
Ask HN: From tech startup to finance. Bad move? - toocool
Hi HN<p>I was the first engineer at a tech startup in SV and, after building and leading an engineering team and scaling the company to ~40 people, I was passed on for a promotion, since the founder decided to bring in an experienced VP of engineering to take on the majority of my activities. I don&#x27;t have anything against this new guy (except that he is not a very talented leader IMHO), but what disappoints me is that I have been completely excluded from every &quot;leadership&#x2F;management&quot; task without being given any constructive feedback, and I am just expected to quietly switch to an individual contributor role after 3+ years of leading major initiatives.<p>The whole thing has been very ego-crushing for me, so I made my resume circulate through the help of a well connected recruiter in order to keep my options open. I got in touch with two very famous hedge funds for a backoffice role (cloud computing stuff: modern infrastructure management, rearchitecting of legacy applications, containers, ...) and the interviews have been very mature (no Google style). I got an offer from both places, they are localed in NYC and Chicago so I would have to move.<p>I have fundamentally two questions:<p>- What to do with the reasonable number of options I have vested<p>- Is this really a good career move? Am I just going to be extremely disappointed in a few months? FWIW, I worked in big enterprises before, but software was their core business, never trading&#x2F;finance<p>Current employment numbers (startup):<p>- Salary: 160k<p>- Bonus: ~10k a year<p>- Equity: ~1% as ISO (after dilutions), of which I currently vested 80% (the startup is definitely on an upwards trajectory, at the moment exercising those options and paying the AMT tax would cost me around ~100k or more)<p>New offer by the hedge funds (they are pretty much comparable):<p>- Salary: 200k<p>- Bonus:<p>- 200k a year (minimum guaranteed by the contract, every year)<p>- 50k sign-on + relocation bonus<p>Thank you!
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qwrusz
I work at a hedge fund. In the front office of a smaller shop, but I am pretty
sure I know both firms you interviewed with. First off, congrats on both
offers, these are not easy interviews or easy jobs to get.

My 2 cents: Try to find someone doing the work you are about to do at the HF
and have a conversation with them. I don't see any comment on here yet from
someone who can speak from experience at a HF BO. That's a worthwhile coffee
or phone call if you can find someone. Don't believe job descriptions,
recruiters, or interviewers at the HF about what you will be doing day to day.
Speak to someone who is a third party about the type of work in general (try
Linkedin, Bloomberg, friends or whatever networks you are a part of to find
someone to talk to). Ask them about the work, day to day, pros and cons,
career progressions, lifestyle, etc...

Second part of the answer. NYC and Chicago, and the two firms, are VERY
different culturally. Think about what city you want to live in and what firm
culture you prefer.

I vote NYC over Chicago if you can. And then go for it, you have little to
lose - if the work sounds interesting based on conversations with people
actually doing it and the city is a place you wouldn't mind trying out living
in, what are you worried about? You can always move back to SF or move to a
different company, HF or startup in NYC.

As for the vested options Q. You haven't given enough info for anyone on here
to answer that prudently.

Some people's sign on bonus will be negotiated to consider vested options at a
previous job. Your offer looks standard and that you haven't negotiated
anything on that part. Up to you if relevant, just sharing people do this. The
HF is fully aware of what options are so you can bring it up with them if you
choose.

Congrats again.

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mswen
I think you should make the switch:

[1] Cash portion of compensation is significantly better

[2] Diversification of experience improves. You have big enterprise, start-up
and now would add trading/finance to the mix

[3] If you keep a tight rein on lifestyle inflation you could easily save
enough money to become your own angel investor in 4 to 6 years from now if you
really find you prefer the start-up environment

[4] If you stay the ego-crushing aspects will continue to weigh heavily on you
and create daily stress.

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a3n
Take the new job. It's a new field, new challenges, lots to learn.

When you're done there, go to some other industry. Medical devices,
alternative energy, aerospace, porn. Live in different regions, different
countries.

That's the beauty of software. If you're open to it, you can learn a lot about
different parts of the economy.

Or did you specialize in whatever your startup does when you were in school?

~~~
toocool
Definitely a sound argument.

I didn't specialize in school, I like to have a very broad set of CS skills, I
found it immensely useful being able to know a bit of everything.

At the same time, in the startup I've been able to specialize in particular
aspects of modern cloud infrastructures, and that's what got me in the door
with these funds.

~~~
a3n
> I didn't specialize in school, I like to have a very broad set of CS skills,

> I've been able to specialize in particular aspects of modern cloud
> infrastructures

That's fine, great in fact, but not quite what I meant. It was more of a
leading question, at a higher level: you probably didn't specialize in
whatever your startup is fixing or disrupting.

My suggestion was at a higher level than what we study at school.

How does a hedge fund work.

How does a medical device work, and not kill its patient.

How does an airplane keep itself flying, and keep its pilots and home office
and suppliers informed about and in control of its performance. How do we keep
passengers comfortable and entertained.

How does an airplane in flight fit in with all the other airplanes in flight
and on the ground.

How does FedEx tell me that my new phone just entered their facility in Wuhan
China (which they just did), and deliver on their statement that it will be
here Thursday at 10:30am (which I believe will probably happen, plus or minus
hours).

In that example, there's at least two parts: The logistics of actually moving
that phone and knowing where it is, and the system that's keeping me, the
customer, informed.

How do first responders know where to go, and how do we know who to send
first? How does a wind turbine work.

"What do people do all day?" (One of my favorite books, and I'm pretty old.)
[https://www.goodreads.com/book/show/313375.What_Do_People_Do...](https://www.goodreads.com/book/show/313375.What_Do_People_Do_All_Day_)

For all of the above, and much else, software is both essential and
incidental. It's the larger picture, what are we actually doing with software,
that's most interesting (to me). We're lucky enough that we can move around
and see all of that.

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ones_and_zeros
200k salary and a minimum 200k yearly bonus? Just take one of the HF jobs and
you can retire in a few years and do whatever you want.

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cascala
Interesting choices you have in front of you.

Hedge fund pros and cons: * higher pay * more volatile pay * what is your
long-term career path at the hedge fund?

Startup pros and cons: * probably a nicer work environment than a hedge fund *
you feel disenfranchised

The simpler argument would be to simply take the job that pays the most. I
think there are very few exceptions to that rule.

~~~
bbcbasic
> The simpler argument would be to simply take the job that pays the most. I
> think there are very few exceptions to that rule

An exception would be where the toll on your physical or mental health is
greater than is warranted by the extra pay.

In my book anything that burns you out is not worth any amount of money <
$enough_to_retire.

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rajacombinator
You probably will be disappointed but it sounds worth doing for a year. You'll
work with some smart people, but the culture is very different from SV
startups. But for 450k it seems worth doing for a year.

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gragas
As a side question, can I ask how much experience you have other than your
work at said startup? Within a year I'm going to have to make the choice
between going the tradition route in tech or joining a high-frequency prop
shop. The starting offer seems to be around 130-150k base with 20-80k bonus at
the end of the first year (which is implied to scale heavily after the first
year, unless things go really poorly).

If you were given the choice, which route would you take?

~~~
toocool
I have about 7 years of full time experience on my resume, being in most
places a functioning individual contributor. In the startup I have been able
to explore other skills such as management and interaction with other parts of
the business, all while being highly technical.

In your shoes, I don't know what I would choose, I don't know what to expect
from the financial world. Money surely sounds nice.

As a further data point: if the interviews at Google/FB/... were not so crazy,
and if I were given some sort of choice on the area to work on at those
companies, I would have definitely tried the interview with them as well, but
what I liked about these hedge funds is that I was interviewing for a specific
role and so the interview process was pretty much focused around that, without
anyone asking me to code an rb tree on a whiteboard.

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gragas
Can you tell us which hedge funds? I can't imagine hedge funds need much in-
house technical work. HFT prop shops, on the other hand, are pretty much all
about technical work.

~~~
toocool
Thank you for your reply. Unfortunately I don't feel comfortable in sharing
the names, but if you google "top 30 hedge funds", they'll be there.

From the interviews it seems like these companies are actually looking for
people with distributed systems experience (think of SV's devops + architect
skills), and willing to pay well for it (I've heard of several people leaving
Google/FB/Netflix/... to join these groups).

~~~
gragas
Interesting. I did not realize that hedge funds would need such advanced tech
like that. I have no doubt that they can afford to pay for it.

