What it’s like designing at start-ups

An unreliable guide for you to survive what you’ve gotten yourself into

Designing for start-ups is not easy. Most of the time, you’re going to be the sole designer — the one-man-show of design authority in a pizza-hungry team of techies dying to ship half-broken features.

“Ew, start-ups are so disorganised, and you have to do EVERYTHING.”

Most junior designers, sometimes even seniors, frown upon taking on the start-up challenge. And for valid reason: It is not everyone’s cup of tea.

Nothing ventured, nothing gained. If you don’t like to gamble, don’t play the game.

You’re probably here because you’re interested in designing at start-ups; or maybe you’ve already signed your employment contract with one (congratulations!), or maybe you’re in the process of interviewing at one and you’re thinking, “Oh f*ck. I actually don’t know if this is a good idea”.

As someone who is proud to have dabbled in not one, not two, but TEN* start-ups, I’m here to provide you with some comfort and guidance on what it’s really like to be a designer working at a start-up.

*Most of which have folded their doors so far, but no matter. That’s just a tiny detail.

Let’s first address the common myths from Ye Olde Hall of Frequently Asked Questions.

Myth #1: Start-ups are risky

This isn’t really a myth, but a fact. Real start-ups are risky, a lot of them have no product-market fit, no clear revenue model, and it’s a lot of figuring stuff out while burning investor cash in the process. Once that money runs out, you’re officially unemployed.

Thankfully for you, you have a risk-appetite. You’re not afraid of being left without a job at minimum notice! Right? Right…?

The two biggest risks I’ve experienced so far working at a start-up are opportunity risks and financial risks. But we can handle that.

Start-ups don’t usually have a career trajectory planned out for you; a lot of growth and moving up the ladder is something you need to plan for yourself and work hard to attain.

So in terms of opportunities, working at larger enterprises will always seem like a more sound idea. There is a clear way you can work yourself upwards with time, and you are very unlikely to get that same structure and stability at a start-up. But, in exchange for the stability and the highly structured environment at larger enterprises, your growth as a professional is intentionally limited.

Financial risk? Well, I don’t think I have to explain this one, but for my word count, I’ll attempt to do it.

Other than the risk of the start-up bleeding dry and leaving you to your own devices, start-ups don’t usually pay that well. This, of course, is highly dependent on what kind of industry you work for and what position you’re in. A junior working in a sketchy start-up? Yeah, you’re not bringing in the big bucks for a while, so you’re not going to be off to a good financial start.

Despite the risk, I’ve found start-ups to give almost complete freedom and autonomy to most of their employees. So if you’re self-driven and ambitious, this is truly the environment where you could grow, unhinged.

TLDR; Start-ups are risky, potentially low-paying with unplanned career trajectories, but you get all the freedom you want to grow as the trade-off.

For the record, I’ve always grew less and earned less at enterprises than at start-ups. So the risk I took against joining enterprises has always paid off.

Myth #2: Start-up working hours are crazy

After surviving my design school curriculum, nothing is crazier than design school to me. So I am very biased on this aspect.

In all seriousness, start-ups can be quite demanding, even compared to cut-throat consultancies that promote the design-slave-trade. You’ll never know when you’re busy, and when you have nothing to do at all because the workload fluctuates depending on the complexity of the project.

After 5 years in start-ups, I would say that the working hours are crazy in terms of not being predictable, but they aren’t crazy in terms of having extra strict deadlines and doing overtime on the daily.

Sure, we want to ship things quick, but start-ups don’t have the budget to blow to make product mistakes like enterprises, so many founders have learned (forcefully) to take a step back when it comes to how long a good product should take to be completed. In a reasonable fashion, anyway, since speed is one of the edge start-ups have over corporations.

I definitely have (and still sometimes) work longer hours on some days, but I’d like to think that the extra hours are my voluntary contributions for the long-term good of everyone*.

*This is how I always get sucker-punched to exploitation, but I still like to believe the world is a good place for hard workers. If we play our cards right.

Myth #3: Start-ups don’t care about design

This is a funny one because when start-ups even bother to hire designers, it’s pretty solid proof that they do care about design, even if the designers are only hired to make marketing materials for social media posts.

The more correct statement would be that start-ups might only care about design superficially, and not deeply. And you cannot fault them for thinking that, since the amount of individuals who can bring design strategy to the table and successfully use it to bring the business any sort of actual value are few and far in-between.

They do care about design, even if it’s superficially initially. It’s up to us as designers to amplify the value of our skills and weave it into business processes to accelerate decision-making. Designers are very much like secretaries in my opinion, we exist to empower others to do better.

Here’s my typical tenure at a start-up, as evidenced in my LinkedIn profile on how I’ve never stayed anywhere longer than a year thus far. But what do I actually do at my time at start-ups?

Well, you’re about to find out. Vaguely.

First month — It’s hectic AF

Your first month at a start-up will be crazy. Forget getting a proper onboarding, forget slowly familiarising yourself with the product or company workflows. When start-ups hire, they are eager to fill up the role to get the work done.

You will be thrown into a mountain of tasks that were due weeks or months ago. Every single start-up I’ve been in has never failed to follow this pattern.

I enjoy this, but many people don’t and come in with too rosy expectations. Your first month will always be crazy, if it isn’t; your job isn’t real or your start-up isn’t.

First quarter — Productivity

After you’ve cleared away urgent tasks and gotten a gist of what’s the workflow at the company, you’re in for a time of huge productivity. This was when I vibed with my team the most and get a lot of designs out through the door.

The great benefit of a start-up is having your designs shipped super quick and seeing your work being used by real customers in the real world. Agile during these moments truly is a blessing.

6 months — Cards unfolding

Most of my start-ups don’t actually make it this far. By this time they’ve either run out of money, or the founders have fallen out and fired everyone including themselves, or the stakeholders just decided to not invest in design anymore.

2nd quarter onward will be when things slow down a bit, and when you can observe the red flags that pops up in the said start-up you work in. It is also a time where you can cut yourself some slack because you should’ve passed your probation by now, so you’ve earned yourself a chill pill.

This is the time where I really observe the design market and the industry events that happen because start-ups are very volatile and are easily affected by world events. If anything happens, I have to get ready to find a new job, and I need to have prepared a strategy for it.

If I feel that something’s not right, I’m redesigning my portfolio right away.

One year — Bankruptcy

So let’s be real, a lot of start-ups are not managed well. And I am just a salary worker, so when people like me are subjected to bad entrepreneurship or management, we can only accept our fate of unemployment.

You can design the best thing in the world but when you run out of money, you’ve run out of money. You can do all your due diligence checking the founders’ profile and track record, but failures will still happen.

There’s no point playing the blame game, you just have to move on.

So usually by this time my colleagues and I would have gotten a notification about the liquidation of the start-up, and it was time to pack up our work and look somewhere else. If we’ve worked hard during this short tenure, we can pat ourselves on the back because we’ll have a lot of cool things to show for it.

I wish I had a more positive outline of what a good tenure at start-ups would look like, but I haven’t experienced it / am in the process of determining if my current workplace is it. Just don’t be overly-positive or optimistic about the experience and you’ll be fine.

Start-ups are not that scary

My start-up experiences have been crazy because I was part of an economy that could not afford to invest in design, and a time where innovation entrepreneurs or companies had a very difficult time finding a product-market-fit in small markets.

I’m sort of an outlier in this aspect, because I chose, intentionally, to work on high risk products that sometimes didn’t make sense from a business perspective.

I do not speak for all designers working in start-ups, and my experience will not mirror everyone’s. But I think start-ups aren’t all that bad.

Start-ups are the gate for you to do meaningful work

The thing that gets me hooked onto start-up culture is the impact we get to make for the people we design for. Meaningful work is not specific to start-ups, but I’ve found that start-ups provide more options to do meaningful work than most ventures.

Want to work on improving mental health? Want to design the future of digital currencies? Do you desire to improve education and learning through technology? The list of cool things that start-ups do is a long one.

I’ve had the privilege to do really meaningful work because I get to choose where I work and what I work on every single time. And that’s a privilege not many people get if they choose to go corporate or consultancy.

Start-ups hire better (probably)

With the whole drama in design hiring today, and the fact that start-ups in general do not like to waste time, you’ll be getting a slightly better* hiring experience with them than at some mid-sized corporate.

*From my personal experience and the experience of close friends. It’s not great, it’s still crap overall. But start-ups are still slightly better and A LOT easier to deal with in general.

This is completely subjective and biased towards my own experiences, but if you are rushing to get a job to pay for a rice bowl, a start-up is unlikely to take 2 months to get back to you. I’ve closed all my hiring processes with start-ups within 3–4 weeks, the fastest employment contract I’ve signed just took me a week.

If they don’t want you, you’ll know. Then you can save your time and focus somewhere else.

Start-ups usually lead to unique portfolios

Portfolios are one of the most important things to designers. If you’re reading this article, you’re probably here because of my portfolio article.

There is no forgiveness to a bad portfolio. There is no forgiveness to cookie-cutter portfolios. There is generally no forgiveness to designers who don’t work on cool, unique things.

And start-ups usually give designers cool, unique things to share on their portfolio. The best portfolios I’ve seen from the community aren’t from people working in Big Tech or some well-known company, it’s from people who worked at start-ups.

And that’s how you’re going to get your big break in design. Your unique work will be noticed and someone out there is going to give you a chance. If you blend in with the thousands of other designers, you won’t get that chance.

How to look for a design job at a start-up

If I’ve convinced you to give start-ups a try, you’ll probably be wondering where to start looking for such opportunities.

I’ve always vouched for Wellfound* (previously Angel.co or AngelList Talent) as a great starting place to search for start-up jobs in the tech space. They have been incredibly reliable, and I’ve gotten 2 job offers directly off there.

*Not sponsored. Really just my honest opinion.

But of course, nothing in life is easy or guaranteed. You’ll also have to roll up your sleeves and put in some work to get more leads.

I typically look at the top 100 start-ups in my region and go down that list, check their company and career page, and apply from there.

On occasion, LinkedIn throws in some really solid leads as well because the algorithm already knows what I’m sort of into.

Figuring out stocks and shares in your compensation

This is something I get asked constantly by my friends, so I’ll attempt to explain this here. In general, sweat equity is useless in my opinion because most start-ups don’t live to see the day of a proper IPO. But that doesn’t mean you shouldn’t pay attention to what is offered to you.

This video and this video will explain the basics of it much better than I can in text.

I am not a financial advisor nor am I an expert in shares, but my general advice is to pay attention to the vesting period and cliff of your equity, not just its perceived value. Typically, cliffs are a year and vesting periods lasts 2 years.

You can negotiate this depending on how much leverage you have.

I’ve seen some offers where 0.03% of equity had a vesting period of 4 years without anti-dilution clauses in the offer. This is when you know your offer is bullshit* and you should just cut the shares option in your compensation.

Or maybe cut the start-up off because that is a huge red flag.

*Again, I am not an expert. I have been offered one share before (What a joke). Don’t let sweat equity be the excuse for start-ups to lowball you. Sweat equity is just a BONUS at most; it is not something you can feed yourself with until it becomes realised gains, which either takes years or never happens.

Plan your stop-loss

I’ve mentioned a lot about taking smart risks for your career, and choosing to work for start-ups is something you need to be smart about.

If you work at a start-up for a few years, and the company is not showing signs of acquisition or any sort of major growth, please look for something else.

Again, everything is dependent on industry and region, but don’t sabotage your career working for some entrepreneur’s failing hopes and dreams. You are a salary worker at the end of the day, and you need to protect yourself and your future.

A good friend of mine did stay at a start-up for 5 years, was underpaid the whole time, but it got acquired by a bigger player and she got a 100% raise, putting her well-above the median market rate for compensation today.

But she is one of the lucky ones, not everyone has such a happy story to tell and not everyone can afford to give a company so much of their time.

If you want to work at a start-up, do so with caution and planning.

Closing thoughts

I never really gave much thought about working with so many start-ups, and how abnormal it is compared to many professionals in the space, especially considering my super short tenures (which I am working to fix, they are not intentional).

The one perk about being weird or having experiences most people don’t is being able to share some more insight about how certain things work in the world, and for that I’ll never regret this path despite the occasional agony and grief it has brought upon me.

I always say my previous start-up will be my last, but it has become a habit at this point to take risks, and perhaps even gamble with my career in order to work on something interesting.

Again, I know start-ups aren’t everyone’s cup of tea. But I hope with this sharing you get a bit more insight on why it is the preferred cup of tea for some of us.