How do I get out of corporate IT?
November 8, 2020 11:44 AM   Subscribe

I'm a software developer that specializes in software that is very outdated. It sees periodic updates but is based off of 15 year old technology and hasn't seen a meaningful large update in 7 years. Modern software development practices like Docker, automated builds and the like have completely passed it by. It is dependent on Microsoft, which itself has largely abandoned updating .NET Framework in favor .NET Core. This has lead to unsteady, short-term contract jobs with large corporations that need to support it. Even successes are horrible as no one wants to deal with it. I've learned I do enjoy developing software and I can't stand corporate environments. How do I get out of this cycle late in my career?

I don't think it would be fair to say I've grown stale. If anything I've learned a lot of about how fundamentally operating systems work, building multi-platform architecture, and dealing with some hard problems. When you're tasked with delivering software that's dependent on a poor, outdated software package and also working within the confines of a very secure corporate environment you actually tend to learn a lot. I based my current software delivery methodology on how Rust is installed as I can't assume anything about a given environment or what's installed on it.

While this might sound DevOps heavy, and it is, that's simply because installing and delivering software in a corporate environment can be a huge burden. Sometimes even things like Docker aren't allowed but if I have a bash script that does a lot more than a bash script should, I can generally get around restrictions. My current contract has a facility in which nodejs was rejected by legal so I was forced recreate my test suite in cpp as that toolchain was the only thing available to me.

The heavy restrictions has actually made me a better developer. The software I write is usually written with the least dependencies, does exactly what is needed and if I can brag, pretty elegant. Mostly because I had to.

Covid has made my job hunt harder, while I saw my only source of income crash. If I could have any job I think I'd want to be in a research lab. I like being around creativity and creative people. I used to think things like MIT's Media Lab were just toys, but now I see the appeal. I've tried to apply to startups but they seem very focused on whether or not I've been apart of a successful startup, went to the right school. I can also see where my resume might have me tagged as someone who has spent their entire time lagging behind the curve but that's not the case at all. If anything I get bored quickly in dealing with outdated technology and try to fit it into a modern tech stack.

What would my next steps be? I don't mind freelancing and taking contracts but, I never liked speaking at conferences or blogging. Has anyone actually made a career out of this and not get shoehorned into a speciality? I'd love to consult and help setup smaller startups or technical companies. My experience has been limited but I did feel as if they were looking for superstars. I had one technical founder tell me they only hire people from "unicorns" which I guess are companies with high ARR. I know there's got to be companies out there that are interesting technology firms not focused on the next TechCrunch article, how do I find them?
posted by anonymous to Work & Money (12 answers total) 9 users marked this as a favorite
You could try finding a "hot" open source project to contribute to and then use that experience and those contacts as a way into the type of company you want to work in. Also, maybe meetups is a way to get to know people. It is rough out there -- especially if you are trying to break in.

Also, if you aren't already doing this, I recommend writing a non-boilerplate cover letter with your application. I am a hiring manager, and 90%+ of the applications I see have no cover letter. Most that do have a cover letter have a bland generic one like "I have XX years of experience in Y technology and think I would be an asset to your organization." I know how time consuming it is to apply but you could put your story in your cover letter and tune it to the company a bit. I did interview someone based on their cover letter & they got the job. [I was going to pass on the resume, but ran the cover letter by one of my leads and we decided to give the guy a chance.]
posted by elmay at 12:03 PM on November 8, 2020 [4 favorites]

You might look to companies that are growing and just exiting the startup phase but not yet full-fledged "corporate" environments. The downside to that is that you're going to be job-hopping quite a bit as most of those companies are headed to becoming corporate environments, but during the transition from startup to corporate, you'd probably enjoy being part of that environment.

elmay's suggestion of contributing to open source projects is good - if there's a project you like and you can make a strong contribution to it, and it's of value to companies, you'll probably get noticed. Possibly even by startups.

Yes, startups and others heavily in the thrall of The Next Big Thing(TM) are looking for "superstars" and also really want someone that will be ridiculously dedicated to the job.

A smaller non-startup is likely your best bet. Especially if the company is growing at a good clip and you can have a hand in picking technologies instead of just working on what other folks have already picked.
posted by jzb at 12:13 PM on November 8, 2020 [1 favorite]

A grab bag of ideas:

Interviewing is largely a numbers game -- both for the people seeking jobs, and for the companies hiring to fill roles -- to land a new job you need to be a reasonable fit for the role and also have a fair bit of luck. Apply for many opportunities!

Use your network. Have you tried reaching out to friends in the industry, former colleagues or former clients to see how they're going and if they know of any opportunities for work that you might be interested in?

It could be helpful to have some line items on your resume with a recent examples of you working with a newer technology, to help give evidence that you're still learning and not only a specialist in one legacy tech stack. This could be an open source contribution, or maybe highlighting any work project or side project where you used some different tech and tools.

You could take a stepping-stone approach where you aim to land a role that isn't your dream job, but gets you closer and lets you gain different experiences. e.g. can you identify any small startups / consultancies that are trying to build and sell software using modern technology to organisations such as the corporates you've got lots of experience working inside? Would you be able to frame your experience of working inside these environments as helping these small businesses to navigate the enterprise sales process, making it easier for them to e.g. pass the client's hurdles for security requirements, testing and documentation, etc, and close out a successful and profitable sale and deployment?

Another possible option to frame your value separately from the tech stack, and instead focus more on what you can bring to a less experienced team as a senior developer. E.g. a number of small businesses may have eager but inexperienced developers, if you find one that's managed to be operating profitably, using a tech stack you're interested in, but is struggling with tech debt etc, you could try to frame yourself as someone with experience of the full software lifecycle and ability to help get tech debt under control through investment in CI, testing, traceability of release artifacts, automated monitoring for production systems, taking security vulnerabilities seriously, etc -- both being able to do this hands on, but also being able to teach the existing team why and how to do it.

edit: also, if you're game to give it a try -- personally i love hearing real "war stories" about actual projects -- talking about what worked and what didn't. I find it more interesting than talks about the latest trendy technology X. Are you able to draw on some of your experiences to put together a short talk you'd be comfortable giving, other people might find interesting and valuable? If so, this could give you a lot of visibility at a meetup and be a good way to grow your nework.
posted by are-coral-made at 12:42 PM on November 8, 2020

If you like the Microsoft environment, give their Azure items a try. They have a great deal of online training materials, and you are well suited to many companies who do want to move older business applications "to the cloud". If there are local Meetups for midsize IT consulting practices, they might be interested in someone with your background.

Research labs can be a mixed blessing. Funds are tied in academic grant amounts, and there can be large swaths of slave, er I mean graduate students you compete against.
posted by nickggully at 1:09 PM on November 8, 2020

Try higher education institutions. The pay will be lower, but the environments are generally much better on morale. I've worked in both higher ed and corporate as a data analyst and engineer and I want to go back to higher ed so BAD, it's just that I needed the corporate experience to pad my resume and make the step up from analyst to engineer.

I would get a few cheap online certifications in the meantime in relevant languages and tools just to show that you're still evolving in your career and work on your portfolio with a project or two. Udemy or Coursera would work fine for that.

HigherEdJobs tends to post these jobs rather frequently.
posted by Young Kullervo at 1:09 PM on November 8, 2020

Also freelancing gigs (even if they are just one or two projects) looks awesome on a resume as well.
posted by Young Kullervo at 1:11 PM on November 8, 2020

I work at a large financial corporation in a very agile modern tech stack area. We are constantly looking for developers. If you’re in the greater Philadelphia area (or interested in moving?), shoot me a me-mail. And if not, just know there ARE corporations out there with innovation labs and new tech stacks that would kill to have a developer like you who is flexible and open to learning.
posted by kellygrape at 1:17 PM on November 8, 2020 [4 favorites]

I was in somewhat similar situations twice in my career, and I found two ways to cope.

The first time came after a decade of earning my living with Clipper (a compiled dBase II, more or less). I had a consulting gig with a company that had some legacy Clipper apps, so they needed me enough to give me a little wiggle room. I wangled a week-long course in their new preferred language (PowerBuilder), and that gave me a foothold for new work.

The second time came after the DotCom crash when there wasn't much work at all. I used the time to take a self-guided tutorial on SAS which was a good match for my background in math and statistics. I earned a certification and pursued it long enough so I know it would worked, but other opportunities opened up.

While I was on the bench during the dot com bust, I sent a cover letter and resume to every business in the local Better Business Bureau. I got a couple luke warm replies, but one guy held on to the resume and called me year later. I was at his company for the last 15 years before I retired.

Don't be afraid of small companies. The pressure can be much less than in a big shop, and they may well want you for legacy apps.
posted by SemiSalt at 2:26 PM on November 8, 2020 [2 favorites]

I can also see where my resume might have me tagged as someone who has spent their entire time lagging behind the curve

I think this suggests you should work on your resume. What you've written here is doing a good job of selling you as someone who is adaptable, creative and puts thought into their work. Sure, companies like when they can find someone who knows whatever language or framework they use, but having someone who can figure stuff out is actually way more valuable and some companies are capable of understanding that. Don't write "deployed tedious old application to corporate network", mention that you borrowed ideas from Rust to overcome challenges X,Y,Z while deploying the thing.
posted by hoyland at 2:32 PM on November 8, 2020 [5 favorites]

Also one way you can free up your time as a contractor is by raising your rates. If you have a tech stack you hate working on but that pays the bills, doubling or tripling your rates might well mean you have a comparable paycheque but a lot more free time to explore new growth paths.
posted by mhoye at 2:48 PM on November 8, 2020 [1 favorite]

I was in a very similar position (developer with expertise in a Microsoft tech stack, looking at greener fields) a few years ago. I was concerned that interesting companies wouldn’t value my experience but things all worked out very well in the end.

I did however invest a lot of time in the transition. I intentionally dedicated months to to learning and building up my resume/web presence. Things like:

- Built tiny side projects in many different programming ecosystems, publicized them on my personal website and GitHub
- Built a new personal website as an exercise to get up to speed with modern web dev and JS
- Wrote informational technical blog posts, submitted them to programming newsletters
- Gave a talk at a user group about a subject I just happen to know well

At the end of all this I’d learned a lot and built up a decent web presence. My website’s front page and my pinned GitHub projects clearly indicated “this person can get stuff done in many programming ecosystems” - intentionally, so potential employers would notice that when doing the bare minimum of background research on me.

YMMV but this is one blueprint you could follow. Feel free to DM me.
posted by ripley_ at 8:04 PM on November 8, 2020

You might want to check out The Recurse Center - it's specifically a program for people who already know how to code but want to jump into something new.
posted by Ragged Richard at 2:17 PM on November 11, 2020

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