sImoN Yee
Product Design

so yo•U •WaNt To joIn a sTA•Rtup

Or, how to hedge your bets playing the startup slot machine

Congratulations! You’ve taken the plunge and are thinking about joining a startup to experience the wide world of entrepreneurship and innovation. Startups can be very exciting adventures to embark on, but they also carry a healthy dose of risk and other factors for you to consider. Please keep in mind that as we progress through this essay, I will be overgeneralizing the nature of startups and enterprise companies for the sake of brevity, and will be mostly focusing on early-stage startups in general, so please take it all with a grain of salt.

Now that we have that out of the way, I will offer some of the insights I’ve gained from playing startup roulette and what the expectations are from a designer’s perspective (though many of the anecdotes here apply to startup life as a whole).

Understanding the Differences Let’s start by briefly going over some of the key differences between large companies and early-stage startups.

No safety net. Unlike large companies where there are a lot of legacy resources and processes in place, there are very few, if any, that exist in a startup. If you happen to be the sole designer on the team, you are the safety net.

For example, if Marketing wants to run a test for a couple of new landing page designs, a large company will likely already have an A/B integration in place that can be easily leveraged. There are no such assurances at a startup. Oftentimes you will be the one that figures out which tools to use, run it by managers for approval, buys the tools, builds the initial A/B test and exports the results.

While bigger companies have a standardized way of doing things and have a bad rap about their methods being antiquated and inefficient (usually it’s justified), at least they are proven and stable. You aren’t going to encounter many procedural surprises in the enterprise world. Not so with startups. Processes can change as frequently as tools (or because of them), and you might have to do a lot on-the-fly tinkering to figure out how everything fits together.

You’re the expert. From what I’ve noticed through the years, this is probably the area designers venturing into startups struggle with the most, and it’s somewhat related to the above point. Basically, you are the design guru for the entire company and will have to answer a lot of questions that you might not have had to deal with previously. While definitely not an exhaustive list, some examples include:

1) The tools that are used:
— Why should this new tool be used over existing tools?
— Do they interfere with existing workflows?
— How do sharing permissions work?

2) The design process:
— How does design work with PMs and other stakeholders?
— What do file handoffs with Engineering look like?
— How do stakeholders provide feedback and keep track of previous iterations?

3) Methodology:
— Apple just released new iOS gestures, what should we do?
— Our PMs want to conduct user research but none of them have done it before, can you help them?

4) Dealing with pushback and conflict:
— We’ve always done it this way and it’s worked fine—why change it?
— Are you sure you want to do something different from what the agency/previous designer did?
— Competitor A does this really cool thing with their interactions—can we try doing that too?

While these are all too common questions that I’ve encountered working with early-stage startups, they’re also not guaranteed. Sometimes startups have had good advisors or strong individual experience and have done a good job operationalizing Design. Also, most of the questions you’re going to get at are going to be relative softballs (We don’t have transparent logo, can you make one?), but the above list serves as a prelude of what to expect.

These are background things that are often taken for granted at a larger company because someone else has defined and maintained a system that works. But there isn’t a “someone else” now, and even if there is, they are likely in the same boat as you.

The point is, whether you get asked easy questions or more intricate ones, your coworkers are going to expect answers for both. If you’re ever asked a question that you don’t have a good response for, answer it to the best of your ability and don’t be afraid to admit that you need to do some additional research. It might be awkward or even embarrassing, but it’s much better to take time giving an accurate answer than giving a BS answer and getting called out on it later when something goes awry.

Compensation There’s no secret here—salaries are generally lower across the board at a startup than they are at a more established company. Startups usually try to compensate for this (no pun intended) by offering equity in the company along with other perks like catered lunches, company outings, happy hours, dog-friendly offices, amongst many other things. A lot of people entering startup land get overhyped on the promise of equity and the prospects of being the next tech gajillionaire, but there are two caveats to be cautious of:

1) In the midst of all the glitz and glamour of Silicon Valley, there’s a sobering statistic to be wary of: half of all startups fail [1]. To put it into perspective, that is a worse percentage than the restaurant industry. Even more sobering is that the article qualified “failure” as a company returning 1x or less to its investors, and most startups consider a return of 10-20x a moderate success, which means that their definition of success may not align with yours.

2) For now, let’s assume that you’re one of the lucky ones and your startup is on track for a successful exit. Fantastic! But unless you are one of the very first employees of a company (usually the first five or ten), the shares given to you would have heavily tapered off by then. There are some exceptions to this, of course—Facebook and Google were supposedly minting millionaires well into the thousands, but those scenarios are exceptions for a reason. The more likely scenario is that you’re around employee #20 and your shares are worth closer to $25K-50K than a million. It’s still a nice chunk of change to have, but it’s important to have realistic expectations so that your motivations for joining a startup are well-intentioned and you don’t end up in a pair of golden handcuffs.

There are also some complicated mathematics involved with stock options, including some with pretty weighty tax and financial implications, that are well beyond the scope of this essay. For example, I once had to write a check for over $6k to exercise some of my shares in a company I worked for—money that I may never see again if the company falters. I happened to have pretty straightforward terms as well as co-workers who helped me navigate the process, so it was something that I had expected. To protect yourself against any unpleasant surprises, it’s best to cover the specific terms of your offer with a tax professional. But for a detailed introduction to the complexities of startup equity compensation, Carta offers a three-part series explaining the process [2].

Now let’s tie it all together: first, there is no guarantee your equity will amount to anything; secondly, take into account the time it took to vest your shares, the taxes you’ll have to pay for, and factor in whether or not the payout was worth taking a reduced a salary for all those years. Is it worth it? Could you make more taking a higher salary and lower equity elsewhere?

Money isn't everything, of course. Each scenario is entirely situational, and every individual has a different tolerance for risk. Use your best judgment and evaluate what’s best for your own situation. The takeaway from all this, however, is that equity should be considered as nothing more than a potential “bonus” if all things go well, but never anything to base your retirement on. Look at it as if it were a lottery ticket with slightly improved odds. But if your gamble pays off and you get that 100x return, then props to you.

A comparison of how startup compensation compares with some of the tech giants. [3] [4]

Advantages Now that we’ve covered some of the big differences, let’s explore the pros and cons of working at a startup. We’ll start with the positives.

Lower barrier of entry: Generally speaking, it’s typically easier to land a job at a startup than it is with a more established company. The main reason is because startups are desperate to hire designers but don’t have many resources to work with. They often don’t know how to vet them, how to interview them, or even where to find them. I’ve advised several startups with their hiring needs and this is a situation I’ve repeatedly experienced.

Contrast this with larger companies who have a set design culture, a higher number of applicants, and look for more specific types of designers, and you’ll start to see why the barriers of entry are so different. The lower entry point is not so much a question of skill as it is of circumstance. What this means, however, is that this can be beneficial for designers who have limited experience or are pivoting from other disciplines. Just make sure that the company has other structures and foundations in place that will help you grow.

Please understand that in no way does this imply that designers at startups are less talented or skilled. On the contrary, because these designers have to learn very quickly in a trial by fire, they often become very well-rounded and work better around constraints. Some of the strongest designers I’ve met hail from companies nobody has ever heard of, but are doing really innovative things because they had to.

Learn/grow faster: Since you have to become the expert in all manner of design subjects, you’ll end up learning a lot of things that you never had to before. Because there isn’t a cornucopia of resources at a startup, you’re always doing something. So if you’re not pushing pixels, then you’re doing user interviews, reading up on the latest tools and trends, researching some front-end framework you’re not familiar with, planning out the next design timeline with PMs, and a whole bunch of other things. Whereas larger companies kind of shield designers from this need to self-educate, it’s highly important and critical to the role at a startup. While yes, you can find designers like this at a larger company, they usually have lofty titles like “Principal Designer” and the pressure to do grow isn’t as critical because there are so many safety nets in place.

As a result of this growth, you end up becoming the designer equivalent of a Swiss Army knife, or in tech parlance—a “full stack designer”—and end up more well-rounded and knowledgeable about design as a whole than many designers at large companies who primarily focus on a few key responsibilities, which brings us to the next point...

Ownership: At a large company, you’ll most likely be iterating on existing features and screens, since much of the heavy lifting has already been done. For the majority of the time, there won’t be a lot of high impact work on highly visible projects, and it can feel like you’re just a small cog in a very big machine. Instead of reinventing the wheel, you’re greasing the gears. This feeling of redundancy is perhaps the biggest reason why designers leave the comfortable environs of rockstar companies and venture off into the wild frontier of startups.

At a startup, you get the opportunity to own whole features, products, and even the entire platform. When showing off your work to friends and family, you get to say you worked on all of it, from the strategy to the icons. This is much more interesting to talk about than some obscure modal that a company needs for compliance reasons.

How do we use this app again?

Working cross-functionally: Being part of a startup involves wearing many hats, regardless of role. You’re the CTO of the company? That must mean you know how to change the printer toner. You used to do phone sales in a former life? Great, you can help set up our inbound phone network. With that said, your role as a designer will often include becoming an expert in other domains as well, especially the teams you work closely with. For example, if you work a lot with Marketing, you’ll likely learn a good deal about conversion funnels, heatmaps, and LTV/CAC ratios.

This is more out of convenience than necessity, as humans tend to pick up on the tendencies and interests of those we spend time around, but it is something that will only help develop your well-roundedness as a designer. You will be armed with much more context and can pre-emptively integrate the business needs of the teams around you into your designs in an organic way, rather than have it as an afterthought or a band-aid solution.

Disdvantages Lack of peer feedback: while being the primary source of truth and in a position of instant leadership can be exciting, it can also be one-dimensional. One of the biggest problems with being the expert is that you live and die on your own expertise. There isn’t anyone with more proficiency to offer alternative solutions, provide constraints, or help you become a more effective leader. Without that kind of feedback, it can be difficult to determine whether you are doing your job “right”.

Lack of community: This is related to the preceding point, but designers are social creatures by function, and sometimes we just want to bounce ideas off each other and discuss designer things with like-minded individuals. It’s much more engaging to chat about the latest design tool or complain about the latest Sketch bug with the person next to you than it is trying to explain the nuances of these conversations to a layperson, or posting it to a design forum and waiting hours for a response.

Having a design community can also cut down on a lot of the time devoted to researching things that you’re not familiar with. For example, if there’s a design workflow that you’re considering integrating into the team’s process, it’s much more efficient having another designer on board who can share their opinions on it instead of spending hours scouring the web for its pros and cons.

Design everything: Since you are the main point of contact for all things design, expect to see regular requests for all manner of things. Everything from employee badges, email newsletters to conference booth signage, swag—you name it. If you’re thinking about joining a startup, you might as well brush up on your print design skills, because chances are high you’ll be creating a lot of physical collateral.

While some of this can be a fun creative outlet, it can also negatively impact your workload and create friction around prioritization. Without a larger design team to 1) filter the requests; 2) properly assign them; and 3) manage the workload; the work can become overwhelming at times. This is especially true when everybody says their requests are “urgent”. It also makes it harder to say no and deny requests, as the lack of a team is perceived as a lack of power. The end result is that instead of working cross-functionally, designers are overloaded and would rather just acquiesce to demands in order to stay float.

Designing swag can be super cool, but not if you're slammed and haven't done print work in years. Wait, is it RGB or CMYK? [5]

Evaluating Startups When chatting with startups to determine if there might be a mutual fit, be sure to ask meaningful questions to ensure that their design philosophy aligns with yours and that it is a place that will empower you to do your best work. Every company will say they value and care about design, but do they really? Listed below are some questions that can help you make that determination.

Who does Design report to? As I mentioned above, being a designer at a startup requires wearing multiple hats. How the reporting hierarchy is structured can offer insight into what the day-to-day hat wearing looks like. A good number of startups have Design as part of the Product team, this usually makes the most since you’re a Product Designer after all. But I’ve also seen Product Design reporting directly into the CEO, which is phenomenal, since it gives Design an automatic seat at the table and instant leverage in the decision making process. Conversely, I’ve also seen Product Design report into Engineering, which doesn’t make a whole lot of sense to me and is something I would consider a potential red flag.

What experience does management have working with designers? How involved were the designers in the visioning and strategizing processes? Do they have an example where working with designers was a success? How about one where it was a failure? What factors contributed to the success and failure of each?

Are you empowered to succeed? Does it look leadership is serious about giving Design a seat at the table, or is Design merely an afterthought—meaning, is Design solving problems together with relevant stakeholders or simply executing off of a PRD written by a PM? When you mention doing usability studies, are they committed to allocating resources, or are you told that there isn’t enough time to conduct one?

What can you accomplish there? Or better yet, what has already been accomplished there without Design? How can Design contribute further to the tasks that have already been completed? Inquire about the timeline for the first six months on the job. How about after a year? What are the priorities? Are there any mentions of scaling the Design team further?

Finally, find out how success will ultimately be measured (and rewarded). What are the concrete metrics that you will be measured on?

The point of asking these questions is to assess the company’s design intent. It’s one thing for a startup to say that it’s a critical component of the organizational DNA, but their actions should demonstrate it. A startup that truly values design should already have tangible elements of it in place, or at the very least, be committed to do so. If it looks like they haven’t even taken basic steps to champion Design, then it should be another red flag.

Conclusion Working at a startup can be a great and rewarding experience. You will learn a lot of new things in a frenetic environment with like-minded individuals. As a result, startup designers usually become much more well-rounded than their enterprise counterparts, and there’s always the potential of a huge monetary payoff—or a reduced paycheck.

At the same time, the startup environment may not be for everyone. Things are constantly in flux and because everything moves so quickly, it can feel like you’re playing catch up all the time. Learning new tools and processes can be incredibly valuable for career growth, but not everybody enjoys the feeling of cramming for a never-ending exam. Larger companies may not seem as sexy, but they have certain merits that are worth considering.

There are a ton of startups out there trying to solve some really big problems, so there’s a lot to get excited about. At the end of the day, you’re the best judge of how to best balance your temperament, life stage, and personal priorities with your career goals and aspirations. Hopefully, this essay helps you make an informed decision.

If you have any more questions about designing at a startup, or startup life in general, please feel free to reach out.

Resources Designer Fund, How to Understand and Negotiate Your Startup Compensation
Google Ventures, How Top Startups Pay Designers
First Round Capital, What to Do When You’re the Only Designer They’ve Got

Footnotes [1] Fortune: "Conventional Wisdom Says 90% of Startups Fail. Data Says Otherwise."

[2] Carta: Startup Employee Stock Options 101
Part 1
Part 2
Part 3

[3] Salaries were calculated by aggregating data from Levels. I tried to get as much parity as possible by comparing similar roles, but because not all salaries were available for each level, I had to settle for an IC4 at Facebook, L3 at Google, and IC5 at Amazon—which all fall into the junior to mid-level range.

Amazon's salary seems low because it generally is, in comparison to their competitors. They also weight their vesting schedule towards the back half, when the numbers explode in year 3. Since I was only comparing salaries for junior-level designers who have zero to two years experience, it made for a larger-than-normal disparity.

[4] Salary data for designers at startups was taken from Angel List. Equity was calculated by using a combination of formulas taken from 80,000 Hours to estimate average equity percentages and exit values.

[5] Image from Kaitlin Sullivan / Blend