Ask HN: Should I checkmate my employer?

It sounds like you may be failing some sort of implicit cultural filters - you've been in the same small workplace for 8 years and apparently your circles don't include highly-paid IT/development people. "International-tier" tech is a fairly distinctive and exclusionary culture to anyone who is not fluent in either its own norms or those of a handful of adjacent academic fields, and the boundary may be policed based on shibboleths that even members couldn't articulate explicitly when prompted. Looking at your post, I get enough of a "cultural difference" gut feeling that reinforces this suspicion - I think the most glaring signifiers are the excessive spacing, omission of apostrophes and commas (though I realise this is more common in the UK) and a certain harshness in verbiage like "aggrieved" and the "The problem/s? They won't..." that is at odds with the nonconfrontational style of the modern workplace. (There was actually an opinion piece on this on the HN front page a few days ago: https://goodreason.substack.com/p/on-corpspeak)

Consider befriending some people in your industry who are in a position closer to the type that you would be interested in, and asking them for feedback on your CV or at least absorbing the way they talk and present themselves by osmosis. I'm not in the UK, but at least in the European location I'm in there are many tech people circulating on local meetup (social) apps.

What throws me off about even the short description you gave is that your claims are... off.

As a hiring manager, I don't care that you filled a 42U rack - I care about why. What did it accomplish? Did you do it with cost efficiency? What impact did it have on the business? What was the ROI on filling that stack? Why do you feel it is better to have filled a rack than to have scaled in the cloud?

Same with LOC and number of repos. Those simply are not meaningful numbers. I could go put 20K lines of code in 20 repos here in the next hour, that doesn't mean I accomplished anything. Tell us what that code does.

You say you need a larger staff, but you don't say what tasks they would do. What is not getting done? How are you managing to keep things running without staff? What more could you do with more staff, and again... what would the impact be on the business and at what ROI?

In short, if you want to tell a story that sells who you are, you need that story to be about how the business is a better place for your being in it. Less facts, more impact.

Throwaway acct.

I left my first sysadmin job after about 3 years because the advice I recieved is that if you work solo for too long, you develop your own ways of doing things, become unable to integrate into more mainstream best practices, and become effectively "unhirable". I wonder if that has something to do with your lack of success in the job hunt.

It sounds like maybe there's a lot of 'institutional knowledge' about how that 42U rack and the rest of the network is assembled that only you know. It would be expensive for your employer to replace you, but with an external consultancy that replaces a large fraction of your infrastructure with something they can manage, they could survive if you left.

If you're willing to take the risk and switch careers, it might very well be worth having that sit-down with your employer where you lay out exactly what will happen to their infrastructure when you leave.

Edit: I would reconsider how you wrote your CV.

- It's not a matter of the degree to which you fit some specific title (didn't go to enough board meetings to be the Director of IT, or whatever). It's not percent score match, it's pass/fail. Were you the director of IT, or weren't you?

- Eight years is a lot of problems to solve, and a lot of weird niche technologies to learn just enough about to be dangerous with. Those are specific examples of your ability to be really good at the stuff you've been doing. Mention it. Plus, who knows if someone else is looking for someone with experience with a weird niche technology?

- Given how long you've been doing this job, PHP dev might be too big a leap to make at one go. Might be worth looking for something halfway there, that's still perceived as similar to what you've proven you're good at.

Step one: believe them as they demonstrate how little they value you.

Step two: Do your job, as described in the job offer, and stop doing extra. They place no value on that extra work.

But in the long term, don’t stay, even if they do give you a raise or exceed another offer. After all, they didn’t value you before; imagine how little they will value you when you’re a bigger cost to them.

Failure may not be so bad. A company that doesn't want to invest in IT when everything is working likely will invest when things break. I would say just make sure your bosses know what's coming and put it in writing. Write a succinct report, with the headline up front, that explains exactly what will happen without additional resources and what you could make happen with which additional resources. Get them to sign off on it. When failures start to happen, point to your report and explain that you're locked and loaded with your plan to fix it as soon as you have the resources.

I would be very cautious about negotiating a salary when you're in the position of knowing you can't get a better salary on the market. Fix what's wrong with your resume, get a better offer, and then negotiate (or not). Just not a good negotiating spot to be in if you know you ultimately have to accept what they say.

Garry Tan has the best career advice: https://twitter.com/garrytan/status/1377661970178973696

    My best career advice: at every job you should either learn or earn. 
    Either is fine. Both is best. But if it's neither, quit.

My suggestions would be focusing on a few cosmetic things:

- Update your resume (you can get inspiration from Dribbble).

- Update your personal site to look nice.

- Update your GitHub account to have a few repos.

These are mostly cosmetic, but that seems to be the problem you’re having right now: getting your foot in the door to interview for positions.

Earn or learn. If you’re not doing either, it’s time to move on.

Learn a new language. PHP (while not entirely garbage in its modern form, though based on your post I'm guessing you're not using it in a very modern way) has a stigma insofar as I (for one) assume someone that has only used PHP is not likely to ramp up quickly because they lack intellectual curiosity.

Honestly, when I'm looking at resumes, I immediately assume anyone that only has experience in one language is at best a junior level engineer even if they have 10 years of experience.

I'd recommend Python or Java. .NET is also an option. Learn them in your spare time (hell, even use them at work, no one will notice) and make sure you build something substantial before you put it on your resume.

A couple of things:

It sounds like you're asking two (or more) different questions. Your title implies maybe getting back at your employer. I think many of us have gone through similar feelings, but ultimately you should do what's best for yourself and not necessarily what'll make you feel good in the short term (checkmating / petty revenge). In my experience, typical advice is to not take a counteroffer from your current employer. Will you really be satisfied at work if they give you that raise? Will you go through the same issue in another several years?

As for the resume development and lack of responses - maybe try applying to worse-paying jobs, and see if you get hits. Take the recruiter calls and find out what it was about your resume that they liked. You could even go so far as to say you were hoping to get a better-titled position etc and see why they say you're not qualified. You can use all this to better edit your resume, or go develop the needed skills at your current work.

I've also been contacted by headhunters in the past, and with just a little bit of prodding, they're very happy to critique and edit your resume because it's in their best incentives to do so.

Find another job.

Are you doing anything beyond just sending out CVs? That's a pretty poor way to find a job, TBH. A CV is required for a job search, but best delivered after you've had a discussion with a hiring manager (at best) or someone at the company (at least) about the position.

In my experience, the best way is to find someone who used to work with you and see if they need help or know anyone who does. You have far more credibility and they'll have more info about you.

The second best way is to meet someone at a technical event, connect with them, and (after a sufficient period of time, don't do it on the first email) see if they know anyone looking.

The third best way is to target local companies who you'd want to work for, and who you know someone at (use LinkedIn or Xing). Meet them for coffee, learn about the company. If it is a fit, ask if it is okay for you to send a CV over.

All of these take some time to implement, which is why it is good that you are currently employed. (Always easier to find a job if you have a job.)

Start now.

A) Sit your employer down and say "I am applying for Jobs in the 80-100K range because <list of reasons>. When I get an offer I will take it, you are welcome to make me an offer to stick around now"

B) Get on LinkedIn and scope out some recruiters, reach out to the ones you like the look of with a brief of the sort of role your looking for. Get on the phone with them and get their advice - they will get you interviews.

Don't stop B if A works. Ultimately you should leave your current employer - they are not going to "get it" overnight so it will happen again in some form.

With your skills I'd expect to see you earning at least 80-90K depending on location. Aim for more full stack or DevOps roles. Consider management or team lead tracks - you clearly have strong organisational skills.

I was like you once.

You have plenty of raw ability, and are capable of a lot, you've proven that. That can be hard for employers to digest when you apply for jobs "through the front door" (e.g. job boards, career sites, etc.).

A bigger question that might help guide you is, what are you hoping to do in your career next? Focus/clarity may help you here, especially to emphasize the skills that give you a better chance of being matched to and landing a job.

Also, I mean this with all sincerity, great for you for reaching out on HN. Do whatever you can to network, because the people who know you and know what you are capable of can be far more helpful in many cases than "going through the front door" applying for jobs. Going through the front door is notoriously difficult.

I don't promise to be able to solve anything, but reach out if you want to chat. I have 20+ years experience and started out much like you.

Email in profile.

I don't understand why you expect more from them. You are selling employment services on the free market. You told us yourself that you are yet to find someone else offering to pay you the same or more for the same thing.

That's precisely how your bosses are thinking.

The key to negotiating job situations is to have several other offers lined up. Fix your CV and skills so that you're more desirable and the problem becomes considerably more tractable.

There's a magic number of job applications necessary to land the job. I can't tell you what that number is, so you have to keep doing it.

And what I would do, rather than use the offer as leverage for a raise is to leave. I would leave them in very good shape, documents for everything, knowledge transfers to my successor and be available for some consults after I leave, etc. I would be the good guy. For me. I need to like my reflection in the mirror.

They are unable or unwilling to pay more now. That won't change if I put a gun to their head and force a raise out of them. Other things will however change, and that is highly unpredictable, but probably mostly in the column of I'm fucked rather than they're peachy and happy with the situation.

Not sure why you would be beginning to feel "aggrieved" -- you don't have evidence you're being underpaid per the market rate, and you didn't feel being underpaid in your previous 8 years. "42U Rack and 20 git repos" in 8 years don't seem that impressive TBH, unless the work involves interesting technical challenges. Did money suddenly become more important to you, or was there some kind of fallout between you and your employer, or did something trigger you want more meaning in, or validation of your work?

I honestly don't know your situation enough to say whether this is actually likely or not, but given that the other replies haven't mentioned this I'll bring this up to you for consideration just in case: I can't help but wonder whether you're interpreting an early "midlife crisis" as a dispute over pay levels with the employer. I mean do you actually feel financial pressure, or are you just disillusioned with your work (or even life)? If you think this might be the case, perhaps instead of trying to get out of your current job ASAP, try expanding your areas of technical expertise and cultivate new skills that seem interesting to you (and preferably valued by other employers)?

If you've worked for 8 years doing all that and aren't getting any interest, your CV may well suck. If you were hiring a new PHP developer, consider the things you would care about in a CV you were reviewing.

It certainly sounds reasonable that you'd be looking for a new role – from what you've said I'd bet your CV isn't coming across the way you want.

The CV check is basically always going to be "does this person roughly look like they have an appropriate level of experience in the areas required for this job". You probably need to make sure you're tailoring it appropriately for the specific roles you're applying for. If you're applying for an IT management role, focus on the procurement and management and less on the "building services" part. If you're pitching yourself as a PHP developer, focus on the services and the development practices you used, and drop all the stuff about building out servers. And don't be afraid to send different CVs for different roles.

Definitely consider using a tech recruiter to place to as well. They're bastards but useful in some cases.

Another option, not sure if you've done it yet, but have an honest, face to face sit down with your employer. What you're experiencing is burn out; tell them so.

What kind of jobs are applying to? Your xp sounds like “rando IT guy” so it might not be translating well.

Seems like it's a good time to work a more leisurely 8 hour day, turn off the pager outside work and take all the vacation you're entitled to.

Agreed your CV probably needs work. But talk to a recruiter in the industry to help you improve your resume, they know far more and have more accurate knowledge than another engineer. Also, not sure how many positions you've applied to but apply to as many as you can, 100 would not a bad number of positions to apply to. It can be a numbers game.

To answer the question in the title - No, you shouldn't. For the same reason if you google "employer counteroffer" every piece of advice will advise you not to take the counteroffer. You've already signaled your intentions and they will no longer see you as aligned, crippling future growth at the organization, and they will oust you once they can.

I suspect you come across as a bit “Jack of All Trades; Master of None”.

On the systems administration side of things going from one system to a rack isn’t nothing, it’s an achievement, but a lot of employers paying £100k may have applicants coming with more breadth of experience or significant scale - either 1000’s of systems, 10000’s of endpoints, maybe they’re looking for specialist knowledge implementing endpoint protection using Crowdstrike?

In the developer dimension for £100k they’re likely looking for a PHP developer who has ‘full time’ written software in a professional setting for a number of years, worked on teams of developers and contributed to big projects and big codebase (~20k LOC across ~20 repositories is ‘hobby’ scale, plenty of places in industry are >=2 orders of magnitude larger), and perhaps they also seek prior experience with the frameworks they may use?

I’m not sure you should be aggrieved, £60k is nothing to sniff at for a smaller-scale IT role with a “Does It All” blend of duties.

Also beware almost everyone is far more replaceable than they might themselves believe. I doubt a SMB would have much trouble finding applicants for a £60k role involving figuring out your stuff. Maybe they’d just hire two people on £40k to have more arms around the problem domain and more resilience against a repeat? Definitely don’t underestimate that trying for “Checkmate” may/will result in an adverse reaction from your employer. Generally employers dislike being strong armed and even if they pay you today they may well begin working on their Plan B.

If you want to take your career in a different direction and focus on something like PHP development you may have to accept this involves taking one step backwards before you can take two steps forward. Maybe that’s a PHP Developer role which focuses just on that, and not 36 other things, but maybe it’s a bit more entry-level because you don’t have the experience today to join as a “Team Lead” of a 10-person team doing XYZ.

Lastly, by far the easiest way to find your next big thing is within your network, not shotgunning your CV into lots of places who have publicly advertised an opening. Look in your local community for topical microconferences or user groups and get involved. Look for more national user groups or communities around e.g. Kubernetes (if that’s your jam) and get involved. Many of those will have Slacks with #jobs channels where hiring managers will post opportunities. Being a participant in the community, particularly if you’re a respected value-adding member, is a foot in the door.

In the UK? Ask Thayer Prime, she will 100% know how to sell you and is in touch with a lot of interesting companies.

It sounds like your unambitious employer treats your work as a cost centre, and achieving a grudging pay bump isn't going to change that.

Your resume is a mess probably. I'm a writer. If you want me to take a look email me John at Biggs dot cc.

70k is pretty good in UK. If you want to go beyond that, you need to he offering your skillset to multiple companies at once, means becoming a consultant to multiple companies like this. I'm sure many SMBs could benefit from this kind of solo wizard who can come in and make their infrastructure rock-solid. How many can you handle at once? Five? Ten?

You would be better off asking this question to a recruitment consultant, ideally one that specialises in whatever it is that you would label your core skillset.

Without seeing your CV, my guess would be that you're missing some criteria that the orgs you're applying to are applying as a front-end filter. For example, maybe you don't have the right degree (or maybe you don't have a degree at all), and the places you've applied to auto-bin CVs which don't meet this standard. This is something a recruiter can likely help with, either by manually bypassing the filter or by pointing you towards orgs which don't have those requirements.

The other thing I would say is that it's pretty clear you actually want a raise, not a move. Is that coming across in your applications? I wouldn't personally waste time interviewing someone who didn't seem like they were genuinely looking for a job change.

There are CV writing/review services available, but I can't recommend one that specializes in technical jobs. Perhaps someone else here can.

Because it sounds like there's something about your CV that is causing it to be ignored. UK standards for this are different, but make sure you don't include things like age, gender, race, or a photo. Do make sure there is correct spelling and grammar. Focus on how you used technology to solve business problems.

The other possibility is that you've hit an industry-wide hiring lull. It's getting towards the end of the year (budget time), and the economy is slowing down.

Spend one or two hours every day learning new stuff. You get raise, you are not in dead end career. Employer does not get screwed by searching for replacement. Eventually they will have to hire more engineers. Everybody wins!

You seem like you’re all over the place, a Jack of all Trades.

Specifically you’re counting the number of U’s in your rack as well as LOC.

LOC isn’t generally seen as a great metric. But let’s assume some people like it. 20K over 8 years averages to 100 lines a day. That’s fine, I guess. But I read this as not you having written 20K lines but the whole company?

I’ve been told by coworkers that £60K is considered a decent salary in the UK outside of FANG, and even in FANG, salaries are 30-40% lower than in SV, not factoring in RSU’s and bonus.

Maybe you aren’t underpaid at all, the size of the company (and the value they provide) justifies that salary.

I think you have a lot of ownership over the tech. And that is a nice benefit. You make the technical and architectural decisions.

> I'm currently earning £60K a year ($70K) and I'm beginning to feel "aggrieved", everyone tells me I should.

Dont let your friends tell you what to think about your own job and salary. And £60K in the UK isnt a bad salary. I would stick with them, and maybe up your game even. If you can find a way to increase their profits or reduce their expenses you would have some leverage. SMB is a different ballgame than corporate.

What's your motivation, you just want more money? Do you like working there? Do you like the people? Then go talk to them, tell them what you want (but figure out what that is first), explain how you're going to have to go look for it somewhere else if it can't be achieve with them.

If it's just money you want, go brag up the CV and spam applications. Something will stick eventually and you can climb the career ladder until you realize the uselessness of this endeavour.

I don’t think you can checkmate your employer and attempting to do that will show them the risk and they’ll start working to mitigate it. You might get a raise in the short term and then be let go in a year.

For the CV question, ask yourself why would a company hire you over another applicant? Make sure you highlight that in the CV and that you apply to jobs where that is your competitive advantage. If you’re trying to change careers somewhat, you might have to make a “lateral move” for the same pay so that you can build skills.

Don't stop applying to jobs. It takes about 50-400 applications to get a job.

Upskill in things you want to do but you don't do at work.

Create and add to your portfolio.

Submit CV and portfolio of projects that serve as proof points.

Depending on your life situation, I would greatly consider starting your own company. If you are willing to work on IT there are always possibilities.

The answer to that question is almost always “yes”. There’s no shortage of IT employers, quite the opposite.

Are you applying to PHP dev jobs? And what type - office, hybrid, or remote, in London or not London?

There's likely something wrong with your CV, have a professional review it.

Its shocking to me how poorly people are compensated in the UK. There's no way a competitive market could exist there. Move to America if you dare... you can actually make something of your life.

Have your CV checked by a (document) designer and copywriter. I've seen many many IT people having an appaling CV that just doesn't get noticed by anyone.

Hire a consultant to look at your CV. I used levels.fyi had a great experience.

If you’re not getting recruiters it’s because you’re not matching keywords. If you can get in front of hiring managers, past the ATS and recruiter screen that is, your resume is good. Otherwise it’s bad.

Your employer can replace you for some annoying short term costs.

If you’re in a small business you might be working for what I call “mom and pop tech company”. These are painful to work with because getting cash for anything is like pulling teeth since they think of the business cash as their personal bank.

Get the CV cleaned up, discuss a transition with your employer, and offer to stay on to support the consultant for a market rate fee. This will save them money. But it’s time to move on.

I started building websites in 1997, started my first post-college job in 2004, and and have worked my way across the spectrum from user experience backwards through the stack to operations and architecture over the last 25 years.

What do I do? What value do I bring to an organization?

“Reliability and cybersecurity are critical features of any project, but these things require a deep understanding that most software engineers don’t have. I build platforms and tools which empower teams to ship highly-reliable, highly-secure software by default, enabling low-friction when it’s time to ship to production.”

PHP and JavaScript were my bread-and-butter for 15 years. But I took the time to learn how to write highly effective, modern PHP with types, and linting, and static analysis to point out poor choices in my code.

Besides teaching me to be a better developer, it also made it really easy to pick up Ruby, then Bash, then Python, then Go, and even some dabbling in Swift along the way. With each new language I learned, I was able to bring new ideas back to my day job.

I have both Dev + Ops skills, so I also do a lot of work in AWS (beyond the “Big 4” of EC2, S3, RDS, and CloudFront), Terraform/Terragrunt (with modules), building AWS base images with Packer and AWS ImageBuilder, Monitoring-as-Code with Terraform + New Relic, built custom cybersecurity scanning tools that identified vulnerabilities and poor configurations across our suite of AWS accounts, and more.

Stay humble, and stay hungry, because there is always somebody coming to eat you. As long as you’re respected, feel free to stay. If you’re not being treated the way you believe you should be treated, then go someplace else. Never let your ego get in the way. Never allow yourself to become too proud to make the right call.

Lastly, but probably most importantly, is that very few things are done by individuals. Most things are done by teams. I teach, I share knowledge, and I work hard to build up the people around me, so that we can work collaboratively together to solve the big problems. I try very hard to magnify the talents of the people around me, rather than preventing them from growing beyond my own limitations. Even though I elected not to become a “manager“, I am still a “leader“.

Find the thing you do which drives value, and market yourself that way. You are not a “PHP developer“. You are a “developer who uses PHP as one tool in the toolbox“.

Just like how McDonald’s is not in the restaurant business; they’re in the real estate business. Google is not a search engine company; they’re an advertising company. Facebook is not a social networking company; they’re an advertising company.

What's on your resume? You sound like a full stack dev + DevOps. Both are in high demand.

To echo other comments about "culture" here, I'd like to give you an example of how cultural alignment helps with certain things.

For years and years I've had this horrible experience interviewing. Go all the way to the final round of on-site interviews (the panelists, day-long, etc.) then get rejected and nobody will tell me why. It's awful, beyond disheartening, and expensive in that it forces me to waste 60+ hours per company for absolutely nothing in return.

So this time around when I started looking for a new employer, I took a slightly different approach. Just like you I'm applying only for jobs that I'm qualified for, but instead of agreeing to just any interview with any company I could get even a modicum of attention from, I changed my way of thinking to "I want to LIKE where I work and the people I work with, and I want to do something more than make some Ivy-league rich kid even richer; I want to have a positive impact on people's daily lives somehow."

That led me to refocus the kinds of firms I was interviewing with. Instead of fintech, devops, or some other silicon-valley elitist crap, I paid special attention to small/mid-sized employers, particularly those who work with charities, non-profits, the poor, unemployed, or the government.

I took some other interviews with the other kinds of aforementioned places, and instead of just sucking it up and desperately suffering an insane interview process as usual, I screened them this time around. I asked recruiters and hiring managers what their interview process was like, and in several cases I ended up telling them I wasn't interested and refused to suffer their insanity. I went so far as to tell one guy his process was elitist bullshit and I had more sane options elsewhere, so why would I bother with them?

Probably not the smartest move, but I was pissed off. Haha :-)

In the end I wound up getting an offer from a government contractor (US) for $40k a year more than I'm making now. Health benefits are roughly equivalent, the retirement plan is better, I get to do the kind of day-to-day work I enjoy (I don't get to do this where I'm at now) and best of all I get to build/improve systems that help people and their families. And that means a hell of a lot more than grinding a job I hate all so some fortune 500 exec can get his next massive bonus while i'm drastically underpaid vs. market rate.

Another little tidbit I've personally noticed is that every job I've ever been hired for had an ex-military person in the hiring process, or as the hiring manager (or their manager). Every single one. I come from a military family (US Navy), though I never served myself (my loss). So my next job hunt I'm going to look for opportunities/industries with ex-military people involved specifically, and I'd be surprised if my luck didn't improve.

Definitely leave your job. You’re clearly done, the relationship is no longer working.

As for landing a new job with the salary you want, it’s a numbers game. You just have to keep searching, keep sending out resumes. And after a couple years at each job you often need to do it again if you want to move up.

I’ll throw in some of my job hunt tips (I just signed an offer this week after a two month search):

- Write cover letters. What I do is I take whatever they wrote in the job description about the skills required, and I jot down one bit of experience I have for each one that’s applicable. Then I massage that into a brief cover letter.

- Look for reasons to say no. Companies can tell if you’re just telling them what they want to hear. It’s important that you’re doing your half of the job, which is thinking about what kind of work environment you can be effective in, and discarding opportunities that don’t fit. This doesn’t have to be a lot of opportunities, but it should be some.

- Be interested in the people and the position. When given the chance to ask questions, act like you already have the job and start asking about the actual work. You should come across as interested in the work, and this also creates opportunities to show off what you know.

- Have a reason why you’re applying. I know the real reason is “I need money” but it’s important to have a story about why this company. Do you like the mission? Do you have an impression of what the people are like? Are you interested in some technical aspect of the work? Have a story from the start, and refine that story as you go through the interview process.

- Enjoy the process. This is hard, because you need to pay your bills, which ramps up the pressure. But it’s really important to find ways to enjoy the people and the process of interviewing. How you relate to people in the interview is how they’ll assume you’ll be in the job. You need to be someone that the interviewer would like to spend an hour with. Enjoy the moment to meet a new person. Enjoy the chance to talk about interesting subjects. Enjoy the game of solving a problem.

- Embrace failing and not knowing. It’s ok to screw up, but if you get scared and sad because you screwed up that’s usually game over. You should have two modes: 1) killing it, and 2) understanding, cheerfully, the specifics of how you’re not killing it. If you don’t know an answer, say you don’t know and be inquisitive. Try to learn something about the subject or the role in that moment. This buys you time and you might be able to course correct as you learn more. Worst case you might learn a little more about what to study for next time. Or you might learn about what kind of positions you’re not qualified for.

- Fudge your experiences a little in the positive direction. Every project has things go wrong, but you don’t need to focus on that. Emphasize what worked, to start. Don’t talk about sour relationships or your coworkers failures. It’s OK to have rose colored glasses about your work experience, the interviewer doesn’t know, they weren’t there, and it helps you come across in a positive light.

- Although you should emphasize positives in your career, don’t be afraid to talk about “learning experiences”. A perfectly acceptable anecdote is “we did X, and had Y go wrong, so I do Z now when I’m in that situation”. That shows critical thinking, adaptability, and honesty which are all positive traits. It can turn a failure into a positive in the interviewer’s eyes.

- After each interview jot down a few words about your takeaway. This can be a positive or negative note. These will help with the earlier point of knowing when to walk away from an opportunity. Also if you can note one thing you did poorly and what you should’ve done instead. Interviewing is a game, and you’re going to lose the first few no matter how qualified you are. You can’t improve unless you analyze your game. Don’t dwell on it, just note one takeaway for next time and move on.

- Lastly, just grind. I’ve got 25 years of experience and I think I’m very hirable, and I still have to send out dozens of pretty high quality applications to get an offer. It’s a funnel, and most of the reasons you fall out of the funnel have nothing to do with how good you are. You’re going to get rejections from companies you were excited about and you’re going to feel sad. Let yourself feel sad. Take a break and do something nice for yourself. And the next day get back in the saddle and send out a couple more applications. Don’t think if it like an ended relationship think of it like a missed basket, or a shot that went off the goalpost. You don’t stop playing because you missed a shot, you take another shot.

Not trying to say you have approached this the wrong way, but one thing strikes me and that is that you have done an impressive job of scaling up ops and development all by yourself.

If you have that much code and that many servers in an SMB, your work is likely critical to the company. Assuming your managers are rational and want what's best for the company, it seems like they might taking you for granted and that they are overlooking a fairly big risk (you leaving).

It's possible that you have done a "too good" job and left them with the impression that your job isn't that hard, and that you could easily be replaced. Things are rarely broken, new features are added on time, and nobody feels the urgency of scaling your one-person team.

I'd use your qualities to communicate these things. Be the employee you wish you had. If that's not appreciated, take the first chance you get to leave.

You're loyal, so perhaps you could proactively list what it is that you do in your job - "in case I get hit by a bus". Show that you care about the company, and that you're trying to help them prevent a bad situation. List everything you do and have done that provides value for the company and what skillset is required for those things. Writing your job description like that will give a better picture of the scope and importance of your work. I assume your managers aren't very technical, so it also gives them an opportunity to check with their advisors and network, in case they think you're exaggerating (don't be too humble, and be specific).

You're also hard-working, so one approach is to tell your closest manager that you think your market value is X, and that your current compensation is too far from that to justify you staying with the company in the long run. "I want to stay at Company, but I can't afford not to switch jobs eventually since working here effectively costs me Y per year."

If that's not getting across, I think that the company needs to feel the pain a bit. See if you can find a way to leave while being as professional as you can. Set the date and give them time to figure out what to do. They will most likely have trouble finding a replacement, and if they do they will not have a lot of time to on-board. You've warned them, been firm but professional the whole time, so now it's your closest managers responsibility. The higher ups, if you have any, will not be pleased that they weren't warned in time.

You don't owe them anything, you're valuable and you have knowledge that will be expensive to replace. If they're rational, they have somehow missed this information. If they're just playing mind games, they need to be called out (not your job).

Just my suggestion. Assuming people are rational and just lacking information often gets surprising results, and builds trust over time.