Senior Art Director

About LetterShop
At LetterShop, we believe collaboration is sustenance. We are a boutique agency weaving strategy and design into communication that captures attention and earns lasting connection. Most days, you’ll find us working shoulder-to-shoulder in our studio overlooking the Hudson River in Dobbs Ferry where we will are sketching ideas, crafting campaigns, and cheering each other on.

Our team specializes in branding for fintech and technology businesses. The majority of our clients are on retainer, and we act as their off-site design team. While we do have some seasonal projects, the majority of our work is with client partners with whom we have developed close relationships over the years. We create everything you can imagine a business would need to market its business, from brand strategy to websites to PowerPoint presentations. If the company requires it, we have the means to make it happen.

We’re a woman-led, tight-knit team of thinkers, makers, and doers and we’re looking for a senior leader to help shape the next chapter of our client experience. If you thrive in creative environments, love rolling up your sleeves with smart people, and find joy in shaping great work and great teams, you’ll feel at home here.

About the role
We’re looking for a Senior Art Director who lives and breathes branding. Someone who finds joy in building cohesive brand systems, sweats the details of typography, and leads with both sensitivity and strength. You’ll guide a talented team of designers, nurture their growth, and inspire them to bring their best ideas forward. Our clients look to us to help them uncover, shape, and express their brands from the inside out. We take a service-first approach to our client relationships—listening deeply, collaborating openly, and building trust through design excellence.

Core responsibilities:

• Lead creative direction across branding and design projects, from concept to execution.
• Develop and evolve brand systems that balance creativity with consistency.
• Provide thoughtful, constructive feedback that helps designers grow.
• Collaborate closely with clients, translating their vision and strategy into powerful design.
• Drive high standards of craft in typography, layout, and digital design.
• Balance kindness and empathy with clear, decisive leadership.

What we are seeking:

• 10+ years of experience working at a creative agency or design studio
• Deep expertise in typography and a love for creating scalable brand systems
• Loves getting their hands dirty and immersing themselves in the day-to-day design work
• Strong written and verbal communication and interpersonal skills
• Experience and willingness to work in an “all-hands-on-deck” team and wear many hats
• Keen eye for trends and what is happening in the world of branding
• Extraordinarily organized and detail-oriented.
• Strong multi-tasker, self-motivated, and an independent thinker
• Must have interest in budgets and ensuring that we continue to provide our clients with value and quality
• A leadership style rooted in empathy and respect, with the confidence to make tough calls when needed
• Experience working with fintech and technology brands is a plus
• Mastery of Figma for design, prototyping, and collaboration
• Expert at the Adobe Creative Suite
• People of color, trans/gender queer individuals, individuals with disabilities, and veterans are especially encouraged to apply

Logistics and compensation 

• This is a freelance to permanent position
• Compensation is based on experience and seniority level
• Upon hire, there is paid time off
• Upon hire, we offer 100% paid healthcare insurance
• Upon hire, there is a 401(k) plan with both traditional pre-tax and ROTH deferrals and employer, 100% vested, safe harbor contributions up to 3% of pay. The plan also provides for an employer discretionary Profit Sharing contribution.
• We work standard working hours from 9:00 AM to 6:00 PM ET. Occasionally, we need to work outside of these hours but this is not the norm.
• Upon hire, this is a fully on-site or hybrid position so the ideal candidate will be within commuting distance of our Dobbs Ferry, NY office.

Please reach out to hello@lettershop-nyc.com with your cover letter and resumé.