How Can I Get a Job at a Startup?

The best teams are built around two things: An idea that matters to the team; and trust.
David Hieatt

I’ve worked with startups for almost seven years – long enough to have hired and to have fired people; to have gained and lost business partners; to have been hired by Escape the City and to then have been frequently pinged with, ‘If you got a job there, how do I?’

Seven years is long enough to feel the truth of what entrepreneur-turned-VC Mark Suster talks about here, when advising those who want to make the leap into startups:

“Make sure it’s in your personality type, make sure you have the risk appetite, make sure you can afford to take the risks given your life situations and make sure you know that there is a high possibility your startup won’t be hugely financially rewarding. If you still want to go for it knowing all this and all that you’ll endure – awesome! It’s the best experience I’ve had in life. But not for the faint hearted.”

De-risking Yourself.

Startups are still testing their way towards their business model. The less proven their business model is, the more risk you are taking – although the startup is also taking a risk by hoping that you will be an effective producer. The less relevant experience you have, the higher risk that they are taking.

So the point of the interview process – which can often be a serendipitous meeting at a drinks event, as opposed to inside a formal interviewing boardroom – is to decrease the risk that a startup would be taking on you if they hired you.

In early-stage companies, there are rarely clear job descriptions – often the founder simply has an idea of the outcomes that they need. Sometimes they have cash to hire you; sometimes funding is still on the way. Get used to uncertainty.

Suster outlines the ingredients of a great entrepreneur but the same applies to great startup employees – the notable attributes tend to be confidence, decisiveness, resilience: “not very status oriented, questions authority, can handle high degrees of ambiguity or uncertainty, can handle rejection, not scared or ashamed of failure.”

Take Jason and Bob. Jason worked in a corporate role but wanted a marketing job at a startup. So did Bob. Just to make the story easier, let’s pretend that I was the startup founder with hiring power.

Jason = Confident; Bob = Not So Much.

Jason met me at a startup event. (There are plenty). We had a mutual acquaintance (often, “it’s who you hardly know that counts“). Jason was interested in my startup and let me know (sincerely) what he admired about my startup’s work when he shook my hand.

He asked insightful questions. He listened to my responses and shared what he’d been working on – outside of his corporate day job; he’d spent evenings and weekends building up his Facebook app skills through reading books and taking various courses.

I told him about some issues we’d been having with our Facebook efforts. He mentioned that while this wasn’t his area of expertise yet, he’d read an interesting article about Facebook apps that he would forward on to me.

I didn’t meet Bob at that event because Bob wasn’t there. Bob had emailed me earlier that week, introducing himself. He had attached his CV and had plenty of information about himself, but hadn’t asked me a single question about my company except for more information about compensation.

I had replied to Bob telling him that I was going to the event that week and that I could meet him there for a quick chat if he was interested. Bob had forgotten to reply to my email, and instead, sent me a quick line the next day telling me that he’d also forgotten about the event.

Jason = Competent; Bob = Not So Much.

Jason emailed me the next day as he’d said he would. He attached the article that he’d mentioned, which he’d found via Linkedin because he was subscribed to a Startup Marketing interest group. He invited me to connect on Linkedin and asked me for feedback on his Linkedin page – as I browsed, I could see that outside of his day job he had worked on some interesting, relevant projects that he had uploaded to Slideshare (Linkedin allows you to display multimedia on your profile).

Bob had mentioned Facebook marketing in his CV and I forwarded him the article that Jason had sent me to ask his opinion on the question that I had about Facebook. Bob emailed me back saying that he didn’t trust the article as he was more qualified than its author (without specifying exactly what made him more qualified) and told me that if I wanted more of his advice, he’d be happy to discuss it but would charge an hourly rate as a consultant.

I went to browse Bob’s Linkedin page, which was fairly barren and cryptic. We had no mutual connections. I went back to him and told him that we didn’t have a budget for external consultants at this present time. Our email trail ended.

I thanked Jason for the article, gave him some feedback on his Linkedin page, and reminded him that we weren’t hiring at this time but that I’d keep an eye out for other startup marketing gigs. He was grateful but said that he already had a few other potential leads and that he wasn’t looking for a full-time job in another area right now – instead, he was going to take his time over the next six months and get to know startups that he could do volunteer projects with, to build up his portfolio.

I told him that we’d be interested in being one of those startups. He came back to me with a specific project he had in mind that would deliver free value to my business (i.e. skimming our Facebook Analytics reports and recommending which posts we should focus on replicating).

We kept in touch over the next month, got to know each other better, and since he was excellent (proactive, competent, confident, honest, willingly accepted feedback) I began to think of relevant people or hiring managers I could introduce him to or how I might be able to hire him in the future.

The Value of Doing Free Work.

Time is a startup founder’s most precious resource. So if you can make engaging with them easy and time-efficient and upside-only for them, they’re going to want to continue engaging with you.

You need to put your hand up instead of waiting for them to give you orders. And you need to be comfortable with uncertainty.

Even after you’ve got the job, everything (salary, working hours, role description) can change quickly and it’s very different from working at a big company where there is a specific square box for you to fit into.

In a startup, it’s more like the job functions exist in circles and they overlap like Venn diagrams – you pick a main circle to join, and you prepare yourself for the fact that other circles will overlap.

So before you even get the job, the startup manager often wants to see that you’ve got the prerequisite flexibility and dedication. It’s far easier to go the extra mile for founders or companies who you genuinely like who are in a space that you are genuinely interested in.

The best way to get to know founders is by working with them a little bit. If they can’t pay you, do it as a hobby. I did this often in the early years of my career, despite being asked by indignant friends – “You’re doing this for free? Why aren’t they paying you?”

I’d explain that this was my way of finding out who I wanted to work for, de-risking myself to prospective employers, and that it was a cheaper learning method than graduate school. I was gaining learning that I couldn’t get anywhere else.

Of course you have to draw boundaries. But you also have to play the game if you want to be in the game, and if nobody’s going to pay you straight away, the best bet is to jump in and just start playing anyway.

Plus, 9 times out of 10, delivering great results through a free ‘project’ would end up leading to great, well-paid work with founders who I genuinely admired. The times when it didn’t work out, I’d simply walk away with no hard feelings, as I would still have learned something and gotten to know some new people.

All of it led me to really getting to know the startup ecosystem and how I could fit into it. I learned that someone is more likely to take a chance on you when you’re brave enough to take a chance on them too.

The more mutual rapport and trust you’ve developed with founders, the more likely you are to become comfortable needing one another. The more genuine interest you have in their company and mission, the more genuine interest they will have in you and your skills.

So what does this mean?

  • Find founders and startups that you genuinely get excited about. It’s important to know what your own mission is. List the areas that interest you then start learning about players in that space and reach out to them. If you don’t know where to start, watch this TED talk and figure out your own personal ‘why’.
  • Give them a free sample. Charlie Hoehn writes about this in his e-book The Recession Proof Graduate – the value of free work for both you and a prospective employer. It gives you a chance to learn about the employer and whether you actually want to work with them, and by initiating, designing and managing the project yourself, this takes the impetus off the employer to have to dream up new work for you.
  • Get in the game. A lot of people ‘want to work for a startup’ but people who really want to be in startup life are already there in some capacity because they can’t not be – attend events, read startup blogs, mix with other entrepreneurial types, start a side project or do a course (at General Assembly or Startup Institute).
  • Do your homework. Read the relevant Quora debates. Have an active Twitter profile that allows you to follow the thought leaders in that space – at the very least, you can just retweet articles you find interesting to keep them in one place for your own reference. Learn this list on your way to work every morning.
  • Develop allies. If you want to build a useful network, you yourself have to be useful – this comes from being well read, well connected, and having a positive attitude about helping others out without expectation of the favor returned. This allows you to build a network of people who are aware that you exist and who know that you are interested in working in a specific area. Start here and here.
  • Show that you’re hungry without being desperate. Reach out. Follow up. Deliver. Keep your promises. Be honest. Do what you say you’re going to do. These simple things matter more than the qualifications you’ve gathered.

I’m still learning as I go, but what I can see clearly now is the meaning of this:

“Some of the biggest challenges in relationships come from the fact that most people enter a relationship in order to get something: they’re trying to find someone who’s going to make them feel good. In reality, the only way a relationship will last is if you see your relationship as a place that you go to give, and not a place that you go to take.” – Tony Robbins.

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