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When it comes to a startup’s earliest hires, it’s most often those who step into the first product or engineering roles who shine the brightest — and receive the most support and advice. Yet the first design hire has the power to transform the entire trajectory of a startup, shaping everything from how users interact with the product, to the branding and creative work that draws in new customers.

First designers agree to take on a role that’s filled with unlimited opportunity, as well as endless minefields. And perhaps even more so than other founding team members, it’s often hazy what this role is all about. Gaurav Bhushan, Head of Design at Keyo, perhaps said it best: “As a designer, you add the most value when things are ambiguous. Yet the gap between ‘what is’ and ‘what could be’ at early-stage startups is as uncomfortable as it gets.”

We heard gems of wisdom like this at our inaugural Founding Designer Track, a first-of-its kind community for those considering joining a startup as the first design hire. While we’ve long curated top-tier advice from some of today’s leading designers on the Review and tried to demystify emerging design roles, it seemed like we could do more to close this gap between designers’ ambitions and the uncertainty around this first foothold into the early-stage startup scene.

With this program (that just recently wrapped), we wanted to bring curriculum and community to a group that rarely steps into the spotlight. To do so, we brought together a truly standout collection of experts to give an inside look at this pivotal role — what it’s really like, pitfalls to avoid and tips to set yourself up for success. Each of these coaches (listed below) has seen firsthand the peaks and valleys that come with building a design culture from the bottom up.

We’re eternally grateful to this incredibly accomplished group for raising their hands to mentor the next generation of design leaders, but we also can’t help but take a minute to brag about those who benefited from their wisdom: the members of our first cohort. This hand-picked group of up-and-comers already lend their hands to designing products you use every day — including Google, Lyft, Facebook, Netflix, Dropbox, OpenTable and more. Keep your eye on this crew — you’ll be seeing lots from them on the startup scene in the future.

To share insights from the program with the broader community, we’ve assembled several of the key takeaways that have stuck with us from these robust, honest conversations. What lies ahead is an inside look at the curriculum and the most tactical gems that emerged from each session.

Fair warning: This in-depth manual is lengthy and meant to be a comprehensive resource to return to over and over. To navigate around, click on any of the links below to skip directly to that section of this resource:

If you’re curious about this unique role, read on to see what it takes to climb aboard a startup as the first designer. Let’s dive in.


Like with any “first” role, there’s no clear career trajectory for a startup’s first designer because there’s no set flight path for any brand-new company. Often folks join a startup without really knowing what they’re getting themselves into — and the breakneck pace that ensues is not everyone’s cup of tea. So if you’re considering taking on the mantle of a startup’s first designer, the first step is to tackle some serious self-reflection work to interrogate whether life as an early employee is right for you and your working style. The program’s experts are here to help you do just that, outlining the must-have qualities to succeed, as well as the highlights and the drawbacks of this role that you might not have considered.

The essential qualities of a founding designer

Before we dive into the finer details of this unique founding role, let’s sketch a blueprint of what the earliest designer role looks like — including the tools you need on your drafting table. To get more specific, when you join a startup as a founding member, there’s a few skills you’ll need when the going (inevitably) gets tough. While it’s true that no one design role looks exactly the same, if the qualities on the punch list below ring true, you may be a great candidate for a startup’s first design hire:

Throughout your journey as a founding designer, you will have every title and simultaneously no title at all.

Even if you’re ticking through these boxes and nodding your head — recognizing yourself in these traits — know that there’s more to it than that. Below, we outline the duality of the role, the brightside and the underside you should consider before taking the founding designer title.

Pros: What lights a fire under founding designers

Taking on a brand-new role at a company that’s still in its infancy opens up a host of unfamiliar challenges. But with challenges come incredible opportunities — the kind that keep you up at night, not because you’re worried or anxious, but because you can’t wait to sink your teeth into them. Here’s a quick hit list of what powers up a startup’s first designer:

Seeing your work out in the world

Rebecca Garza-Bortman, First Designer at Masterclass

Designers, at their heart, are creators — and nothing fires up a creator more than seeing their work come to life. “Even now, I still get really excited about seeing something I designed — something I created that didn’t exist before — out in the world. Nothing beats that feeling for me. Honestly ask yourself: How much of your work do you want to see out there? At an early-stage startup your work will be seen, but at a large organization or in a consultant role, projects move much slower (or may never even see the light of day) when the company is juggling the priorities of countless other departments,” says Rebecca Garza-Bortman, Founding Designer at MasterClass.

Garza-Bortman also notes that the sheer range of what a startup’s first designer gets to take on is exhilarating. Whether it’s imagining what a class with a famous expert could be, flying to Florida to help with production at Serena Williams’ house, or designing the company’s first office space, no two days as MasterClass’s first designer were the same.

Sometimes, that work might show up in ways you never dreamed it would. As Soleio Cuervo, (one of Facebook’s first designers) shared at a session, he certainly wasn’t expecting to design a t-shirt for Justin Timberlake's appearance in the film “The Social Network.”

Hackathon poster by Ben Barry. Still from "The Social Network" featuring hackathon t-shirt.


Startups offer an attractive level of influence that’s unattainable at larger organizations. You don’t have to convince hundreds to go along with your next big idea — you only need to convince a few co-founders. But this goes beyond an impressive “founding team” title to hang your hat on.

Let me be clear here — influence is not solely about having a big fancy title. As an early member of the team, you’re an owner of the business successes and failures. You will have a big hand in crafting the environment, culture, design and experience the way you wish to see it. You’ll grow your skills both as an individual and as a designer,” says Faire’s Katie Witkop. “As the company grows, members may be added to the team with shinier titles and executive roles. You can’t let that distract you. Use influence, tenacity and humility to achieve effective leadership.”

If you think you can’t have immense influence without a big title, then you actually don’t have influence at all.

Cons: The most common challenges early designers will face

As with any early-stage startup role, there are plenty of potholes to dodge. Our coaches were honest about the roadblocks first designers need to face along the way.

Losing sight of good for perfect

Whether earned or not, designers often have a reputation for being perfectionists. There’s more to design than making every pixel perfect — simplicity and speed are essential skills at a startup. “Speed is not a dirty word. For better or worse, speed has been — and continues to be — one of my top skill sets as a designer. It’s allowed us as a company to take big bets, iterate quickly, build our brand, and strengthen my position on the team over time. Now I know what you’re thinking, ‘How can quality design be done when you’re rushing?’” says Witkop.

Design process is important, but losing sight of good for perfect is not a privilege available to a design team of one.

“Moving fast and iterating quickly allowed us to build a company successful enough to hire a team of five designers down the line. Don’t be afraid to revise and redo when you later have a team to support you,” she says.

Finding your place within the company

Anthony Short, First Designer at Segment

Design may align most closely with product and engineering, but beyond this immediate circle there are a whole host of other stakeholders you’ll need to lend an ear to. “It can be challenging to find a leg to stand on when you’re working with other departments. For example, marketing is held against very particular metrics, and if folks don’t hit them they’re at risk of being fired. Whereas design is not held to strong metrics and may want to push for things that can’t be measured,” says Anthony Short (Segment’s first designer).

“Although design usually sits on the product team, marketing and sales are our partners as much as product is. It’s super important to take the time to develop these relationships and have empathy for those departments. It’s a really delicate balance of allowing other teams to have input but also protecting your vision as the ultimate authority. You were hired for a reason,” he says.


So you’ve decided you want to take the plunge and become designer number one at the next great startup. You’re ready to take on the challenges, hold on through turbulence, and create something from nothing. In the midst of excitement for this big career transition, it can be tempting to grab the first opportunity that lands in your lap. But if you’re able to, it’s worth taking the time to rigorously evaluate which startup to join. If there’s a mismatch in scope of the role, tension with the co-founders, or an unstable business model ahead, you might get soured on the founding designer experience.

How do you find the right opportunity, and evaluate (without the aid of a crystal ball) if it’s really the best path forward? There’s no set of criteria that point to the next rocketship you should grab a seat on. But with the right amount of due diligence, you can set yourself up for finding the best fit for your skillset. Here’s how:

Reaching the right people

Perhaps even more so than a typical job search, finding a startup that’s in the market for their first designer is a game of networks. At the very early stage, most founders aren’t working with recruiters and lack the funds to leverage traditional job posting boards. (Although many venture capital firms help the companies they've backed with recruiting in the early days, so be sure to check out sites like our own First Round Talent portal here.) That means you’ll have to flex those networking muscles to come across opportunities you might not have seen otherwise.

Jared Erondu (First Designer and now Head of Design at Lattice) shared a practical pointer for expanding your network: "Design and tech communities are often undervalued. You never know if you might form a relationship now with someone and start a company with that person five years from now. If you’re interested in someday joining a startup as a founding designer, prioritize joining these communities now," he says. To put this advice into practice, consider a few of the many fantastic communities and mentoring programs to choose from, including the Creative Lady community, Designers Guild, Designer Fund and Out in Tech. Plus, amidst the drastic 180-shift to all remote work, there’s never been a better time to hop on a Zoom call and get connected with those outside of your current geographic bubble.

Getting to know the founding team

After getting your name out there and putting in the work to expand your network, maybe you’ve come across an opportunity that piques your interest. While you may be over the moon excited, several of the instructors cautioned against ignoring founder red flags for the sake of the chance to shape a new product.

For the program attendees, this piece of advice was particularly impactful: “As designers we’re overly invested in product quality, but product is not the be-all or end-all. Being reminded that the success of a business does not hinge entirely on the product — with exceptions — is both liberating and scary,” says cohort member Kaye Mao, Interaction Designer at Google Health.

When it comes to evaluating the founding team, start by reflecting on your own priorities and what you’re seeking in your next career move. Journal about what your dream role might look like — how you work with the co-founders, what drives product decisions, and design’s seat at the table. Then, start seeing where the opportunity in front of you aligns. The instructors recommended honing in on three key areas: personal priorities, company philosophy and the importance of design.

Jared Erondu, First Designer at Lattice
Sara Lin, First Designer at Parastructure

As the interviewee, it may feel like you’re the one in the hot seat, but as the potential first designer at a startup, you’d be making your way across uncharted territory — so it’s in your best interest to get a rough lay of the land. But interviewing with non-designers about design can be incredibly challenging, and may require you to wade through a lot of hand-wavy marketing speak. You won’t have endless time with the founding team, so it’s important to make sure your questions pack a punch. Consider these prompts from Anthony Short (First Designer at Segment) for sparking more illuminating discussions with the founding team:

Evaluating the upside

A quick caveat here — even if you’ve found your dream founding team, you’ve still got to do your own due diligence to make sure the startup has the legs to go the distance. There’s no secret formula here, but in his session, Jared Erondu of Lattice suggested putting on your investor cap. Here are a few specific areas to consider:


You’ve landed your dream gig as the first designer at a startup with a founding team you click with. You’re in the door, but the hard work is just beginning. What comes next? To put it frankly, success isn’t assured. To excel as a founding designer, you’ll need to carve out a path for yourself without any tracks to follow.

David Dat Nguyen, First Designer at Gusto

Across each of the sessions, the coaches emphasized one core responsibility above everything else (and no, it’s not to avoid Lorem Ipsum, although that was also a unanimous plea): The single most important goal of a founding designer is to establish design as a critical function for the business. It’s pulling up a chair so you have a seat at the table. It’s battling for your voice to be heard. David Dat Nguyen, First Designer at Gusto, put it quite succinctly: “You need to be ready to rumble.”

If that sounds daunting, we don’t mean it to be. However, it does get to the magic of what makes programs like Founding Designer Track so special. If you want the inside, warts-and-all look at what it really means to forge a new path as the first designer of a fledgling startup, you need to lean on the guidance of those that have tread the path before — if not multiple times.

So how do you plant your flag amidst a sea of (often conflicting) voices and company concerns? There’s no one-size-fits-all answer here. What each company cares about, and how you center design’s mandate, will vary wildly from startup-to-startup. Instead of leaving you hanging to figure out how to pull it off on your own, the instructors got incredibly tactical about what’s worked — and what hasn’t — for them as they forged a similar path. Consider these five key areas that are critical to proving design’s mettle.

Make design the cultural backbone

Design’s role will vary widely depending on the product, the industry and the makeup of the founding team. But as an overarching goal, consider design as an extension (and a driver) of the broader organization’s culture. “Crafting the design culture is similar to crafting the company culture. We emulate the companies, products, and people we admire. So what does your startup aspire to be? Establish a foundation for what design is at the company by building off of what the company values and prioritizes,” says David Dat Nguyen of Gusto.

Soleio Cuervo, former Head of Design at Dropbox and an early employee at Facebook, echoes this sentiment with an apt metaphor:

Think of design culture like the skeletal system of an animal. Just like a skeleton reflects the nature of the creature it resides in, design culture exists within the context of the broader company culture. It must work in service of the entire entity.

Design must evolve as the company grows and continue to reflect the product’s core values. Consider this example from Teresa Man, Lead Designer at Superhuman:

Teresa Man, Lead Designer at Superhuman

“Superhuman’s DNA is rooted in how fast the user experience is. As the lead designer, I know this is the one thing that cannot be compromised. Email is not a new paradigm, but because at Superhuman we are so focused on speed, we have to think about what design we can embed that reinforces that fast behavior,” says Man. “That might mean removing icons and buttons and text that people are used to seeing in their email experience. The idea is that if we show them a button they really don’t need, they will click on that button and it will slow them down. We deliberately did not include any back buttons on the mobile app — the only way to go back is to swipe. We are tailoring the design to drive home how users can work more quickly, which reinforces our product’s core differentiator.”

But for design to be reflective of the entire company’s culture, you need to open up design input across the company — not just within a narrow group of stakeholders. At Superhuman, Man has embedded this ethos in a few key ways. “Everyone has access to my Figma files, and we post different design ideas on Slack that anyone can discuss and vote on. We also host design sessions with everyone at the company and pay a lot of attention to feedback from those that are closest to the customer. It’s high-lift, but we really take the time to walk through the design process with the customer delight and onboarding team to share why certain design decisions were made and listen closely for their input. No one knows our customers as well as they do.”

Anthony Short of Segment also reminds us that tapping into this customer mindset is critical for balancing your lengthy to-do list with company-wide goals:

Being at a startup is like if you’re in a dark room. You sort of know where you are, but can’t really see all that well and you’re only focused on what’s right in front of you. Don’t forget every now and then to turn on the light and see which direction you should be going in with broad user research and exploration.

Showcase your chops

Amir Hadjihbib, First Designer at Checkr

With limited metrics to evaluate design against, it’s no surprise that senior leadership questions what design brings to the table. But, according to Amir Hadjihabib, who was an early designer at Zendesk and the first designer at Checkr, “Across any startup, the primary goal of great design should be to get more customers.” To do so, you must remain in lockstep with the other leaders driving the strategy for the company as a whole.

“There should always be a strategy that defines the role design plays. You must align with the founders to ensure you’re working on the highest-impact business goals. You’re partnering with the CEO to get customers and you need to know what those overarching goals are so you can look at them with a design lens every day,” says Rebecca Garza-Bortman of MasterClass.

When Garza-Bortman joined MasterClass as the first employee and designer in 2013 to design the initial product and brand, the company invested heavily in branding from the very beginning — not because of chance, but because that was Garza-Bortman’s secret weapon. “The company wanted to offer a premium experience, and the visual language needed to align with that luxury. One of my first projects at MasterClass was imagining how the company branding interacted with a single class (that we hadn’t even filmed yet) for Annie Leibovitz,” she says. “That one speculative page design was used to get prospective instructors pumped to be a part of the company, and set a quality level and tone for future classes.”

Guard your time

Working at a startup can be like trying to decide which of the ten different burning fires you need to put out. When someone’s asking you to jump in and help, it can be incredibly hard to say no, even when you’re already overextended. By closely aligning with the priorities set at the highest level, you have more reason to say no. “Focus is paramount; if you’re doing a good job, your startup will want more. By mapping to the strategy you provide clear boundaries and guardrails,” says Hadjihabib. Katie Witkop of Faire is in full agreement here — you can’t battle each blaze simultaneously:

Sometimes acknowledging a smoldering fire, and actively telling yourself to worry about it another day, is completely justifiable and often the right call.

More tactically, as a founding designer your schedule is likely to fill up with “quick syncs” and other back-to-back meetings with cross-functional teammates. “Protect your time for the important work. Typically at startups, when the company finally gets a designer on board the team is extremely excited to build a bunch of stuff. You need to invest your time in what is important to the company goals,” says Garza-Bortman.

Katie Witkop, First Designer at Faire

It may take a bit of practice, but you’ll start to get more comfortable clicking “no” on that meeting invite. “At a young startup, your job will change every three months — this is a good thing. As the founding designer your job is to be nimble, agile and work on whatever is highest priority for the business to be successful. With all the work you'll be doing, you don’t have time for meetings that aren’t relevant to design,” says Witkop. “My CEO understood this well — he used to barrage me for taking any meetings except product kick offs, design reviews, and all-hands on Fridays. Now, I am now a fierce defender of my schedule, and feel comfortable pushing back meeting times or organizing them so that I protect undisturbed hours of the day to design.”

Controlling your schedule — at a company that is in rapid growth and unstable at times — is one of the best ways to take back your sanity and have time to do quality thinking.

Get comfortable flying solo

Another pain point? As the only designer, you need to be comfortable evaluating your own design. “Yes, getting feedback from your cross-functional partners is super important, but they won’t be considering it with a designer’s eye. You’ve got to be able to look at your own work and remove as much bias as possible,” says Sara Lin, First Designer at Parastructure. Here, Lin includes a few tactical tips for turning a critical eye to your own work:

Build a system — but not a Rube Goldberg machine

As an artistic, creative designer you’re probably more of a right-brained thinker. Perhaps you’d feel happiest left to your own devices to dream and create. But as a critical cog for your startup, you need to be interlocked with all the other gears so you can all turn and move forward together. This is where that operational, methodical left side of the brain comes in.

“When you join a larger company, you may not really need to think about processes and infrastructure. Those systems have probably been in place long before you arrived and will live on after you leave. But at a startup, you need to be thinking about how to set up the design team for success in the future — even if right now you’re just a team of one,” says David Dat Nguyen of Gusto. “It’s not just about getting something done and then immediately moving on to the next project. You’ve got to think about the processes that can help scale quality. What are the points of friction with other departments that are causing crossed wires? Remember: A design team is only as happy as its cross-functional colleagues,” he says.

Keep in mind that it’s a balancing act — you want to introduce lightweight processes so it’s not a free-for-all, but don’t get carried away and try to copy-paste FAANG design processes onto a small, scrappy team.

“Don’t get bogged down by Medium posts that promise tried-and-true solutions to design processes and workflows,” says Anthony Short of Segment. “At large companies, designers often have each step outlined, including research, testing, exploration, prototyping and design sprints. But at smaller startups, the communication layers are shallow, with only a few people at the company. Many of the steps involved at larger companies do not apply to a startup and add an unnecessary anchor to your speed. Think about what’s needed for the company stage you’re in and don’t over-engineer something because of one person’s opinion on how it should be done.”


Life as the first designer doesn’t mean that you’ll always be the only designer. Hopefully, at some point during your company’s journey, you’ll start hiring to grow your team and amplify the impact of design in the long-term. (If you’re taking notes, Teresa Man of Superhuman suggests that the usual ratio is nine engineers to one product manager and one designer.) While it may be tempting to stay heads-down on direct execution, hiring should be treated with the same careful eye and painstaking effort you give to all of your design projects. “Being a good founding designer is half execution and half thinking about scaling the culture and the team,” says Andrew Lee, Product Designer at Notion.

For starters, there’s the old mantra to hire slow and fire fast. Instead of rushing the process or skipping over best practices because you're pressed for time, focus on growing thoughtfully. As you scale design’s imprint, keep your eye out for these common challenges:

Building a balanced team

Stephanie Hornung, First Designer at Asana

There might be temptation (and pressure from other stakeholders) to hire a designer with your same skill set. After all — you’ve been such a great first designer, why wouldn’t they want the same type of person to continue building out the team? “The founders already know how to work with ‘Stephanie,’ so most likely they will want to hire someone that they can plug in, who is similar to your process, so that it's easier to bring that new person onto the team,” says Stephanie Hornung, First Designer at Asana. But there’s a few key reasons you may want to resist that temptation.

To attract diverse talent beyond your immediate circle, you’ll need to start flexing your networking and personal branding muscles. There’s no way around it — this will require an investment of time and resources. But to mix our metaphors, it’s worth it’s weight in gold when you find the person who fits in at your startup like a missing puzzle piece.

“You’ve got to be willing to play the long game — building your talent pipeline is a mix of recruiting and networking. And when you’re small and want to grow fast, then expect to spend more than 20% of your time on recruiting,” says Hornung. “Coffee chats are a super valuable tactic for getting to know people outside my close circles. Don’t approach it from a recruiting standpoint, think of it as learning from each other. Even if they’re not right for the job, they can help point you to someone else who might be.”

Another helpful strategy? “Building up your personal brand is a great way to attract diverse talent. Look for opportunities to write articles on your personal blog or Medium page. Volunteer to speak at the local MeetUp in your area. Get people excited about your ideas and wanting to work with you,” she says.

Hornung also reminds us of another critical factor. “When you bring someone onto a small organization who has a different approach or process or is from a different background, you need to go through an honest assessment to make sure that the startup is an inclusive environment for everyone to work. Hiring diverse talent is just the first step, and you need to do the work in your organization to make space for new voices.”

Preparing non-designers to interview designers

You’ve winnowed down your candidate pool, now you need to assemble your panel. This can get a bit tricky, because when you’re the only designer at the company, you are guaranteed to have non-designers evaluating designer traits. “Identify the people in the room and if they can understand design. Consider those who have a good handle on customers. You want to find engineers, PMs, and founders who are product-centric,” says Jessica Ko, First Designer at Opendoor.

To make sure everyone is evaluating within the same scope and expectations, develop an interviewing rubric. Include high-level criteria that don’t directly relate to evaluating design, but speak to how they will be as a teammate, such as “Does this person show empathy concerning completing goals?” or “How excited would you be to collaborate with this person?”

Jessica Ko, First Designer at Opendoor

According to Ko, the single most important skill to evaluate for when hiring the next designer at your startup is a beginner’s mindset. Here are her tips for evaluating this somewhat nebulous criteria:

Hiring your own boss

Katie Witkop of Faire has hired plenty of designers over the course of her career, but when it came time to hire her own boss, that was an added wrinkle. “You need to nurture your team and allow it to supersede you. Two years ago, Faire’s CEO told me that we would need to hire a Head of Design that can build a 100-person design organization. I had the choice to try and stretch up to that role, but painfully acknowledged that it surpassed my management experience and ultimately was in another direction than where I wanted to personally grow,” she says.

“From them on, we started the search for a Head of Design. We looked for this role for over a year and a half. When we found the candidate we eventually hired, the CEO and I finally felt like we’d found who we were looking for. He was thoughtful, process-oriented, and interested in the recruiting and development of designers,” she says. To find your next great design leader, borrow these questions from Witkop’s own interviewing arsenal:

Most founding designers dream of owning their organization, leading through title and management — and originally I was no exception. But ultimately finding and recruiting my boss has been one of the things I’m most proud of, because I designed a business that could grow beyond its founding members.

Making sure design is a team sport

As your team grows, your role takes on a whole new meaning. No longer a one-person-band, you’re responsible for pointing the team in the right direction. It’s overwhelming, especially for folks that have limited management experience, but there’s also beauty in a blank canvas to paint on. Keep these core focuses in mind:

Soleio Cuervo, Early Designer at Facebook & Dropbox

Finally, Short implores you to rethink what it means to be a leader, beyond the flashy title. “Don’t stamp your feet to get a new role. Be okay with your current role, while knowing that you eventually want to get to a higher level. Focus on building your relationships up to take this next step. You need to earn your leadership — it’s not given, you need to build up the people around you; people need to believe that you can lead them.”


Like any “first” role, operating as the founding designer can feel a bit like you’re on an island of one — out of reach and misunderstood by others at the company. “Life as the first designer is actually quite lonely. You’re constantly working with engineers or salespeople or others that don’t quite get what you do. Sometimes you look up and you realize you’re missing someone to lean on when everyone is relying on you. So be prepared for that, and jump at the chance to hire a second designer when you get that opportunity,” says Stephanie Hornung of Asana.

Superhuman’s Teresa Man has seen this across her career in other roles — but couldn’t quite put her finger on what she was feeling until she started meeting with other design leaders. “Even though I might have colleagues that are design-driven, it’s definitely not the same as jamming out some sketches, concepts and prototypes with another designer. It’s crucial that you build your support network of creatives with those outside your startup to help cope, and maybe geek out on some good (and bad) fonts together.”

Patrick Weiss, former Designer in Residence at First Round

In addition to seeking outside mentorship and design communities to help lift you up in these lower points, any startup employee must first and foremost take care of their mental health and stress management. “There’s no way around it — building a company is incredibly stressful. You will battle impostor syndrome and there will be plenty of days where you’re wondering ‘What have I gotten myself into?’ You have to start thinking about managing that stress before it hits you like a ton of bricks — not after,” says Patrick Weiss, former Design Expert in Residence at First Round.

“It's easy to feel like you're the only person struggling with something—especially as a solo designer on a team of engineers. While the details may differ, nine times out of ten someone has solved your problem before, and all we need do is ask for help,” reminds participant Bryce Daniel from Snackpass

As you consider your next role, remember that titles may sound impressive and important, but it’s not what will keep you motivated to put in long hours, stomach criticism and stretch your skills.

Seek out responsibilities, not roles. Think about what gives you energy and shape a role that leverages the responsibilities that you’re best equipped to own. If you don’t find happiness in the things that you are doing, you will almost certainly burn out. Sometimes when a small company grows big, the culture evolves in a way that no longer resonates with you. That’s entirely okay,” says Soleio Cuervo, formerly of Dropbox and Facebook.

If you find you’re no longer feeling fulfilled by your role, heed this advice from Rebecca Garza-Bortman. “About a year after we launched MasterClass, I wasn’t feeling as challenged in my role — the design function had been built from scratch and scaled, and maintaining the system was not motivating to me,” she says. “Instead of waiting until I was totally miserable, I knew it was time to go. It’s an incredibly hard decision to walk away from something you’ve helped bring into the world, but I wanted to leave on a brighter note and not one of bitterness.”

Leave the party while the best song is still playing.

“For me, this was a poignant reminder that it’s okay to leave when you feel like you’ve done your best work and go where you’re needed instead of seeing a startup all the way through to IPO,” says Kaye Mao of Google Health. “There isn’t one specific way to be successful, you can define success for yourself and follow your own joy.”

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