Joining an Early Stage Startup

Sunday, February 20, 2022

This is a record of some thoughts I wrote out for a designer I was mentoring who was considering her next career move. I wrote it in mid 2020, and only made a few minor edits since. It's probably a mix of things I read online one time or another.

On Joining a Startup

You might like it if have a healthy risk appetite. The higher the risk, higher the reward after all! If you get in early and help grow the company, then you have equity that you've grown! If you have 1% of a $2m company, and that company ends up being worth $200m after 4-5 years, that's a huge financial reason to join! You have to believe in the team, the product, the market, and invest your time wisely.

Get the the magic in the air feeling of working with founders. You get the energy of being on a team of "dreamers". Everyone is bought in, there's often few politics and no red tape. Everyone's excited to build things and send the rocket ship to the moon.

Have big impact. Design and build something well, see customers love it, and see that it generates more revenue for the company!

Work with quick deadlines, while being able to embrace ambiguity. You might work on an entirely new feature and build it in 2 or 3 days. Need to build out reporting? Get something working fast that checks the box.

You'll work on 3x as many projects in the same amount of time. You'll learn by shipping a lot of things. You'll design onboarding, integrations, settings pages, core feature experiences, design systems, and more from the ground up. This isn't done for you, you have to figure it out and put it out there. Afterwards, you'll have experienced shipping many types of projects. You learn a lot quickly.

Learn all aspects of the business. You'll learn how to run a business, and be on top of metrics like how much ARR (annual recurring revenue) you have, and how big your customer contracts are.

Growth is everything. Your entire job will be to grow the company. Every project is about growth in one way or another, whether it's about acquiring new customers, or retention of existing.

Wear all the hats. Be the researcher, marketing designer, product designer, and PM if you want. Learn to code. Learn to sell. Do customer support for a day. There are lots of areas to explore and practice.

Join to get a bigger title. Want to get a higher title? Join a startup and have lots of responsibility, then go somewhere after with all of the learning and experience gained.

Want to start your own company someday? Learn from the people that just started one. You get to work directly with the founders.

Form deep relationships with your colleagues. It can be a bit of an emotional and mental rollercoaster, and you'll lean on your co-workers throughout the peaks and valleys.

These are some of the reasons I joined a startup, but it's not for everyone.

Bigger Companies

Working at a bigger company is a different type of experience and trajectory. At big companies, people are focused on promotions, since that's the way to make more money and grow in their career. That is entirely okay, but you're more focused on choosing the right projects, teams, and getting good optics internally.

At big companies, there's likely to be a good design culture, since you'll spend a lot of time with other designers on your team. At a startup in the early days, the only time you work with other designers is with your customers, or with contractors. It sucks sometimes, but you sort of optimize for other types of learning.

Big companies often have big stock packages and big salaries. You could get a 20-30% higher salary, and big stock package (100-200k over 4 years) at most big tech. Some startups pay well, especially if they've raised lots of capital. You can get a good salary, and stock options that have higher potential to grow.

Big companies have more room for you to focus on your craft, and lean into specific skills slowly. You can certainly spend time going deeper.


In the end, it's your decision! There are certainly benefits to both, and it depends on your priorities, goals, and interests. There are many other great reasons to join a company, and this is just a handful of thoughts that have percolated for me.