Advice for a middle-aged hacker seeking new challenges minus techbro BS
March 6, 2020 1:22 PM   Subscribe

I'm a software engineer in my early 40s who has been fortunate to not have to deal with much Silicon Valley disruptive culture nonsense throughout my career. My career aspirations may force me outside of my comfort zone, so I'd like some advice on how to sniff out warning signs in the interview process, what questions to ask that will help me make an informed decision, and, if I do make a change, how to best survive as an older engineer in an industry that often exploits workers while paying lip service to work-life balance.

I love technology itself, and am happy to be able to apply my technical expertise to solve real-world problems. What I can't stand is the Silicon Valley ethos, the main aspects of which I'm trying to avoid are (a) routine expectations of insanely long work hours, regardless of an individual's productivity, (b) "move fast and break stuff" attitudes toward treating coworkers with respect and complying with regulations, and (c) the obsession with company valuation, stock prices, etc. that turns engineers (labor) into bourgeoisie who somehow think the company's interests are aligned with their own.

I've largely been able to insulate myself from these forces by avoiding tech startups entirely, changing jobs only once since finishing my undergrad, and, for the last fifteen years, working for a university in a government-funded research unit. However, I feel like I've hit a ceiling in terms of my career growth in my current role, and many of the attractive things about my current situation (cutting edge research, stable funding sources, engaged and responsive management) have faded over the years, to the point where the known risks of staying put may outweigh the unknown risks of making a change.

I don't really need help comparing the pros and cons of the two positions I'm in the final interview stages for right now, as there are too many variables to consider (location, stability, company size, salary, benefits, etc.) but I could use some advice on:

(a) warning signs to look out for that are specific to or highly represented in startups

(b) the right questions to ask during interviews that can help me get candid answers about the company's culture in a way that doesn't come off as too snobby

(c) online resources that might have more candid details about the companies that might not be apparent during the interview process. (I know about Glassdoor but am unsure how well it represents what is actually going on at these companies.)

Also happy to read more general stories from anyone who's left a secure tech job for a more volatile but possibly rewarding startup and lived to tell the tale. What has gotten better/worse?
posted by tonycpsu to Work & Money (17 answers total) 14 users marked this as a favorite
 
People in Silicon Valley don't routinely work insane hours. Silicon Valley is primarily large, blue chip publicly traded companies where people punch the clock. Startups are all over the map and some are insanity and some are people just doing their own thing and being their own bosses. And if you think software developers aren't already peak bourgeoisie, well, you're wrong. But on your questions:

(a) warning signs to look out for that are specific to or highly represented in startups

Just ask. Even the shittiest people in the world aren't really trying to trick you about who they are. Shitty people somehow think they're geniuses and don't usually hide it. Ask how what hours people work. Ask how many women work there. Ask what their family leave/sick leave policy is.

For true startups ask how much money they have, what their runway is and how many people work there. If there's six months of money and four engineers, yeah, maybe take a pass. Ask how fast the company grew the last year and how much they expect to grow next year. How many people were hired in the last year? If a 200 person company hired 100 people in the last year, it's a different world from a 200 person company that hired 10.

(b) the right questions to ask during interviews that can help me get candid answers about the company's culture in a way that doesn't come off as too snobby

Just be matter of fact. Honestly asking questions makes a candidate look smart IMO. Don't couch questions or justify why you're asking them, just ask them. Startups know they need to convince smart people to work there versus an established company. And if they seem edgy or cagey or avoid the questions, well, you have your answer. Well-run companies are generally happy to answer these questions in interviews.

If it's really a startup ask how many people are on the cap table. Ask about how much funding they have and from where. Companies with more friends & family money are likely to last longer than ones with pure VC money IMO. Ask specific questions about their business that show you did your homework. Ask who their customers are.

You'll notice that I'm not suggesting to ask if they use git versus SVN. Or if they do standups versus weekly status emails. Because I don't think those things matter much, but if you have a strong opinion about the nuts and bolts of the dev process, ask those questions. No point in spending time for a job you're not interested in doing. The key factors that determine whether a company will be terrible are general culture and money IMO.


(c) online resources that might have more candid details about the companies that might not be apparent during the interview process.


Glassdoor is as good as it gets with the caveat that it has a bias towards disgruntled employees. You can try Linkedin and see if you have any contacts-of-contacts that are willing to say something nice about the company. This is pretty hard because for truly new and/or small companies everyone who has the answer you want probably still works there.
posted by GuyZero at 2:03 PM on March 6 [7 favorites]


This is a very targeted answer to the culture part of your question, but as a bit of a left field item I always recommend asking for a copy of the travel policy for larger companies, or at least a description of it. It's a slightly odd but not dangerous odd request - companies that can't deal with it or require many levels of approval just to tell you some basic information are going to be hard to get stuff done in.

More importantly though - it's one of the few places where companies have to back up all of their culture talk with actual dollars. Think "We have a flat organization" meets "only VPs and above get to fly business class". Or "we really value employee time" meets "flying internationally you must leave after a full day in the office if a flight is available". Or the company has offices in London and SF and the threshold for business class travel is *just* over the distance of that flight.

I'm not looking for anything specific, just consistency of values. If a company says "cost cutting is our first priority" and they have a policy with economy class / cheap hotels, great - that's consistent and you can decide if that's what you want. But if they say they trust employees and have a flat org yet there are multiple levels of pre-approval and oversight depending on your job title...that's a red flag.
posted by true at 2:12 PM on March 6 [6 favorites]


Here are my heuristics. This is a list of things you can verify from the outside, either because it's public information, or a fact you can ask about in the interview. There are lots of values that bro-tastic workplaces don't have (see e.g. Key Values), but verifying them from the outside is difficult.

And again, these are heuristics. Not all young founders are jerks, etc.

These correlate with bro-ness:
  • cryptocurrency, chatbots, VR, esports, mom-as-a-service, market-making (HFT, betting, gambling, certain bits of fintech), microtransit (rideshare, scooters, etc.)
  • business models that require a large, commission-based sales team
  • young founders
  • "ninja", "rockstar", etc. (although I think most people have got the message on that one)
  • geographic pattern matching: San Francisco
  • an onboarding process that includes things like Snap Council
  • low cash/high stock comp (this can obviously work out very well, but young guys are more comfortable with it than most people)
  • rapid head count growth (again, this can be a good sign for various reasons, but it does tend to bring out the worst in people)
These anti-correlate:
  • concrete, generous family leave and pro-parent policies
  • strong 401k match
  • remote-first (not just the head of sales works from his summer house)
  • women in senior positions who were promoted from within (not women they added to the board because they're about to IPO)
  • engineering inside a unfashionable legacy industry, e.g. defense, retail banking, etc. I personally wouldn't choose to work in these environments, but there's a certain amount of ... maturity there

posted by caek at 2:17 PM on March 6 [10 favorites]


Have you ever considered pivoting into service design or UX? Perhaps as a developer in a multidisciplinary agency?

I've found that UX teams are much more chilled and understanding places, perhaps by the very nature of having to constantly consider others' perspectives as part of the work.
posted by doornoise at 3:19 PM on March 6


"Unlimited vacation" is a red flag that there will be no room to take time off.

"Competitive salary" means below average.

Flat affect is a big techbro trope in my experience, particularly at the top of the company, founders, tech leads.
posted by rhizome at 4:15 PM on March 6 [3 favorites]


Tech company hiring manager here.
(a) warning signs to look out for that are specific to or highly represented in startups
Chaotic, badly or inadequately furnished office environment. Founders and leadership team with limited work experience. No one with visible gray hair. Alcohol-centric social culture. "We can't afford to have any process, we're moving too fast!". Compensation emphasizes equity component while salary component is well below market rate. Benefits packages that emphasize optional quality-of-life/"wellness" items ("we'll reimburse you for your gym membership") but do NOT include defined/regulated items like a 401(k) match or accruable PTO.
routine expectations of insanely long work hours
This expectation is not universal or routine in my experience. You should feel free to ask about customary schedules/work hours.
(b) the right questions to ask during interviews that can help me get candid answers about the company's culture in a way that doesn't come off as too snobby
Go ahead and just ask about areas of concern. Thoughtful questions reflect well on a candidate, and as hiring managers, we want to address people's questions so they feel comfortable moving ahead. Snobbishness tends to come across in how people talk about their background or as inflexible attachment to a particular working style.
posted by 4rtemis at 7:10 PM on March 6 [2 favorites]


You should sign up for Blind and ask questions there - it is full of tech bros and the ethos you dislike, but you can also ask really blunt questions and get candid answers. (Also, if you're not looking at Blind or levels.fyi or something you're probably off by 50% in salary expectations)

In terms of warning signs, I dunno, the real thing is that the way to get a chill experience is to be on a team where your teammates and manager are chill. The culture of the larger company is going to make a little difference but your immediate team is going to be 90% of your experience, and at most companies you don't get to pick it. (If you do have an opportunity to join a company where you get to pick your team after hiring, you should take that opportunity.) You can try to suss out what the founders are like but I have worked at companies with all kinds of executive leadership and the impact on my day-to-day life has been virtually nil. I have worked at places where people a couple levels up from my immediate manager were idiots and mismanaged the team out of existence, but until that happened I had a pretty good time, and I was just fine afterwards, so it's really not that big a deal.

Oh, and that whole paragraph only applies if this is a startup with more than a hundred people or so, but startups with less than that are for chumps, so don't take one of those jobs.
posted by inkyz at 7:33 PM on March 6 [2 favorites]


Thanks for all of the responses so far!

I confess that my lack of private sector experience outside of the "fashionable legacy industries" as it was eloquently described above may be causing me to worry a bit too much about the work/life balance issues and paint with too broad a brush about Valley / startup culture. The one interview I had with a local startup about five years ago went poorly, in large part because I wasn't getting good answers about work/life balance, so maybe I'm letting that bad experience color my perception of the entire sector.

The two companies I'm in entering the in-person interview stage with right now are startups -- one is a large (~1000 employee) late-stage startup in SF that recently received its Series F funding, while the other one is a tiny (~30 employee) local company that just got their Series B.

The advice about smaller startups being for "chumps" is obviously relevant to the second company I'm interviewing with now. Is there a particular reason to avoid these smaller companies? Is it just that the failure rate for these smaller companies is so high? Is the fact that this company isn't located in the Valley relevant here in some way? This one was founded in 2013 and seems to be growing responsibly.

I've gotten good vibes about both from the people I've talked to during the phone interviews, but I thought I might not be asking the right questions, or asking them in the right way. It's good to know that the majority think just asking directly is the right call, and the advice on things to look for that are already public information is very useful.

In terms of salary vs. equity, I am not going to take any position that doesn't at least provide parity salary and benefits-wise before taking into account any future income from stock options. From Glassdoor and that Blind site, it appears that my minimum salary requirements would be below the median for what the position I'm applying for at the larger company typically pays, so assuming they like me, I don't think I'll have a problem getting what I need there. Meanwhile, the CTO I interviewed with at the smaller company is aware of my salary needs and hasn't told me to piss off yet, so while I'd expect the number there to be smaller, I think I can at least make a lateral move and have the upside for more if the equity ends up amounting to anything.

One follow-up question here: is it reasonable for a prospective remote employee to demand the same salary from a SF-based company as they're paying to locals? Or does the cost of living factor mean that I should expect them to come in low, assuming I'll take it since it's well above the prevailing wage here?
posted by tonycpsu at 10:14 AM on March 7


The advice about smaller startups being for "chumps" is obviously relevant to the second company I'm interviewing with now. Is there a particular reason to avoid these smaller companies?
I don't entirely agree with this advice (but then I'm a chump who worked for a < 100 person startup for a while, so take my perspective with a grain of salt) but these smaller startups are, broadly, less likely to have established product/market traction and also less likely to have the general "adult supervision" support structures in place that go along way to maintaining long-term employee quality of life. They are inherently unstable and success is absolutely not guaranteed. Unlike with larger companies where employees with a canceled project or bad team fit have a chance of finding a landing place elsewhere in the company, in a small startup there is nowhere to go but out. Your equity probably will not be worth anything. It's a real emotional roller-coaster, and your company may start to feel like a family in the best AND worst of ways.

I have few regrets about my small-startup time—I learned a lot and made some great personal connections—but you should be clear on what you want to get out of the experience and prepared for the possibility that the company may fail and/or be a dysfunctional horror.
Is the fact that this company isn't located in the Valley relevant here in some way?
Probably not very. Welcome to MeMail me with specific details about the situation.
it appears that my minimum salary requirements would be below the median for what the position I'm applying for at the larger company typically pays,
Don't lowball yourself on salary.
is it reasonable for a prospective remote employee to demand the same salary from a SF-based company as they're paying to locals?
Yes if you are senior staff with desirable skills. Larger companies are more likely to have strict salary bands with regional CoL adjustment, but I've heard that some places are phasing those out as FT remote work becomes more common.
posted by 4rtemis at 11:10 AM on March 7 [1 favorite]


I understood your question to be about bro culture, rather than work life balance. In my experience, work life balance is much better in tech than in the technical groups of legacy industries as long as you're an individual contributor with no reports or project management responsibilities. The relative lack of structure means that management in tech can be very hard on personal/family life. But for engineering ICs who aspire to lives outside the office it's a pretty great deal. (With the exception of deadline-driven parts of the industry, like videogames, product agencies, etc.)

I don't agree with the advice that smaller startups are for chumps either. They are different in character in many ways, and if you're particularly concerned about the bro element, they may not be the best place on average. To the extent work is about earning money: I think they're better for people who are either financially secure or young. But at their best: you'll have more autonomy and responsibility at a small startup, and the work will be more interesting.
From Glassdoor and that Blind site, it appears that my minimum salary requirements would be below the median for what the position I'm applying for at the larger company typically pays
Unless you don't care about money, the implication of this observation is that you not understand what the market rate is, and you should do some more research. If you are concerned about cultural mismatch, work/life balance, etc. in moving into this world (and I think that's reasonable!) then you should understand the upsides too, so you can understand offers and negotiate from an informed position.
One follow-up question here: is it reasonable for a prospective remote employee to demand the same salary from a SF-based company as they're paying to locals?
IMO it's certainly reasonable. If they don't want to pay remote people the same they'd pay local people then, well, they're welcome to hire local people, and good luck to them. But will you get it? Depends. Larger companies with offices in many cities often do formal geographic benchmarking and of compensation, and can argue from an informed position about your local market. The hiring manager may tell you their hands are tied and not be lying. A smaller company, which has never benchmarked compensation outside the Bay Area, will usually be more accommodating.

I'd personally be a little bit skeptical about a company at Series F. Taking SV VC funding suggests you're on board with the basic premise of growth followed by exit via acquisition or IPO. Making it to Series F, however, suggests you might be having trouble with the exit bit, if not the growth bit. With that in mind, I'd discount stock comp from this company heavily, unless you have very concrete information about a planned IPO. I wouldn't discount the stock from the Series B company. I'd just assume it was worthless, and then it's a nice surprise if it's not.
posted by caek at 2:23 PM on March 7 [2 favorites]


Another idea is to look at the photos and names of whatever executives or board members are listed on the company's site - usually in the About section. Check out their LinkedIn profiles, recommendations from others, recommendations of others. Google them. Assess from what you can find if they seem like people you'd like to work for.

If there are photos of other employees you can evaluate their age and how comfortable you'd be working with them. Obviously there will be a ton of bias on the company's website about their own culture and photos are hardly enough to use to judge a company, but you can draw your own conclusions based on what you discover.

I've been trying to get a role with a large company whose job descriptions all include a multi-paragraph assertion of their commitment to diversity and they're consistently rated one of the best companies to work for nationwide. Everyone I've interviewed with there has been supportive and accepting.

In my own job search I've also gone to meetups hosted at companies I'd like to work with. It's a great opportunity to speak with other developers there, ask them what they're working on, what the culture is like. You can also get a feel for what the office is like.

A couple years ago I secured a third interview with a large Seattle-based company who was opening an office in my city. The night before the interview a hundred or so of their employees came down to my city and hosted a happy hour at a nice restaurant. Everyone I would be interviewing with came up to me and introduced themselves and every employee that I talked to raved about the culture at the company and how much they enjoyed hanging out with their co-workers inside and outside of work.

I had been skeptical of working for a corporate behemoth that has a storied record of treating employees poorly, but I have to admit that next time I find myself out of work I'll be applying there.

As a 49-year-old dev I also feel the urge to not work with techbros. While I've inevitably been one of the oldest people on the team by far and one of few women - if there actually are others - I've been OK with taking care of my own work-life balance, choosing not to participate in extracurricular activities as well as bringing decades of experience in the industry and my own old-school nerd sense of humor.
posted by bendy at 7:22 PM on March 7 [1 favorite]


Also in terms of salary, ask for more than what you want. I've been contracting for a few years and my baseline hourly rate is the hourly equivalent of the last salary I made as an FTE in the Bay Area. I usually tack $25-30/hour onto that - more if the recruiting company offers zero or limited benefits. I also worked for a year at a ridiculously-high hourly rate and I may bring up that number.

I saw a video a few years ago with some good advice. Never bring up money first and when they make you a salary offer - no matter how high it seems to you - say "I'd be more comfortable with ($offer + 15K)." Chances are good that they'll counter. They've already expended time, money and energy to bring you on and you are making it clear that you have the confidence to believe you're worth more. You're also letting them know that you aren't desperate for this job and that you're willing to walk away if the conditions aren't to your satisfaction.

I'll never forget an experience I had in my naiive early 20's. I was offered a job and asked what salary I wanted. I think I said $26,000 and I got it. A year or two later my asshole manager laughed and told me that he was planning to offer me a lot more. Now I consistently play my cards close to my chest and never bring up money first. When they ask me what pay-range I'm seeking I'll say something like "Obviously it would depend on the culture fit, the demands of the role, etc." Whatever is important to you.

I've been job-hunting for five years now and haven't gotten an offer for an FTE but these are things I've learned in my experiences in hundreds of interviews and in advice while networking. Hmm, on second thought maybe this isn't good advice at all...

And finally, a job is never a lifelong commitment. Every job I've ever had I've learned more about things to require and things to avoid in my next job.
posted by bendy at 7:45 PM on March 7 [1 favorite]


is it reasonable for a prospective remote employee to demand the same salary from a SF-based company as they're paying to locals? Or does the cost of living factor mean that I should expect them to come in low, assuming I'll take it since it's well above the prevailing wage here?

This is an open question. Some pay the same no matter where the remote person is located, some calculate COL adjustments so that Iowans get 40% less than SVers, or whatever. I think the best strategy is to have an idea of the market range and just decide based on everything else if their offers are reasonable.

Never bring up money first and when they make you a salary offer - no matter how high it seems to you - say "I'd be more comfortable with ($offer + 15K)." Chances are good that they'll counter.

I would still not supply a number there. The advice I like is just to say something vague like, "Hmm, it seems low," and leave it at that. Say you have another call in a minute, to juice their FOMO, and let them decide what kind of increase (if any) they'll make with a second pass.

It's a hardnosed strategy and it's hard to say something like that and leave a silent ball in their court, but the conventional business wisdom is to pay you as little as possible so it's perfectly reasonable to make that their problem only. You don't sound like you have to take the first job that offers you anything, so you have plenty of room to negotiate and they're probably in a bigger hurry to get someone than you are to fill that need.
posted by rhizome at 1:53 PM on March 8 [1 favorite]


> It's a real emotional roller-coaster, and your company may start to feel like a family in the best AND worst of ways.

Yeah, that's pretty much what I'd like to avoid. I've got enough fulfillment from my family, friends, and to some extent the work itself that I don't really need the drama of my personal happiness being tied to the company's. All else being equal, I'd probably go with the larger company, but all else is never equal, and I don't know that I'll end up getting offers for either, so I'm at least trying to have an open mind about smaller start-ups.

> Is the fact that this company isn't located in the Valley relevant here in some way?

Probably not very. Welcome to MeMail me with specific details about the situation.


Eh, it's not like I'm trying to keep my identity secret or hide the details about the companies here -- just wanted to keep the advice more general and not have the early responses be derailed by comments about the specific companies.

This is the larger, SF-based company, and this is the smaller local (Pittsburgh-based) company. The two situations couldn't be any more different, but the roles I'm being considered for both sound great.

> it appears that my minimum salary requirements would be below the median for what the position I'm applying for at the larger company typically pays,

Don't lowball yourself on salary.


Yeah, I think I phrased that really awkwardly. My point was that the minimum I'd need to feel comfortable leaving my current position is well below the average according to those sites, which means it's likely that I could get a pretty significant bump (and have upside in the form of options) without forcing them to put me in the 90th percentile or whatever. I still intend to get the best offer I can, but if I'm getting a 20% or more raise from where I'm at now and like everything else about the job and the company, I'm not going to walk away from it because they're "only" slotting me in near the middle of their salary band.

> I'd personally be a little bit skeptical about a company at Series F. Taking SV VC funding suggests you're on board with the basic premise of growth followed by exit via acquisition or IPO. Making it to Series F, however, suggests you might be having trouble with the exit bit, if not the growth bit. With that in mind, I'd discount stock comp from this company heavily, unless you have very concrete information about a planned IPO. I wouldn't discount the stock from the Series B company. I'd just assume it was worthless, and then it's a nice surprise if it's not.

Thanks for explaining this so clearly. Everything I've read suggests Databricks is aiming for an IPO rather than an acquisition, ad an IPO is certainly what I'd prefer considering who the buyers would be that might be in a position to absorb such a large company. I hadn't thought that the long period of "gestation" here might be a sign of problems proving the company's worth to a potential buyer or the public at large.
posted by tonycpsu at 5:25 PM on March 8


I don't have any specific insight into Databricks's IPO plans, but I do work for a pretty direct competitor of theirs. Feel free to Memail me if you want to get into the details. I know enough about Databricks to know they are a solvent, successful business, so you certainly shouldn't assume from what I say about Series F that they are in commercial distress. I'm sure they're doing fine. And you should not take life advice from a stranger on the internet.

However, two notes of caution. 1. Anyone going up against behemoths like AWS faces very serious headwinds. 2. 2020 is not going to be a good year to IPO. Recent "successful" IPOs have by and large not been successful, WeWork left a turd in the swimming pool, and well, the markets are in free fall right now. My guess is very few tech companies will IPO any time soon. If they attempt to tell you the stock will be worth $X when they do eventually IPO, ignore them. It's not necessarily a bad faith exaggeration. It's just that, in the present macro circumstances, nobody knows anything.

But back to your original question: data engineering as an industry is full of huge nerds, and the people who run the companies are more likely to be Romney Republicans with firm handshakes and kids in college than they are bros. There will be a sales team, and they may not be your cup of tea, but it's not boiler room stuff when you're selling to the Fortune 500 and the US Government. If you're remote then work/life balance is what you make it.
posted by caek at 10:26 PM on March 8 [1 favorite]


If the company is at 1,000 people already you're not going to get any significant money from an IPO unless they're going to let you directly purchase pre-IPO shares. Even then it's not uncommon to do a "reverse split" so whatever number of shares you think you have suddenly becomes 1/10th of that overnight. The key thing to understand is what % of shares you have relative to the pre-IPO float and whether they're all the same class of shares - some insiders are more equal then others.

Anyway a 30-person company isn't something to be scared of but it's definitely higher risk than a big established company.

And other have said, try to avoid naming a number first and whatever number they give you initially push on raising it. It's all a dumb game and even people who deny playing it are still playing it. So play the dumb game.
posted by GuyZero at 10:51 AM on March 9 [3 favorites]


TIL that it's illegal in CA for employers to ask for your salary history, and they also have to provide salary range information on request. (previously on MeFi). This makes me feel much better about the salary negotiation process with CA employers if I end up getting to that point.
posted by tonycpsu at 2:02 PM on March 10 [1 favorite]


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