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

80 points by throwaway41441 8 years ago | 50 comments

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's still the job experience I'm most proud of.

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.

I think companies look at my 8 years at big enterprises and think I'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.

What could I do now to make myself more employable at startups?

amirathi 8 years ago |

> 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 8 years ago | |

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 8 years ago | | |

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.

karthikb 8 years ago | |

And the first impression does not have to be made by you! With several years of experience, you probably have a strong personal network. An introduction with a few sentences recommendation can go a long ways.

cfusting 8 years ago | |

Fluff.

It's very hard to find good people. If you're good at what you do you'll easily find an appealing position once you sort out culture. Stay away from the megalomaniacs deluded enough to think you have time (or reason) to do in depth research on their company along with the many others you are applying to.

This isn't an internship, you are already valuable.

ryanwaggoner 8 years ago | | |

Rude.

No one said anything about doing in-depth research before applying, and while good people are hard to find, they're not unicorns. If you're walking into an interview without any background knowledge on the company or position that you're hoping to get hired for, you're at a severe disadvantage to those that do show the tiniest shred of initiative.

Your attitude strikes me as remarkably entitled and arrogant: "I didn't spend any time learning anything about this company, what the challenges are, etc, BUT I'm really smart and talented, so you have no choice but to hire me."

Sounds like looking for applicants who show they care even a little bit is a great heuristic :)

ryanSrich 8 years ago |

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 8 years ago | |

what profile would you hire for pre-PMF?

jpzisme 8 years ago |

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 8 years ago | |

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 8 years ago |

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 8 years ago |

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 8 years ago | |

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 8 years ago | | |

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.

lynnetye 8 years ago | | |

Without even knowing you, I want to say that you're probably not too picky. You may have overestimated your skills though, or maybe you've just forgotten which of your skills are most appealing to startups. My full-time job is connecting with, talking to, and helping startups hire software developers. It varies from company to company (and from department to department), but I wouldn't say that fresh graduates are the top choice from an employer's perspective.

Feel free to reach out to me by email if you think I can offer more specific advice/help/resources.

jtchang 8 years ago | | |

I'd be glad to do a quick mock interview and try to give you some advice. I've done a lot of hiring with various startups.

sharemywin 8 years ago | | |

You might be asking for too much money.

awillen 8 years ago |

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 8 years ago |

> 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 8 years ago | |

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 8 years ago | | |

> 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.

masudrhossain 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago | |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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 8 years ago |

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

kespindler 8 years ago |

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 8 years ago |

Start your own.

trevelyan 8 years ago |

Work for cheap

egfx 8 years ago |

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