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Ask HN: What's left for early startup engineers as the company grows?
463 points by tootall on Jan 13, 2015 | hide | past | favorite | 186 comments

I joined a startup ~2 years ago as employee #2 (software engineer), and thus I've had the responsibility of essentially building every technical aspect of the company from the ground up, which I loved. Now, the company scaled up (about 45 people) but, instead of being happy, I feel like everything's been taken away from me:

- Technical strategy: I strongly shaped the technical direction of the company defining a lot of critical points, and now they brought in a VP of engineering

- Management: I managed an entire team of 10 people without ever missing a deadline of the whole team, and now they brought in an engineering manager

- Customer facing roles: I was having a lot of customer interaction and support, now they brought in a support engineer and I don't even know who our users are anymore

- Infrastructure management: I took care of building a state-of-the-art scalable and fully automated infrastructure in the public cloud, and now they brought in an operation guy

- Developer: This is the only thing I still do, full time

Essentially, and I understand it's just my ego speaking, I feel like there has not been any career advancement for me. The only benefit has been the gazillion things I learned in this ~2 years journey by doing the above roles.

I've been told that now, since I don't have to worry about the other things, I can focus on what I'm able to do best, just writing code (which I agree, all the tasks I did were less challenging than some critical parts of the code base I wrote from scratch), but still in the "about us" web page of startups just the management is going to be listed and take the credits. Where did I fail to claim my part when the company was growing?

I understand this is a first world rant and and I should just "be happy" it has been a success so far, but still I find it hard and I would very much appreciate the opinion of other people who went through something similar.

Thank you

I'd focus on a repeating theme in your post, "and now they". This suggests that you already see a division between the management of the company and yourself. You haven't been part of the decision making process and feel that all possible angles have been locked out by an outside agency. How much feedback have you given to the company management that you would be interested in those positions before they where "taken" from you? Have you done a gap analysis between your current operating skill set and the expectations for those position? What skills have you tried to improve outside of "developer" recently that would show you are trying to expand your role?

You need to get past the "been told", and start communicating what you want to achieve. It might be too late at this company, but I would bet not, just because these roles are already filled doesn't mean they will stay filled, or that tasks won't outgrow the current holder. Think ahead, and aim for a goal, communicate with every means you have that your ready for that goal.

"Fortune favors the prepared mind." - Louis Pasteur

Sure, but I think this is just normal as a company grows.

When the company is tiny, you have a ton of hats. As the company grows, those hats become too big for you to wear all of them, and so you ("they") hire some people to take some of those hats from you.

As a developer, if you don't have clear aspirations toward management, usually you go nowhere: your influence erodes until you end up "just another developer", regardless of your tenure in the company.

If you do want to keep doing development, then you need to push management (early on) to create a technical track that's parallel to the management track. There should be technical positions (that come with no direct reports) that are at the same level (both prestige and pay) as manager, director, VP, etc. They need to be well defined, and it should be clear how it's expected that a developer will progress to those levels.

So what I'm saying is that I don't think the OP's real problem is that he has fewer roles, but just that, as the company has grown, he's remained a "leaf node" in the org chart, which just gets deeper as time goes on. If you think about the management hierarchy as your own hierarchy, that's just naturally going to happen. If you have parallel tracks, it stings a bit less.

Or, the OP is basically just built to work at small companies, and he should plan on joining a company when it's small, and then hopping to another small company when it gets too large. That's a perfectly valid strategy, too.

That sounds good too, but aren't you presupposing that this course of things is normal. The OP is saying things turned out differently than expected, and such dissonance really bugs him. Why would he work harder to communicate when working hard has failed so poorly in the past?

Second and third world people probably have similar problems too.

In my experience, what other people thought you communicated and what you thought communicated are often very far apart. Its an amazing thing, Humans are so good at communication but also so bad. I know with my significant other multiple times we have both got upset with each other for actions/inaction that we thought we had communicated with the other, when either we hadnt or hadnt clearly. We have been together for 10 years, and it still happens.

Communication is possibly the hardest thing to get right between two people, because it seems so effortless.

Don't even try communicating with a group of 100 of these so called people; surely three of them will found a religion based on misunderstanding your point, especially if you are the OP.

As a technical founder I actually face the issue on the other side, which is how to keep those that have been around for 5+ years challenged and motivated. Here are a few things I've learned that might help with perspective:

1. You shouldn't be afraid to ask for what you want. As a founder, it's tough to always know what goes on in everyone's mind. I try as much as I can but when I'm a part of the conversation I will be able to help much more than just being looped in after a conclusion is reached.

Every good developer wants to be challenged. Some want to stay on the technical side, others grow into managers, and some like to blend the two. Talk to the ceo/founders and let them know how you feel. I'm sure they appreciate what you've done so far and will be happy to figure out the future.

2. You're at a very unique position where not only do you know how the entire system works but you also know how it's supposed to work. This gives you the ability to contribute to any of the different roles you mentioned in a really meaningful capacity.

One of the comments said something about not being good at those. I mostly disagree with that on principle. Just because you don't have the training doesn't mean you won't be an awesome manager. Some companies actually don't hire managers but rather promote. I believe LinkedIn is one of those companies, and they do it because they want those the manager will oversee to really trust the manager. That's something that, as a developer, you can do when you've seen the person's work.

3. The skills needed to get something off the ground are somewhat different from those needed to take it to "the next level". It doesn't mean you can't have both, but it is a question you should ask yourself. Do you like the rush and the excitement of creating something new? Or do you like the joy of seeing a large system run smoothly at super scale with time to sleep? Or both.

"Just because you don't have the training doesn't mean you won't be an awesome manager."

While this is true, it's worth remembering that management isn't a promotion, it's a career change: http://fractio.nl/2014/09/19/not-a-promotion-a-career-change...

It took me awhile to realize that management is, generally, not a skilled profession. Not saying that certain skills can make you better or worse at it, but that you don't need them to be effective.

In a skilled profession, not having them means all the difference. You can't wire up a house without the skills. You can't build a web app without knowing a whole lot of stuff, at least not within any time frame someone would pay you to make one in.

It doesn't mean that management is stupid or boring. It means that you can bring more of yourself to it because there's not this huge body of best practices that you have to adhere to in order to succeed in it. There's lots of room for eccentric practices, The Office showed that exquisitely.

You can carve out a place for yourself. If your days are taken up by meetings, take your laptop to those meetings, listen with half an ear so you can still contribute, and code whenever you can't. Don't ask for permission, you're a manager, you're busy. You're always busy, you decide what you're busy with.

There's this hierarchy I've noticed of office workers. You can be paid to do stuff other people tell you to do, I call these drones.

You can have responsibilities, in which case you can justify doing anything so long as it fits into the responsibility and you can make your bosses believe that. I justify posting on HN this way.

If one of your responsibilities is someone else in the company, then you're in management, and you have a lot more latitude to order your day, if only because you can simply order your subordinate to take care of your responsibilities. You generally use this power to think and strategize about how to improve your department's role in and contribution towards the company.

Once you get promoted into management, this is how you're expected to spend your days, but you don't have to. You can still code if you want to, so long as you're meeting the additional responsibilities that are thrust upon you by managing others. They're your responsibilities, you can meet them however you see fit. That's what management means.

If you don't know how to do this, you might get stuck attending pointless meetings. If you do, then you can avoid most any meeting that you weren't personally asked to attend by someone you report to. If you're at a meeting, your job is to contribute to the shared understanding of whatever business situation they're having the meeting about. If you can do that while coding, so much the better, you're multi-tasking.

Even if you don't have any direct reports, even if you don't have any responsibilities, you can create them. You can't make people report to you, but you can sort of take responsibility for them if you notice they're slacking or whatever.

You can also take some role the company needs filled and start taking it seriously. There was this great segment in The Office where Pam, as part of the sales staff, starts taking on "Office Manager" roles, and eventually leverages it into a newly defined role and salary, in hilarious fashion.

You don't have to use subterfuge to gain responsibilities, you can simply ask your boss for one or notice something that needs attention and tell your boss you're taking care of that from here on out. If your boss notices you taking responsibilities, then they'll start to re-categorize you from a drone to someone who can take charge of something. Managers call this "initiative".

You are describing bad management. You don't need skills to be a bad anything. There are plenty of bad programmers going around who don't actually have any useful skills either.

There is a particular set of skills involved in not getting fired even though you don't actually have any skills. However, this skillset will not save you if the company institutes blanket layoffs or goes out of business, nor if you ever need to look for a job with no skills. And if you're getting by without any tangible skills or output, chances are everyone else around you is doing the same. This makes the chance of the company going out of business and you needing to find another job quite a bit higher.

YMMV, but I've found it's a significantly less risky strategy to just go learn the skills, practice them, and refuse to work with people who are obviously faking.

Most companies have bad management. I would go so far as to call it the norm.

You're obviously better off with skills. I never said you weren't. But you don't absolutely need them to be an effective manager of other people's efforts. In fact one of the best ways is to just get the hell out of their way.

> In fact one of the best ways is to just get the hell out of their way.

One of the fundamental purposes of management is to help other people get the hell out of your way. In software, the purpose of a manager is very often to stare down requests and reject them on your behalf because you're busy doing something more important.

> just get the hell out of their way.

That is a skill.

Not one you can learn from any textbook or 'theory of management'. That's what I meant. Just because there are skills involved doesn't make it a skilled profession. That would be like saying collecting baseball cards is a skilled profession just because it takes a certain amount of knowledge to know which ones to collect. Sure, but that's doesn't make it a skilled profession.

"Skilled profession" isn't defined by what you can learn from any textbook or theory. Just try mentoring a fresh CS grad out of MIT or Stanford - they will know all the theory and textbook algorithms, but there will still be huge gaps in their knowledge of how that translates to solving practical programming problems.

A skilled profession is one that involves skills, i.e. things you can practice at to get better in. Retail clerks and fast food workers are generally not considered skilled professions because no matter how much you practice or improve, the customer will generally not care. Management or even something like professional basketball is a skilled profession, because there are large differences in the performance of workers based on their level of experience and practice.

As a founder I manage various teams full-time. I don't consider myself to be a manager because ultimately I don't report to anyone, but I disagree with most of what you're describing.

Skills - You may have only worked with bad managers because to be a good manager, much like anything else, requires certain abilities. While some have those it's practice and experience that make you really good.

> You can't wire up a house without the skills. You can't build a web app without knowing a whole lot of stuff, at least not within any time frame someone would pay you to make one in.

You sure can wire up a house without skills. The house will probably end up burning down due to the many mistakes you'll make but it doesn't mean it won't work. On the same token you can manage without skills, but those you manage will burn out, produce less, be unhappy, and pray that you'll disappear one day (or get fired).

Delegation isn't as simple as just telling others what to do, that's a gross misconception.

> You can have responsibilities, in which case you can justify doing anything so long as it fits into the responsibility and you can make your bosses believe that.

Really? Don't you feel behaving in such a way won't help the company you're helping build?

I do agree that finding things to do and potentially developing something that may not get the attention it needs is a good idea, but that's good for any stage of the business.

> Really? Don't you feel behaving in such a way won't help the company you're helping build?

You're helping the company by meeting your expectations and goals, which are set by your higher-ups who have clawed their own way up the hierarchy and so are presumed to know what they're doing. So long as you're doing that, you're a good employee.

What you do with the rest of your time is up to you. Certainly don't start working on side projects or screwing around, but you can do stuff like investigate future profit centers for the company, catch up on industry gossip, take people in your company and other companies for lunch, (networking) do personal / life stuff like taking your kid to the doctor.

All of these things are things that help the company in a roundabout way and may be overlooked by someone who doesn't properly understand what managers do.

The secret to clawing up hierarchy is that you don't claw your way up the hiearchy. That's a path to middle management.

You become a entrepreneur, you network and get hired directly into a position(Cofounder). You get into finance, and enter VC/Private equity firms so you get placed on boards etc

So i don't assume that the top people, are the best skilled.

I quibble with your stating that you can be a manager without some critical skills. I think the skills defined under the (now defunct) concept of emotional intelligence are vital to being a successful manger. Without empathic skills you can't get anyone, but the most committed employees to perform well. It seems self-evident, but many people I've met including very poor supervisors lack the ability to really put themselves in others' shoes.

I'll quibble with this. There are plenty of managers that wield authoritarianism and plenty of subordinates that yield to it.

I'd agree that managers with soft skills perform better, but even the old-school ass-kicking types can still eek out a performance. And even be rewarded by the higher-ups for that attitude.

> I quibble with your stating that you can be a manager without some critical skills.

Why couldn't you? All that would need to happen is a company asks you to take on the role.

one question, why do you say that the concept of emotional intelligence went south?

This is seriously one of the best comments I have read on HN. Thank you! What I think is important is very often no one tells you these things, and programmers are often systematizer types - if they're not explicitly told "this is how things work" they are slow on the uptake or conjecture reasons why you're not supposed to do them.

What you are describing is a completely redundant role. If that was all managers were, why do companies, including smart ones, have them at all?

What do you believe that middle-lower managers do then?

One thing you need to come to grips is that regardless of how smart you are, the VP of engineering is probably someone that has a lot more experience and clout than you do. If they aren't, then the senior management of the company is terrible. If your company has grown to the size of 40-50 people, that's the time when they need real experience to help drive them forward. They can't take a chance on a great programmer who has never managed an organization before or grown it from 40 to 200 people. So you need to accept that.

But you should stick by the VP of Engineering and learn whatever you can from them. Be their right-hand person, and try to become someone that the entire company goes to for technical issues. It's not hard to be the de facto CTO, just make sure you are a part of all the technical decisions, and a positive guiding force for the company. As you become more and more the face of technical decisions, eventually you'll be recognized for it, or you can go to another company in that higher role.

Why is it acceptable for the Founder/CEO to continue leading the company at 40+ employees but not acceptable for the engineer to lead an engineering team at 40+ employees? Seems like a double standard.

> Why is it acceptable for the Founder/CEO to continue leading the company at 40+ employees but not acceptable for the engineer to lead an engineering team at 40+ employees? Seems like a double standard.

It is a double standard, but however it's hardly that cut and dry.

Post Series B, if the board does not believe the current Founder/CEO can take the company to the next milestones of growth, they will replace them.

Typically engineering teams need to scale sooner, so you you see a more experienced manager be brought in before the CEO is considered for replacing.

The CEO may also has the additional benefit of having the investors and board help him or her in their decisions.

reason number 472 to never take funding.. if your business can not be bootstrapped successfully, it's likely your business is going to never turn a profit. Funding is silly, i'd never subject any business i'm involved with to a board room full of investors that don't give a shit about me or my business and only care about PROFIT! MOAR PROFIT! blech.

So glad we're bootstrapped.. we're not doing millions a month in business, but we don't need to.. we've been profitable for nearly a decade, a SaaS service since 2002, and we do about 100k/mo in revenue. Pays the bills, pays our people, and we're all so much happier with life.

>if your business can not be bootstrapped successfully, it's likely your business is going to never turn a profit. Funding is silly...

Well, this just isn't true at all. Many companies have very high costs up front due to the nature of their business. This is especially true in hardware startups, but can also be true in software startups.

I guess, but there are so many better ways these days, if your product is worth building to get it built than to give up a huge piece of your pie. Crowd funding, etc.. if you have 10 years of R&D well you're better off just taking the idea to another company.

This is a generalization, but I think owners get their priorites mixed up when they are sitting on millions in free money.. their burn rate is insane.. they spend money on the wrong things, etc.. fancy offices, whatever, and they aren't even profitable. We work from home, and share a co-working space as well as an office with 2 other companies..

Office life is over rated and is a giant waste of startup funds. =/

The board is just a bunch of old white dudes with money. The fuck do they know?


balls187 suggests they know how to make money--which is perhaps true, but not necessarily in your field of endeavor or business, unless you've picked them.

kelnos is closer to it, which is that the board tells you what to do because they're the board and that's the power you've granted them.

Again, in neither case, do we actually need to assume they are making the best or even informed decisions. There are some great stories of boards I've known locally suggesting really dumb things that hurt and even killed companies.

Assuming you're correct (very debatable), it doesn't matter: they're the ones funding the company, so they get to make the decisions. This doesn't always work out well, but it's not unreasonable.

One could make the same argument for hereditary monarchy. Which I would take as a sign that maybe it is unreasonable.

Except that taking funding is a voluntary action. Living under a hereditary monarchy is not.

Presumably how to make money.

Investors are like companies, 60%-80%(Dubious estimation) are not that great, but every so often there is a good one.

Are you implying that young, poor black people know better?

What are you thinking? You can't just point out that decision-making in Silicon Valley lies with a clueless investor class.

You've got to keep the charade going: keep them writing checks and thinking their input is valuable.

One BIG reason to start your own company but never ever become an employee at a startup.

EDIT: The only benefit of working at startup (and a significant one) is to learn how startups work. If thats taken away from you then there is no point in risking your career.

Frequently in VC backed companies, founders are removed from the CEO role if they aren't showing the ability to monetize and determine "what's next." Sometimes the founder goes to a glorified secondary tech role like a fellow, and sometimes they leave the company all together.

We are doing it differently. We don't think a tech driven business can be run by non tech leadership. We also don't think it can be run without business leadership. So we have two CEOs, on from tech and one from the business sector we are in. It works really well.

The two are not equivalent, as you need different attributes in each case. The CEO needs to have the product vision and complete information about the company (see http://www.bhorowitz.com/why_we_prefer_founding_ceos for discussion), which typically only the founding CEO can have. You'll note that this is a continuation of the role they had when the company was small, though of course it requires a massive amount of learning.

However, for all other roles in the company, the important thing is having the experience to scale and lead that part of the company: sales, marketing, product, support, engineering. When the company is young, those roles will be filled by allrounders: people a few years experience who do everything in that area. As the company grows, you'll want to hire VPs who have the skills to lead those areas, often people with >15 years experience as a practitioner and/or leader in those areas.

It's not just engineering: you want a VP of Sales, a VP of marketing, a VP of product, etc. Those people will have the skills to take your existing sales/marketing/product/engineering org, and scale it without damaging it. If you have that skillset in your engineer #2, than it would make sense for them to do that role, but it's unlikely that they do, and certainly doesn't seem like it in th OP's case.

Ownership has its privileges.

I understand, but you are right it's a double standard. The Founder/CEO usually got that position for reasons other than their their technical know how. Personally, If a CEO doesn't understand most of the nuts and bolts of the company they are running; bye! bye!(That is unless they are brilliant in other areas in business.)

Your observation is known as 'Founders Syndrome' (http://en.wikipedia.org/wiki/Founder%27s_syndrome)

> Why is it acceptable for the Founder/CEO

Chances are the Founder/CEO has a controlling share of the company's stock.

Not to be snarky or anything but the first thing that pops to mind: "Because it's his company".

This x1000. The last thing you should do is withdraw, and leave everyone high and dry. I've seen this situation, where the 3 remaining of the original cohort, for some reason, resented the new CTO, and basically abandoned the company. Only reason they're still here is they have an ownsership stake and are friends with CEO. They could've been hugely impactful to the success of the company, but instead, they're sitting back to watch the everyone else fail.

Also, with this crew in particular, they really weren't that good. They begat a lava layered monstrosity that doesn't scale and isn't maintainable. Make sure that's not you.

What is wrong with leaving everyone high and dry? The CEO has no qualms about doing that to devs.

If an engineer leaving puts the company in a bad spot, then they are understaffed and need better management that can foresee and handle those transitions before they happen.

It's all part of proper engineering culture.

This is what happens when one person stops communicating to another due to lack of awareness; the other assumes the worst, and stops reciprocating. They are the only one who knows what's going on, yet it almost always comes down to them saying "Why should I be the first to re-establish communication?". You should do it because you're an adult, and the other person isn't a mind-reader; if you don't, you don't deserve any sympathy when the shit hits the fan.

I think even before you bring responsibility into the picture, there's a lot for each actor in this situation to gain from reestablishing communications(I certainly can't see what they would lose, except for face). This is assuming the other party is mature and rational though.

You're suggesting he owes them something, and it really sounds like he doesn't - they've passed him over for career advancement, so he needs to find somewhere he'll be appreciated

I don't understand why this attitude is a problem in this context.

It's their last and only pressure point in the political game that happens in the company.

If you don't feel that your skills are fairly compensated and you can't leave (due to contracting or vesting time) you don't have any other options.

Being a dick is not an option or a negotiation tactic, it is just that being a dick. Note I'm speaking to my experience, where tbe people in question do everything but actively sabotage the CTO in question.

"Being a dick is not an option or a negotiation tactic"

I disagree. Leaving is not "being a dick", it's looking out for yourself. If you don't, nobody else will. It's apparent this is the case with the OP: He was pretty much built the entire company up and was there for the company when they needed him (I would imagine late hours, weekends, etc).

Now that they don't need him anymore, they pushed him off to the side. I've heard this story 1000 times and experienced it first-hand.

I don't work for startups for exactly this reason. If I'm spending my life building your company, I better be getting 50% in equity. It's really not worth the fooseball table in the lunch room and the Red Bull in the fridge. This is why you need to get the young and naive to fill these roles.

I agree, leaving is not being a dick. Staying and not helping, or actively hindering new staff through lies and misdirection about implementation details of a complex application in a complicated domain is.

I see a number of posts saying that you're probably not experienced or qualified enough to hold these other positions. However, I don't think the VP of Eng, Dev Mgr, or OPS Mgr could do what you do...essentially help start and build a company from day one.

Those skills you've developed don't have much value at your current company any longer. They are most likely keeping you around for historical value and once the systems you built get replaced its over pretty quick. Take those skills elsewhere and brand yourself as someone who takes a company from 2 to n employees.

Not everyone has your skill set so learn how to market them. I'm on my second company where I was an early hire. I learned that you're way more valuable in the beginning then you are at the end. Eventually I got pushed out by management types because I held on to the notion that I helped build this company and deserved something for it. Don't wait too long to realize it.

+1, witness how the company needs changed from generalists to specialists.

The experience is probably quite frustrating since every specialist they hire is supposed to handle their aspect of specialization better than you (otherwise why hire them?) - the support manager probably has better and more complicated pipelines for support, the ops guy probably owns various issues that were put on the backburner before.

Wrong way to think about it is try to squeeze yourself into a specialist position, and then keep wondering how did things get to be so bad.

Some right ways to think about it would include addressing some areas where specialization is missing (research? next-gen architectures?) or just moving on (to a different place).

The rub is:

* the OP will need to pay a lot to buy their vested options when they leave each company

* the fair market value of common stock will have probably increased so they'll also need to pay immediate income tax on every gain

* they likely won't have a market for their shares until acquisition or IPO (five to ten to never years)

* the shares they do have will be diluted 10x or more through Series A/B through F, and they won't benefit from readjusted new 4-year-vesting grants

* they'll learn a lot and profit little from serial startup monogamy

Try to join when stock has low paper value, exercise the options immediately so there is no gain and no tax. Then you vest shares, rather than options, and can take them with you.

Not that many startups allow 83-b elections early on. It costs them a few $k when someone does this. It doesn't necessarily have to (it's just paper filed with the IRS by the employee), but that's what they're told and that's what they went through when they did their own 83-b paperwork. So that's what they think everyone needs to do. Honestly, there really aren't any legally required paperwork involved with 83-b, but the entire ycombinator crowd is convinced that there is. Perhaps it's bad knowledge by the YC figureheads?

Since this affects 100% of startups and can have a huge financial impact on early employees, one would expect it to receive more attention. Since some startups allow the election, it is clearly possible. It needs to be a standard part of compensation negotiations. Early employees can obtain independent, professional advice on the topic, rather than burdening their friendly neighborhood VC.



> Honestly, there really aren't any legally required paperwork involved with 83-b,

I've consulted with several good (by recommendation, and by their work on other issues) tax professionals, and each and every one stressed that without filing a 83-b election notice within 30 days of grant (and a copy with your returns) and paying the associated tax, you will NOT enjoy favorable 83-b treatment.

Do you claim they are wrong? How do you retroactively get 83-b treatment if you don't file in the first place?

This is great advice. I will also add that if you want a leadership role, model your resume around your leadership experience at this company. You've led a team of 10 people. So say that on your resume. It was your high water mark and you don't have to tell people that you're not leading 10 today. Go out and get that leadership role if that's what you want.

What's the financial outlook for this career path? I've always heard bad stories about early hires dealing with a below market salary(for a while) with worthless stock options. Is this a myth? It never made sense to me since I feel an early hire should make significantly more than average, since they don't have the power/equity advantage of a founder, probably have to work long hours, and a large part of the success of the company rides on their shoulders.

Interesting question you might ask yourself, do you want to be in management or not? Do you want to be customer facing? Or not?

When companies are small the jobs are all blends because they have to be, you just don't have the resources to do more. But as the company gets bigger (presumably through growth and not just a funding bump :-) you can allow folks to focus full time on specific roles which, in theory, gets you better execution of those roles.

A friend of mine once said you often could figure out what role you liked "best" by the first thing you did when you got in, did you check the build? (developer) did you check email? (manager) did you check the web? (marketer) A bit simplistic but it does make for interesting introspection.

As employee #2 you're well connected with the CEO and the other founders, and you can talk about what you want in your future. You should sit down and have that talk with them.

What if you check HN first thing you get in?

Time to cash out.

Then, you should write for techcrunch. </snark>

That's a valid point. I remember when I started my job, I spent about 1/3rd of my day working on support cases.

I made it very obvious that I did not like doing it, but was merely being a team player until the company hired the right people.

Again, that's why it's important to communicate where you expect your career to go.

The rub with startups is that leadership may not have experience with developing careers.

From what you've written, it seems like you really don't have a lot of experience developing careers either, which is one reason to bring in an experienced engineering manager. It's not a knock on your skillset managing a 10 person team and delivering. Just a realization that management isn't something you can just quickly learn on the job.

My advice: have a discussion with whomever the new engineering manager is, and explain your career aspirations and the current dilemma you have.

Agree with this advice. You should talk to your manager and work out a plan to achieve your career goals within the company. This is a significant part of your manager's job responsibilities, and assuming they are good a good manager, then they will be more than happy to work with you on this. You are obviously an important part of the organization and if they have any common sense, they will want to retain you. And if, for some reason, it turns out there is no good way to grow within the organization, then start weighing the pros and cons of leaving.

Also, remember that transitioning into a management role is an advancement only if you want to be a manager. It's a career change, and is not suited for everyone. This is why many tech companies have pure developer track advancement opportunities.

As employee #2 he should be talking to (presumably, his friend), the CEO, regardless of who his manager technically is.

Exactly. If he doesn't have an open line with the CEO, then I would leave, assuming I have some percentage of options that had vested. I would stick around long enough to vest, then go start your own thing or be a cofounder of something.

I know this situation well. I am employee #1 in a 55 person company and I feel like I might as well be employee 55. But, since I'm remote, I can do my thing, write code, and generally be left alone while getting paid regularly. So being cut out of the loop does have some advantages, especially if you're remote.

> I'm remote, I can do my thing, write code, and generally be left alone while getting paid regularly. So being cut out of the loop does have some advantages, especially if you're remote.

There is the opposite end too. I joined a 100 person company, and some early founding employees were clearly resting and vesting, while I was working nights and weekends to iterate and replace prototype software written by early team members. I was grateful for the company they built, but was curious why they had an entitled approach to their positions.

Software is meritocracy based, not loyalty and tenure.

As employee #1, in what ways do you think you should be treated differently than the other employees?

Software might be about meritocracy but power is not.

It's not entitlement so much as ownership, they don't feel they are entitled to 5% of the company, they own 5% of the company.

Depending on how much equity they have collectively they might be able to fire the CEO if push comes to shove.

At a company with 45 people, all of the roles you mention probably should be dedicated roles/teams. You didn't do anything wrong, you were just successful at growing a company.

If you want to wear a lot of hats, go join another early stage company (the items you mention make an awesome resume). If you want to grow at the current company, pick an area or two (development+strategy or management) and let the ceo know what you are interested in.

This exact situation happened to me. If you are at such a distance from the founder that he doesn't care about your place in the company — namely you're not considered one of the "important people" — your problem is two-fold:

1. Your immediate job won't be as gratifying.

2. (And this is a bigger deal) You won't be in the room during the exit when the money is being handed out.

Re 1, as I saw it, given my equity stake, I should just put my head down and wait for the liquidity event. This worked well, though was a large blow to the ego. Given personalities and priorities of the founder, agitating would have put my equity stake at risk.

Re 2, despite the fact that you may have an iron clad equity stake, there is often money that is handed out in an exit which goes beyond equity. In my case it was about $90mil in retention money. If you're seen as one of the "important people", you'll be in the room when that is being divvied up and can get your hands in the cookie jar (at that point it's just a land grab.) If not, you're shit out of luck, since no one at that point will be looking out for your interests.

So, I would say I would take the long view and not worry too much about the ego/job satisfaction. If you end up set for life, the resentment will fade. (I'm 3 years post liquidity event and the resentment is for the most part gone. Both for the name on letterhead issue and being left out during retention.) I would, however, do all I could at this point to re-establish myself as one of the 'important people' so you can be in the room when the cookie jar is open. In my case, it was impossible since in my obviously biased view the founder was an ass and an idiot, but perhaps your situation is still salvageable.

You've got a bunch of options, depending on your interests and skills.

You could be a repository-of-lore brilliant coder / guru. Sounds like this is roughly what the CEO has carved out for you right now.

You could be CTO/Head of Engineering. You may or may not want this job or be suited to it, based on what you've said so far.

You could sink down into the organization as a (hopefully) really rich mid-level engineer and enjoy the ride.

You could do it again as a founder rather than early employee somewhere else.

I think you should figure out what would be best for you, what you want, and then see if the CEO agrees and will make it happen. At some level, if you're a few years into vesting, and the company is successful, it may not significantly change your financial outcome to stay -- you have early stage stock in a successful startup. More could be nice, but it won't change your outcome 10 or 100x, like moving to a founder role would.

Lots of good options; just don't do the west coast thing and stew on it while you write increasingly bitter tweets and blog posts. :) Today is a great day to get some clarity!

> At some level, if you're a few years into vesting, and the company is successful, it may not significantly change your financial outcome to stay -- you have early stage stock in a successful startup.

somewhat related question - doesn't the huge taxes on the options exercise upon leaving make that huge difference between leaving and staying? How does people manage it? Doesn't it forces you to stay until the exit?

I'm sure you're right there are some tax consequences; I'm definitely not an accountant, though.

In a friendly situation if the company is in good shape, there are probably lots of options, including some sort of buyback to get enough cash for the taxes, or finding an investor who'd like the shares. If the company isn't doing as well as advertised, those possiblities are probably harder to get sorted.

For the US - Depends on if you're exercising and holding or exercising and selling. If you didn't get the opportunity, or forgot, to take an 83(b) election as a founder, then you've been paying income taxes as your shares vest. If you were keen on taking that 83(b) election, your tax liability is negligible on liquidation and you pay nothing until that point for usual ISO arrangements.

I've heard that before. You were very productive coding, almost too busy and if they promoted you then they would be one good coder short. It was easier to hire somebody fresh with an outside look to think long-term. I expect you will soon be heading a 'special projects' group as a perk to keep you motivated (that group might build a second website or launch in another country or create prototypes so that could be great). The only thing you could have done would be to insist on becoming a/the CTO from the beginning and not let them hire anybody on top. Were you cut for that from day 1? Often investors add pressure to replace parts of the team with 'more experienced' experts, that can also affect founders (being stripped of CEO and president titles).

I went through the same thing at a start-up I founded (with others). It ran for 10 years and I never jockeyed for a management position. I just stayed a developer. In the end the fact that I was a founder who played a giant role in building the company meant nothing. I got sucked into one of many layoffs. No severance. Just back vacation pay and a fake tone of regret from the new engineering manager who made the call. The other founders had already left years before me and went on to even bigger and better things. I stayed because it was comfortable, but I regret not leaving years sooner.

I would guess most people there don't even know who you are, right? They might even know, but they probably don't get it because what you did in the past doesn't matter. Your company is becoming more corporatized and in that environment all that matters is your title. Since now it's likely just "developer" or "senior dev" or something, you're just another scrub with a good backstory.

If I were you I'd update my CV to reflect the contributions you made then start working your network to find the next thing.

> Where did I fail to claim my part when the company was growing?

Seems like it is not too late; just talk to the CEO and VP of Engineering and say you want a new role created called Chief Architect or Principal Engineer. As employee #2, it seems perfectly fair that you should get some additional recognition above and beyond simply "developer". If they like you and want to keep you, then I think definitely they would not object.

This is the right move. If they say no, or don't come back with a compelling alternative this means that you don't have a strong enough relationship to be recognized for your potential future contributions. It is important that you are likely to only be recognized for your potential, not your past contributions.

Early employees of a startup are in a rotten deal. They took slightly less risk than the founders, similar pay cut, but with order of magnitude less equity, and with more work in designing and building the product, running operation, doing marketing, and selling to customers. When the company goes under, their loss is the same as the founders. When the company does well and scales up, their positions and roles will be diminished substantially, and their equity would be diluted again and again with each round (later grant is often not at the same scale as the initial option grant).

Early employees are basically jack-of-all-trade doing essentially the same job as the founders (minus the fund raising) in building up the company but with much less of the upside. If you could, be the founder. Don't be the early employee.

I have to respectfully disagree with you. You may be spot on in some scenarios, but you couldn't be further away in others.

As a co-founder, I didn't take a salary until a year into the startup (same with my other two co-founders). Even when we received our accelerator funding, all of it went towards our first hire's (an engineer) salary and operating expenses. At this point, our risk was significantly higher, not slightly. If the company didn't succeed, I can tell you our first hire was next in line for a cushy market job, and he was being actively poached, not us.

After we graduated the accelerator we raised a ~$1M seed round. We hired more two early team members at market salaries. Each of the co-founders were taking $33K salaries. Why? We wanted the budget to hire great people. So no, definitely not a similar pay cut. In fact, it's increasingly hard for early stage startups to hire good talent at less than market rates because there are plenty of amazing startups hiring above market. Our risk at this stage was even higher, because failing would burn most of our bridges with our new investors (maybe a couple wouldn't hold it against us), where as if our engineers went on to start something, no investor would think twice about their history working at a failed VC-funded startup.

We didn't increase our salaries again until we were generating revenue. Even now, three years in, I'm taking $20K less than the starting salary for a junior person in the role I have. While I want to increase that a little more as our revenue grows, I don't think it's fair to take a market salary at our stage.

And I won't even begin to dignify early employees do "more work in designing and building the product, running operation, doing marketing, and selling to customers" with an answer.

I'm not complaining, but to say being an early employee is a rotten deal is unfair. If our startup goes under, I definitely have the more rotten deal. It only looks like I had the better deal if we succeed.

And if you want to start a startup, you should, that's the only way you'll know how truly hard it is.

How hard it is based on the situation you are in. You could have investor contacts, alumni of a fancy university for credibility, developer friends willing to work with you etc, etc

It ranges from fairly hard but doable to impossible.

Make demands if you still have power/clout left. My story was pretty much just like yours -- I was engineer #2 (after the CTO), I pretty much built the company along with the CTO. I have patents with me as the inventor on them through the company.

Early on I was promised equity in the company, but never got anything in writing (I knew nothing about startups when taking this job).

I was actually treated pretty well as an employee, given good raises, position upgraded to Director level.. but that equity thing was always out of reach, and they kept pushing it off with various excuses. I trusted the CTO, but the CEO was a greedy type.

By the time I put my foot down, it was too late, and they had no problem letting me go. If I had made demands about 6 months earlier they would have been forced to do something or end up REALLY hurting. But I had knew that I had waited too long, so I secured a job before I tried anything. I learned a lot at the company, so I'm grateful for that, and I'm working at a much better and more interesting place now :)

> Where did I fail to claim my part when the company was growing?

One problem I had in my youth was that I really wanted to be recognized for what I did without a lot of blowing my own horn. If I self-promoted, my victories felt hollow: was I getting kudos for my work, or for my self promotion? So I energetically avoided calling attention to my accomplishments.

Eventually I came to realize that this was a little crazy. I can't expect managers and clients and investors to automatically appreciate all the stuff that it has taken me years to learn to do well. I've discovered that there is a reasonable level of taking credit that is neither sleazy nor slighting of my colleagues. Being modest and self-effacing is good, but it can be taken too far.

So let me answer your question with some more questions: Do the executives know that you did these things well? Have you told them you wanted a position other than as a line developer? Do they know that you're unhappy? Are you regularly discussing your career plans with them?

If you, like I once did, find that stuff revolting, then I'd encourage you to find someone to help you practice those conversations. You shouldn't let your ego speak all the time, but it is ok to let it out of the cage once in a while.

You have to ask for equity at the beginning otherwise you have no leverage down the line. They don't want dead equity on their books so they are more likely to give you the position you want if you already hold vested equity.

If a company refuses to give you equity, you shouldn't join that company - People don't change like that; if the employer has an exploitative attitude at the start, it's not going to change.

Also, you have to be assertive when you talk to them or they won't respect you and will just use you and put someone less qualified (but more assertive) in your place.

It really sucks, but this is life. You have to lock-in the value of everything you produce before you even start! You can't give other people options because they will screw you.

Not all managers are like this, but most of them (by far) are! I think Silicon Valley might be an exception - Mostly because CEOs there are younger and more optimistic.

If they haven't elevated you into a senior management role after doing all those things successfully then they're probably fucking up.

if you believe in the company, and the founders, go to them and fight for what you've created and your position. If they don't listen and help come up with a solution to retain you, it's probably time to move on.

I would focus on technical strategy. It is by far the most high-level, important thing you can do on the engineering side and your point of view should be critical. Is there a CTO? Nothing beats a system wide view to really know where to focus.

I was in your position in 1996 when I worked at WebLogic — I was the first server engineer after the founders. To give you an idea of what a crazy career path that can lead to, see my LinkedIn:


I'm still an engineer and code everyday. Just have a lot of other jobs :)

It's time for you to start your own startup. I'm dead serious. You have demonstrated a lot of necessary skills. All you need is a cofounder and an idea. Take your time and be selective. As an experienced technical person you will be much in demand as a cofounder; you have the upper hand and can pick whom you want to work with. Or even do it solo if no one shows up that you feel good about.

Your career path is your responsibility. Don't expect anyone else to care about it, though occasionally someone might.

Maybe not even the cofounder.

Congratulations! You literally built a company and now have what it takes to found your own.

I would vest in peace, learn from senior management (seems like your company hired good senior folks) cultivate relationships both in and out of the company (VC + advisors)... then start tinkering in your free time. Once your options vest you should be ready with an MVP and solid contacts to hit the ground running.

> Where did I fail to claim my part when the company was growing?

One thing that might have been better if you cared about not being hired over: ask for the title of CTO or VP of Engineering when you were hired. If they give it to you, you know you're on the same page. And if they won't give it out to you when they're least proven, you can bet that it's unlikely they'll consider giving it to you later when they have more options (and can bring in a new shiny person whose only limitations are those they can discover before hiring).

That's in the past, though. The good news is that you've got a good story here that counters any claim that what you do best is "just writing code." Sit down with the management that's trying to define you that way. Remind them everything you've delivered, just like you told us. After that recap, tell them something like "I've enjoyed contributing to the company's success in all these ways that go beyond writing code, I see continuing to contribute and grow in this way as an important part of my career development." Don't make this about competition with the new VP and ops guy -- let management know you intend to do everything you can to help the new hires make their big contributions too. Just let them know you need a continued technical vision/management role, a title that reflects it (though it's probably not going to be VP), and a path for the future. If possible, come up with some new ideas/initiatives of your own before this conversation, and maybe even a title to suggest. Sell them on a vision of how letting you contribute in this way is going to make everybody more successful, just as it's gotten them to the point where they're at.

And if they don't respond to that... if everything you've written here is true, I suspect there's no shortage of other startups/businesses that might be pretty interested in having you help them succeed.

I have a similar story in some ways. Employee #1 at a startup, wrote much of the initial codebase, been with the company now for a bit over 7 years. We’re 20 people now, and have dedicated people for support, UX, QA, product management, etc etc all of which I used to have a hand in in the early days. I manage a small team of developers (not all the dev, just the clientside team), I still code a good bit (obviously less than before) and I’m involved in a lot of product discussions to figure out what we’re going to build. We’ve struggled a lot with figuring out the right title for me, and as long as the actual work is the right mix for what I like then I don’t really care all that much. But I’ve been recently brainstorming appropriate titles that better reflect what I do, beyond just being a developer (which has been my title since day 1), and I’ve come to settle on “Technical Director of Product”, which I don’t think is a real job title in any normal world. I make sure that I’m heavily involved in product decisions, because the thing I’ve found the most satisfaction in is defining and building product, and shaping the direction of the company through influencing the product development path. And I’m grounded in the technical side of that, which is an important distinction to me, since too often “product people” have no technical background and just lob things over the fence to engineering without understanding the tech side of the house.

So for me the important thing was trying to understand what parts of the job I really want to prioritize (in my case active coding and product definition) and regardless of title making sure I inject myself appropriately. So that means if there’s a conversation about a new product we’re thinking about building I make sure I’m in those conversations from the beginning.

If you’ve been with the company from essentially day 1 you likely have a decent amount of political sway, even if you don’t know it. I’d start by figuring out which parts of the things that you listed you actually want to stay involved in. As another commenter mentioned, if you really want to wear all those hats then maybe finding another brand new startup is the only real choice. But if there’s one or two areas that are dearer to your heart then I’d try to figure out how to make that your day to day activity. And I’d hope given your history with the team that you can have a dialogue with the founder(s) about how to make that happen. At the end of the day the title doesn’t really mean shit, but if you’re not loving the work then you owe it to yourself (and they owe it to you) to figure out how to make that right.

The main question I have, which I don't see addressed in your description: do you have a meaningful equity stake commensurate with the contributions you perceive you made?

You might need to adopt the "owner's" mentality - which is that as long as these people are growing the value of the company, you are free to focus on what you enjoy the most, while they work to make your equity more valuable.

That said - if your contributions in all these areas are truly valuable, at a small company, there's always a case to be made for someone to be spanning functional areas, if they have the expertise and chops to add value. Probably worth a conversation internally. As others have said, assert yourself a bit.

Let me tell you the blatant truth which no founder will tell you: You are just a worker bee for them. They will do whatever it takes for the startup to be successful. So even if you gave your blood and sweat, and single-handedly built the product in the last 2 years, if they think (I should underline they think) that a vp of engineering will do a better job than you - then they will go out, hire that person and probably give them more equity than you.

You should think about what's best for you next. If you think you are not going anywhere, you should cash out and leave.

Interesting thread, and I feel it applies to me too... I just recently left my role as a VP Engineering in a 20 people startup. I think there is some disparity here as I am UK based and titles here are a bit different...

When I started, there were already a few people working on it, but because of an office move, nobody stayed. In a way, I am engineer #1, just with some code to maintain already. I had experience as a lead engineer already, but my job here was much tougher, I had to change my role every 6 months, from only coding to only devops, hiring, managing, doing all tech strategy choices, doing resource allocation, doing management meetings, etc...

I was eager to improve as a manager, but I still loved coding. It was very hard to hear that the company was hiring a CTO and leave me no authority. Now that person is full-time.

I tried to be very clear about it, I am aware of my strengths and weaknesses. I also fully understand that a founder needs to think about what's best for the business and not just people's carreers. I also made it clear I was there to learn, but the reality is that I never felt I was given a chance.

I stayed there a few months to get some learning from the new CTO, vest some more options and then I left. I left because the situation was toxic for me, with a mixture of resentment and miscommunication from their side. I personally think there's not much you can do in those cases... just start again.

Now onto the next adventure...

When they were hiring all these people... how did you react? did you express interest in these roles?

There are tough questions to ask yourself, and I applaud your introspection. One of the challenges of a rapidly growing company is keeping up with it. Hiring is about finding the right person for the right time. When a company changes drastically through growth, expectations and functions change. The person who did x may be unqualified to do y. In short, the company grows faster than the individual. Another dynamic is that as the organization grows, the need for generalists gives way to specialized employees.

I think this is a very powerful statement you made: "all the tasks I did were less challenging than some critical parts of the code base I wrote from scratch". This tells me that the problems that interest you the most are coding and architecture problems, and that you are happiest when solving those problems. Employees will have the greatest positive impact when they are focused on tasks that they enjoy. But it seems that you desire something more. What is dissatisfying about the current situation? Are you bored with the coding? Are you jealous of others getting recognition? Are you frustrated with the direction of the organization? Are you frustrated that you are no longer "that guy" whom everyone depends on? All of these circle around the same question: where do you want to be?

Leadership comes in many shapes and sizes. It's not just about how many direct reports you have. Fundamentally, great leaders shape the direction of an organization. Employees look to that person for advice, encouragement, and approval. It sounds like the company decided to hire others for formal leadership roles. A very difficult and powerful question is to ask yourself "what is the VP doing that I wasn't able to do?" There is a tactical reason that the CEO hired the VP, and it isn't because of credentials. Perhaps it's his/her ability to communicate across teams, or gain the confidence of management? Don't let your ego tell you "nothing, I'm better than them"; there is a reason they are VP. Different jobs require different skill sets, and understanding where you are strong and weak is critical your success. Being an engineer who kicks out mission critical code is fundamental to the success of the business, but it is extremely different than developing and managing a team. With a humble attitude that is always looking to improve, there is no stopping your career growth.

Take all those awesome skills you have learned and do those for yourself on the side.

You have learned why every good developer has side projects, gotta keep the dream alive. Two of my engineering heroes did just that, Scott Adams and Mike Judge. They can also be technical related in games, apps, etc on your own. It is much better that way in the end if you like products to launch with any amount of control.

> Scott Adams has always had several side projects because they gave him energy to endure his boring job. One of these projects became the sketches for Dilbert.


Harness the energy of that boring job into something great, it is the American Dream of Engineers across the land subjugated to the power structures of now.

When you have your own things on the side you are also a little less ego driven at work as you have controllable areas on your own products and it lends to smoother teams somehow. Encourage others at work to have side projects, watch how it makes them relax and work better at work.

Most of all, always do quality work, even if it isn't fun make it fun or gamify it. If you are in a situation that prevents you from doing quality work, then you should move on.

What is your title? I'm guessing it's developer or engineer. If you view yourself as such, others also view you as such, and you won't be considered for management roles, because you're not a manager. I've chosen this for myself deliberately, and i accept that the cost is that i have to define my role more narrowly. I don't think how long you are at a company matters that much, or even should matter much. As the old saying goes: what have you done for me lately?

I've seen this transition happen myself, where the company grew, got cut up into a bunch of departments, all of which got a manager, mostly external hires. I feel like this way of organizing companies (departments, hierarchical, middle management, etc) is an anti-pattern. Everybody does it because everybody does it, but every dividing line you add reduces efficiency, and I've seen firsthand how damaging middle management is to the agility at the individual level. I don't know what the antidote to this anti-pattern is, but i feel like company structure is a territory ripe for innovation.

Is there a certain role you feel you were overlooked for - VP of engineering? Manager? Or did you want to continue being an engineer? If it was the former, the time to voice your desire has probably passed. If it's the latter - and you really do just like writing code but want some sort of recognition - well, take the money I assume you'll earn and think of that as recognition.

1) if you haven't already take a vacation. 2) What do you want to do? What do you want to focus on? You used to have a lot of different tasks that you probably did a good job at given your constraints but probably didn't excel at. You're now being given the chance to specialize and focus on only a few things. As others have said, your co-workers probably haven't thought too much about growing your career. Once you decide what you want to do have a talk with your vp of engineering and possibly your early co-workers. Your vp should be willing to give you the opportunity to grow especially since you already have a lot of technical knowledge and general company knowledge. Also they presumably hired the vp because he has experience with bigger companies our more mature companies. Take the time to soak up some knowledge. While not a first choice, don't be afraid to leave for better opportunities. You've proven that you can build up a product and accept general responsibilities.

Are you really young?

I would expect the first engineering employees to know the most about the stack and thus naturally become the engineering leadership as the team grows, which it sounds like you were. If they felt the need to hire above you, it sounds like you were lacking some cross-section of experience that the founders/board want. You should ask them.

You helped found a company and fell in love with the work of a founder. You can't re-found the same company, so found again!

I'm going to be honest here and say you're like the best person for the job you have. The guy who got VP? He's a more qualified manager than you. The guy who does support? He's got 8 years experience and a masters degree. You? You're the best developer they have. This practice is even more common in enterprise. I worked in tech for the largest company on the planet (take a guess) and it was routine to find the best developer was as most a team lead, never management. HR strategically will shoehorn these people but cutting off their avenues for growth. In my experience however, if it's money you're after these companies will happily shell out. It's not money their trying to save, it's expertise. It will also pretty common in enterprise for guys to NOT want to be moved up. Not everyone wants to put their neck on the line, and once you move up it's impossible to move down.

Here are my thoughts with limited knowledge of your situation.

As employee #2, you are a technical co-founder, period. The problems you have outlined will not be solved be staying at the current company. It's apparent that the owner has chosen to keep you as 'just a dev', even though your contributions are outmatched and significant. It seems opportunity to seize more than what you could have has unfortunately passed you by.

From what you're describing in your post, it seems you're showing regret. Other people have been hired for these positions, even though you built it.

The thing is about being an early employee is that it's a blessing and a curse. Most people don't realize this but the thing is the feeling you get for being the guy that put this company where it's at today is unmatched.

The problem is that once it's built, you go into maintenance mode and it turns into a corporate machine. Everything you enjoyed and discovered during the process is now going through "procedures" and "process". The freedoms gone, other people are here now and they start getting the ears of the owner instead of you.

You feel like you own this company, you should, you built it and partied with the owner for years (guessing here). The biggest regret at this point is that you probably don't own enough (equity) or you were never made co-owner.

You have a choice, stay and give your last effort to be in the position you earned. Or leave, full well knowing that you will likely not be #2 at a successful startup again. We all know that startups getting successful is about the same as winning in the lotto. However, you could be the guy you are describing in your post, the VP of Engineering that gets hired for a startup that is starting to grow...

In either case I wish you the best of luck and as another dev can appreciate the weight of your decision.

I would move on to starting the next business, but maybe you need the steady paycheck? You started company A, company B will be even better.

On a related tangent, I would love to know how someone in his shoes could get crowdfunded to start a new business. What do you advise? (Maybe I should start a new thread and ask.)

First, congratulations.

Second, let me focus on the management point. You wrote: "I managed an entire team of 10 people without ever missing a deadline of the whole team, and now they brought in an engineering manager"

a) Do you think the (now-bigger) team needs a full-time manager? b) If yes, did you want to become that full-time manager? c) If yes, did you make your desire known?

If the answer Yes, Yes, No, that's ok- lots of people want to continue being individual contributors. It's still on you to work with management to define the right structure that works for you and the company. Maybe you become some sort of Chief Architect. Maybe you help hire the manager.

Either way, if you were as pivotal as you say you were, you should certainly have the CEO's ear to bring this up in a constructive way.

Quite frankly you should see this as an opportunity to start your own thing. More importantly I would question why weren't you promoted especially being the one of the first employees? Assuming you have done nothing to piss the founder off, you should be truly appreciated for what you have achieved whilst motivated through career progression etc.

Also bare in mind that this is a normal process for SOME companies as the more they grow the more people are hired so as to try and achieve more (this is debatable) work thus higher revenues.

Personally, I would see what you really want from life and if you are seeking credit/appreciation for your own work then

start a new business or co-found a product or join a startup that is prepared to give out equity

It's important to understand it's business, not personal. I strongly dislike the comments in this thread that say "Leave". That's an emotional reaction but it doesn't help you advance. In fact, you'll slide back down the ladder. You should just explore what is the best option in front of you and do that.

Really, if you want more responsibility, you have to sell someone else that you're the best person to have that responsibility. No one should give it to you out of loyalty because that is a disservice to all the other people in your organization that are relying on you to fulfill that responsibility.

It doesn't sound to me like you know what you want to do--mostly because you have not explored your options. I will hope you have a good relationship with the founders. In that case you should have an open and honest conversation with them reflecting about your experience so far, that you're proud of the range of experiences you've had, and hence why you think you're ready to do something more--but you're not sure what.

If they are friends, they'll help you. You can ask them to give you feedback on what they felt you did well and what they felt others could do better, so they hired externally. This will give you something tangible you can work on.

If they are really loyal back to you, they'll create an opportunity for you to develop skills that will lead to advancement.

Of course, this conversation is very shocking and anxiety inducing for the founders so how you frame it is important. If you are not accusing them of passing you over, but really genuine about learning and developing yourself, most people will want to help you.

If not, you may find a better opportunity elsewhere. Again, it's just business. Keep in mind, sometimes you have to sell yourself into a role that you're not quite sure you can do--and then do it.

p.s. If you asked me, it sounds like you're interested in a engineering management role, which is not the same as a CTO role. If you have a conversation with the founders, you could focus on that.

>In fact, you'll slide back down the ladder

Money, titles, who cares? Life satisfaction is much more important than climbing ladders.

If you are doing less things than you used too is typically a sign of growing company... hopefully you will have your efforts payup in a big way... best of luck!

I have always felt that working in startup is like giving a kid 10 toys to play with and taking one toy away every year. It's very normal not liking and feeling of giving up something you own but it is as important for a company to get away from generalized to specialized resources with the growth.

a senior management leader once told, his goal every year is to find, train and pass on the baton of some of his existing responsibilities to next person until he has nothing else left...

Nash, http://joday.com

I'm in a similar situation, but with a much better outcome. In my case, however, as the company grew I made it very clear what I wanted my role to be.

It's best not to assume that the people you work with know what the best role is for you. I started around the same time as another engineer, but our roles diverged. This was, in part, due to both of us being open about where we expect our career to go as the company grew.

So, if you want to be something different, have the discussion with the people who hired you. They clearly have seen your talents and shortcomings. If it doesn't go where you want it to go, then it's probably time to find a new job.

All I see here is positives. Congratulations on building a startup.

Never been in your situation so my suggestions may not be appropriate. From the order you specified the tasks I think for you Technical Strategy aspect ranks highly. I think it gave you great challenges and satisfaction. If that's true then I suppose a role would be that of a CTO given that one of the founder is not playing that role.

Here is Fred Wilson's take on CTO vs VP of Engineering. http://avc.com/2011/10/vp-engineering-vs-cto/

This seems relevant: http://jacquesmattheij.com/first-employee-or-cofounder although in this specific case it's not much help.

I think ChuckMcM's advice of chatting with the founders a bit sounds good. You could try and spin it in a positive way... "I was doing all this stuff, and even if it was really crazy at times, I felt like I was growing a lot and contributing a lot, and I feel like I'd like to continue that somehow. What do you think?"

I have been approximately you a couple times. If it were me in your shoes again, I would leverage the huge amount of knowledge/skills I've acquired and jump into a new opportunity. There are basically 3 directions: 1) start your own company that you will build yourself, 2) find another startup in a similar spot to where you were 2 years ago, or 3) join a big company. I will say a likely outcome of joining a big company is you will be expected to focus, having relatively shallow but deep expertise (i.e. specialization of labor).

Maybe it's time to move on.

A company I was at started growing so fast (factor of 10) that it lost it's identity and with it a lot of the things that made it enjoyable/interesting. We opened new offices downtown and in other cities and from then on it was time to pass on the torch.

Clearly, it wasnt about keeping the old guard, but about growth. I did learn a lot and am respected for what I was able to accomplish.

It was a great experience, but sometimes it's good to realize when you're just the launching pad.

Bowing out gracefully was the key for me.

I'll be brutally honest. Most of the early employees at most startups aren't very good engineers. In fact they're pretty mediocre. That's why we get the term of technical debt. Take your options and experience and move on to the next gig. Move aside so the better, more experienced people can clean up your mistakes without you fighting them every step of the way.

Maybe it's a psychological thing, but really good engineers are never employee #1-5 at a startup. They just aren't.

Two paths I followed when I faced similar growth issues:

1- Time to create company product #2. Ask for a tiger tea, break out of the hierarchy, and have fun building something from scratch.

2- Move on. Find a great idea or another co-founder, and repeat the startup experience in another startup.

I've done both of these paths. Both can work. Both play on the strength of a generalist who can get a company off the ground, but then who doesn't fit into the subsequent culture of a growth-stage company.

If I was in your position and not in a lead role I'd be upset too. Either they think your too valuable to lose as a developer or they don't think you can't handle those jobs. Either way you need to express your desire to grow. If nothing happens then it is time to find your next gig. It sounds like your a kick ass developer so I'm sure that won't be hard. Just make sure your next gig knows you want to do more than just development.

Eerily close to an experience I've had in my career. Nobody is looking out for your career except yoursel and as the company grew, they left you behind, that's that. I'd attribute this to poor management, as you typically want to keep the core members, but sometimes this does indeed happen.

I suggest you leave and take this experience with you and be more aware during your next professional engagement. At this point, being in the company is holding you back.

You can find analysis and hints on this and other similar situations in the last book from Ben Horowitz "The Hard Thing About Hard Things" http://www.amazon.com/Hard-Thing-About-Things-Building-ebook.... I'm reading it now. There are a lot of interesting insights about how startup Companies scaling works.

Perhaps if you can't advance inside the company it's time to advance outside the company.

They may well consider you as "an engineer with little prior experience, and we only gave him that role because we couldn't afford someone experienced yet". To the next firm, you are an engineer with experience building a company's central product from the ground up and leading a team of 40+ people in a high risk start-up environment.

(pardon, I misread your post and got the number of people you led wrong, but the principle of the post is the same)

You can play the lottery ticket game and move on, taking your 2 years of vesting with you.

Only do this if you think you've set the company up for long-term success and it will still be successful even without you there.

Also only do this if you think you can make out better in the long-term (more money, more equity, equally sure thing elsewhere), otherwise just buckle down and ride out the remaining 2 years.

Unless you think your current company is trash, then just bounce.

Who do you report to? Did they discuss these hires with you? If you have a good relationship with the founder, you should frankly express what you'd like your trajectory to be and come up with a plan to make it happen. If this isn't something you can discuss with your founder or whoever you report to, then you should look for a better place to work that is willing to listen to you and to help you grow.

Were you considered for these roles or entirely left out of the process? How much have you actually talked to your management about this?

Speaking as a founder who has tried hard to replace myself (so that I can focus on what I do best, which by definition doesn't fit into an org chart), maybe you'd benefit from switching gears completely, and using this opportunity to learn and experience the business side of things. Probably it would be hard to find a better chance to get a front row seat.

People have taken you for granted and don't care about you, period. 1. Be vocal about what you want, be it a raise or promotion! This is America. If you don't ask, you don't get anything. 2. You have other options! Go make your own awesome startup. If you have so many skills like you said, why not? 3. Just out of curiosity, are you white?

I was in the same boat, not sure if I can give advice but I just took another corporate job while my company grows and I advise them and help where projects actually sound fun, otherwise I just don't care

In the meantime I work on building my own sellable tech.

Hope that helps, I'm working on a sweet e-commerce platform right now and building just little sellable tools

I was in the same boat, not sure if I can give advice but I just took another corporate job while my company grows and I advise them and help where projects actually sound fun, otherwise I just don't care

In the meantime I work on building my own sellable tech.

Hope that helps, I'm working on a sweet e-commerce platform right now and building just little sellable tools

I am unable to see what exactly "you" want from the company. Did you speak to the founders about your career aspirations and they turned you down ?

Did you want to be a manager ? VP of Engineering ?

The way I see it, being developer seemed a natural thing for you. I also assume you must have got significant stock options and you must be drawing lot more salary as well.

If you don't know what you want, you have two options.

You can learn to be happy with what you have, or you can determine what you lack, and work towards getting it.

Almost no one chooses the first option. When we don't actively work on the second, we often embrace our dissatisfaction without mindfully working to change it.

I guess my question is, since you are employee #2, why are you not any of the guys you have named that "takes care of things". Like, it would be pretty normal for you to be that VP of engineering or Engineering manager. Have you sought for a more senior role?

Lots of good advice here. Sounds like you're in a good position and appear to bring quantified value to companies, particularly to startups. Just reflect on what you really want out of this short life and go with it. That includes the willingness to walk away.

I know how you feel, there are many great engineers out there in the same situation. I think you might be turning the corner to be a founder. You know what needs to be done to scale a company to success the question is can you do it for yourself or just for others ?

Go get yourself another job: your a bootstrapper, not a long time runner. Do the same somewhere else. Plus you learned a lot since then, so you should be able to get more responsibilities/remain fullstack longer!

Could be worse. I know someone who was an early employee of a startup. She had the desk nearest the front door, so she ended up being the receptionist. Five years later, she's still the receptionist.

I went through this exact situation. I joined a company when it was just the founders and me, and then we grew to dozens and then hundreds of people. As we grew, I felt these same slights: I was left out of strategy meetings, I was not mentioned on the website, managers were hired over me, etc. Overall, it felt disconcerting as more and more happened outside of my control, and without my knowledge. At first I was frustrated, then I realized I had the best of all possible situations.

Some notes:

1) If you do not have much experience scaling a team, then it is sensible for the founders to bring in someone with more experience. Scaling team requires more than just hitting deadlines. It is about recruiting, retention, recruiting, managing personalities, career growth, recruiting, managing up, communicating across teams, etc.

2) Everyone's role changes as you grow, for better and worse. For instance, early on the VP gets to have fun setting direction and designing the overall product and strategy. Later on the VP might be spending 90% of their time dealing with conflicts, recruiting, firing, managing up, etc. They may long for the day when they got to play a big role in product development. Early on as engineer, I had the benefit of being able to build an entire product by myself. Later on, the advantage was that I could take vacations and did not have to deal with bugs and outages 24/7.

3) You will have to specialize to some extent. You cannot be the jack-of-all trades role forever, no one can. If you want to eventually have a VP/CTO role, then you will need work with your VP to develop your management abilities. For instance: ask for mentoring, start reading books and articles on management, ask to have a junior engineer put in you, help out with interviews and recruiting. (Note to actually get a VP role, you will probably have to switch to a smaller startup in a few years, using your cred from this gig to get you the job.) If you want to do greenfield development, work with your VP or founder to carve out a role building out innovative/experimental/skunkworks features. If you want to do scaling and architecture do that. There are lots of ways to interesting work and build valuable skills, but you are going to have to choose a course. (In my situation, I alternated between doing experimental/greenfield features and doing scaling/rewrite work on existing tools.)

4) With regards to customer facing roles, I highly advise that your company have a policy that every engineer spend a half-day in support at least once a month. It is essential that developers stay connected to the customer, both so that you can intuitively understand how to solve their problems, and to increase your empathy and motivation.

5) Try to figure out a way to get looped-in informally to the strategic aspects of the business. Make some sort of effort to have lunch or beers with a founder once a quarter. If you have 1:1's or have a wiki where decisions are discussed, then that can be a good thing. The execs understandably want to keep management and strategy meetings to a small number of people, otherwise the meetings suck. But finding a way for you to informally connect and give your two cents can be valuable both for you and the execs.

6) If you want to raise your profile and get your name known, use whatever leverage you have to get some favors. Ask to have yourself put on the web site as "Founding Engineer." Figure out a way to have the founders to introduce you to useful people, and to help you get into some of the more prestigious invite only events, whatever they are in your area. You have to use judgement and be diplomatic, because you might also lose out on advancement if you are seen as angling for a quick exit.

7) Generally, I would recommend sticking with the company as long as it is on an upward trajectory (unless you have a compelling alternative). You will learn a lot as you go, and your reputation will increase with growth.

Eventually I realized that I had the best of all worlds. Why does one want to be a VP? Usually money and status. What sucks most about being a line-level employee? Lack of agency/control. But in many ways it is less fun to be a VP, than to be a high-status engineer, who has enough sway to avoid micromanagement, enough credibility to control his or her own destiny, who can spend their time working the craft that they love. As engineer #2, you get status by virtue of your early employee number, and hopefully and you will get good money from equity stake (if not, then that is truly unfortunate). So hopefully you get the money/status benefits of being an executive, while still getting to work your craft, and still getting to stay in a peer relationship with your fellow engineers.

You will need to fit into one of those positions (if it makes you happy) or leave. You have a valuable set of skills and it's a great time to work on your own ideas.

I am currently in a similar boat as you.

Do you think the company's management already knows that you'd prefer to keep a more management-oriented role? They may be mistaken in assessing your desires...

I would just leave and solve an interesting problem at another company. You have a large chunk of equity. Unless you want recognition - that's a different topic.

Maybe you're experiencing small signs of burning out. Have you thought about taking some time off to think what makes you tick (or even changing a job)?

I'm looking for a technical partner for this concept.


1) Locate VP of engineering and/or engineering manager.

2) If you want their job: assert dominance.

3) Otherwise: flip finger, leave, start your own startup.

If it's a promising company, ride it out 2 more years for vesting. Were you interested in any of the roles you mentioned?

Leave. That's what I did when I got to the same point as you. Much happier now as technical co-founder of a startup.

People have taken you for granted. 1. Be vocal about what you want, be it a raise or promotion! This is America. If you don't ask, you don't get anything. Are you an American? 2. You have other options! Go make your own awesome startup. If you have so many skills like you said, why not? 3. Are you aware of your own weaknesses? Maybe there is major weakness about you that stopped you from getting promoted but you are not aware of it!

Personally if I could eliminate all the aspects of my job that aren't just writing code I would be ecstatic.

Shoot me an email (it's in my profile), I can share my experience with this in private.

Why must companies grow anyway?

Because if they don't they'll be out-competed by those that do?

sounds like you're in a great position to craft the position you want, and then shop around your experience to other startups

if you get a bite, go back to your startup, say you have another opportunity, see how much they want you

> Where did I fail to claim my part when the company was growing?

You don't give us a clue to answer this. Your whole story is about things that happened. You haven't told us about what you wanted. You haven't told us anything that you did to get what you want. Did you know what you wanted? Did you do anything to try to get it for yourself?

> I should just "be happy."

I call bullshit. If you were happy to passively accept what's being handed you (money, responsibility, acclaim), you wouldn't have made this post. Honest mindful gratitude makes a person happier, but cloaking bitterness with false gratitude, which this sounds like to me, will make a person ever more bitter.

You have to start with what you want.

If you want to keep doing everything like you did before, then you should make a career as early stage CTO. If you want reward and acclaim for that, then you have to negotiate it up front, usually as a nice slice of equity. Be advised, there's risk in that.

If you want to grow with a company, then you won't be able to do everything you were doing before. You will have to focus. And you have to assert your case that you want the role and can be successful in it. To grow with the company in one of these roles, you'll need to cede the other roles to new teammates. You will probably have to mostly stop coding. You will have to embrace the thousand headaches that come with the new role as the company grows.

These are two possible career strategies. There are others. All start with knowing yourself. All depend on asserting yourself.

Are you an owner or an employee? Employees get treated like employees.

I hope you negotiated for a whole whack of equity.

I'd be interested in speaking with you. Bring your experience to my early stage, funded startup and let's talk about how you want to advance your career:


BTW, where are you located?

Did you file an 83b for your equity?

I'd be interested in speaking with you. You have the experience I need for my early stage, funded startup:


BTW, where are you located?


Jack of all trades, master of none. Go to another start up or specialize.

Get involved.


Side project.


Be pragmatic: there will be other opportunities which are equally interesting and staying isn't helping. You could be CTO at a different startup. Further, you should be approximately at your zenith at the company and they should be able to provide a strong reference, if you stay dissatisfied your performance and appearance will suffer - along with your potential for future employment.

Also happiness is about the journey (career, parenting, etc). If you're not on a journey you won't be happy!

He's probably got a 4 year vesting schedule and maybe a more recent evergreen grant with another 4 year vesting schedule. As intended, that's a good incentive to work on the problem before giving up.

The thing missing from the post is a description of what he wants. If it's more recognition, I bet he could talk to the founders and work something out. To them it'll be a justified and free way to keep a great engineer.

> Leave.

If he's got options, they'll be vesting -- typically over a 4yr period. He's 2yrs in so if he decides to leave, then he'll lose half of them. If he's willing to do that, then he'll have to exercise what he already has vested. Does he even have the cash to do that?

It's easy to suggest that people just 'move on' but it's important to remember the context.

>If he's willing to do that, then he'll have to exercise what he already has vested.

Not necessarily. It depends on the terms of his or her options grant. Many companies give employees a 10 year exercise period after they leave (advocated by Sam Altman: http://blog.samaltman.com/employee-equity).

> "Many companies give employees a 10 year exercise period after they leave"

I suspect many companies don't do this, as there'd be no need to advocate for it otherwise.

A 10-year exercise window has to be extremely rare to the order of non-existing in SV startups. Maybe it's picking up stream since the article was written and I am not aware of it. Can an employee vouch for his/her employer (company) that does this? Do more recent YC companies do this?

In fact, even Quora hadn't actually implemented a 10-year exercisable window by the time (or right before the time) Sam's article was written: see comment at https://news.ycombinator.com/item?id=7610668. Note that the article simply mentions it as an idea; not as an ongoing implementation. I wonder if it is now actually implemented at Quora.

Except after 90 days ISO become NSO, so you lose tax benfits. But maybe he 83b'd them and already purchased as employee #2

Very easy to say, but if you have significant equity (which, as employee #2, you really should) it's a lot more difficult to just step away.

"The journey" is all very well, but if that journey involves checking out for a year while you wait for a payout then so be it.

One company, a good friend of mine was employee #1 and I was something like employee #40. After the IPO it turned out we'd gotten the same package equity and options-wise, which is to say, not much... Being an early employee, 99.9% of the time! means getting screwed.

> if you have significant equity (which, as employee #2, you really should)

That's the big unknown here.

If he does have significant equity (even 2.5% or more is good), then what's the problem. He gets to share the long-term benefits without any of the stressful responsibilities and can be solely devoted to doing what he's best at. If a brief mention on About Us page is all he cares about, bring it up at your next review and say that it's not about ego specifically but more about career advancement and personal growth.

If he doesn't have decent equity then he should've quit long ago and hanging around any longer isn't going to be any more satisfying. Unless he is super critical to their development (i.e. only he knows how module X works), then he could negotiate a better job title at the threat of leaving but that could be a risky and burn-bridges move.

I'd be surprised if he has any "equity". He may have options, but that is a significantly different thing. Most onerously of course is that if he leaves he will likely have to shell out actual cash on a lottery ticket. Who knows if he can afford to do this, or if it makes sense to do this.

That is a long way of saying, under almost any reasonable scenario, whether he has significant options (vested or no) should not be the determining factor on if he should stay.

He should stay if it he enjoys the job, they are compensating him enough in real compensation to overcome his lack of enjoyment, or he doesn't have other job opportunities.

I will say, as a long term employee (though to be fair, it's not that long term) he should have the ability to more forcefully outline what he wants to continue with the company. If he doesn't, either he's fooling himself about his real value, or he is doing a poor job communicating it to the company. In either case, it's his issue.

Being early employee with 3% quickly turns into burnt out employee with 0.2% after a couple of funding rounds in adverse conditions with a brand new VP engineering who doesn't have the bandwidth or interest to find out how really vital you've been and how much more you still have to contribute. No shiny options package for you. Enjoy the holiday ham and the subsidized yoga.

Rather than checking out..... consider spending time trying to get mentored by the new managers. Think of the way Larry Page was mentored by Eric Schmidt. Also spend time reading about how to manage a large team.

Also consider... do you want to manage a large team? Or do it again from the ground up?

>>involves checking out for a year

Woah, I'm not saying you shouldn't be getting paid. The trick is getting paid while you are interviewing for new positions! Just make sure your interviewing for them.

as a founder, the most striking thing about your post is that you haven't defined or communicated what you role you actually want.

you need to figure that out, ask for it, and if you don't get it, leave.

I don't understand this "first world" business. Is it a generational thing to be ashamed of not living in a shithole?

This is a common problem. The startup has "grown above" you and it's time to consider moving on, because unless you start playing politics you're going to get demoted with each new hire. Negotiate a better title and salary (you'll probably get something) so you can get a better next job, and see about getting investor contact (preferably of a social nature rather than "presenting to" investors, because you want social equality in order to get investor-level mentorship that persists even if they can't fund your next bit) but you'll probably be out the door in another 6 months.

Don't take it personally. Even if it is personal, it's not worth getting bitter about it. The pro-young ageism only works for Stanford kids; if you're an average 24-year-old, this game still treats you like shit in most cases. The "social climbing" dynamic in startups isn't uncommon. It sounds like they don't have a culture of internal promotion. This will burn them, later on, because people will catch on to the social-climbing/no-internal-promotion culture and everyone will start doing bare-minimum work... but you probably won't be there when it does.

Ask for a VP-level title, even if it doesn't involve you managing anyone. If you don't have the experience to be the VP of Engineering, then you can't expect them to give you that title, but you should get something at the same level, so that you have political equality with these new guys. Even if it's a meaningless VP title ("VP of Technical Culture") it at least shows that they're committed to giving you the credibility that you need to continue contributing meaningfully to the company. No one's going to take you seriously if you're Employee #2 and don't have a title, and you can make this argument in the negotiation. And saying "no one's going to take me seriously if I don't get <X>, and I won't be able to do my job" is a great way of saying "I'll leave if I don't get <X>" without actually saying it; it has the added benefit of speaking from a perspective of their needs (your ability to do your job) rather than yours.

If you want to be a founder or CTO in your next gig, demand investor contact. If they won't give it, the words you want are, "If you're not willing to give me this, the right thing to do is to accelerate my equity vesting, so we can separate cleanly." You're not actually threatening to quit, but you're strongly implying it in a way that (a) makes it clear that your needs aren't going to go away, because you've started to think seriously about the future, but (b) doesn't commit just yet to one course of action. (They could re-up your equity, or give you the investor contact, in which case you'd stay.)

If your founders are good and this just happened "accidentally" or because you had your head down and didn't fight for yourself, you can improve your position significantly. You may not get everything you want (you might have to settle for a Director title and investor contact only to the more junior partners) but you'll make progress and be ahead of most people your age. On the other hand, if they're deliberately fucking you up the ass, then expect them to denigrate your work. Again, don't take that personally either; they're taking a political decision (to grow above and demote you, because they're social climbers) and back-rationalizing it. So don't let that, should that happen, embitter you either; just move on.

Good luck!

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