Ask HN: Startup to enterprise and back to startups – how?

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?

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.

> 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.

> 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.

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.

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.

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.

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.

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.)

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

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.

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 :).

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.

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.

Work for cheap

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.

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.

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.

you should apply to work with us because we love this type of stuff: https://www.chargehound.com/jobs

Start your own.

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.

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.

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.

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".

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.