Illustration by Laura Thompson

The first step to getting work is building an impressive portfolio. The second step is less obvious: pitching your portfolio, and yourself. The perfect pitch—does such a thing exist? It depends on who you ask, so we asked five art directors, each hailing from a different set of coordinates across the media and publishing landscape. How do they find and commission new work? What should designers not do? Some art directors like receiving midweek emails, others want you to know what “a big book” means (it’s not what you think), and essentially all of them are looking for new talent on Instagram. Whether you’re starting out as a freelancer or hunting for new gigs, we’ve got you covered.  

Question 1: How do you get their attention?
Inside the minds of five art directors…

The art director at The New York Times:

“There’s always this ‘it’ factor with new work. If you’re owning the style you’re developing, that will be apparent, and then I know you can reproduce that same level of work. I’m able to infuse more fun and personality into the Parenting site at the Times; it’s not straight news, so not everything has to be neutral. I probably get 100 promo emails a week, and I look at as many as I can. But on Monday morning, it’s going to get buried. Same with Friday afternoon. 

I use Diigo to create a tagged database of illustrators. If I have a story that needs a figurative illustration, I type that in and comb through websites, Instagram feeds, and cold emails that I’ve saved, and they’ll pop up. That’s why I suggest sending pitches in an email, because then you’re one step closer to my database.” — Deanna Donegan, art director for NYT Parenting 

The design lead at a big tech company:

“Within tech, art direction is a newer function. Lately we’ve been working with two to three outside contractors a month, and that’s increasing. I’ve gotten unsolicited DMs, printed zines, or small self-promos. That stuff actually works, but it doesn’t work all the time. I might not have something for you at this moment, but in a few months, who knows? There’s a lot of power in imagery to set the stage and mitigate concerns about new tech. If your work is on the nose in feeling like it belongs within the tech sphere, it’s less of a fit. If we’re talking about AI, we’d rather make the technology a little more relatable and approachable with work that has a confident pencil line and feels more human.” — Damien Correll, art director at Google Design

The book cover director at a big publishing house:

 “Most book cover art directors can’t handle all their titles in-house, so they’re all looking for freelancers. There are fewer kids in art school thinking about books, but there’s so much work to do. We’re all looking for a new person we can trust, meaning someone who delivers a great set of comps in a timely manner and works to give real revisions until the project is done. Before you email an art director, look at the books they work on, or their imprint(s). Also, get to know the publishing cycle. There are three seasons: You launch books, work on covers, and finalize before sales seasons. The best time to send me a little blip is right when I’m assigning books, so mid-March, mid-summer, and around the end of October. That’s when I have a list of books to assign.” — Jason Booher, art director at Penguin Random House

The Condé Nast art director:

“We have a very specific editorial style—very graphic and pop-y, with a lot of whim and whimsy. It’s not too serious; we have fun with food and fun with our illustrations. Most of our work is done internally, because of the changing landscape of magazines. I have two staff photographers and a full design team, and I lean on them a lot. We can’t afford to commission everything out, but we do use outside people for illustrations. Expressing very specific interest in why you like our publication and why you think you can bring something to the table, that goes far.” — Michele Outland, creative director at Bon Appetit

 The head of a branding agency:

“We have one or two freelancers working on different projects at any given time. We’ve found that we’re successful when we bring on people who want to work with us, because our work is sometimes in the political area and often deals with race and gender. The other reason is we often work on really long projects where you have to be patient. You don’t always see your work out in the world tomorrow. We just rebranded Carnegie Hall, and that project started in 2018. We typically hire people who reach out to us directly through our ‘work with us’ email address. An email that is well-written and well-informed about what we’re doing out in the world, it means that person knows what they’re getting into when they come to us. Things that feel too canned aren’t good. We can’t respond to every email, but as of a few months ago we set up a system to file them so that when we’re hiring six months or a year later, we know who to go to.” — Bobby Martin, founding partner at Champions Design 

Question 2: What about social media?

Take your Instagram feed seriously 📸

“The number one place I find new people is on Instagram,” Donegan says. These days, Instagram can stand in for a portfolio. Don’t kill yourself trying to get a follow from every art director—most said they find new work while surfing other people’s likes and follows anyway. Focus instead on your presentation, or open a separate account just for work. “I react to a curated feed,” Outland says. Donegan agrees: “When you post, you’re showing art directors what you can do tonally. So if I come to you it’s because I’ve seen what’s within your range.”

Take your spec work seriously, too.

Find a prompt and then make some stuff. “Just work to make your portfolio more cohesive,” Donegan says. If you’ve never done a book cover, design a dozen. “I once had an art director who told me to go make 10 book covers in 10 days. I ended up with six decent covers,” Booher says. “Don’t do the classics; that’s like doing an identity for Coca-Cola or Nike. I recently did a redesign of 1984 and I was sweating balls because it’s like, How many people have tried this? Do a non-fiction title, or your favorite book. Go to The Strand or your local used bookstore and get a dollar book that’s really weird and random, and then you have all the copy in front of you.” 


Question 3: Anything I shouldn’t do?
Four common pitfalls to avoid…

Don’t just say, “Hey, here I am!” Anyone who’s written a cover letter has heard this advice, but it’s worth repeating: Tailor your pitch to the person or company you’re pitching. “Tell me why a recent piece moved you, or how you feel your work might sync with ours,” Outland says. Also: Say, “ ‘I’d love to illustrate for Bon Appetit (or Healthyish, etc.)’ instead of just saying ‘your publication’ in the email.” Martin agrees: “Addressing us as Bobby, Jennifer, and the Champions team, and speaking to something we’ve done and put out in the world, it lets us know you’re paying attention.” Tiny changes, major mileage.

Don’t only send your portfolio as a PDF. A busy art director can click on a website or an Instagram handle much faster. They also can’t save a PDF to Pinterest,, or Diigo.

Don’t get too swept up in a design trend. “There are certain waves where you see young illustrators latching onto a style of someone who they know is getting work,” Donegan says. “Most art directors are going to know who you’re emulating, so it’s not going to be a successful approach.” 

Don’t skip straight from getting the assignment to submitting a fully-rendered piece of work. “Seeing optionality early is always going to net a better result,” Correll says. “If someone gives you one piece to talk about early on, then it’s clear there’s already a path taken, and if you have to negotiate it feels like you’re going backwards.” 


Question 4: How do I know what they’re looking for?
Some helpful tips for cutting through the jargon…

Human: “ ‘Bring a more human touch’ means, ‘let’s make this look like it wasn’t made on a computer.’ ” — Correll

Clean: “A generous amount of white space, or an austere, minimal design.” — Correll 

Playful: “There’s naïvete to the line work, or it’s colorful. It could be really reduced shapes or abstraction. Proportions play into this. But usually it’s color.” — Correll

Gesture: “The pose of a figure in the piece. Maybe a person looks excited, but we need them to look calm. Or it’s the relationship between two figures.” — Donegan

A big book: “It’s not literally big. It means all the elements add up to something that feels important and large. If it’s fiction, it means it’s a big-deal writer.” — Booher

An idea book: “It’s simple, but there’s a concept, like the matchbooks on the cover of Malcolm Gladwell’s The Tipping Point.” — Booher

Commercial: “This isn’t bad, it just means you’re setting certain signals. You need it to be brighter and less conceptual.” — Booher

Process: “If I ask ‘what was the process in coming up with this,’ what I’m really asking is ‘why does this look the way it does?’ I’m just trying to get people to talk about their work.” — Martin