editione1.0.2Updated February 27, 2023
You’re reading an excerpt of Land Your Dream Design Job, a book by Dan Shilov. Filled with hard-won, personal insights, it is a comprehensive guide to landing a product design role in a startup, agency, or tech company, and covers the entire design interview process from beginning to end, for experienced and aspriring designers. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.
What’s the one unfair secret way of getting your foot in the door when applying to jobs? Easy. Connect with people first. The best strategy is not to cast a wide net by applying everywhere but to be focused on the few opportunities where you can make an outsize impact. Your future employer appreciates this effort too—they’d rather hire someone with the necessary skills, with a passion for the company’s mission, and who has done their homework over someone who’s just looking for whatever they can get.
When you are applying, your best bet is to use a variety of channels, from reaching out to alumni to promoting your portfolio in other channels. All of these will help you raise visibility and increase your chances. However, these tactics won’t be as effective if you haven’t figured out the strategy first—understanding how your skills fit with the types of jobs you’re looking for.
Broadly speaking you can apply to jobs in two ways: casting a wide net by applying to several dozen companies or targeting your search to companies and roles that fit your skills and needs best.
By casting a wide net you can reach out to several dozen companies in a short amount of time. Unfortunately, that means you’re right there in the sea of resumes and portfolios, with a lower chance of standing out. You’ll get some responses, but the rate will be in the low single digits.
Even if you do get a response, it’s hard to tell if the role is a good fit for you. When you’re desperate, it might feel like anything that looks decent enough is a good fit, but it might not be the right opportunity for you, leading to frustration when you actually start working there.
In general, I’m against this approach. It’s time consuming, it has a low success rate, and it doesn’t lead to much learning in the process. Too often I see heroic funnels from junior engineers and junior designers looking for an entry-level position. They list out all the companies they’ve submitted their application to—sometimes in the hundreds—that led to few responses and even fewer interviews.
This is why I recommend you take a more deliberate approach in your search.
important A close cousin to the wide-net approach is the passive auto-pilot job-searching strategy. By having your portfolio up-to-date, your social media set up, and your LinkedIn outreach preferences turned on—you’ll get a trickle of recruiters reaching out. These won’t always be the most relevant matches, and you’ll still need to vet them, but it’s a low-effort way to capitalize on the hard work that you’ve already done.
My recommendation is to target your job search and apply to places and roles that fit your skills and needs best. This doesn’t mean excluding yourself from roles that might be a stretch (that’s OK!). Rather you should be picky with your job search—by doing your homework now, you’ll save a lot of time later.
You’ll focus your efforts and ultimately will be able to find a satisfying job with a culture that fits you best. It will also give you a sense of control and the power to persevere in a process that might at times feel opaque and frustrating. Being intentional in your job search will help you stay focused and lend you a sense of autonomy and ownership over a process that sometimes feels chaotic.
With a targeted job-search approach, we’ll take a look at how you can use your superpowers and your personality to stand out.
One effective way to apply to jobs is through an employee referral. With a contact inside the company, you shortcut the tedious part of the process and your portfolio lands squarely right in front of the eyes of a recruiter or a hiring manager. How you ask for a referral makes all the difference.
The best referrals come from people you’ve developed a strong relationship with by working together. Think of these folks as people in your tight-knit inner circle. These are the folks that not only can get you in the door but write a glowing review so that the interview completely flips. Instead of selling yourself, they work hard to get you in and sell the opportunity to you.
However, these are not the only referrals to act on. As a designer you’re uniquely positioned to interact with people cross-functionally. This means right out of the gate you have a broad and diverse network of folks that you’ve worked with before, such as:
customer support specialists.
The list goes on. Eventually some of those folks join other companies, or they might know someone who works at a company you’re interested in. You might not have a strong relationship here, and these folks are usually weaker ties, but that’s OK. The important thing is that you still had a shared experience, which makes it easier to reconnect regarding future opportunities.
These are folks you might have just met, perhaps at an event or maybe you reached out to them directly on LinkedIn. For the most part, you’re still strangers. Getting referred by them is harder, but like the first type of referrals, it’s important to build the relationship first and make a genuine ask.
Let’s imagine you were in their shoes. You’re probably busy, stressed about a deadline, and somebody you just met reaches out about a job opportunity at your company—what do you do? Would you immediately submit the referral? Or would you not bother altogether, given everything else that’s happening? To make sure your request doesn’t fall by the wayside, make it easy for the person referring you to submit your application.
Highlight the experience and projects relevant to the job you’re applying for. Show them that you’ve done your homework about the company, the team, and the project. Follow up by saying that you think you’d be a good fit and that you’re interested in learning more. Ask yourself—how can you make the person who’s going to refer you look good?
At the end of the day, referrals are just one way to get in, and while they do increase your chance of being seen, they’re not a panacea when it comes to getting the job. Any company with a strong recruiting or a hiring manager will do their due diligence and may reject your candidacy if it doesn’t meet the job requirements. It’s in your best interest to show why you’re a good candidate and how you meet or exceed the criteria in the job post. This isn’t to discourage you in applying—just think of this as one tactic out of many that you could use in your job search process.
The best way to connect with a company is by reaching out directly. Whether it’s identifying the hiring manager or the recruiter, you want to initiate the conversation and start there as opposed to submitting your portfolio online and hoping for the best.
Yes, this approach does take work and it won’t be easy. You may need to ask around and reach out to a couple of folks before finally reaching the hiring manager, for instance. However, because it’s not easy, most people won’t take this route. So this is yet another way for you to differentiate yourself and reinforce the trait of taking action and being proactive.
If you know the hiring manager for the role, reach out to them directly with your application. If you don’t know the manager or who’s doing the recruiting, look them up. This will be harder for larger companies, but for startups or mid-size companies, usually you can poke around their site, LinkedIn, or AngelList to at least find the recruiter who posted the listing.
Reaching out to the hiring manager or the recruiter directly increases your chances of getting seen, boosting yourself directly to the top of the queue. It’s kind of like that scene from the movie The Pursuit of Happyness, where Will Smith’s character has no luck going through the gatekeepers, so he tries his luck and reaches out to the CEO directly. The call goes well and the CEO asks “Can you be here in 20 minutes?”
So if you get to this stage, have your pitch ready. Tailor your portfolio and show relevant work, thus making the decision to bring you on easier for them. Not only does it show that you’ve done your homework but it also shows that you’re going to go above and beyond.
Lastly, you don’t necessarily have to talk to the hiring manager or a recruiter. Sometimes it’s hard to find those folks on LinkedIn and it’s not clear if they’re the ones hiring for the role—occasionally people might still have the name of their previous company listed as current on their profile months after they’ve already left. So diversify your outreach. For example, you might reach out to a product manager or an engineering lead who’s working on the same team.
storyA few years ago I found out about a networking event where one of the speakers was from a company I wanted to apply to. I connected with the speaker there and followed up with an email to talk about a potential design role. However, except for one email response, I never heard more. It took a second event a few months later, where I connected with the recruiter from that company, to have a more productive conversation. In the end, it takes luck, creativity, and an openness to try different methods to get to a concrete response.
A low-key way to get your foot in the door is by setting up an informational interview. This wouldn’t be as high a commitment as bringing you on-site for the hiring manager or the designer you’re talking with. However, you still need to fully commit to learning all you can about the company, the role, and the design culture there and come prepared with specific questions you’d like to talk about. Better yet, send these questions in advance to the person you’re interviewing so they can come prepared too.
This approach works best for companies you’re interested in that might not have design roles open right now but you want to start the relationship early. Be sure to follow up after the interview with a thank you, and if the right opportunity comes up, feel free to broach the discussion around jobs—if someone would be interested in a design role at the company, how might they apply to work there?
Recruiters come in all shapes and sizes. To simplify things, I’m going to focus on in-house and recruiting agency recruiters. This model is not unlike that for designers. In-house recruiters have a deep understanding of the company and are sometimes embedded on the teams they’re hiring for (design or engineering, for example). Agency recruiters work with multiple companies and bring the advantage of breadth—potentially placing you in a company that’s a great fit for your (and their) needs.
In-house recruiters are usually your first point of contact when it comes to getting the lowdown on the company, the team, and the job itself. A good recruiter will do their best to answer your questions and make sure you’re left with a good impression (even if you might not be the right fit just now). Use them as a resource to understand the role.
important Recruiters can be your best ally. Treat them well. Focus on high-quality recruiters—equip them to succeed and they’ll in turn help you.
Even if the role or you aren’t a good fit, it’s not a bad idea to still connect and stay in touch periodically. Sometimes things change internally and a position that was open is no longer there. But this doesn’t mean that another opportunity might not come up soon after.
storyWhen one of the companies I joined was struggling, a recruiter who I connected with previously recommended me for a design role at a new company that she just joined. Be sure to keep those lines of communication open.
With an agency recruiter, you can potentially have a lot more flexibility since they work with multiple companies. You may also develop a strong relationship with them over time. The best agency recruiters also act as mediators. They work above and beyond to not just find a good match but to give feedback to the company and you (the candidate) on what each of you thought about the other.
For example, when I was working with a recruiting agency in the past, they would usually brief me on a role and the client first to gauge my interest. If I was interested, they would then set me up with a phone call or an in-person interview. After each interview, we debriefed to understand what the client was thinking. Not every recruiter might have this process in place, but it doesn’t hurt to ask.
At the end of the day, agency recruiters are usually compensated based on commission. This could be a good thing and a bad thing. It can be good in the sense that they’re also motivated to get you a high salary (since they’ll get a percentage cut). However, it may be bad if the recruiter gets sales-y and tries to push you toward a role that you might not be interested in at all.
Of course, not all jobs that will come your way will be a great fit with your goals. In those situations, it helps to step back and see if the opportunity resonates with you based on the future mapping exercise that you’ve done earlier. If you have a good relationship with your recruiter, they will try to get you a good match; but bear in mind, some opportunities will take time to surface.
Sometimes recruiters get a bad rap for reaching out to designers with UX engineering roles. It’s a tough job, and many entry-level recruiters start off by spamming everyone with semi-relevant job titles. Don’t worry about those but focus on the ones that have their stuff together. Recruiters who have taken the time to understand the design industry are worth their weight in gold in connecting you to the right opportunity, so use them wisely.
If you went to college, you have an alumni network. Universities usually do an adequate job at keeping records on their alumni—after all, who else are they going to call for more donations, though in my experience, they don’t do a good job of promoting these resources to the alumni themselves. Most of the time they do exist, so it just takes a bit of time to search for them on your alma mater’s website.
As an alum, you’ve paid a ton of money to go to school, so make sure you get the most out of your investment.
Here are some resources your school might have:
Official local alumni events in your area, or see if you can find your local event organizers to potentially organize an event together.
Online database of all the people who graduated from your school—great resource if you’re looking to connect with someone.
Informal groups that have been created and organized by your alums for professional development.
Identity, affinity, and interest groups.
Emailing lists informing you of (career or networking) events, latest school news, or alumni stories.
Usually there are tons of resources available for alums, and in my experience either they’re not well advertised or not very well maintained, but they do exist! You never know what famous alumni went to your school. If you went to different schools for your undergraduate and graduate degrees—your potential network is bigger by default.
Same advice applies if you’ve recently done a design or UX bootcamp or have gone through workshops. Although those networks tend to be smaller, they also tend to be more specialized. Leave no stone unturned. It’s highly likely there are resources out there at your disposal that you might not be aware of.
Here are some low-effort online strategies to help you land the first interview. Using a blend of different methods, both offline and online, will help maximize your chances of landing the phone screen.
What if instead of applying to companies, the companies applied to you? Reverse job auction sites flip the traditional model of filling out the same form repeatedly for different companies. Instead you submit one candidate profile and companies bid on your profile over several rounds.
Although you won’t find the giants like Facebook or Google here, the caliber of tech companies is high. You’ll get outreach from smaller startups and mid-size companies, as well as larger and more mature organizations like big consulting companies that are building up their design teams.
Some of the sites you can check out in this category:
Hired offers a personal assistant to help you navigate the job process. To my knowledge no other platform has a free service like that. That said, some designers didn’t have as much luck due to being either new to design or because of applying internationally. It can be a mix, but don’t let that stop you from trying these platforms out.
When applying to any job, the best approach is to establish a personal connection first. Without it, applying online is playing a game of numbers, and the odds are usually not in your favor since you’re competing against many qualified candidates.
Yet it would be a mistake to ignore job boards altogether. Sites like LinkedIn provide advanced intelligence on companies, people, and salaries offered. If you do choose to apply through a job board, try to find out who the hiring manager is and follow up with them directly.
In addition to job posts on Dribbble and Behance, take a look at these other design resources too:
CreativeGuild by Creative Mornings
These days most recruiters are on LinkedIn. Usually they’re given a specific criteria to find and filter candidates—for example, mobile app designer in the gaming space at a mid-stage startup. While some designers forego LinkedIn altogether, I think it’s a missed opportunity, especially when you’re new to the industry. With LinkedIn, you can get a summary of profiles for applicants applying to the same job.
Use LinkedIn as another channel to promote your work. Be sure to fill out your profile and use it as an opportunity to brand yourself. Then flip the switch on your profile to let recruiters know you’re actively looking for jobs.
With LinkedIn you can get a summary of profiles for applicants applying to the same job.
If you haven’t used it in a while, you can usually get the gold subscription for a free one-month trial. I found it helpful to get the inside scoop on jobs, profiles, and a (rough) salary estimate. LinkedIn premium now comes with LinkedIn Learning, which makes it a good value.
You might discover new common connections who changed jobs recently.
Check out who your competition is for the job to get a rough idea of their skill level, but don’t let the job requirements or their experience deter you.
Finally, examine the company to see if there are any common connections. LinkedIn will also show people you went to school with who now work at this company. Use this information to get a referral—and remember, referrals can come from people you’ve just met.
If you’re specifically interested in working with startups, AngelList is a great resource—think of it as a cleaner, curated LinkedIn for applying to startup gigs while getting a transparent salary estimate.
As a side note, AngelList has one of the best newsletters and blogs for tech careers hands-down.
In July 2020, there were 1,939 product design roles in startups all over the world.
Sometimes when you apply to a job through LinkedIn, the posting has been live for a few weeks and the company may have already extended an offer. You can avoid this fate by setting up job alerts and get a consolidated list of new jobs as soon as they’re posted. Most job boards have this feature as well.
If you truly want to get ahead, reach out before a job is posted. Doing so gets you in front of the line before a line even exists. A good way to do this is by setting up an informational interview to learn more about the company and the team.
Set your job preferences.
Aside from the usual suspects like job boards and networking sites, designers are hacking together existing platforms to share job posts. Here are a couple of places I found useful.
Designers Guild is a designers-only community that’s managed by Marissa Louie, Stedman Halliday, Ivy Mukherjee, David Martinez, and Brad Monahan. Designers Guild is a safe space for designers to ask questions and have meaningful conversations about design.
Every month there’s a post on who’s hiring. It’s against group policy for recruiters to join, so the posts are usually made by hiring managers themselves or by designers working for those companies. Usually these posts net a significant number of responses and the caliber of tech companies is high. Most importantly, it sheds a layer of opacity since you can reach out to the person who posted the job.
Twitter can be a good source for connecting with designers directly and for searching for design jobs via hashtags. Yes, this approach might be time consuming, but there are useful pockets of design gigs in the ecosystem.
When you’ve applied to jobs, there’s often a delay on the other side in getting back to you. The hiring manager may be busy, reviewing other applications, or gone on vacation. That said, when you’re looking for work while unemployed, every day counts. Believe it or not, you have more control over the situation. You can either continue applying to more places, or follow up with places you’ve applied to.
Since we already covered various strategies for the former, we’ll focus primarily on the latter half—the follow-up. A big part of getting the first (phone) interview is figuring out what’s happening on the other side. Did they get your application? Is the job still open?
You can get to an answer by proactively reaching out to the employer:
Send a personalized email. Reiterate your interest and let them know about your application.
Call on the phone. Potentially leave a succinct, actionable voicemail that gets them to respond.
Meet in person. At a networking event or even for coffee.
Your approach should be personable and focused. You’re not looking for any job. You’re interested in this specific position that this company has, and it would be their loss to not hire you.
What comes to mind when you think of sales? Mad men? Do you view it as a necessary evil? The truth is, promoting your work, letting people know of your achievements, is a big part of career success long after you get the job. Think of applying to jobs as a sales process with a cycle. Every application you submit is like prospecting. You’re generating a qualified list of companies and roles that could be a good fit. Then you develop that relationship further through various means of contact.
An important part of sales is understanding your clients’ needs. After your conversation, you might discover that this is not the right place for you after all. Or they might reveal specific requirements they’re looking for that you can mention to them in your presentation.
Here’s a general format to follow. Think of this as similar to a pilot’s checklist, ensuring you’ve got the obvious and basic things covered before takeoff.
Catchy title. Grab their attention.
Address by name. This shows that you’ve done your homework in finding who the recruiter or the hiring manager is.
Be clear. State up front that you’re inquiring about a specific role.
Tell them how they know you. You either have chatted with them on the phone or this is the first time reaching out; maybe there’s a connection you have in common.
Get specific. Show them relevant projects that you’ve done that are in this industry or close to the work that they do.
Build enthusiasm. Get them excited by being enthusiastic in your message about this job and the value you can bring to the team.
Close with the ask. “When would be a good time for us to chat?” Suggest a couple of time frames and mention that you’ll follow up with a phone call next week if you don’t hear back from them.
You can use this general format for the initial outreach or incorporate parts of it in a thank you email after the conversation. If this is their first time hearing about you, you want to make sure you start off the conversation strong.
In my experience, you will usually get three basic responses. Here are the underlying messages behind them:
Yes. Come on in, we want to get to know you better. It looks like your skill is on par or slightly above average. It’s possible you could be a good fit.
Maybe. We’re not sure about you based on what we’ve seen. We might be looking at other candidates. This job might not be available soon and we’re unsure ourselves.
No. We perceive your skill to not match the job requirements. You might be too strong or not have enough experience yet. We might not want to tell you this due to legal limitations.
If you do get an outright rejection, treat it as a gift. In today’s world of recruiters ghosting candidates and candidates ghosting jobs, having some transparency is helpful so you can focus your energy on quality opportunities.
One point to remember is that a no is a not now. Take the rejection as an opportunity to follow up, thanking them for their time, and ask if you can get their feedback on areas where you can improve. Suggest that you’d like to stay in touch so that when the timing is right the next time, you’ll both be on each other’s radars.
Sometimes you won’t hear back (yet). People are busy, emails get lost, or sometimes folks just forget to respond. Reach out again in about two weeks, or better yet follow up with a phone call (remember, you already mentioned this in your email above).
A few years ago I was applying for a product designer role at the same company but in a different department. Because it’s an internal job board, you would think I’d get a response quickly after submitting the application. However, it took at least a month and a couple of follow-ups to understand that although they were actively interviewing, they never received my application to begin with.
So don’t despair if you don’t get an immediate response—there many reasons why that could be the case. The important thing is to get clarity on where you stand in the process and keep moving your application forward.
Nobody calls anybody these days. That’s why reaching out with a friendly phone reminder is a good tactic. It also flips the dynamic; now instead of waiting for them to interview you over the phone, you have a little bit of leverage to interview them before the official interview starts.
Your phone call should follow the same principles as your email. Get in an enthusiastic frame of mind, mention your application and how excited you are, and inquire what the next steps are. Sometimes you might even be able to get away saying you’ll be in the area next week and wouldn’t it be great to do a quick chat in person.
It helps to practice this conversation ahead of time. Do a quick rehearsal with a friend. Consider writing out the key points and questions before the call. You won’t have a lot of time on the phone, probably two to five minutes if the conversation goes smoothly, so make that time count.
The key points are also helpful if you’re leaving a message. In that case, also make sure to leave your number—repeat it slowly twice at the end of your message along with your name.
If all else fails just show up at their office, right? That tactic of showing up unannounced might get you escorted out by security. Ideally, you’ve been able to move the process along so that you’ve sent an email, called, and now you’ve set up a meeting in person.
Another way you can meet your prospective employer is by looking at which networking events they’re participating in and where they might be headed off to next. Usually, smaller companies announce conferences they’re attending or presenting at, or if they’ll have a presence such as a booth to demonstrate their services or product.
In my experience, some of the best ways that I’ve connected with employers was by following up with them at professional networking events. If I’d already submitted an application or even when I had already interviewed with them, it was useful to chat with them in an environment that’s more relaxed.
Hopefully this chapter gave you some new tactics to try. The key principle that helped me when I was going through this process myself a couple of times was getting clarity and feedback.
When I wasn’t sure what was going on on the other side, I reached out. I got plenty of rejections along the way, but having a clear answer was more helpful than no answer at all. As you get feedback rolling in, use it as an opportunity to further improve your application, your communication skills, and the types of companies you approach. Good luck out there—and keep learning!
Think of networking as another powerful tool in your job-searching arsenal. Aside from the short-term benefit of finding a job by networking, it opens up the possibilities of making mutually beneficial long-term connections that can last over the course of one’s career.