how to pick the right startup to join [full guide]

In Part 1, I broke down the types of roles I think you should be looking at if you’re early in your career, non-technical, and trying to break into startups.

Most of them sit somewhere around revenue: sales, growth, marketing, demand gen, or increasingly, GTM engineering.

You can read the full article here.

But knowing what you want to do only gets you halfway there. The next question is arguably harder: which startup should you actually join?

There are thousands of startups you could work for. Every year, YC alone produces hundreds more. Add every other accelerator, seed fund, Series A company, and startup that just raised a round, and you have way too many options to evaluate one by one.

I don’t think the answer is to browse LinkedIn until something looks interesting.

When I was deciding where I wanted to work, I tried to make the process much more mechanical. I came up with a small number of things I cared about, decided which ones mattered most, and used them to narrow down the companies I was willing to spend serious time pursuing and tracking.

Basically, I made a decision matrix (really not that complicated I promise).

Step 1: Start with your non-negotiables

Before looking at companies, figure out what you actually care about. These are going to be different for everyone, but when I was looking, mine were roughly:

1. The founders had a good track record. Ideally they had previously founded a company, worked at a startup that had reached meaningful scale, done great things or otherwise had a track record that made me believe I could learn from them.

TLDR: I wanted to work with founders who have seen “excellence”, Kimia (NationGraph’s Co-Founder sold his company to Ramp and then spent years there witnessing hyperscale).

2. The company sold into the U.S. I wanted exposure to the U.S. market and companies selling into a large customer base. Nothing special here, just believed that if it’s B2B it has to have some U.S exposure to be successful.

3. I found the market interesting. I don’t necessarily think you need to be obsessed with the industry before joining. But you should be curious enough by the thesis and compelled by the problem to want to go and solve it!

For me I spent years telling founders as a VC to avoid selling not the government because of how slow sales cycles can be. For me to realize that in reality NationGraph solves a lot of those problems in government procurement.

4. Strong investors were around the table. This mattered to me, although less than the other factors. Having great investors isn’t proof that a company will succeed. Plenty of heavily funded startups fail. For me, I just viewed it as another signal that smart people had spent considerably more time doing diligence on the company.

And most importantly your list might look completely different.

• Maybe you care about working in person. Maybe you want to move to San Francisco. Maybe you want to work somewhere with 20 people or fewer. Maybe compensation matters more because you have financial obligations that make taking a huge risk unrealistic.

Take a lot of time to think about these factors. This is probably the hardest part in my opinion to nail down.

Step 2: Weigh your factors

Not every criterion should matter equally so make a spreadsheet and write down your criteria down the rows and the companies you’re considering across the columns. Give each criterion a weight from 1 to 5 based on how important it is to you, then score each company against it.

For me for example: the quality and track record of the founders would have been something like a five. The investors might have been a two.

Multiply the score by the weight, add everything up, and you have a rough ranking. That’s it! It’s not that hard, it’s only a bit of mental math and then thinking deeply about what you care about.

All you have to do is multiply the weights by the company score and tally the score to get the total weighted!

For the record, I wouldn’t blindly join whichever company Excel tells you scored 84 instead of 81. The point isn’t to outsource your career to a spreadsheet. It should just force you to answer a much harder and honest question:

What am I actually optimizing for?

When two offers look equally exciting, or when you’re deciding which five companies deserve 90% of your job-search effort, having an answer to that question is incredibly useful.

This is roughly how I thought through my decision to join NationGraph

Stage of the startup matters more than you realize

One of the things I would explicitly include in this decision is what stage of startup you actually want to join. People talk about “working at a startup” as though joining a 12-person seed company and joining a 700-person Series D company are basically the same experience.

Well unfortunately they’re not and quite different!

Generally, the earlier you go, the more risk you’re taking and the less structure you should expect. But also the greater the reward to be reaped at the end.

At a seed or Series A startup, your job description might be directionally correct at best. You could be an individual contributor reporting directly to a founder or senior executive. There may be nobody above you who has done your exact job before. and processes aren’t documented because half of them don’t exist yet.

You are going to spend a lot of time figuring things out yourself and for some people that’s the entire appeal.

You get autonomy much earlier than you probably would at a larger company. You can take ownership of things that would be three levels above your pay grade somewhere else. If the company works, you also joined early enough that both the experience and your equity can become meaningful.

The tradeoff is obvious: the company might not work out like 99% of startups fail.

Toward Series B+ and beyond, and some of that risk starts to come down. Ideally, there is stronger evidence of product-market fit, more customers, more revenue, and a clearer organization around you.

You’ll probably also get more structured learning. There are managers. There are established functions. Someone may have actually written down how you’re supposed to do your job. But you give something up too.

Your scope can be narrower. There are more people between you and the founders. There’s less blank canvas to take over. And, generally, you’re joining after more of the company’s value has already been created.

Neither is inherently better. They’re just different bets that you’re making and you should be aware of those differences as well.

When you’re young, you can probably afford a little more risk (mostly)

This is personal, and there are obvious exceptions, but I generally think being young is one of the better times to take startup risk.

If you’re 21-25 y/o and have relatively few obligations, the downside of spending a year at a startup that doesn’t work is very different from the downside when you have a mortgage, kids, or people financially depending on you.

That doesn’t mean you should join a terrible seed company because someone gave you a cool title and 0.1%. It means I wouldn’t optimize all the risk out of the decision.

If I found a very early company with exceptional founders, a market I believed could become enormous, signs that customers genuinely wanted the product, and a role that gave me an absurd amount of ownership, I’d be willing to accept that it might fail.

Because the upside isn’t only equity. It’s what happens to your career if it works.

Being early at a company that goes from 20 people to 500 can compress years of learning into a very short period. Your responsibilities grow because the company is growing faster than it can hire people to fill every gap. If you’re good, you can end up owning things much earlier than you would in a more established organization.

That’s the kind of risk I’d personally want when I’m young.

How do you actually find these companies?

This is probably the easier part.

If you spend enough time on X and LinkedIn, you’ll start seeing interesting companies constantly. Funding announcements, product launches, founders posting about what they’re building, investors announcing new investments, people leaving larger companies to start something new.

You can also be more systematic. Go through YC batches. Look at the portfolios of funds you respect. Browse accelerator directories. Look at which companies have recently raised. If you want to get nerdier about it, you can use tools like Exa or Parallel to web scrape pull together and research companies at scale.

I wouldn’t overcomplicate this part, though. There isn’t a shortage of startups. The hard part is deciding which ones deserve your time.

I’d rather have a list of 20 companies that fit my criteria extremely well than a Notion database containing 2,000 startups I know nothing about.

Once you’ve built that shortlist, then you can do the work from Part 1: learn everything you can about them, figure out where you could be useful, create proof of work, and find a way to get in front of the right person.

Do the extra diligence

Talk to employees. Talk to former employees if you can. Use the product. Look at customers. Understand why people buy it. Ask what the company has accomplished since its last funding round. Ask what would need to be true for the next two years to go exceptionally well.

You’re evaluating them too, as much as they are evaluating you.

Some gut check questions to ask yourself

After all of this, I think the most important criteria are actually difficult to put into a spreadsheet. Go ask yourself these “gut check” questions to make sure you’re ready to make the choice when the time comes.

List of non-exhaustive questions to ask yourself in the process.

Here are some of my favourites below that I used:

• Are you going to be given enough autonomy to do great work?
• Are the people around you exceptional?
• Are you going to learn from them?
• Do you think you’ll like working with them?

You can join the hottest startup in the world, backed by every investor whose logo looks good in an announcement, and have a terrible experience if you’re working for someone you don’t respect and doing work nobody trusts you to own.

Especially early in your career, I would optimize heavily for the people.

POV: At the Nationgraph office having fun

Your manager, founders, and first few teammates are going to shape how you think about work. You’ll copy how they communicate, how they make decisions, how quickly they move, what they consider good enough, and what they expect from you. You want the bar around you to be high.

The best situation, at least for me, is a company where you feel slightly out of your depth but the people around you trust you enough to figure it out. That’s where a lot of learning happens.

You can’t eliminate the risk of joining a startup, but you can be much more deliberate about which risks you take.

And when you’re early in your career, I think choosing the right people, the right amount of responsibility, and the right learning curve matters a lot more than finding the perfect job title.

As much as you’re placing a bet on a company you want to make sure they bet on you too.

Part 3 next will cover how to get the job once you know what role + company you want to work for.

With gratitude,

Chris