Chief Brand Officer at Flodesk


RebeccaShostak (Chief Brand Officer at Flodesk)

Rebecca Shostak is the co-founder and Chief Brand Officer of Flodesk — a simple, intuitive software platform specializing in stunning email marketing and e-commerce. She began her career designing merch for Linkin Park and Rihanna.

California, United States • August 15, 2023

What led you into design?

As a kid, my peers were into dolls, painting their nails, or pop culture—but I just wanted to build things. I'd try to get people to start clubs (which made me kind of unpopular), mostly because I wanted to design the logo and brochures.

My mom had friends who sewed, so when they visited they'd gift me these bags of scraps and cloth instead of candy or toys, which got me so excited. I loved to make things and play with materials. My favorite place to go, even when I was young, wasn't a toy store—but an art store. I would see the colors and creative materials and couldn't wait to get my hands on all of them to start making things. So even from a young age, I was a designer.

I started learning how to use Photoshop at ten years old and became an Adobe fiend. I was hooked from the start and spent almost all my free time working—to the detriment of my social life. When I wasn’t on the computer I spent my time on pen and ink drawings, paintings, scratchboard, and fine art.

When I was 13, I was on the cover of Silicon Valley magazine. In the interview I said that when I'm older, I want my own business and graphic design firm. I don't know where I got the idea from, but it was something that was in me from the start.

One thing that shaped my transition from the fine art world to graphic design—precisely, computer-aided design—was my high school robotics team. I became captain of our 3D animation team there and fell in love with all things computer graphics.

I studied both graphic design and English in college because I have always been really interested in the way words and visuals interact. I like to think of myself less as a traditional designer and more as an expert in visual communication. I also won a lot of awards during this time, including being the youngest person to win an Adobe Design Achievement Award, which encouraged me to continue pursuing this direction for my career.

In my first job out of college, I got hired by a company that does merch designs for a lot of big artists. They brought me on primarily because my style resonated well with women. I did a lot of work for the Umbrella Tour for Rihanna, like her t-shirts and calendar. I also did a ton of work for Linkin Park, which was great because they were my favorite band growing up. I had a lot of fun walking into various Hot Topics at the different malls in L.A. and seeing my t-shirt designs lined up on the wall. When I pointed them out to the clerks, they didn’t believe me that I’d designed them!

What does a typical day look like?

My days are spread out like a fan because my design team is in Europe and our engineering team is in Vietnam. I wake up early and get on calls with my Europe team. Then I'll work all day with the American team—and in the evening, I'll hop on calls with the engineers.

When we started Flodesk, I executed everything from the product design to the product templates, our brand, and all of our marketing graphics. We've been hiring, so now I'm more of an art director, manager, curator, and giver of feedback. Instead of doing all the work myself—which is something that designers often have a hard time letting go of—I'm trying to impart my thoughts and my creative processes to my team members so they can be independent thinkers and do an even better job than I could have.

What's your workstation setup?

Where do you go to get inspired?

I'm lucky to be married to someone who's both an architectural historian as well as a practicing architect. He brings up a lot of interesting historical references and essays about how the continuum of history and culture has shaped design and architecture. We talk about philosophies that informed buildings over the centuries, which gets me thinking about what that looks like when you translate them into graphic design.

I frequent design and art museums, too. It's important to understand the past as well as the present because, from that, you can extrapolate the future. I'm big on design history, fine art history, and cultural history—especially Western culture from the past 500 years.

There's so much to learn from it. I especially find it fascinating how you can map culture to art and design. For example, industrialism shaped modern art and design principles, while Greek philosophical revival shaped the Renaissance. Even the present is inspired by these old philosophies, although most people don't realize it. They're very much present with us to this day.

I also make an effort to walk around when travelling. There are so many creative small businesses popping up everywhere from Lisbon to Mexico City. I notice a lot of small “concept” businesses, restaurants, and popups that have curated menus and are highly brand conscious—they really care about the way their stores and displays look. If I see a line out the door, I'll go and investigate because I'm fascinated by what makes people want something. Why do people want to buy a product or engage in an experience? What makes people willing to stand in line for hours? I like exploring what's happening in the real world and understanding what excites people. Then, I try to bring that into the digital world.

Another big inspiration for me is the Flodesk member base. I bring that up because knowing your audience when designing is essential. It's not about my own style—but rather getting inspired by what our customers love and how they express their brands. It then becomes my job to extract the essence of their brand and bring them templates that are a high-design version of what they're trying to do so that we can inspire and elevate their work.

What product have you recently seen that made you think this is great design?

I love Notion. I use it both personally and for work. It has a snappiness to it with its typography, spacing, and design system—making it a delight to use. It works as I would expect it to. It has advanced features that it tucks under the hood, so I don't feel overwhelmed with the UI. And it looks beautiful, right? It makes me feel like I'm organizing myself in an environment that inspires me to be creative.

Creative brains have trouble switching between administration and creativity, which is critical to business success. Notion provides an excellent bridge between those two where you can go into organizational mode and work on being more of an administrator, getting your to-do lists together without feeling like you're completely leaving your creative flow.

What pieces of work are you most proud of?

Flodesk's builder. I would consider our builder system for creating your emails, forms, checkouts, and workflows one of my most significant masterpieces of all time. Even though there are always improvements to be made, it has evolved through countless iterations like a rough stone smoothed by the ocean over time to become this seamless experience where people can get lost in a creative flow. Email builders are a tool that used to be stressful in legacy software, but Flodesk’s builder genuinely aids people to design exciting things. We often get compared to MailChimp as the “easier version” because it's so painful for users to design even the most basic emails within MailChimp. When they come into Flodesk, we hear it's like a breath of fresh air.

Creating a piece of software that can instill that kind of feeling in someone and help them get the output they want is amazing. I'm proud of my original designs and where the team's taken them—creating a tool that's powerful but feels so simple and speaks to the creative mind.

What design challenges do you face at your company?

Our biggest challenge right now is the transition from designing things as one-offs to systems—in everything from brand to product. In the early days, we built quickly, fast, and dirty. I approached product design more like a print layout than a living piece of software; the result was a lot of inconsistency, from our UI components and UX patterns to how I built the templates themselves. I even used Photoshop from some of the earliest iterations of the platform. 

It was the same with our original brand. There were no strict guidelines; my cofounder Martha and I just designed a cool-looking landing page on the floor of her San Francisco apartment using my favorite font. Whenever we posted on social media, I used different graphics and fonts. While this created a human touch to the brand (and product, to an extent), it was inevitably unsustainable. Today, our design team focuses heavily on bringing a systems-based approach to everything we do—from products and templates to brand assets. I'm excited about these necessary initiatives that unlock our ability to scale our design output, but cleaning up the "design debt" left behind by our original one-off approach takes a significant investment in terms of the team's time.

What music do you listen to whilst designing?

Any advice for ambitious designers?

I want to reiterate what Brian Chesky said—we need more design entrepreneurs. Look at the number one most successful company on planet Earth: Apple. Apple differentiates itself with a huge commitment to design. Design is not only a sense of aesthetics but the way things work and feel. You'll encounter many people—VCs, mentors, and people in the business world—who will tell you that design is not a differentiator and that you need something else. But I disagree. I think that great design is the biggest differentiator you could have. Your design skills are valuable. Lean into design if you want to build a company that lasts. Don't be discouraged.

The other thing I'd say is to lose the ego! It won't serve you when you're building for someone else. The difference between a designer and a fine artist is that design is creativity for a function. It's usually a function you hope to get in front of many people, whereas fine art is about self-expression. Don't turn your design into self-expression if you're trying to build a company or want to serve others. Listening to your clients, customers, or users is critical to creating successful designs.

Anything you want to promote or plug?

Flodesk is for the creative mind, so I'd encourage anyone who's a designer and wants to get their email list started to try Flodesk free for 30 days. It's a much better way to grow a business and make money than by putting your efforts into social media.