In Part 1, I broke down the types of roles I think you should be looking at if you are early in your career, non-technical, and trying to break into startups.
In Part 2, I went through how I would actually pick the startup you want to join, from what stage to target to the criteria I personally used when making that decision.
The next question is: how do you actually get the interview and stand out once you're in the process?
For some context, I've landed more than a dozen offers from VC-backed startups across internships and full-time roles.
I've also been on the other side of the process, seeing firsthand what candidates do to get my attention and what actually makes someone stand out.
FYI: Most of this is applicable whether you're technical or non-technical, but I'm obviously I'm not going to tell an engineer how to pass a coding/technical challenge. This is more about everything surrounding that: getting someone's attention, approaching the interview, and showing that you'd actually be good at working at a startup. Also to note I am generalizing most startups here.
This will be a long article but I promise you if you read everything you will be one step ahead of most people in the startup interview process.
The startup interview process is "slightly" different
FYI: This is a generalisation, some startups may be widely different.
Unfortunately the lay of the land is that there are ONLY so many startup jobs BUT a lot of smart people who want them.
A good role can have hundreds of applicants, and if you're early in your career, your resume probably doesn't look that different from a lot of the other people applying.
Maybe you went to a good school, had an internship or two, joined some clubs, and have a couple interesting things you've worked on. But sorry to break it to you, so did a lot of other people!
However, the good news is that startup hiring tends to be less formal than the recruiting processes most people coming out of school are used to.
If you're applying to a Big 4, McKinsey, BCG, a bank, or a Fortune 500 company, there's normally a fairly rigid process you have to follow.
- You submit through a job portal, someone from HR screens the application, you go through whatever interviews or assessments they've designed, and hopefully you make it through the funnel.
There isn't always much room to do something completely different and force yourself into the process.
But startups are sometimes can be different.
- Sometimes the company barely has a careers page. The person interviewing you might be the founder or decision maker who wrote the job description last week.
- There might not even be a recruiter actually and because of that, there are considerably more things you can do outside of the formal process to get someone's attention.
This is to YOUR advantage if you have "high-agency".
You can email the founder something with substance and send it to them. You can notice a problem with the company and try to solve part of it before they ever ask you to. You can do a lot more than submit your resume and hope someone picks it out of a pile.
We will deep dive into this "show and not tell" method more in a bit!
But before getting into what those things actually are, I think you need to understand the type of person most early-stage startups are trying to hire in the first place.
This will help you understand what founders are looking for specifically.
What makes someone a "good" fit at a startup?
This obviously changes depending on the company and the role, but I think there are a few qualities that are the most important for most startups.
The first is being a self-starter.
At an early-stage company, you're probably not going to be hand-held through everything. There might not be a playbook for what you're doing because nobody has done it before and maybe your boss might not have the answer either.
You could be given an objective that is basically "we need more pipeline" or "figure out how we should be doing content" and it's your responsibility to turn that into something tangible!
The way I think about it is taking the ball as far as you can yourself. For a simple analogy:
- If you're driving toward the penalty box in football and you have space in front of you, keep going. You shouldn't have to stop every 5 feet and ask your teammate where you should run next.
- Eventually you might hit a defender and need to make the pass, and that's completely fine. That's where your boss and your teammates are there for that.
- But you should have taken the ball as far as you reasonably could before needing someone else to move it forward.
Work at a startup is pretty similar. There's a huge difference between going to your manager and asking, "What should I do?" and going to them saying, "Here's what I'm trying to accomplish, here's what I tried, here's what happened, and here's what I think we should do next. Am I missing something?"
The second person is going to thrive considerably more in an environment where everyone has too much to do already.
the non-exhaustive list of what some startups might be looking for in people qualities!
You need to be able to execute
The second thing, and probably the one that founders care the most about is your ability to do things or execute.
I've met incredibly smart people who are very good at "strategy" but not particularly good at execution. They can tell you what the company should do, what the marketing strategy should be, or what someone else should build, but when it comes time to actually open the laptop and do it themselves, they aren't as effective.
That becomes difficult at an early-stage startup because there simply aren't enough people for everyone to only be a strategist.
- Someone eventually needs to build the campaign, make the landing page, send the emails, talk to the customer, research the accounts, organize the event, or whatever else needs to happen.
Especially when you're early in your career, I think you should optimize for becoming an executor. However, that doesn't mean blindly doing things without thinking about them. You should obviously understand what you're trying to accomplish and have some kind of plan.
But there is a point where thinking becomes procrastination, and a startup usually benefits much more from someone who can plan reasonably well and then actually try go do the thing.
There are other qualities that matter too that are similar:
- Hunger and determination are big ones. Founders generally like people who have some kind of chip on their shoulder and really want to make things happen.
- That being said I don't think you need to manufacture this or pretend that working 100 hours a week is your life's purpose, but there is a noticeable difference between someone who is casually interested in a job and someone who is going to keep figuring things out when the obvious answer doesn't work.
Lastly I'll add taste, although this depends much more on the role.
- If you're going into marketing, content, growth, design, or anything where there isn't always an objectively correct answer, you need some ability to recognize what good looks like.
- You can know every marketing "framework" in the world and still make painfully corporate slop content that nobody wants to read. This is hard to learn but a good first step would be to see how startups "position" themselves on socials.
So if you boil all of this down, the person I think does well at an early-stage startup is reasonably smart, can figure things out without constant direction, has good judgment, and most importantly can execute.
if you have at least more than half of these traits, you're in a very good position to land yourself a startup role.
Which brings us to the actual interview itself: how do you prove that you're this person before they hire you?
Do the work without permission
This is probably the single piece of advice I give most often to people trying to break into startups: do the work without permission.
some ideas to execute this method.
I sometimes call this permissionless work or show don't tell.
The basic idea is extremely simple. Instead of spending the entire interview process telling someone what you would do if they hired you, find a small way to actually do it before they hire you.
Let's say you're applying for a sales role:
- Go pretend you already work there for a few hours. Figure out what you think their ICP is, open LinkedIn or Sales Navigator, use Clay if you know how, and find ten companies you genuinely think should buy the product. Find the right people inside those companies and maybe even write the messaging you'd use to reach them.
If you're applying for marketing:
- Go through the website and find something you think could be better. Maybe you redesign the homepage. Maybe you come up with a content strategy and actually make one of the pieces. If you're applying for events, come up with an event the company should run, who should be there, why those people would attend, and how you'd get them in the room.
It doesn't have to be some massive project that takes you two weeks. The point is to put yourself in the position of if I started this job tomorrow, what would I actually do? Then do a small version of that today.
This works because most applicants don't do it.
A lot of the messages you get when someone wants a job look basically the same:
- "Hey, I love what you're building. Here's my resume. Would love to chat." There's nothing inherently wrong with that, but it also doesn't tell me very much, particularly if twenty other people have roughly the same resume.
One of the best examples I've personally seen was someone who reached out wanting to work with us at NationGraph and tried to rebuild his version of our app himself. They just went and did it without any permission
Was it perfect? Obviously not, and that's not really the point. What stood out was that this person had spent enough time understanding what we did, formed their own opinion about what could be better, and then actually went and made something. They showed me some of the qualities I talked about above without needing to write "self-starter" anywhere on their resume.
Now let me show you how to do this.
The PDF method
The way I tend to think about this is what I'll call the PDF method, although it obviously doesn't have to literally be a PDF.
Basically, at some point in the process, send the person interviewing you something useful that they didn't ask you to make.
The PDF is not supposed to be some 40-page consulting deck that takes you a week to put together. It should really answer one question for the person hiring you: if this person started tomorrow, what would they actually do?
There are a few different ways you can approach this.
One is a 30/60/90-day plan.
- This works particularly well if you've already had an initial conversation and understand what the company needs. Lay out what you would spend the first 30 days learning or fixing, what you'd start building or testing by day 60, and what you'd hope to have working by day 90.
The closer you can get to actual output instead of hypothetical ideas, the better.
This becomes particularly useful after you've had your first conversation with the founder or hiring manager because now you have information that the other 300 applicants probably don't. You know what they're thinking about. You know what problems they actually have. You know why they're hiring for the role.
Listen for those things during the interview and then use them.
I put the a few examples of my own PDF methods here! If you like my content feel free to subscribe and support, it would mean the world to me 🙏
What I did when I joined NationGraph
This is roughly what I did when I was interviewing for @trynationgraph.
I had an initial call with Kimia, one of the founders, right before I was flying to London for a holiday.
I knew I had an 8 hour flight ahead of me, so before boarding I downloaded basically everything I could find about the company so I could go through it offline on the plane.
POV: 8 hour flight to London, raw dog just building a case study for NationGraph
During the flight, I studied the company, the market, the product, the positioning, and everything else I could get my hands on. I then wrote a PDF laying out my thoughts on the business and everything I would do if I joined.
When I landed, I sent it to Kimia.
I also sent him a photo of myself working on it on the plane, which in hindsight is a little ridiculous, but I wanted to make it obvious that I was serious about the opportunity.
This was Kimia's reaction many months later when we debriefed on it:
proof that it worked i guess!
I think that moment was an important part of why I stood out. I didn't necessarily have the most experience, and they weren't hiring me because I had spent ten years doing growth at startups.
The bet was much more around whether I could execute, move quickly, figure things out, and care enough about the opportunity to actually do the work. What I had done also showed a huge amount of hunger + determination to get shit done.
Instead of me spending another interview telling them that I was hungry and a self-starter, I had spent an eight-hour flight researching their company and given them something tangible to judge. That's really the entire point of the method.
FYI: I went through the normal interview + case study process but doing what I did, improved my chances a lot!
Execution is your advantage
I think this method is especially powerful if you're 0 to 3 years out of school or generally still early in your career.
The problem you have at that point is fairly obvious: you don't have much experience because nobody has given you the experience yet.
You can't magically add five years of operating experience to your resume. You can't point to the three startups you've already scaled because you haven't had the opportunity to do that yet.
But you can show hunger.
- You can show that you move quickly. You can show that you can take an ambiguous problem and turn it into something tangible. You can show that you're reasonably smart through the way you think about the company and the quality of the work you produce.
That's what I think you're really trying to demonstrate when breaking into a startup.
What you're actually showing them is what you're going to be like once they hire you.
And if you don't have years of experience to prove that yet, sometimes the easiest thing you can do is just start doing the job before someone gives you permission.
If you made it this far, thank you! I will be posting more exclusive content here and on my substack here. If you like my content feel free to subscribe to support, it would mean the world to me.
Part 4 will be about how to excel in your first 30 days in your new role.
Thank you for reading up to here if you are still here. Godspeed and good luck!
With gratitude,
Chris
