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Creative Director

Product | Chicago, IL | Full Time

Job Description



Creative Director

Creative Director – Sittercity, Inc.

Sittercity is a high growth, fast-paced and dynamic web company founded in 2001.  We are America’s largest and most trusted online solution for connecting families with high-quality, local caregivers, including babysitters, nannies, tutors, elder care providers, pet sitters, and housekeepers. With over 2 million members nationwide, Sittercity connects families with pre-screened caregivers by providing detailed profiles with photos, parent reviews, background checks, up-to-date availability, references and caregiving experience. In fact, every 30 seconds Sittercity connects a family with the local caregiver that meets its unique needs. 

Our Creative Director is a newly open opportunity for our organization.  We are looking for someone to make a high impact for our company in the open marketplace.  This is an exciting opportunity – one we trust will be both personal and professionally rewarding. 

Position Summary:

The Creative Director will develop original creative design concepts and approaches, owning all phases of creative development including conceptual, visual design and user experience. You will work closely with our business team leaders to shape all phases of creative development including conceptual development, branding (working with the marketing team) and visual design while possessing reasonable depth and expertise in content development, user experience and technical implementation.  Strong knowledge of website design is essential. 

In addition to this, you will be responsible for mentoring and managing the efforts of a creative team across multiple projects. As the Creative Director, you will maintain and enforce the highest creative standards while remaining aware of project goals, milestones and budgets.

We are based in Chicago but will support work-from-home with some travel to Chicago.


  • Promote continual creative improvement and actively contribute to a culture of innovation, excellence and accountability.
  • Conceive and create experience-oriented design solutions that fulfill strategic business objectives.
  • Responsible for articulating and defending conceptual and directional choices.
  • Serve as overall creative lead but responsible for inspiring and motivating creative staff.
  • Direct all phases of creative work from concept through production.

To be considered, you will bring the following:

  • A strong understanding of web standards, interface design principles, responsive design accessibility and CSS.
  • Advanced skills with Adobe Suite (Illustrator, InDesign, PhotoShop).
  • Ability to thrive in a fast-paced, deadline driven environment.
  • Previous experience managing creative projects from concept through final execution.
  • Ability to be flexible and creative in a wide range of project types.
  • Information architecture and wireframing.
  • Marketing and Agency experience a plus.


  • Bachelor's Degree in Fine Arts, Commercial Art, Graphic Design, or similar.
  • 6+ years designing for the web and digital channels.
  • Must have impeccable references and portfolio.

Please include a link to your portfolio.

Our Workplace:

We operate in a casual and fun environment in the River North neighborhood of Chicago.  Perks include weekly on-site yoga classes, unlimited healthy snacks, weekly lunches, quarterly outings, and work-at-home Fridays.  In addition, we offer a very competitive benefits package including Health, Dental, Vision, Short-Term Disability, Long-Term Disability, Life Insurance, 401(k)  as well as 3 weeks of paid time off to start. Sittercity is a Recipient of the 2012 Work-Life Seal of Distinction Award from the Alliance for Work-Life Progress.                                                       

Sittercity is an Equal Opportunity Employer committed to hiring a diverse workforce.  We consider all applicants for employment without regard to race, color, sex, sexual orientation, gender identity, religion, age, national origin, disability, veteran status, or any other basis as prohibited by federal, state or local law.  Sittercity participates in E-Verify.

Interested applicants, please apply at