A Designer’s Guide to Working in Tech

Big Companies   Mid-Stage Startups   Early Stage Startups

A shift in how we work

Many of us who trained as graphic or industrial designers could never have envisioned a career in technology — and then suddenly, given the rare combination of timing, opportunity, and market, we find ourselves thrust into an industry that we’re not just new to but is also rapidly changing how all people work.

Our training is still suited for more traditional paths in the arts and design, instead of preparing us for industries that are rapidly changing and emerging.  And as startups and technology continue to “eat” more and more of the world, our talents have come into higher demand at those companies—to make technology products more innovative, useful, empathetic, and beautiful. While it may be hard to see on an individual level, this shift is as large a societal change as the industrial revolution. And this growth has created an environment where, much like being a skilled software engineer, being a skilled designer can translate into hundreds of different career paths each with their own risks, rewards, and opportunities. This is a good problem for an industry (and an individual) to have, but can be intimidating as we are whisked along to new and foreign places in our careers.

Just like most designers I have met and worked with, I have experienced these feelings first hand. Throughout my career, both the nature of my work and the types of companies I’m doing it at has changed dramatically. I’ve worked at big tech companies (Google, Apple) doing product design, design agencies (IDEO) doing graphic design, in-house design teams (adidas) doing brand and apparel, and freelance (all of the above). Most recently I started a company (Oyster), designed the products and brand, and built our team and service to scale, and then acquisition (to Google). Now, in addition to my role at Google, I’m investing in early stage startups and helping founders with product and design. Each experience has utilized my fundamental design skill, but has also pushed me in a wide range of ways that I would have never anticipated while studying graphic design at RISD.

Some notes on this guide

This guide attempts to share insights specifically into those areas beyond design practice that tend to be the most uncomfortable and foreign to designers. Throughout, I’ll take an in-depth look into the hiring, work, learning, risks, and compensation of companies in every stage from new ventures to global conglomerates, and the movement between roles at each.

This is a collection of resources and stories from my own experiences, and those gathered from other designers and leaders, to help people at any stage navigate a career that will take them between many roles, companies, and markets. It’s important to try and evaluate the opportunities in these different companies in terms of what is best for you, what you want to learn, and ultimately, what you want to build and create.

Understanding the opportunities in tech

Today, we are in a period of maturation in tech, a very broad term, referring to a rather specific set of companies; primarily those that exist in what we consider today to be the “consumer internet” such as Pinterest, Airbnb, Slack, and Spotify. These businesses have leveraged design to differentiate their product and brands to build meaningful advantages against competitors and incumbents.

As this industry matures, designers are moving from working broadly in the tech industry at-large to specializing in specific trades and segmenting further by company size. This specialization often happens along two interconnected pathways—market and stage. Market-specialization is becoming an expert working in something specific like e-commerce, social networks, autonomous vehicles, or personal finance. And, within each market, there is a diversity of companies and opportunities at different stages. Designers carve out their sweet spot in terms of the company stage that makes the most sense for their lives and ambitions, perhaps choosing to work primarily in small teams with startups, on their own schedules in freelance, or with the support of bigger companies.

And, because of all of this, you should equip yourself to think of the opportunities ahead of you not necessarily as parallel options but completely different paths and roles.

Big company

Big Companies

I’ve worked at what qualifies as a “big tech company” at three separate points in my career — illustrating both how fluid the tech job market can be as well as the unpredictability of where your career will lead you. The draw of a big company is that you will be afforded more opportunity to develop design skills, work on heads-down design, and focus on your area more than you’ve ever done before. In the summer of my junior year at RISD, I was an intern with Apple’s Human Interface Group where I worked with a small design team on interfaces for the iPhone and MacOS — my first experience working in anything like tech. After working at IDEO after graduation, I took a job at Google working on Maps as a lead designer — a new experience connecting and partnering with large engineering organizations. And finally, I now find myself back at Google, after selling my company Oyster to Google Play in 2015 — a unique experience combining the environment of a big company with the task of building & leading a new team and projects across several offices.


  • Google, Microsoft, Facebook, Netflix, Microsoft, Amazon, Uber, Airbnb, Twitter, Spotify
  • Public companies or 10B+ valuation; private companies likely to go public
    2000+ employees and often 100s or 1000s of designers
  • Large product portfolio and several product teams operating somewhat independently within a larger organizational hierarchy.
  • In order to court the best talent and operate in a wide range of markets, these companies tend to have many offices distributed worldwide.

Hiring at Big Companies

  • Big companies are (nearly) always hiring. The industry giants are constantly backfilling for vacant roles, staffing up new projects, and tend to hoard design talent. They are increasingly aggressive in hiring designers right out of school and out of adjacent industries (advertising, graphic design). For this reason, don’t be discouraged if you don’t have direct experience, these companies need to hire and design talent remains a very rare resource in tech.
  • Given their scale, the hiring process can feel removed from the job you’re interviewing for. The person you’re working with most closely during the hiring process often a) isn’t a designer and b) will never work with you directly if you join the team. This can feel a little alien, but tends to be the way big companies operate for organizational efficiency. Interviewers are trained employees that know what the company is looking for in new hires. This applies to any role but if you have a friend or connection that works there (or any contact really), always reach out first. Companies today often offer employees a referral bonus and coming in through a warm reference is nearly always better than simply applying directly.
  • Judge the opportunity on the team and project. When going through the hiring process at any big company, you should judge the opportunity by the team and product, not just the company’s reputation for design and product. A company like Google or Microsoft is so large that team A and team B could be led and run in completely different ways. Push to get to know the people you’ll be working with every day before signing on the dotted line. During the hiring process with Google Maps, I visited and spent the day with three separate teams (Maps, Chrome, Android) getting to know the managers, work environment, and team. The Maps team appealed to my background, interests and sensibilities — and became my new teachers, mentors, and friends.

The Work at Big Companies

Organizational layers give shelter for focus but also insulate you from the gears that turn business. The design team you will join is part of a bigger team that usually includes product management and engineering. This team is part of an ever bigger cross-functional sub-organization that rolls up functions like marketing, customer service, and business strategy. In short, there are layers. Layers are both a blessing and a curse. They give you the chance to specialize, learn on the job, focus on trying new technologies & tools, and offer role-related mentors within close reach. But they can also insulate you from larger business goals, the challenges of growth, and the complexity of technologies and processes that are outside of your focus area. If you want to understand the broader business goals and how your work can affect them, you may have to seek out those people and metrics yourself.

  • Your team’s quality is a huge determinate of your success. You’ll find that your design team is your tribe and that their ethos, mission, and work ethic will affect and shape yours. If you’re a junior employee, your success on that team will largely follow how effective those around and above you are. When on Google Maps, the leadership inspired and brought the team together around a shared love of the history of maps — a passion that extended to the work and way the entire team approached cartographic design. If they have a great relationship with executive leadership, you will too. If they’re embroiled in corporate politics, that may be your experience as well. This is a good lesson in surrounding yourself with positive and impactful colleagues and mentors. If you’re having trouble with the quality or personalities on your team, the good news is, if you don’t like what you see, you can work to transfer internally to something new.
  • Personal advancement may feel like a predetermined track. Career advancement, salary increases, and benefits are carefully planned and organized across the company. As you advance, the ladder typically forks—either to double down as an expert individual contributor or to move into people management. Navigating this part of corporate culture can be especially hard for designers who were never trained to think of their craft as a pre-determined career ladder. Work hard and progress into new roles that have fulfilling projects and responsibilities.
  • Leadership roles focus on creative management more than creative direction. One of the most concrete takeaways I’ve had from working within leadership positions at big companies is that the more senior the role, the more likely it is your responsibilities skew toward management and staffing and away from creative direction or vision. This seems to stand in stark contrast to agencies or other smaller companies where the senior design staff also act as creative leaders or visionaries. While it’s really dependent on the team size and organization, this bias toward team growth, hiring, and strategic planning seems to be the norm for leadership roles in larger companies.
  • Shipping work takes a lot of time (and people). I’ve often likened the impact an individual designer can have quickly at a big company to turning an oil tanker’s course a few degrees. It might be a big change, but its effects won’t necessarily be felt for a while. This is especially true if you’re working on a core product for the company. The entire product development process will be extended to meet goals for all teams involved: infrastructure engineering to ensure scalability of projects, proper legal and marketing checkpoints, in-depth user research. Don’t be shocked if you soon find yourself in regular meetings with 15-20 people from all across the company, some of whom you don’t even know by name. Big organizations are political; maneuvering those groups of people to get what you need (or want) takes a whole set of skills you never anticipated needing.

Skills & Learning at Big Companies

  • Your design skill will almost definitely deepen. The draw of a big company is that you will be afforded more opportunity to develop design skills, work on heads-down design, and focus on your area more than you’ve ever done before. The resources the company has should afford you to push the envelop with design concepts and development methods. Use the opportunity afforded by this to turn routine projects into opportunities to challenge your skills, design toolkit, and core abilities.
  • Your responsibility largely ends with your domain. Until you reach the senior ranks of your team, it is unlikely that you will be responsible (or have much exposure to) marketing, hiring, product strategy, or management unless you specifically seek it out and make it a priority. Even then, big companies, especially ones with growing and profitable business-models often have a more siloed relationship to that type of shared responsibility than a startup.
  • Learning opportunities abound. You will have seemingly infinite access to internal growth programs, education, and workshops that can cover things far beyond your role—want to learn to write python? Learn from one of its original authors. Want help planning your personal financials? A finance VP from the company will lead a regular workshop. Big companies are worlds unto themselves and there are a ton of opportunities to seek out smart mentors who are happy to share their experience. This can feel especially daunting coming straight from a small academic environment but embrace it and try to immerse yourself in the culture of learning.

Compensation at Big Companies

  • You’ll have great perks. Things like lunch, your gym, or your home internet is often included in your compensation at a big company. Big companies also have fantastic retirement savings programs (matching your contributions, etc) that you should take advantage of. Take all of this into account when assessing compensation—it could equal something equivalent to a 10% boost to your overall package.__
  • There is a ceiling on your financial outcome, but it’s largely guaranteed. You’ll likely have a salary bigger than anything you’ve ever seen or expected (especially if you’re a new grad or moving from another industry). But remember, your net income is relatively locked in and as you’ll get raises as you move up the ladder. While there may be more speculative projects you can join that offer a bit more variability in your income, chances are you will be very secure and can be putting some money away. If the company is pre-IPO you can expect a good return whenever those shares become freed-up—but the financial risks and returns are an order of magnitude greater than a public blue-chip tech company.
  • Learn about your company’s stock-based compensation plan. It’s common that a large portion of your annual compensation will be in stock grants that vest over a period of months or years. While most plans for public companies are similar in structure, take the time to learn about the specifics of your plan, when you get paid, tax rules, and how to plan your finances. And remember, pre-IPO companies play by a completely different set of rule and structures. It’s as much a responsibility as developing good communication skills or being a good leader — just because it’s money, doesn’t mean you need to treat it as taboo.

Stray Observations of Big Companies

  • Not everyone sees the job as their “calling.” Unlike a startup there are many on your team who will probably see the company as a job, not a mission or calling. This can be for any number of reasons — a more balanced work-life, a more relaxed way of life, different stage of career, varying ambitions, etc. While it may be difficult to get comfortable with this, embrace it — you will get some valuable perspective beyond your own work and stage of life.
  • Internally the company will feel like it’s own universe. Big companies are building more incredible things than ever before — sci-fi style projects that are only rumored about on the outside. Once on the inside you will be hit with a tidal wave of new information that only gets shared internally; resources for every imaginable topic, new skunkworks projects, internal development (dogfood) versions of your favorite apps, and ground breaking technological achievements.
  • Make use of your free time to build your network. At a big company there are often thousands of leaders in their field all around you — well beyond design. It’s an incredible opportunity when used correctly. Try using your lunch and free time to meet new people both socially and professionally — even if they’re not on your team or product. The network internally is huge (see previous bullet) so seek out people with common values and interests — it will make work more personal an fun and pay off in the long run as you continue your career, either at the company or elsewhere.

Medium company

Mid-Stage Startups

Mid-stage startups are “off-to-the-races” and are often high-growth companies that have been in their market for a few years, either having established some sort of leadership in customer base, technology, or capital raised. This is an opportunity to join a company that is significantly lower risk while still having the chance be a part of a fledgling team and have a hand in shaping the company’s direction and future. What you may lose out on against bigger companies are some of the structures and perks, and a more favorable work-life balance. When compared to early-stage startups, you may feel like you’re inheriting a more mature product or design language versus having the opportunity to build it as your own. Mid-stage companies can be very case-by-case in how mature and organized their design and product processes are. I’ve seen all walks of this in companies I’ve advised and while this can be a bit frustrating if you’re considering joining a company it often follows how central design is to their core product or how senior of a role design holds within the company’s leadership.


  • Stripe, Shyp, Omada Health, Casper, ClassPass, WeWork
  • <1000 employees.
  • Likely still have one main office, perhaps a satellite sales office in New York, customer service operation in Nashville, or an engineering office in San Francisco.
  • Post Series B or C in funding but IPO might not yet be on the horizon.

Hiring at Mid-Stage Startups

  • Don’t be surprised if the hiring process feels a little disorganized or (on the complete other end of the spectrum) overly formal. The size of the recruiting team and hiring process at mid-stage companies can vary widely. Some have already invested in building out operational systems of a larger company. Some have yet to dedicate appropriate recruiting resources for their stage of growth and are still operating “by the seat of the pants” nature of an early stage start-up. If anything about the role or the interview process seems ambiguous, mention it to the recruiter or hiring manager. Do consider this as you’re making a decision; I’ve found that the hiring process and how a team introduces new hires is closely correlated to the actual culture of the company.
  • Hiring is often more opportunistic. Hiring pace and volume may be a bit situational based on new fundraising or growth in a specific product area but chances are they’ll be opportunistic—if someone great applies or contacts them, they’ll be more biased toward hiring or tailoring their needs to a specific candidate. If you don’t see anything on their careers page, browse LinkedIn or Google and find designers that currently work there and email them directly with a short, complimentary note expressing your interest and background. It will go a long way and may have a higher likelihood of success than emailing founders directly.
  • You’ll likely be evaluated by employees at all levels of the company. You’ll meet a few senior leaders within the company during the hiring process. This could include founders or leaders within your focus area. Remember, given their work, they’re probably interested in learning about you beyond your design skill (they’ll leave the designers to evaluate that)—so be prepared talk to them about the company’s mission, business goals, and their vision for what’s to come. They’ll leave impressed with your perspective and you’ll learn more about the inner workings of the company and how it’s doing. Depending how thorough the process is, you will see a lot of the people you will be working with during the interview process.

The Work at Mid-Stage Startups

  • You won’t be the first designer and will have other designers or a team to work with. While these startups are not giant organizations and everyone may still sit on the same floor, you’ll be a member of a small design team that may still be charged with design throughout the entire company (product, brand, marketing, etc). This will make your little group more visible within the organization as you and your teammates are the go-to people for a range of problems and tasks. If you’re interested in broadening your design skills while still having the support mentors, this is an ideal opportunity.
  • Your work will affect the company, right from the get go. At this stage, the design team is probably a pretty small percentage of the company—and depending on the product and focus you will likely need to punch above your weight class. Depending on the size of the team you may get a lot of exposure to a broad range of design work: marketing, branding, product, interaction, prototyping. Your skills will be in high demand and you may find yourself working with senior team members across the company.
  • There are opportunities to push yourself into new areas. If you have entrepreneurial passions you may be able to broaden your experiences— from building a design culture and establishing design’s place in the company as it grows—from creative and product development processes to user research, hiring, and project management. Many growing design teams I’ve worked with have earned recognition from their designers’ passion projects, whether it’s pushing forward and hosting meetups on design tools like Framer or implementing creative marketing efforts (like the time at Oyster when we rented and designed a free coffee truck for Book Expo America).
  • Your work will ship early and often. You will have a hand in the development of internal styles, processes, and product planning. You will still have a support network of other designers and senior team members but you may be expected to start treading water on your own more quickly. Having the opportunity to ship early gives you a quick view into how a product comes to life at your company, but even more critical is how the team responds after launch — customer feedback, bug reporting, and future version planning.
  • Company growth creates new opportunities for individuals. As your interests develop you may find some openings and fluidity to your role as a designer to specialize or level up quickly as the company grows. Most companies have a bias toward internal promotion and would prefer to grow and cultivate internal talent. Opportunity to grow across the organization, even if it means moving teams, is there, but you have to go and take it.
  • Leadership responsibility can vary wildly. Mid-stage companies will often still have their entire design organization consolidated into a single creative team, as was my experience at Oyster. For leaders, this means you may be managing an organization that is responsible for marketing, visual design, branding, product design, and perhaps more. This can lead to variability with whom you report to (even project to project) and, as the company grows, can cause some complications when the team needs to be broken up and specialized further. On the upside, this type of role and team organization allows you as a creative leader to present a unified perspective and voice to nearly every aspect of your company’s offering. In my own work, this has been a critical aid in rapidly building an emergent brand and product while maintaining consistency and quality across the experience.

Skills & Learning at Mid-Stage Startups

  • You will become an expert in the company’s market and focus. While this should be true of any company you work at, mid-stage startups (and smaller) are going through a lot of the growth pains and spurts that give their employees a crash course in whatever their market may be (real estate, media, finance, food systems) and that will mean you need to be excited to learn these things! After 4 years at Oyster, I now know more about the media industry, digital rights, subscription economics, and books than I ever thought I wanted to. By no means does it need to be your life’s passion but when evaluating opportunities, I’ve often asked myself “If I could work at any company (big or small) in this market, would this be the one?” This question, while simple, forces you to evaluate along a diverse set of points: opportunity, product focus, brand, reputation, etc.
  • Developmental perks may still be extracurriculars. While mid-stage startups may start to feel the pressure to offer many of the development perks that big companies provide, it is a bit more ad-hoc or situational. You can expect team talks from interesting visitors and perhaps an annual stipend for external classes or conferences. If you’re interested in learning a new job-related skill but your company doesn’t offer any education on it — ask and maybe you can take an off-site course or program.

Compensation at Mid-Stage Startups

  • The floor for your compensation should be aligned with the market. While it’s still likely your all-in cash compensation may be lower than at a big company and they will over index a bit on stock options (see next point), the position of the company should make it a fairly secure and competitive opportunity. In short, these companies should have the money to pay you market, so push back if they aren’t.
  • Your options are very likely worth something. While not guaranteed, the company has probably gotten to a point where it’s built something of relative value that could be attractive to acquirers or further rounds of fundraising. Startup equity is an entire discipline unto itself and you should absolutely learn the questions to ask to understand how your stock package stacks up and what its “potential” value is.

Stray Observations of Mid-Stage Startups

  • The early team is likely still there. You’ll be part of the early cohort of the company and get exposure to senior leaders in the team that will be your network for years to come. The network you have within the company will go on to serve you well as the company grows, so make good use of it — take the time to meet and get to know more senior team members and connect beyond the task at hand.
  • The company’s reputation will become your own. While this isn’t necessarily always justified, if you join a mid-sized startup before it breaks out (and IPOs or results in a great acquisition) that will very much work in your favor. The earlier employees of successful startups can often “ride the wave” to new opportunities or more senior roles while still in the afterglow of whatever comes of the startup. It’s certainly a bit circumstantial and out of your control, but not a bad thing to take advantage of.

Small company

Early Stage Startups

At this stage it’s all about the market, the team, and their focus. If any of those don’t fit with you, it’s not the right place — it’s as simple as that. While Hollywood has begun spinning a yarn on what startups are like, (surprise) it’s largely untrue. They can be stressful, lonely places where you’re forced to push yourself beyond your comfort zone. Startup life is not for everyone and for many, it can be too much. With that caveat, early stage startups are a special place and offer very unique working environments where the fruits of the team’s collective labor turn quickly from ideas to products to (hopefully) happy customers and users. Some of my happiest days at Oyster were when it was just a few of us in a small office working on a focus vision for our product — and then getting to see people use it!


  • Remix, Wake, And Co, Abstract, Delighted
  • < 30 people
  • Single office, and depending on the product and market the team is still likely largely engineering focused.

Hiring at Early Stage Startups

  • Be prepared to be evaluated and interviewed by non-designers in the hiring process. This is likely true at other companies on this list but at an early stage startup you may be the first designer joining. You may speak to people with little to no exposure to design in their work. Prepare by practicing your communication of design processes, principles, and how you will build great products to non-designers. Everyone finds their own way to do this but I find that building presentation decks of your work (even if you don’t use them) force you into thinking through the process as a linear narrative.
  • Evaluate the opportunity along the lines of team, mission, and market. At this stage you may be evaluating the company before it ever even launches a product. When deciding whether the early stage startup is right for you remember three critical elements: team, mission, and market. Do the founders and early team have the leadership and vision to blaze their path to success? Is the company riding a wave in the market that they can use to their advantage? Why are they pursuing their mission, is it passionate belief or something else? There are a plethora of questions here but forming conviction behind these three items will help bring clarity to your decision to join.
  • A word on design hiring projects vs. spec work. Like the other companies on this list, they may ask you to complete a design project or exercise. However, this might not be as organized or well set-up as what larger companies ask of you. This is natural and you should understand that a small company will want to get a feel for your work and process because each new person is such a big percentage of the team. These projects should be paid exercises in nearly all circumstances. It’s more about the gesture than the amount but if the company values design they should value your time and work. Request details on how they arrived at using this project and if they can give you any resources to help you formulate your approach. Any good team will respond reasonably and it’s a good test for how they deal with iteration and product process.

The Work at Early Stage Startups

  • You will define the product and design culture. As an early (or perhaps first) design hire your work will define both the company’s product as well as design’s place within the company. This is no small responsibility, you will have a big say in the development of design review processes, systems, and anything else that is visual or creatively driven.
  • You have to be your own advocate. As a solo team member you may be collaborating with co-workers with far more experience and expertise in their field than you. While this is true everywhere, at an early stage startup you will not have the team or mentor to advocate for your work and opinion. Additionally, you will become the voice of design throughout the company — lending your expertise and pushing for design throughout the organization.
  • Being an enthusiastic utility player is a must. Your work, which will still largely comprise of a core role of product design, will also be pushed to expand in any direction the company needs creatively. Be flexible to meet to the company’s needs. If the startup turns sharply to direct marketing and a growth focus, be ready to spend more of your energy creating and testing banners, writing ad copy, and optimizing your acquisition funnel. This is the reality of an early startup and an environment where utility players thrive.
  • Growing the team. While you may come in as the first design hire, there will (hopefully!) be a time when the team expands. Building an early stage design team is a topic and discipline unto itself but there are a few keys to call out. Hiring new designers should be a cross-team responsibility — from determining what the needs are to writing job descriptions and interviewing candidates. This helps the team prioritize design and can aid in embedding the culture into your company early on. Additionally, you and the team may find that it makes sense to hire someone more senior than you. It’s natural for this to feel a bit strange. However, use this as an opportunity to handpick a mentor that you’ll learn from everyday—a pretty rare opportunity. Work with the team to find someone whose skills and experiences fill in gaps in your practice and create a nice overlap with the work your team does.

Skills & Learning at Early Stage Startups

  • Your skill set will broaden. Being a utility player at an early stage company is a blessing and a curse. For those seeking specialization or honing one part of their craft, it may be a maddening experience of spinning plates. A friend in an early-stage B2B company told me about how her recent work with company clients gave her an opportunity to learn new techniques and skills in user research and client management. If you can embrace this breadth and creative variability, you can leverage it to explore new design disciplines, push yourself out of your comfort zone, and impact the company far beyond your role. You may even uncover a part of the process you never thought you’d enjoy and later emphasize that in your role as the company grows.
  • Learn on the job or make it your own priority. Unlike larger, more stable companies it’s unlikely you will have as much time for side projects to explore new tools and ideas. The work at an early-stage company is often at it’s best when it intersects your passions and learning areas—this is why so many early-stage companies describe themselves as mission-drive. If you can find this match, it’s a great opportunity to meld your learning on the focus/industry your company works in with your design learning on the job. The result can be interesting intersections between the core product you work on and your own design pursuits.

Compensation at Early Stage Startups

  • Your salary may be below “market rate”, so your equity package should be outsized to compensate. The annual salary in a small startup is often a bit lower than that of a larger, more stable company. To provide upside, early stage startups offer larger equity packages that can often reach full digit percentage figures — but, keep in mind, that value is all variable and will only be worth something if the company is successful. If you’re joining a company and sacrificing salary it’s important to try and understand what your equity could be worth. Behance founder Scott Belsky offers a good question to ask: “Based on the equity you’re offering me, what would my stake be worth if the company were acquired for $200 million; for $500 million; for $1 billion?” — you can edit those figures based on your situation but this question gets at the root of much more complex economics behind startup equity.
  • Perks and non-salary compensation will be more variable. Compensation in early stage startups begins to diverge with bigger companies on perks, benefits, and bonuses. Of these items benefits can be the most difficult to deal with as medical, family, and other coverages may be especially lacking when compared with what larger companies can offer. It’s something to be aware of as you plan your career and a great topic to push on with any HR-related conversations you have.
  • The risk is real so make a plan for it. There is a very real amount of risk associated with joining an early stage startup. You’re making a bet on the team, product, and market. And while the media loves to celebrate the success stories, you should always be prepared for the downside. Funding can run out, products can prove to be unsuccessful, and the market timing just may not be right. While it may be difficult, it is wise to have a plan for these scenarios. Understand your finances, personal burn rate, and how long you can last without a steady income if you were suddenly out of a job. Try to have a rainy day fund that will float you between jobs in case things don’t work out.

Stray Observations of Early Stage Startups

  • Move the ball forward or no one else will. The reality of a small company is that if you aren’t the catalyst to get the work done, or don’t put in the extra effort to find a better solution—it’s just not going to happen. There is a level of commitment that comes to joining an early stage company that is unique in the working world. Try to find opportunities that are an amalgam of what gets you energizes you creatively, pushes your intellectually, and has meaning personally. It will make the late nights and longer hours worth it.
  • You’ll (hopefully) make friends for life. At its best, the team within a small company represents the special quality that comes from a group of people working on a common collaborative goal. Building a tight and high quality network early in your career is much more valuable than any fancy title or near-term compensation. From folks a few years more experienced you’ll get mentorship and learn good habits. I still consider my co-founders at Oyster two of my closest friends and advisors and have equally tight relationships with many of our early employees.


Much like the industrial revolution over a hundred years ago, we are in a period of rapid change and growth in the way we work. Gone (for the most part) are the days where you work at a single company your entire career. Gone is the expectation that a job cannot also fulfill a deeper personal mission or passion.

This revolution, created in part by the internet, has enabled a rapid growth in the types of companies and jobs this guide outlines—a diverse array of opportunities, focus areas, and working styles. And while change at that scale that can cause some serious disruptions — it’s our responsibility as designers to affect and ultimately drive how these high-growth, newly powerful companies take on the opportunity handed to them.  Personally, it should be a moment to rethink processes, pathways, and how you plot your career.

Our training as designers can afford us the ability to unpack complex problems from multiple perspectives, empathize with others, and create innovative, inclusive experiences. And if we are thoughtful about identifying the opportunities that are being laid out in front of us by tech, then there is challenge and fulfillment and success to be had.