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

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

#1

Post by 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'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?

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

#2

Post by 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?

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

#3

Post by throwaway41441 »

rajjalan wrote: post #2

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?

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.

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

#4

Post by 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.

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

#5

Post by tixocloud »

throwaway41441 wrote: post #3
rajjalan wrote: post #2

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?

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'…

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.

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

#6

Post by 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.

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

#7

Post by 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.

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

#8

Post by dvtrn »

JSeymourATL wrote: post #7

> 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,…

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.

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

#9

Post by 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.

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

#10

Post by 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.

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