
Ask HN: Startup to enterprise and back to startups – how? - throwaway41441
I started my career 15 years ago in a startup. Worked there for 4 years and went from zero clients to over a 1k enterprise customers. I learned a lot and it&#x27;s still the job experience I&#x27;m most proud of.<p>Somehow I ended up getting seduced by a position at a big name IT enterprise, joined other enterprises and now working remotely for 3 years for a medium-sized company.<p>I think companies look at my 8 years at big enterprises and think I&#x27;m not a good fit for a startup. The truth is, I never felt at home in enterprises and was always fighting the processes and complaining. Go figure.<p>What could I do now to make myself more employable at startups?
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amirathi
> What could I do now to make myself more employable at startups?

Startup hiring is a fuzzy science at best. Apart from abilities it's a lot
about what impression you make in the first few interactions with the team.

Before talking to the team, invest a good amount of time researching on the
space the company is operating in. The problem space, adjacencies, incumbents
in that space and their offering, know what's unique about the company and the
product. Learn terminology. Understand key metrics. Go overboard. Know
everything you can beforehand. Use this knowledge in your interactions with
the team. Ask pointed questions. Recognise and complement if there is
something clever about their positioning and the business advantage they have
because of it.

You want to leave them with the impression that the guy is not just
experienced but is sharp and understands what we are doing here.

~~~
nickreese
I'm in the process of hiring for our company / startup and you hit the nail on
the head here. I'm amazed at the number of people who have done 0 research on
us, yet tell us how impressed they are at what we've done.

My favorite line to follow up on these empty complements is: "Thanks for the
kind words. What do you think we're doing that is unique? What would you do
differently if you were in my shoes?"

In that past week, 2 of 8 interviews have had this empty praise. Neither of
the 2 could provide a meaningful example of how what we're doing is truly
unique... and it is in the job ad clearly spelled out. One of the 2 hadn't
even been to our website.

Interactions like these make you want to put up huge filters to weed out the
people using a "resume shotgun" interview process but in my experience the
amount of effort you invest in hiring pays dividends once you do hire.

~~~
cfusting
Seriously? It's hard enough to find talented people. Why do you expect them to
research and understand your company along with 100 others they are applying
to?

Smart people will grasp your product once they get going; I'm more interested
in their intelligence, skills, and experience. If your product is sufficiently
complicated that a solid engineer might not understand it's market appeal
three weeks in good luck selling it.

Sounds to me like you like it when people who interview flatter you with their
understanding of your amazing invention.

~~~
ryanwaggoner
Applying to != interviewing at.

It's reasonable to not do in-depth research on every company you apply to
during a job search (though some would argue that the smart applicant does
exactly that and applies to far fewer jobs with a more personalized, targeted
approach).

It's completely unreasonable to walk into an interview without having the
foggiest idea of what the company does. This isn't complicated; take an hour
or two before an interview to learn about the company, the competitors, and
the space in general. Yeah, you might get hired by someone without doing that,
but you're at a disadvantage against other applicants who understand that
"talented" isn't enough.

------
ryanSrich
This is one of the harder parts of hiring for a startup. Where I've struggled
in the past is finding the right balance between someone hungry enough to work
at a startup (let's be honest, a lot of people just want a 9-5 with a steady
paycheck, and there's nothing wrong with that) and someone with enough
structured background to help improve process/efficiency.

It sounds like you might have this mix. The more you can show that you are a
"startup" person, the better. The best way to do this is by researching the
startup and playing to the hiring manager's needs.

Of course, this is entirely dependent on the type of startup you want to work
for. Pre-PMF startups are incredibly fun, but require a very specific type of
person. If you're looking at startups with $10+mm in ARR then your enterprise
experience is going to be much more well received.

~~~
mpfundstein
what profile would you hire for pre-PMF?

------
jpzisme
Don't get down on yourself, man. I went through a job search last year and
applied to ~400 companies and got strung along by several start-ups, one of
which even said they were very impressed and asked when I could start, only to
change their mind the next day.

Eventually, I found one that was a great fit, and I've been here for over a
year and am extremely happy. What I've seen at least in the Bay Area startup
scene is that many companies have unrealistic expectations and are waiting for
unicorn candidates that magically fit all of their wildest dreams.

If you were at a company that started from nothing and became successful, a
startup that has sense should be interested in you.

~~~
siruncledrew
I've noticed there's a hiring difference between startups that have at least
2-3+ years of proven financials and startups that don't. At some early stage
startups (say <11 months runway in Seed/Series A) hiring seems like a shit
show because they often don't have HR or recruiters/talent acquisition yet.
They realize they are small and are trying to get the most bang for their
(well, someone else's) buck.

Not all do this, but some things I've seen/heard done by a handful of small,
"scrappy" startups:

\- Interviewing candidates knowing they don't have the budget to even give
them a job. It's a shitty thing to do because they are essentially knowingly
wasting someone's time only to say "Yea, you're a great fit, we just need a
few months to be ready to onboard someone for this role!"

\- Putting up unrealistic salary ranges on angel.co to look competitive to
attract more applicants, then giving an offer that's 10-20% lower in salary
than what was given (or pulling the "another applicant is willing to do the
$100k advertised job for $80k, but we want to hire you, would you be able to
come down to meet that number?" card).

\- Giving applicants "day in the life" interviews, where you sign an NDA, work
a full 8 hour day, then don't get compensated for it. Sometimes 6-10 people
are given these kinds of interviews for a 1 person job opening, and it's
mostly just getting free work.

\- Bosses setting an expectation for a great work-life balance in the
interviews, talking about how "they value their employees time", then
expecting everyone to work 10 hours per day or be on call at whatever whim
someone needs work done.

\- Assuming that because someone is foreign, they must be used to working long
hours for little pay and not complaining about it. Even with contractors,
there was a boss who hired a team in Ukraine, was invoiced $20k, then only
paid them $15k without any legitimate reasons and said "well, that's still a
lot of money for you so just be happy with it." It's amazing how shitty some
people are when they make themselves seem so outwardly exuberant or buddy-
buddy in person.

------
snowmaker
As someone who's hired a lot of engineers at a startup, a very simple and yet
highly effective thing you can do is to address this head-on in your cover
letter. Just say what you said in your post: that you really loved working at
a startup and specifically want to go back to one. That makes a big difference
by telling me that a startup isn't your back-up plan if you don't get hired by
a big company; it's your first choice.

Also, (and sorry to promote our own stuff) but you might look at
workatastartup.com, a website we built to help engineers join YC startups. I'd
be happy to look at your application and give you some feedback if it would be
helpful.

------
rajjalan
May be you are talking to the wrong startups? We are a startup and we love to
hire with such a mix of experience. Experience working at large and medium
enterprises is really valuable(in addition to working at a startup). Did you
get that feedback from multiple companies or is that something you are
assuming based on not getting foot in the door?

~~~
throwaway41441
Got direct feedback from one that I lacked skills in fast growing startups and
two feedbacks that I wasn't a fit (even though I had all requirements in the
job description). So that got me wondering what I could improve.

I think I'm competing with fresh graduates. I applied at startups with 20-200
employees initially. Really looking for that experience of taking something of
the ground and scaling.

I know we shouldn't take rejections too seriously but reality is it was always
easy for me to find a job. Maybe I've been too picky and overestimated my
skills, maybe companies are being too picky now. I'm not sure but I'm thinking
hard about this.

~~~
tixocloud
Might be talking to the wrong startups but also might be dealing with leaders
who lack vision.

Spend time to figure out what your strengths and weaknesses are with those
"fresh graduates". As a startup founder, I would take a 10x engineer any day.
Fresh grads bring great energy and enthusiasm but experienced heads make sure
my business is going to make the simple mistakes.

Don't sell yourself short. You're definitely valuable to any organization
(startup or otherwise) as you've seen the best and worst of both worlds.
You're an incredible asset.

~~~
ryanmarsh
Having worked at and hired in both startups and the enterprise the startup
cop-out is to stereotype someone with an enterprise background and expect them
to behave just like an enterprise, bureaucratically. This is a major fear
within startups because they often don't have the spare time/energy to reshape
someone's mindset. It's unfortunate and leads to a lot of skipped candidates
but expediency !== efficiency.

There comes a stage in each successful startup when they start looking for
adult supervision and explicitly seek enterprise experience. If you are
looking for early stage work you should make it obvious that you get the
startup's space and have a fast-execution mindset.

------
awillen
A lot of good advice here - one thing I'd add is that if you're really having
problems find a job at a very early stage startup, try something a little
bigger but not a huge enterprise. Companies that have raised a B or C round
and are trying to scale their business are often looking for people who have
experience working at the scale they want to achieve.

Even if you'd rather be somewhere smaller, it'll probably be a better fit in
the short term, and after a couple of years you may have an easier time
transitioning to something earlier stage.

------
JSeymourATL
> Got direct feedback from one that I lacked skills in fast growing startups
> and two feedbacks that I wasn't a fit ...

Hilarious - Are they right?

Consider the source -- frankly, many startup leaders lack the executive
seasoning and managerial savvy to make a balanced scorecard assessment of
talent. Their hiring criteria often boil down to 'hot or not'.

Get clarity on your targets -- specifically, WHO is the Founder, Co-Founder,
Early-Stage manager YOU can most help? That's the person you want to speak
with.

~~~
dvtrn
_Hilarious - Are they right?_

How would one find out? If as OP stated, their skills lined up and matched the
job requirements, how will they ever know?

Startup recruiting seems a lot like modern dating: a lot of terribly
communicated expectations resulting one party effectively "ghosting" on the
other, ending in a lot of frustration and apathy from one party at the other
_because_ of said terrible communication-and that resentment or 'baggage'
being unknowingly carried with them to the next interview cycle.

"Not a good fit" can mean anything from asking too much salary, to being just
a month short of the necessary 5 years of experience for a tech stack that's
been around for 3, to not wearing the right color shirt to the interview.
You'll never know what "not a good fit" means because it seems like once a
company decides you're not the perfect unicorn, rockstar candidate with a
pocket full of ninja stars, you never hear from them again.

But don't worry, your resume is kept on file for other roles.

~~~
ShabbosGoy
> How would one find out? If as OP stated, their skills lined up and matched
> the job requirements, how will they ever know?

Job hunting as a software engineer has just become a literal grindfest.
There’s very little signal you can obtain from the entire process, but you can
gain a lot of noise.

~~~
dvtrn
It doesn't help seeing people give hiring managers and recruiters so many
excuses for just plain _shitty_ behavior at large.

I have to painstakingly detail and format my resume so YOUR job software can
parse it, make it easy to scan and read but the job advertisement itself looks
like someone let their cat walk on the keyboard?

Granted it's a minor thing in the grand scheme of how much cruft jobseekers
put up with just to get _noticed_ and have a snowballs chance in hell of even
getting a screening call-but I'm beginning to hold a lot of contempt for the
job hunt. More than just the stress of needing a job and the people involved
who seem to-by many indications-look at job seekers as subhuman.

------
masudrhossain
Well, some questions rise up for me.

Did you get the interview? If you got the interview, it might be how you
interview with them. I'm a startup founder and i try to hire people I can go
to the bar with and seems very talented.

What kind of startups are you applying to? If you're targeting startups who
does not or never plans on selling to enterprise customers, then they might be
denying you because of that.

If you're interviewing with them and they ask you questions, just remember
that you have to answer in a manner of "We'll get that done in 1 hour, and not
10 hours like you would with enterprise". And jobs are mostly a numbers game.
They could simply be using your enterprise experience as an excuse.

------
matchagaucho
A good cover letter / introduction.

Startups depend on Generalists to make autonomous decisions that are aligned
with a company mission.

Enterprise Specialists often get disconnected from the company mission and
need a lot of direction, which is a liability for startups.

A cover letter, or in-person introduction that says _" I understand your
mission and this is what I would do in the first year to achieve the company
goal"._

Although phone screens and coding interviewers are looking for tech skills on
the surface, the underlying motivation is "I'm too busy to train/manage you.
Just preemptively tell me what you're going to do and how you'll do it".

------
nathanwallace
Career change is often best one variable at a time. For example, change
company size but stay in the same industry. Double jumps are generally harder.

Perhaps, focus on startups that reduce the number of change variables. For
example, startups focused on satisfying the needs of enterprise IT customers
should value your inside knowledge of the pain points.

Keep looking - the right thing will be out there. (For example, my company,
Turbot, is actively seeking remote employees with enterprise experience and a
pent up hunger to get stuff done.)

------
mikekij
As a startup -> enterprise -> startup guy, I see your 8 years of enterprise
experience as a huge plus, honestly. If you’re having trouble getting back
into startups, it may be one of two things:

1) employee thinks your risk averse

2) ageism. Unfortunately is real when applying to startups.

As for 1, I think proactively addressing this in a cover letter / interview
would be helpful.

Hit me up if you’d like to talk. We may be hiring.

~~~
czbond
Agree here. I've been both, and what I find is most lacking in early, mid-
stage companies is "process" and "ability to think of execution
strategically".

------
fecak
I have advised hundreds of clients that have made this same transition, and
it's not as complex as you might think. Much of the problem is how you talk
about that enterprise experience, which includes both on a resume and in an
interview. The company name and size are not really an issue if you position
your experience properly and understand your brand and value.

------
icebraining
If by startup you mean the "rocket ship" type, why not try a third
alternative, specifically a small software shop? You may find them more open
to people who don't fit the mold of the recent graduate willing to work 16h
days, yet they're still small enough that everyone knows everyone and
bureaucracy is still minimal.

------
charleyma
What type of roles are you specifically looking for? Engineering, sales,
marketing, business, etc

Also what type (industry) and what stage startup are you applying to?

For example, "startups" like space-x I'm assuming value having a ton of
enterprise experience versus something more consumer facing like Snapchat two
years ago.

Different stages as well as industries will be looking for different potential
+ proof of experience and you should highly tailor your resume + interview to
those expectations!

If it's more on the business side, happy to chat further if helpful :).

------
ccajas
You seem to be an example of survivorship bias. The majority of startups fail
within 4 years, so your experience made you more marketable towards enterprise
work as you progressed.

Your experience is not the norm for people working at startups, so you
actually have an upper hand, just not necessarily in the smallest of places.
Look for companies that are undergoing a rapid growth, just past the make-or-
break point. These places need people who are experience working with problems
regarding scale, and solutions that they require.

------
awinder
Depending on your priorities, midsize is usually a great place to get autonomy
wins of small startups mixed with the scale to actually be solving real
problems. I’d be curious if you don’t like aspects of your workspace or are
otherwise convinced that startup really is the place to be.

I’m also gonna take a stab at reading this so take with a grain of salt. I
think the companies are not getting back to you because it’s super low odds of
mutual fit. 15 years in and looking at early stage startups, you probably are
not going to be a fit unless you are replacing a key team member or part of
founding team. You have experience level, trading off for the very unglamorous
aspects of early stage means the value prop to you would only make sense with
significant stock package and likely a high salary. To get into that, you’re
really talking about opportunities coming in from your professional network,
or a number of other low odds vectors for getting in the door.

If you want to go down that path I would suggest really building some solid
relationships at either bigger companies nearing IPO or midsize, basically you
need to expand the pool of people you’re close with who might create new
startups

------
godot
This might seem a bit shallow, but I think it comes down to the set of skills,
a lot. To give you an example of what I mean, if you have Node.js and React on
your resume, chances are you'll be pinged by tons of startups (and some very
early ones) in no time.

There are so many startups in San Francisco right now, and we're in a strange
situation where both demands and supplies are high, but the matching isn't
always great and companies (especially startups) are still struggling to hire
because they can't find the right fit. (sometimes true, sometimes because of
terrible interview processes, sometimes because of not finding candidates like
you who might actually be a fit but don't look like it on paper)

If your resume contains things like C#, .NET, etc. chances are many/most
startups will overlook you for other candidates. (Not saying or generalizing
what your skills might be at enterprises, just giving an example) Vs if you
have Node, React, Docker, that sort of stuff, you'll look like an attractive
candidate to them.

------
amattn
The biggest, lowest hanging fruit thing you can do is tell them you are only
interested in working at startups and you are only applying to startups. You
need this in your resume, linked in profile and also make sure to mention it
during the phone screens and onsites.

As an engineering hiring manager for (mostly) startups, I love candidates that
have both BigCo and TinyStartup experience. Diversity of thought and usually
by then, the candidates have a sense of where they want to work.

If you find that your tech or skills or experience don't line up with startups
then you may have some work to do.

Most BigCos need specialists. Most Startups need generalists. Depending on
your field, you might need to study up as some other posters have mentioned. I
wouldn't study haphazardly however. Apply to a few startups (or industries)
you are interested in and take notes of the questions they ask you and
especially the questions you struggle to answer. Those are the areas to spend
your time getting up to speed on.

------
lmeyerov
There's a silver lining: As an enterprise startup (graphistry), we value
enterprise product experience!

As long as we think a candidate would be productive in our stack, or quickly
ramped up, works for us!

We'd be more curious if you have the startup attitude, where the support, and
bottlenecks, are yourself and our can-do team.

------
dumbfounder
My suggestion is to start listening to the This Week in Startups podcast and
wrap your mind around startup mentality to understand what they are looking
for in an early employee. If you can get excited about the startup mentality
it will hopefully come across in your interview.

------
zerkten
Where are your former startup colleagues these days? If they are still working
close to the startup field, it'd be good to talk with them, even if you you
aren't looking for a direct referral. If you can get candid feedback from them
it may help. Their gap analysis might be quite scary at first, but they can
likely suggest ways for you close the gaps. And the gaps might only be at an
appearance level. You've done the startup thing, I'm sure you can do it again
if you persist.

------
epicureanideal
Talk to some people at a startup, and ask for an interview. Honestly, if you
have a good number of years of experience and want to work in startups,
there's no barrier keeping you out. You'll be plenty employable right now.

------
SandersAK
you should apply to work with us because we love this type of stuff:
[https://www.chargehound.com/jobs](https://www.chargehound.com/jobs)

------
kespindler
Wanna email me your resume (email in profile)? We're tackling an underserved
part of the consumer finance world, backed by top VCs and still early stage.

------
numbsafari
Start your own.

------
trevelyan
Work for cheap

------
egfx
Work QA at a game company. Work 18 hour shifts for $15 per hour. That will set
you on the path.

