Shana Cinquegrana, a.k.a. SHANAshay, is a bonafide 99designs veteran with over 200 contest wins under her belt—most of them in her signature illustration style that appeals to female-run businesses ranging from beauty and fashion to publishing, food and other forms of entrepreneurship.

We sat down with her (virtually) to chat about her New York City bar tending days and how she found her lucrative niche. Read on for a long-overdue designer profile.



Name: Shana Cinquegrana
99designs handle: SHANAshay
Location: New Jersey, USA

You’ve been using 99designs for about 5 years now. What was your career looking like before you discovered the site, and what does it look like now?

When I joined 99designs, I was a new mom forced into “bartender retirement”. It was a tough transition for both me and my musician husband when my daughter was born. We had been living in NYC for 15 years—I was a bar tending and making art, but once I got pregnant I knew I would have to find a new way to continue my craft. I buckled down and learned digital art because it was the only thing I could do from home while taking care of my baby.

Looking back I see that 99designs gave me a new creative outlet which at the time was just as important as making money. I’m not the type of mom who is happy to crawl around on the floor and play with toys all day. I need to have my own career success to be happy. My freelance career was built completely from the ground up, and completely via 99designs. Thankfully I now have a lot of great clients so I stay pretty busy.


You clearly have a real knack for character illustration—generally females. Were you formally trained?

Well, for as long as I can remember I’ve loved to draw. I first moved to NYC to study fashion design at FIT (Fashion Institute of Technology), and there I learned a lot about the industry and the basics of fashion illustration there, but my true inspiration came from working as a bartender in the city. I am endlessly inspired by people, and nightlife shenanigans was the perfect backdrop.

Any examples?

Back in the day I used to draw comic strips of bar scenes from the bartender’s point of view featuring snippets of the typical annoying things bartenders have to deal with nightly. I lived and worked in tribeca in 2001, so the 9/11 attacks had a huge impact on my life and my art.

It was around then that I began painting these sloppy, sarcastic bar scenes on wood or whatever I could find to paint on. The NYC trash yields some really great materials! I sold a lot of paintings and went on to have several shows around the city including murals and some outdoor art. Now, looking back at those paintings makes me cringe. My current digital work reflects who I am now, but I know those old paintings were totally me back then.

A collection of Cinquegrana’s paintings from her pre-digital days

It’s interesting to see how this style transitioned into your current one, which speaks to female entrepreneurs so well. You really found the perfect niche, didn’t you?

Yes, I feel very connected to this market because I am this market. In the beginning when i first discovered 99designs I would browse for contests that let me draw what was fun for me, which drew me to women in my same boat. That grew into a body of work with a common thread. For me, having a narrow-focus has been a good thing. I do what i like and now people have come to expect a certain thing from me, which is great.

I will also say that motherhood has definitely softened me, and has given my style so much more joy and humor. I really want to connect with women on a sincere level. My style is not sticky-sweet, nor super high-end. I aim for somewhere in the middle where real people live. I like things kind of sarcastic and playful. Many times, if i had it my way, I would do things a little differently than the client wants. I find many clients want way too much detail and expect their logo to be a full blown illustration that tells the whole story of every aspect of their business. I respectfully disagree.


But it isn’t easy telling a client “no,” is it?

In the beginning, I was really just learning how to both use Adobe Illustrator AND communicate with clients. Back then I would give the moon and stars to please a client. But once I had several wins under my belt and was starting to feel more confident about my skills and my eye, things shifted.

I think it is important to express your opinions and recommendations to a client because it builds their confidence in you. I find myself telling many clients “less is more”. I usually present them with simplified silhouette versions because I know eventually they’ll realize what I’m talking about. If they don’t agree, or don’t get it, it is time to move on. It is easy for us to undervalue ourselves as artists, but I try not to waste time on a client who does not share my taste.

Do you have any other advice for designers using contests?

My advice for any new designer is to play to your strengths, and to keep open to feedback and critique. Developing a thick skin is key because not all the feedback is going to be good, but also remember to trust your instincts. Keep it pro and positive. I know how passionate we artists are about our work, but honest communication is everything. There is always a way to stand up for your ideas without being defensive. It’s not all about winning the contest; it is about putting out high quality work you can be proud of.

Some of my favorite designs land in the “eliminated” pile, and often times “the winner” is far from what i feel is the best design. Keep it moving and don’t get too emotionally attached—easier said than done, I know! If anyone in a contest inspires anger in me, i imagine them sitting at my bar. Face to face i know we could find something to agree on and laugh about. This is a highly competitive climate but it’s important to remember we are all real people.


How about with regard to improving your skills as a digital illustrator?

I’m self taught in Illustrator, so entering a ton of contests was really how I honed my skills. There will always be more to learn about both design and being a businesswoman. I’m excited to learn! My daughter is now almost 7 andI’ve been teaching her Illustrator since age 3. She inspires me to keep up with the times and embrace change.

What are your hopes and plans for the future?

I’m interested in working with web developers and licensing out my illustrations. I’ve got a ton of original illustration in my 99d archives, so i would love to send them out into the world. I’m interested in brand development and social media design as well, and would love to team up with more people on the business end of things. I also think it would be fun to do some more grown up/sexy illustration and move into a more “fine art” direction.


We’d love to hear a little about where you live now. What inspires you there?

Currently my family lives in New Jersey, about an hour outside of NYC. We moved here because the public schools are better, but my heart will always be in the city. I love the multicultural experience, food, wine, art and music. Now that I’m in the suburbs I’ve found a handful of like-minded mommies to connect with. I’m a huge believer in yoga and good nutrition to keep balance in life. A lot of good inspiration comes from unexpected sources, like your backyard. It is good to step away from the computer!

Lastly, a bartender question: what’s your favorite drink?

WELL … I love to taste good wine and craft beers, but I drink vodka or scotch (with water or club soda). I’m a calorie conscious drinker who has learned to avoid sugary drinks because they lead to bumping hangovers 🙂 I do however have the ultimate respect for good mixology!

Questions for Shana? Give her a shout in the comments!