Soft Skills Engineering - Episode 504: Should I quit my AI job before my first day and professional button-clicker
Episode Date: March 16, 2026In this episode, Dave and Jamison answer these questions: Hi Jamison and Dave. Eight years into my software engineering career, all of it at Series B and C startups, I’ve been craving two t...hings: a recognizable brand name on my resume and the chance to work on real scale problems. After a long search, I finally got both. The catch? I got them in the wrong order. I accepted an offer at one of the hottest and fastest-growing AI companies in the application layer space. Exciting work, smart people, real momentum, but not quite a household name yet, and not quite facing the kind of scaling challenges that come with a billion users yet either. Two weeks later, I finally heard that I cleared the interviews from a big brand name tech company. I’ll be honest: it wasn’t my first choice brand name. I bombed interviews at a few others and this was basically my consolation prize. Here’s the thing about this mega tech company right now: the culture has … shifted. It feels less like a tech company and more like a social experiment with a $1.5 trillion market cap. So now I’m torn and the clock is ticking. My start date at the AI company is in a few weeks and I’m currently in team matching at the mega tech co. Do I renege before I even badge in? Do I start, survive team matching, and then quit? Or do I just honor my commitment and forget about the brand name for now? More broadly: under what circumstances is it ever okay to renege or quit shortly after starting? Have either of you been in this situation or been on the receiving end? I need stories, I need wisdom, and honestly I need someone to just tell me what to do. I’ve changed from a java developer role to OIC integration on oracle cloud. I’m not sure if that was a good move as it doesn’t feel like I’m doing much coding but lots of clicking. I was thinking that having cloud experience would benefit me but now I’m not sure. I’m not sure if I should run back to a java developer job or give it a chance and how much time would be a fair chance?
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it takes more than a vitamin d supplement to be a great software engineer this is episode 504 of
the soft skills engineering podcast where i'm your host jameson dance i'm your host dave smith
soft skills engineering is a weekly advice show about all the non-technical things that go into
the technical field of software development like how to make up for my chronic lack of sunlight
yeah it's true i got an unrelated blood test and it's everything's fine by the way you are really
low on vitamin d like yeah occupational hazard like i probably should have assumed that i don't
know if you realize this jameson but you did poetry at the beginning of this show but it got
edited out so jameson had a little stutter and he kind of slowed down and stopped and i just thought
that is so fitting for episode 504 gateway timeout oh yeah i experienced beautiful brain level
gateway timeouts quite frequently so i have mechanical sympathy there dave do you want to
thank our patrons yes i do thanks to those that are contributing at the level where we shout out
their names every week and extra thanks to those who have completely sacrificed the coherency of
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just head over heels in love with yeah okay here we go the first one is my name is bread because
i like toast brian wolford is in germany angel wood instead of will angel seth angel i thought
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back to yeah like overflowed and wrapped to this yeah i guess it would have changed though i don't
know i think the hacker got the information they came for and moved on and this is just a copycat
joker i don't know who knows yes we don't know who these people are we just love them i've never
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user documentation will devil will angels great grandparents name of angel got mangled at ellis
island oh it's angel and angle well angel's great-grandparents name was angle not angel
maybe is it pronounced data or data braden canes john grant britney ellick closed parenthesis
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All right, shall we read our first question, Jameson?
Yes, I will do it.
This is from a listener who claims their name
is badge in or bail out, but I don't believe them.
Hi, Jameson and Dave.
Eight years into my software engineering career,
all of it at Series B and C startups,
I've been craving two things.
a recognizable brand name on my resume, and the chance to work on real scale problems.
After a long search, I finally got both. The catch, I got them in the wrong order.
I accepted an offer at one of the hottest and fastest growing AI companies in the application
layer space. Exciting work, smart people, real momentum, but not quite a household name yet.
And not quite facing the kind of scaling challenges that come with a billion users yet either.
Two weeks later, I finally heard that I cleared the interviews from a big brand name tech company.
I'll be honest, it wasn't my first choice brand name.
I bombed interviews at a few others, and this was basically my consolation prize.
Here's the thing about this mega tech company right now.
The culture has shifted.
It feels less like a tech company and more like a social experiment with a $1.5 trillion market cap.
So now I'm torn, and the clock is ticking.
My start date at the AI company is in a few weeks, and I'm currently in team matching at the mega tech company.
Do I re...
Oh, how do I pronounce this word?
I know what it means.
Renege?
reneg that's how i've heard that reneg all right reneg do you do i reneg before i even badge in
do i start survive team matching and then quit or do i just honor my commitment and forget about
the brand name for now more broadly under what circumstances is it ever okay to reneg or quit
shortly after starting have either of you been in this situation or been on the receiving end
i need stories i need wisdom and honestly i just need someone to tell me what to do
well you've come to the right place the two most indecisive advice podcast hosts on the planet
here's what you do quintuple your patreon contribution to the soft skills engineering
podcast question answered okay i want to make sure i understand this right if they're in team
matching have they accepted an offer at the mega tech company already no i think okay i think
typically at least the way i've been through the process is you go through all the interviews then
you go into a team matching phase and then once you've chosen a team and they chose you
then you'll get an offer like an actual formal written offer but it's sort of an informal offer
that we want to hire you and yeah i don't know i don't know you know what is that right let me pull
up my notes it is yes it is essentially an offer uh but i don't think it's like signed sealed and
delivered the fact that the question asker said renege makes me feel like they at least said yes
informally to something at least to the next stage right yeah i have a few thoughts about this
one thought is it's a very different problem to scale up than to join something that is already
a large scale so if this company has a 1.5 trillion dollar market cap it's probably not
gonna i don't know quintuple in the next couple of years right i don't know maybe it will stranger
things have happened but there are a lot of problems of scale that already have some solutions
and a lot of the scale you're working with is just keeping this gigantic complicated machine going
not necessarily oh we're being crushed under this traffic weight and how do we how do we deal with a
billion users you already dealt with those problems to reach that scale in some way and kind of fixing
them and improving them. And there's some experiments with new product directions and
new areas where you scale up a little bit, but a lot of it is fitting into this enormous machine
that has a lot of solutions already. And I feel like you learn more about organizational scale
and communication overhead and coordination than you do about just raw, how do we work with
10 million cores and because there are probably teams working on that already and they probably
have an answer yeah not only right not only are they working on it but it was solved years and
years ago yeah we did it yeah we did it before anybody else did because that's how we got here
absolutely can still be valuable i remember that when i was at a mega tech co i remember that same
story where i was like oh how exciting we get to do thousands of transactions per second and all
this stuff and i realized like it's actually easy once someone else did all the work yeah not only
that, but you don't even really get exposure to how it works. I remember my team, probably no one
on my team, really had a deep understanding of how all the infrastructure was working to
service that high a scale. And we just kind of worked in the system and everything was great
at that high scale. At my mega tech company job, we actually did work in a part of the system that
dealt with a ton of traffic. We worked in this application proxy layer and much of the traffic
for people paying dollars to this company went through this layer it also had a ton of stuff
above it and below it so we weren't like the only important piece there but we were we were close to
this scale and i still feel like i just worked with a lot of solved problems and incrementally
improved stuff and tweak things and interesting yeah having said that i do look i am so glad i
got to work at one of these companies i learned so much that has i mean just literally okay last
week i had to write a real high stakes incident report it was going to be published publicly a lot
of like real high stakes situations involved anyway big deal i wrote it it was an effectively
job well done got a lot of positive feedback from various organizations and and people who would
know and someone on my team asked me like dave how did you learn how to do that isn't this your
first time doing that and i was like no i wrote many of these and read many of these at that
mega tech company and i'm so glad that i did because it was like i don't know i just once
you see the work done and you work in that it just changes you for the better that's true i think i'm
probably undervaluing even though i didn't have to solve from scratch all these problems it did
help calibrate things a little bit and just seeing the existing solutions was super interesting and
valuable oh yeah definitely so i i i'm probably being overly negative about the importance of it
But you shouldn't come in to expect to join the team and then be handed this unsolved problem of we can't possibly keep up with this scale.
You go scale it up for us.
Yeah, definitely.
That's way more likely at a fast growing small company.
Yeah. And isn't that the interesting tradeoff you have to make?
So if you join one of these well-established megatech companies, you're not going to solve the scale problems, but you will get a front row seat to see how they were solved.
but then if you decide to join a smaller company you will have to solve all the problems but only
if they happen and there's kind of like this 50 to 1 chance that your particular startup will
actually encounter those problems because the chances of it being crazy successful and getting
that many users it's kind of low yeah i mean you mentioned a billion users how many companies have
a billion users you can probably count them on your hand yeah exactly and of those companies
it's probably a vanishingly small fraction of employees that that sort of like we're on the
bottlenecks of scaling up to that so even then yeah it can be tricky to land exactly that experience
totally so if scale is your thing that you really want to get that's just not in my opinion there's
just not a reliable path to get it yeah i i have my own biases to this question which is i would
absolutely join the fast-growing AI company because it sounds like fun. And joining a $1.5
trillion market cap company that's an established name that has some, I don't know what it means
that it feels like a social experiment, but it doesn't sound, it sounds like there could be some
downsides. I guess I'll put it that way. There's some downsides to every job, but there might be
some internal chaos or politics. I don't know. Once your market cap is $1.5 trillion, then
governments matter a lot to what you do yeah i don't know well i was gonna say the good news is
if you join this fast-paced startup and you're in team matching at this megatech company just like
let the team matching go because it might take a few weeks or months for that team matching process
to all the way go through and by then this startup might actually be out of business so this
could work out well and you also said you said ai application layer and that's like that's like
the riskiest place to be in ai yep you could be a prompt by then yes exactly opus 7 or whatever
your whole product could be a prompt on one of the uh big ai labs oh boy i think there is
it just generally feels like a a somewhat dishonest thing to do to to accept an offer
at two companies at the same time sort of let it play out if you haven't actually accepted
something. I mean, you could use this for negotiation. If they really want you, then
maybe there's a dollar amount or a specific team at this megatech company that would make you feel
better. I think it's possible that there will be connections that will look unfavorably upon you
if you accept and then renege. I'm going to keep trying to say that word so I remember how to
pronounce it later on. But the good news, the company will be fine. They'll be okay. If they're
that big this is a situation they have probably been in many times before and so you're not going
to leave this team in the lurch or anything like that but at some point there is some reputation
risk to being somewhat dishonest with your commitment to join this company that then
evaporates i would say in that one like follow your ethics your ethical code your own internal
conscience more so than the reputation risk these companies are huge they interview so many people
And if you do something weird where you're like, oh, this thing, whatever, got another offer or not going to actually proceed with it, they're not going to remember you.
Like, there's no institutional knowledge.
Nothing is personal for these companies.
And the recruiter you worked with probably won't even work there next year.
Yeah, I guess that's a good point.
Yeah, I think I would just join the AI company.
It's one of the hottest and fastest growing.
That sounds good.
Sounds like you're scaling.
and even if you're not at a billion users yet going from a thousand to 50 000 is still that's
quite a scaling problem yeah it'll be it could be really fun really cool yeah it's not it's not all
about the magnitude that you end up at sometimes just the the like percentage difference is is a
fun problem of its own and jameson guess what i have an answer for you on the sequencing of
events oh between offers and team matching and stuff so i interviewed at one of the big tech
companies and the offer came after the team matching like the formal offer okay now this
i actually didn't i decided not to accept the offer so i never got it on in writing but i had
a verbal call and it's interesting the verbal offer actually came about a week to 10 days after
maybe even two weeks after all the team matching meetings i did like five or six team matching
meetings where i met with various team managers to ask about their team and see if it's a good
match and it was like yeah it was probably like four or five days after the last one where i
actually got the call i hadn't even chosen a team yet and they gave me like the verbal offer so
probably this person doesn't even have an offer in hand yet okay i'm sure this differ or can
differ from company to company but was the verbal offer for a specific team so we did the team
matching and this is the team that no the offer i don't think the offer was team specific i think
it was okay just it was just and then and then you'll join one of these teams probably yeah
exactly like whichever one you i think after you basically the way it works is after you meet with
each one they express an interest level and then you get to pick and if your interest aligns with
their interests then you go and i think they might have even told me like these ones don't want you
or these ones do want you but but realistically the teams all the teams are basically super
trusting in the hiring process at the like the global level and so if you got to the hiring
process they want you and the reason they're meeting with you is because they have an opening
yeah you know so it's not like they're going to be like well i know you passed the extremely
rigorous and painful interview process but i didn't like the way your left eye twitched every
time you said the word chrome yeah it is made a bit trickier by the fact that you have accepted
the offer at the ai company because otherwise you could also just bring this up in a discussion with
them and say i really want to work on these kind of problems i have this this other thing i believe
will turn into an offer and at that stage it's i think very wise to say i want to make the best
decision for me like what help me how can how can this company be the best decision for me you're
not you're not i don't think you're being evil or sneaky or unethical by doing that if you've
accepted the offer already it's a little bit tougher to go back and say actually i need more
money to keep my acceptance or i need to make sure i work on this team or something like that you
still can yeah that one that one is trickier oh that one is painful the smaller the company
the worse the reputational damage and the more painful it is and i've had people do this where
i had a verbal agreement with someone and then i went to go prepare the offer go get it approved
you know which you know takes time and effort and then i prepared it got it all written up sent it
out to them in writing and then they came back then they were like i want more and i was like
you know the time to ask for more was when we were talking about it you know so that that's
And the smaller the company, the more they'll remember.
But having said that, walking away from an offer before you start is, in my opinion, no problem.
If you find something else between the time you got the offer, even if you signed it, and then your start date, just take the better offer.
I think people get super, I don't know what the right word is.
They feel like they've signed something more than what they actually signed.
when you sign an offer letter, all you're saying is, I acknowledge the terms of employment at this
company. And remember, in that very offer letter, it says to you, your employment is at will. We can
fire you at any time for any reason or no reason. To be clear, this is either in space law or the
United States. It's very possible you have a much different contract in other areas. Yes, I think
you're right. You're definitely right about that. But so in the US, if you sign an offer letter,
you have not really committed to anything. The company has made a commitment to you to pay you
a certain amount. Um, and you have agreed to things once you start, like there'll be some
kind of employment contract you typically have to sign, but between offer letter and start date,
you're under no obligation. And I've actually hired people to join me who were in already in
that window with another company and it works out fine. Like it's just not, it's just not a big
deal. Yeah. I don't know if I've hired people that way, but I, I've definitely, I remain
pessimistic about them actually joining the company until their start date yeah for sure
check in and try to avoid this happening to me being aware that it could yeah i do that a lot
too it's like oh every whenever i sign an offer letter for someone and their start date is like
more than a few weeks away i'm like oh boy this makes me nervous right because we're gonna we're
gonna shut down the recruiting machine right and yeah that machine takes time to get going again
and so if they bail between that it does create pain for me but it's also like within it's
perfectly within their right and in my opinion it's perfectly ethical too now having said that
this question is is not really about that time window between offer letter and start date this
question is after start is it ever okay to renege or quit shortly after starting and that's where
things get a little more tricky reputationally and ethically i mean you agreed to join this
company at a negotiated salary and and offer terms and for you to show up like a week later
after starting and say, well, I want more money. I think the manager is going to think poorly of
you because they're going to be like, look, your, your highest leverage time for negotiating was
before you started, because are you going to quit? You know? And I guess your answer is actually,
yes, because I have this other offer. So I think you need to make a commitment and just ethically
and like my own personal preferences are once I commit to a company, I, I lock in and make that
successful. And it would take a really, really big unplanned event to change my mind on that.
Well, have we answered the question?
Oh, I think we did.
But what did you say?
Just tell me what to do.
You said go to the AI company.
Oh, yeah, go to the AI company.
And that's what I'm saying too,
because this big tech company will be around for a long time.
But opportunities like this to go work in AI,
that's like a once in a generation probably.
Yeah, it will be around.
This specific team or this specific company
might not even be around,
but there will be more big tech companies.
They're always hiring.
And some of the attraction, I think,
is this perception that there's a there's a different bar which there definitely can be
and you've at least proved to yourself you can exceed the bar you could probably do it again
right you could yeah probably get another offer yeah good luck right best of luck let us know
what you choose yeah if we end up using your product then make sure my prompts get extra
prioritization they get the expensive model at the cheap model price yeah yeah put in a good
word with the robots for me okay dave all right you want to read our next question yeah let's do
it this comes from an anonymous listener who says i've changed from a java developer role
to oic integration on oracle cloud i'm not sure if that was a good move as it doesn't feel like
i'm doing much coding but lots of clicking i was thinking that having cloud experience would
benefit me now but now i'm not sure i'm not sure if i should run back to a java developer job or
give it a chance and how much time would be a fair chance great question click ops is what you've
pivoted to you've heard of devops yeah but have you heard of click ops i'm trying not to sound
snooty oh i don't think i've ever worked with a person employed to click buttons in cloud uis like
this maybe i have and i just don't know it maybe jobs can be changed into this type of thing but
i guess i i don't understand why that role needs to exist if it was like a a i don't know
professional services role i could see you doing this work as part of professional like on behalf
of an external yeah or sales engineering or yeah i don't know dx or something like i could see this
being part of the role but just you get work requirements passed to you where the way you
fulfill those work requirements is by clicking around in oracle cloud ui feels both like it
wouldn't be very satisfying and it maybe wouldn't teach you that much about general cloud things
and here it comes if anything could ever be robotized that sure could every everyone's
building clis or mcp servers or just prompts where you could literally do computer use that
feels very risky and handing your your agent a a working ui to configure cloud resources but
guaranteed somebody's doing it so but you're saying that maybe this job will exist to just
check on that robot maybe or undo the deletion fix all the damage yeah oops we accidentally
your database uh oh i'm very you're absolutely right i i should not have clicked the button
the shameful confession that you did if you tell a robot and i'm really sorry do that yeah
you're right i absolutely should not have done that i've seen a few of those example
prompts from people yeah explain why you did that it was just a mistake
yes where i wake up every morning and i'm like am i in an episode of the twilight zone is this
really what computers are now yeah they can be if you are naive enough in your trust yep i was
thinking that having cloud experience would benefit me yeah it would but to what end to the
end of clicking yeah i don't know this sounds like a bait and switch where the you took a perfectly
happy java developer who's just cruising along writing all the java code having a great time
probably even using some ai to write the java code and the java developer's like hmm i'm sick of
writing all these desktop swing applications yeah it's time for me to time for me to get into the
cloud and so you get a job and it's a little bit of a bait and switch like yes come to our cloud
environment and it's like we we work with the cloud yeah yeah and and i've actually worked on
teams it's been 10 years but i've worked on teams where there were developers who wrote the code
and then there were operations people who took that code in like built form and found ways to
deploy it securely and scalably in the cloud environment. And those were two separate jobs.
And it was kind of like a pass it over the fence kind of thing. And that might be what's happening
here. It's like, oh, my job is when the developer teams need a new whatever stack or, you know, a
new compute or new data store or new whatever, I click the buttons, make it happen, and I send
them credentials, you know, and that could be exactly what's happening here. But for a long
time, the trend has been moving away from that model where there is no line. And that's actually
what devops is supposed to be it's supposed to be where your developers do the ops not i'm a devops
person or you know that was like the whole point was that the developers do the ops not that you
have a devops person yeah so i suspect that this person got trapped into that kind of a scenario
yeah do you think they work at oracle or they work at a company that builds on oracle cloud
probably probably the second one right maybe it's some kind of service provider or something
I mean, I could very easily see this just being someone building applications at some random company.
They're running on Oracle Cloud, and this person's job is to set up the Oracle Cloud stuff.
Yeah.
And there is room for this to a certain extent because many developers do not have the expertise on things like network configuration and routing and DNS and some of the more, I'll just say, hardcore infrastructure stuff.
Yeah.
Like they understand like sockets and HTTP and things like that, but they don't necessarily know about like network peering and tunnels and private links and all that stuff and route tables and ASNs and all.
Anyway, and so that could be where this is going is more of like a network administrator role.
But either way, I think that you would probably be happier to go back to the Java development role because if all you're doing is clicking and clicking, I don't think this is a job for you.
There are nuances to all the different cloud providers.
They all have different products.
They all are trying to convince you why you should use them instead of the other thing.
There's certainly some common functionality between them.
So I think there's utility in knowing your specific cloud provider in detail.
I think even if all of the docs are in the weights of all the models and there's, I don't
especially if you're creating and destroying resources,
I feel like that's going to be an important area
for humans in the loop for quite a while.
But if you're doing all that by hand...
You mean like six to 12 months?
Maybe. I don't know.
Yeah, every pronouncement comes with a huge grain of salt.
But if you're doing it all by hand,
I think there's an opportunity,
even if you are staying in the same role,
to automate that.
and that's the way you can demonstrate value.
I think what you don't want to do is just keep doing it
until someone squints at you and says,
I bet we could prompt our way out of your headcount.
Yeah.
If you are instead doing it all in terraform,
and so there's this framework that you can use
that frees you up to do other stuff with your time.
Can you take it a level of abstraction higher
so that your manual labor is not as required
or important in the day-to-day execution of these tasks.
Yeah, I mean, there's a real value add there to be had.
Yeah, and there's always, I think, a fear that,
well, if I do that, what is my job?
Then maybe I don't have another job.
And there's a long history.
Yeah, you got to ignore that fear.
Yeah, well before AI of people automating themselves
out of their current job,
and they immediately find other important things to do.
Yes.
Especially because you've demonstrated
you are a capable person
who can do important, useful things
that are high leverage like automate a job that used to take a whole person great it turns out
we don't need that specific job done anymore but there are a ton of jobs that could be done by
someone capable enough to automate a whole chunk of of work that used to be one person's job so
you're saying you can be not only responsible for eliminating your own headcount but that of all
your peers as well no i i think that's that's the thing i'm arguing against that's unlikely to happen
It's more like there's a ton of stuff that your company would like to do that they haven't because they don't have capacity.
And now you can say, well, I've got some.
I could do that thing.
That thing you thought we couldn't do.
It's true.
And the same creative mind that is capable of turning a manual job into a fully automated job by identifying the problem and then solving it is not maybe by its very nature, but definitely by the skill acquired is the kind of person that will identify other really cool, really valuable things that can be done.
And there seems to be an infinite amount of demand
for that kind of work.
Yeah, at least for the next six to 12 months.
Right.
Yeah, so I think I agree with the broad point
that just staying in this job and doing it as it exists
is not a good move for your experience and growth
and just career.
And I think it would be better to go back to writing code
as a job than that.
But there are some opportunities to stay in this same role
and turn it into a better role.
Agreed, for six to 12 months.
Yes, for six to 12 months. And then you get to do something even higher leverage, maybe.
Or maybe the bottom has fallen out by then. You get to clean up the mess somehow. I don't know.
Or maybe tomorrow you show up and AIs have deleted all the resources and it's your job to fix them all.
That's the next six to 12 months for you.
Yep.
Well, have we answered the question?
I think we have. Good luck.
Good luck. Let us know how it goes.
Yeah.
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