Reaching Out Directly

5 minutes


Updated October 11, 2023
Land Your Dream Design Job

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.

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.

Talking with the Hiring Manager or Recruiter

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.

Diversify Your Outreach

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.

Setting up Informational Interviews

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?

Working with Recruiters

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

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.

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