like bad options. All of these come with a lot of sunk cost and uncertainty for a guy in the middle of the game.

But I am kind of at a loss and have about 0 months to make a plan so that I can afford to send my kids to school.

One option you might not have considered is technical sales. You could leverage your CS degree and your ability to deal with/manage people here. I'm a sales engineer about your age and make enough to send my three kids to private school if I wanted to. I'm a mediocre programmer and have an irrelevant bachelor's degree. I understand enough of the tech and can program enough to build demos and tools for customers, but that's about it.

If you've got people skills, you could try to work as an junior sales engineer (or regular engineer) somewhere and then quickly climb the ladder or jump ship to a better paying sales engineering role. Good sales engineers are really hard to find since it's kind of a weird skillset.

This is something my wife has suggested. About four years ago I almost made the switch to get into this at my previous employer. I had gone as far as getting technical certifications for their product. But before I got an opening I was recruited away to my current role, doubling down on business operations stuff.

This is good to hear. Do you think sales engineering is hard to come into of you aren't already in the company / have experience with their solutions? What would get me looked at from the outside?

Conversation skills and general people skills are the most important. You can turn a intelligent and curious sales person into a sales engineer, but it seems nearly impossible to teach a highly intelligent and skilled engineer people skills.

Straight up sales experience is great, if you have it. Also, I'd play up times where you advocated for something within your company or with a client. Bonus points if you can quantify the impact of your efforts. More bonus points if you can describe successfully navigating a complex problem with a customer or another team -- what was the problem and how did you scope it? Who were the stakeholders and how did you identify them? Did you define clear success/fail criteria to asses the results of your work on the problem? How do you handle customer objections? Are you good at asking questions to discover what the customer really needs (because often customers have misidentified their own problems)? Any stories you can share that answer these questions will help you.

For the technical side, you'll just have to target companies whose product seems "crammable," for lack of a better word. This depends on your technical chops. You have a CS degree, so I'm assuming you can probably figure things out on your own and teach yourself, if so there are a lot of companies available to yoy. Sign up for a free trial of their software, play around with it, read the docs, see if it's something you can learn or whether you're in way over your head (but tbh you'll feel like you're in a little over your head no matter what -- that's normal). Make sure you do the obvious stuff like reading the site's main homepage, the "About Us" page, etc. You'd be surprised how many people show up to interviews poorly informed about the company and/or the product.

I'd also at least skim "Mastering Technical Sales: The Sales Engineer's Handbook". It's no-nonsense and not as dry as it sounds. It will give you a good idea of the sorts of problems and questions that SEs have and give you an idea of whether it's something you want to do or not.

as a coda here, unfornately I don't actually hold a CS degree. I switched majors halfway through. Nor do I ahve prior sales experience.

I am pretty confident, I could do (and enjoy) technical sales, as I peruse job listings, I am doubtful about getting to an initial interview with my background. I've put this to the test by applying to several, but I am not hopeful.

A path to Sales engineering looks like I'll have to come up through strategy 3 or 4 above anyway (entry level sales or entry level software dev). We'll see, I guess