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.
Ask HN: Startup to enterprise and back to startups – how?
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Re: Ask HN: Startup to enterprise and back to startups – how?
#32This 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…
what profile would you hire for pre-PMF?
Re: Ask HN: Startup to enterprise and back to startups – how?
#33you should apply to work with us because we love this type of stuff: https://www.chargehound.com/jobs
Re: Ask HN: Startup to enterprise and back to startups – how?
#34Start your own.
Re: Ask HN: Startup to enterprise and back to startups – how?
#35A 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.
Re: Ask HN: Startup to enterprise and back to startups – how?
#36> 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 uni…
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.
Re: Ask HN: Startup to enterprise and back to startups – how?
#37As 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.
Re: Ask HN: Startup to enterprise and back to startups – how?
#38You 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.
Re: Ask HN: Startup to enterprise and back to startups – how?
#39Earlier quoted context omitted.
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…
> 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.
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.
Re: Ask HN: Startup to enterprise and back to startups – how?
#40A 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".