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Ask HN: What's left for early startup engineers as the company grows?

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Re: Ask HN: What's left for early startup engineers as the company grows?

#61
post #25
post #14

Earlier quoted context omitted.

> 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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#62

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…

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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#63
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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#65
post #6

Leave. 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 t…

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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#66

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…

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.

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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#67

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…

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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#68
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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#69
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.

http://blog.habrador.com/2014/01/how-scott-adams-growth-hack...

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.

Re: Ask HN: What's left for early startup engineers as the company grows?

#70
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.

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