How to land your dream startup job!
To a lot of people, working at a startup is an unattainable pipe dream. I know it seemed like one to me. I’ve already covered why I think you can still kick ass without a technical degree, but here’s some tips on exactly how you can get started.
(FYI: I’ve been desperately unemployed, so I’ve made a lot of these mistakes myself. And now I’m one of the people responsible for hiring at Aviary, so I see a lot of these mistakes every day.)
Startups are certainly becoming more common - especially in Silicon Valley, Silicon Alley, Silicon Prairie (I didn’t make that one up), and Silicon… Swamp (oh my god I made that one up but it’s real) - but that doesn’t mean they’ve lost what made them so magical in the first place. These companies have a ton of flexibility, and that changes the rules.
These companies don’t have an HR department, so there’s not a person in a suit reading your resume. Most of them probably don’t even have a dedicated hiring manager, so it’s likely that the person reading your resume isn’t looking for the traditional things you’ve been taught to say. And almost definitely, everyone in the company is (happily!) exhausted, swamped with terrible job applications, and looking for someone who stands out. That’s where you come in!
Step one: searching for the right job
I may not know you, but if you’re anything like every single one of my friends who have been looking for a job for the last 10 years, you are probably doing the following:
- Searching job boards like Monster and Indeed (I hope you are not still attempting to use Craigslist) for general titles like “project manager” or “junior developer.”
- Sending out a resume you haven’t really looked at in a year.
- Sending out a cover letter which, the first time you wrote it, was really really genuine and passionate! But now is… not so much.
- Feeling really bored and sorry for yourself, and complaining to everyone around you that the economy sucks and there are no jobs.
First of all, let’s get that last one out of the way - the economy definitely sucks, and there are definitely not *enough* jobs, but we can find a good one for you. Because you’re good enough, you’re smart enough, and doggone it, people like you!
Feeling better? Cool. So here’s what you should be doing. First, please never search a generic job aggregation website ever again. You might get lucky enough to find some legit corporate job on there, but startups just don’t use them.
So if you can’t use those garbage websites, what option does that leave you? Well, the hard one. The one where you need to sit the hell down, with no distractions, and think about what you want to do. Wanting to work at a startup isn’t enough (and is too general to help point you in any one direction). Assume a startup’s a given. What problem do you want to solve? Which companies do you really respect? Which industry do you want to be in, long term?
Hopefully you can answer one or more of these questions and that’ll get you on the right track. If not, a website like Made in NYC (or your town’s equivalent) is a great place to get some inspiration. If that’s not an option - if you’re not lucky enough to live in Silicon Swamp - try thinking about which products you use on a daily basis that you love. And think about moving.
(Note: don’t be scared to reach out to your dream job. I know it seems like they’ll just say no, but you seriously have nothing to lose. And if they DO say no, ask what you can do to get there in a year. Ask if you can take the person who rejected you out for a coffee. If they’re unresponsive, find someone else in the industry - or me! - and ask them where you went wrong. Don’t give up!)
Step two: updating your resume
Ok, so I’m going to assume at this point you’ve found something (or multiple somethings!) you think you might someday be able to be passionate about. Now you have to do some actual work, but the good news is that you can make other people do most of it for you.
That’s right: show your resume to everyone you know. Show it to your mom and your sister and your best friend and that guy you went on a date with last year. If you’re too embarrassed to show it to them, think about why. This is the trick: if you can’t show your resume to the people who care about you, don’t you dare send it to a stranger.
Send it to all these people, and really listen to their feedback. Don’t get defensive. If they say it’s boring, jazz it up. If they say it looks ugly, use a template in Word (or ask a designer friend to spruce it up for you). If they say it seems like you’ve never done anything, or that they can’t tell what you’ve done, think about why and fix it.
Step three: choosing a job
You might think you already did this in step one. But this is exactly why people often get stuck at step one and give up. You’d love to work at Barkbox, but they don’t have any non-technical positions listed? Or worse, they have non-technical positions listed, but you’re not qualified for them? This is not where you sigh and give up. THIS IS WHERE YOU REMEMBER HOW AWESOME YOU ARE.
You just spent days or weeks revamping your resume to make yourself sound as incredible as possible. Even YOU should be completely convinced at this point. Yes, it’s good to research what positions are officially available at your dream company, but honestly? Don’t even worry about it, because:
No startup will pass up someone perfect.
This should be your mantra every day while you’re applying to jobs. Get it tattooed on your hand Memento-style if you have to. If you are smart, passionate, awesome, and in love with a startup, you can convince them to hire you. They will create a position for you. That’s one of the great things about startups!
So even if they don’t have your ideal job listed, write to them and tell them what your ideal job is. Convince them (in a charming, reasonable way, of course) that they just didn’t realize they needed you. Which brings me to…
Step four: writing your cover letter
I know what you’re thinking. I know that you want to just whip up a generic cover letter so you can send it out to as many companies as possible in the least amount of time. Great idea. How are you at math, hotshot? Because I’d love for you to tell me which of these is better:
- Emailing 100 people and getting 0 jobs.
- Emailing 1 person and getting 1 job.
We good? Okay. So cover letters seem daunting, but they’re actually the easiest part, because all you have to do is be yourself. Show your personality, and your passion. Explain why THIS ONE COMPANY is the one for you (because, remember, you’ve hand-picked it and you actually want to work there). Make a joke or use a silly pun. Nerd out and tell them that you love the dinosaur on their 404 page or whatever.
The goal of your cover letter is to prove that you can fit in.
Do not, under any circumstances, do the following:
- Attach your cover letter as a document. Write it in the email like a normal person. (Similarly, send your resume as a PDF. Not a Word doc. A PDF. No exceptions.)
- Start your cover letter with something formal. If I see “Dear Sir/Madam,” “Dear Hiring Manager,” “To Whom it May Concern,” or any of their relatives, I will not read further.
- Bypass the application process outlined on the company’s website. If they tell you to email email@example.com, don’t email their CEO or designer directly. The ONLY exception to that rule is if you have a direct connection to that person. Otherwise you just look like you can’t follow directions.
- List everything on your resume in your cover letter. It’s obviously good to give a quick overview, but remember that the point is to explain (show, don’t tell!) WHY you are a good fit. (Protip: prove that you are smart and get things done.) They’ll get the details from your resume if they want them.
- Fill your cover letter with all the things you think you could do better than the company itself. It might seem like a good idea to point out flaws in the company’s website (typos, broken links, etc) but I promise you - the company knows about them. The company hates them as much as you. The company will project this hatred onto you.
TL;DR: you need to remember two things.
- You have ONE chance to impress this company. Try your hardest, and mean it, and you’ll do well.
- You are great, and you can be an important asset to their team. Convince yourself, and you’ll be able to convince them.
There’s a ton more material here, but this post is already dangerously long, so we’ll leave it at that for now. I hope this is a good start for you to help you get moving in the right direction.
And if you need a second pair of eyes on your resume or are paralyzed with fear, email me and I’ll remind you how awesome you are.
Finding your value as a non-“skilled” startup employee
I’ve been working at Aviary for 3 years now. One of the things I’ve always struggled with, and keep hearing my friends fight through, is the vast discrepancy in perceived self-worth and “value” between different groups of startup employees.
GROUP 1: The highly “skilled.” (I’m sorry for all these quotations, but I can’t help it - these are the right words but also so silly and wrong that I can’t take them seriously.) This includes engineers and designers, who either have gone to school for years to learn a professional trade or who have spent their lives teaching themselves because they are talented geniuses.
GROUP 2: The highly experienced. This includes employees who join the company at Director-level and above. They could be in any department, but come at a higher default price and with some built-in respect because they’ve been doing their job, clearly successfully, at other companies for a while.
GROUP 3: The rest of us. An employee from group 3 might commonly be referred to as a “people person” or a “jack of all trades.” These titles are meant to give us some sort of imaginary soft skill to cling on to when we consider (and try to prove) our worth, but mostly just make us feel bad about ourselves because people in the first two groups don’t have to prove anything.
It’s a given that groups 1 and 2 have higher starting salaries - they bring more obvious contributions to the table initially - but no one ever talks about the other implications of this rift. (Well, more accurately, they talk about it, but only in frustrated whispers among members of group 3.)
When I first started at Aviary, I was brought in to do customer support and office management. These are (arguably) two of the “easiest” jobs to do in that they don’t require any specific skillset or previous experience; an employee in these roles just needs to be a “people person” who can “wear a lot of hats” and be generally nice and considerate. The reality, though, is that most people would (and do!) suck at these jobs.
Being good at customer support can make or break a company’s relationship with the people providing its revenue. Being a good office manager can mean the difference between employees staying or leaving. These are CRAZY IMPORTANT THINGS. Startups literally cannot function without these roles, which is why (sometimes confusingly) an office manager is often one of the first hires in any new, small company. The “skilled” employees can’t do their jobs if they’re answering support emails or building furniture all day.
Anyway, I was so excited when I started at Aviary (it was a fun place to work! all my coworkers were so smart! we were building things that people loved!) that I spent most of my time feeling incredibly humbled and grateful for the opportunity. This is definitely part of what made me so effective at my job, but I think it was also my first Big Mistake, which has stayed with me for the past few years. At times, it kept me from being happy, it kept me from pursuing new opportunities, and it made me way less productive than I could have been.
Not understanding your own value is a terrible problem, both for you and for your company.
I’ve come a long way in my career at Aviary. I’ve held more job titles and responsibilities than I can count, and by now I understand my value at the company and the fact that the “soft skills” I have to offer are JUST as important as the ones provided by my coworkers. But it took way too long. I spent a lot of time feeling resentful and, well, confused. Sometimes I struggled with feeling like I was the only one not “contributing” anything or building anything directly (for a long time I was the only non-“skilled” long-term employee we had on the team), which made me feel like I didn’t belong. I spent a lot of time (on weekends, of course) teaching myself a bit about programming, trying to learn Photoshop (miserable failure), reading books about startups - trying to find some way to convert myself into a “skilled” employee.
What I want to tell you (and I’m getting quite near the end, now) is that this doesn’t help. I mean it’s great if you actually want to do those things, but what I learned is that I *like* the things I do. I’m really good at the things I do (thank you to my coworkers for lecturing me about this endlessly until I believed it). There are very few people who could do the things I do, just as I can’t realistically do all the things my super talented team does. It does not help to try to turn yourself into a different kind of person.
So, here’s what can help:
1. Read everything you can find about successful people in your own specific line of work. For me, the biggest turning point was discovering Joel Spolsky and devouring every single thing he’s ever written. This was maybe 2011, and my title at the time was Program Manager. Joel was at one point a PM at Microsoft and wrote this amazing article about why PM’s are basically the best people in the world and no one can function without them. I’m paraphrasing (just barely), but it was the first thing that made me feel like what I was doing was an important contribution to the company. Other good examples:
- Customer support: read the Uservoice blog. They will make you feel so awesome about your work. Remember that you’re not just answering bullshit repetitive questions; you have the ability to make someone’s day. That is a big deal.
- HR: Um, hi, building a good team is the ONLY thing that matters. If you don’t have a team, you have nothing. Plus, hiring (and retaining) good technical people is pretty much becoming impossible these days because of all the competition, so you are some kind of unicorn if you can actually pull it off. This has never been my full-time job so I haven’t read a ton of stuff on it, but Lori Dorn is a great place to start.
- QA: Read this killer piece by Spolsky. Oh man. That guy REALLY loves good QA people. (I can relate on this; ever since we hired our QA lead last year, the quality of all of our lives has improved exponentially.) (See what I did there?)
- Office management: I don’t know of any good reading material, but I’m sure it’s out there. I could tell you some stories about office managers who’ve dramatically contributed to the success of their companies. Also, ours is a member of the Office Heroes League. You should join it.
- Account management: This is my current job, so I feel you. Look, being super organized and keeping your paying clients happy is an incredibly important job. And no one else wants to do it! And it’s hard! I don’t know of any influential account managers off the top of my head, but I’ll talk you through it if you want.
Etc. Seriously, do some googling and find people who you can really identify with, and who can reassure you that you are awesome and important and valuable.
2. Be honest with your boss. It took me a while to open up about how I was feeling, but ever since I did I’ve been getting a pretty much constant stream of positive reinforcement from our executive team. And sometimes that’s what you need in this kind of gig - someone to acknowledge that you are building something important, too, even if it can’t be distributed through Testflight.
3. Find. A. Mentor. Just find one. Go to relevant meetups and ask people you respect to teach you. Ask your boss if she knows anyone. Send an email to someone you respect on the internet. Ask my OG mentor to help you out; he lists his services right on his tumblr. Speaking to someone who’s been through what you’ve been through is so invaluable. Having someone outside of your team (that part’s important) to talk to will make all the difference in your life. A bunch of us at team Aviary have stayed in touch with our former COO, who has talked us each through many panic attacks over the years.
Here’s a quick list of some of the skills that commonly go unmentioned, but are incredibly valuable at a startup and will totally get you a job, even if you don’t think you’re “qualified” to get one. It’s important to remember that these so-called “soft skills” are just as difficult to master and are crucial to the success of any business.
- Empathy (seriously, this is a big one)
- Awesome communication skills (both out loud and in writing)
- Brevity (your awesome communication skills mean nothing if you’re sending 10-page emails) (I realize the irony of saying this in a crazy long blog post)
- Willingness to help with anything
- Eagerness to learn everything (often called “hunger” but I can’t bring myself to say that)
- Confidence and humility (you need both)
- Ability to talk to anyone, and ideally to make them smile
- Basic understanding of the internet, social media, etc (you really can’t get out of this one)
I’ve always told people that getting my dream job at Aviary was a fluke. “I had zero skills,” I confide when they ask. “I only got the job because I already knew the founder. I just got lucky. It was just good timing.” I have a million excuses. But honestly? Recently I’ve come to terms with the fact that I got this job because I deserved it. My boss hired me because I had already proven to him that I had all of the above, and that outweighed the fact that I had no startup experience or technical skillz. And building that trust with him, becoming the kind of person who was a no-brainer to hire, THAT - not spending my time trying to morph into someone else - was exactly the right use of my time before my startup career began.
Don’t beat yourself up for not fitting into a cookie-cutter “skilled” job description. Make your own job description (more on this later). Go get your dream job because you deserve it.
And email me if you need any help!