The Easiest Way to Get a Job at an Early Stage Startup

In this article, I’m going to tell you seven steps that you can take to get a great job at an early-stage startup. So I’ve worked in early-stage startups for my entire career, and I’ve used this exact process and actually to land my latest job. And so this is something that I think really works because anybody that I’ve given this advice to has seen success with it.

Step #1: Find a startup you’re interested in

Why is this important?

Well, if you’re not interested in the startup, you’re probably not going to stay there for very long, and startups are volatile, so you have to be interested in the work that the startup is doing in order to actually want to apply for them.

So where can you go to find startups that are interesting? Well, you might find it useful to check out sites like Y Combinator. That can be a major talent base of just up and coming startups. Or you might want to check out different tech accelerators like Techstars for their latest batches, because there might be some hiring that’s happening in those respective communities.

But you also just might find it useful to check out a site like AngelList, where you’re going to see a massive directory of startups that have some job openings and opportunities for you. Something to consider is whether or not you want to be in the B2B world or the B2C world. That’s typically the dichotomy where they’re either selling to other businesses or they’re selling to consumers.

And then from there, there’s an entire rabbit hole in terms of the types of businesses that they might be selling to, as well as the types of consumers that they might be interested in. But what I’d be considering at this point is what’s the overall industry or space that this startup works in? Who are the founders and are they still involved with the company?

The reason why that’s useful is because in the case where they had some founders but they’ve all left, that might signal not all that much confidence in terms of this particular idea and also whether or not you like the team or the vibes that the careers page is giving you. Sometimes the careers page will be super aggressive and they’ll make statements like, if you like to have a 40 hour work week, then you don’t want to work here ’cause this isn’t the place for you.

You’ll need to determine for yourself whether or not you value that, or if you’re looking to just find a place to grind out at. But either way, find something that’s interesting to you and then from there, move on to step number two.

Step #2: Identify at least three opportunities for the business

Step number two is where you’re going to take a look at the business’s website, and you’re going to identify at least three opportunities for the business. This can be something that’s related to just experiences or observations that you can make. The great way that you can think about this is ask yourself, what do you noticing as you explore this startups website. Are you noticing a missing marketing page? Are you noticing something that’s kind of off in terms of their pricing page?

Are you noticing an opportunity in terms of how they could potentially sell more effectively or get more signups? These are the sorts of things to be thinking in the back of your head. Because you’re going to use these later on. The reason why we’re going to come up with these three opportunities is because we’re going to work them into a cold email.

That’s right. Cold email. At this point, just jot down a few different ideas for opportunities, and then from there, rank order the opportunities in terms of what you think is going to drive the biggest impact for the business to the least impact for the business.

Step #3: Cold email their CEO

Step number three is where you’re going to cold email their CEO or whoever is the executive that is hiring for the role that you’re interested in. When you see these job listings for early-stage startups on AngelList and other websites, you are going to be able to do some reverse research and find the CEO or founder of that business. The reason why you want to find this email is because it’s usually not all that hard to figure out. A lot of these early-stage startups kind of followed the pattern of either just the first name of the founder and then the domain, or it’s like the first initial and then their last name, or it’s just their last name.

But what you can do is you can look up an email validator tool to figure out what is an active email and what is not or you can just see whether or not they have the email publicly listed on the website.

Step #4: Cold emailing the CEO with three opportunities

Whatever the case may be, though, you want to email the CEO at this point, and the reason why is because this is step number four when you’re emailing the CEO, you’re going to share the three opportunities that you thought about for their business, and then you’re going to ask for 30 minutes of their time to learn more about what they’re working on.

The reason why we started out with outlining three opportunities of growth for their business is because this is a case in which you’re going to pattern interrupt the CEO and the sorts of emails that they’re typically getting from different people, and then from there, in return for that sort of outline of different opportunities for their business, you’re going to be looking for 30 minutes of time to chat more about the opportunities as well as just learn more about the vision of the CEO and what they might be working on.

Step #5: Check out whether or not you vibe

It’s really important that you see whether or not you get along without this person as well as you figure out what they might need help on next. This can be a great opportunity for you to get connected with somebody new and also just build a new relationship.

And the reason why this is so effective is because, if you see yourself and you’ve already come with all this value for the CEO, well, it’s probably going to be a productive conversation where you’re going to be able to figure out whether or not you can get along with this person as well as whether or not the skills and experiences that you have in the past could potentially be useful to this business or if all of your observations of opportunities were just completely out of thin air.

Step #6: See whether or not you align

Step number six is to see whether or not you align with the sort of CEO or founder that you’re meeting and whether or not you can help, and also if you want to help. So it’s all about at this point, alignment. This means asking yourself, did I like this person? Do I feel like I can get along with this person? And do I want to pursue this relationship a little bit further. What you’re doing at this point is you’re really just kind of doing some blind dating with founders to see whether or not you found a founder that you want to work for, that you’re inspired to work for, as well as a place where they might be able to value the sort of experiences that you have.

In the case where you do feel alignment, this is where you’ll actually stop a little bit before step number seven, and you’re just going to continue the conversation with that founder. You’re going to ask them how you could potentially help, whether that’s as a consultant, first, whether that’s throwing your name into the ring in terms of the job that they might have out there posted, and just explore that conversation a little bit further.

Step #7: Repeat the process

In the case where you don’t vibe though, that leads me to step number seven, and that’s where you just repeat this process until you find some organizations that are really interesting and align to you. This process straight up works. And the reason why I can say that is because I personally used this process a little over two years ago to find my current job.

And also I’ve shared it with different friends and mentees in the past, and they’ve also used it and seen great results. In terms of whether or not you’re being successful with your cold emails, I was personally seeing over 50% open rates, and I was booking one in two meetings of people that did open my emails.

And so if you want some sort of benchmark, that might be something to think about. In terms of my subject line, what I was using was a subject line as simple as three opportunities for company, and then I would just do this for a couple companies that I found interesting.

3 reasons why this work

When we take a step back, there’s really three reasons why this works so well.

Number one, the execs are regularly bombarded with spam emails that add little value to their business. Number two, at early stage companies, they often don’t have application tracking systems, and so the best way to apply for a job is actually to go directly to the founder as opposed to trying to submit something through some sort of portal.

And then number three, by leading with value, with those three opportunities, you’re going to pattern interrupt, which then helps you differentiate yourself from all the different candidates that might be interested in that role as well.

Other tips that I give you, make sure that you provide one or two sentences in terms of your past experiences and why you might be interesting for them to connect with. Be really specific and make it clear to them that you only wrote that email for them and not for anybody else’s eyes. If anything is bulk templated, then they’re going to ignore it.

You can use or Hunter when it comes to trying to identify these sorts of emails for folks, and then in the case where they ignore your first email, what you can do is you can bump your email with a video message that just digs a little bit deeper into those opportunities.

That’s another great way for you to stand out. Some great tools for that can be either Loom or Screencastify in terms of recording that video and attaching it. Hopefully, you try this out for yourself when it comes to finding your next gig. It can work for things beyond just early stage startups, but I find it most successful in these sorts of worlds.

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