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Commission Creative Problem Solving Jobs in Chicago, IL

Smartly

Creative Director, Brand & Content

Chicago, IL · On-site

Experience as a conceptual Art Director, with a portfolio that demonstrates strong campaign thinking and creative problem-solving * Ability to translate strategy, messaging, and business goals into ...

Jobtailor

Creative Director

Chicago, IL · On-site

$110 - $170/hr

Advanced problem-solving skills * A deep understanding of brand strategy and marketing principles ... Adobe Creative Suite Proficiency * Brand Strategy Understanding * Cross-Functional Team ...

Smartly

Creative Director, Brand & Content

Chicago, IL · On-site

Experience as a conceptual Art Director, with a portfolio that demonstrates strong campaign thinking and creative problem-solving * Ability to translate strategy, messaging, and business goals into ...

Smartly

Creative Director, Brand & Content

Chicago, IL · On-site

Experience as a conceptual Art Director, with a portfolio that demonstrates strong campaign thinking and creative problem-solving * Ability to translate strategy, messaging, and business goals into ...

Big I Illinois

Client Service Representative

Skokie, IL · On-site

$50K - $53K/yr

Candidates should be energetic and organized with excellent problem solving skills. Worthy Insurance focuses on providing creative insurance solutions to the healthcare, social service, and real ...

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$107.7K

$162.8K

How much do commission creative problem solving jobs pay per year?

As of Aug 26, 2026, the average yearly pay for commission creative problem solving in Chicago, IL is $107,746.00, according to ZipRecruiter salary data. Most workers in this role earn between $73,700.00 and $150,900.00 per year, depending on experience, location, and employer.

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Creative Director, Brand & Content

Smartly

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 17 days ago

Job description

Creative Director, Brand & Content

Smartly is looking for a Creative Director to join our Brand & Content team and help shape how our brand comes to life across campaigns, content, events, digital experiences, and marketing initiatives. Reporting to the SVP of Brand & Content, this role combines creative leadership, people management, and conceptual thinking to create work that is distinctive, effective, and aligned with our business goals.

You'll lead a team of designers, develop strong creative concepts, and partner across the business to bring Smartly's story to life. This role is ideal for someone who began their career in design, has evolved into a conceptual art director, and enjoys helping creative teams produce their best work.

What You Will Do
  • Lead, coach, and develop a team of designers, creating an environment where people can do their best work and grow their careers
  • Develop creative concepts and campaigns that strengthen Smartly's brand and connect with target audiences
  • Provide clear creative direction and feedback throughout the creative process, from brief through final execution
  • Partner with Brand, Content, Product Marketing, Communications, and other stakeholders to translate business objectives into compelling creative solutions
  • Elevate the quality, consistency, and effectiveness of Smartly's visual identity across all channels and touchpoints
  • Review and approve creative work, ensuring it meets strategic objectives, brand standards, and quality expectations
  • Help establish and refine creative processes, workflows, and ways of working that enable the team to scale its impact
  • Stay current on design, advertising, and cultural trends, bringing fresh thinking and new approaches to the team's work
What We Are Looking For
  • Experience leading and developing creative teams, including direct people management responsibilities
  • Strong background in graphic design, brand design, visual communication, or a related creative discipline
  • Experience as a conceptual Art Director, with a portfolio that demonstrates strong campaign thinking and creative problem-solving
  • Ability to translate strategy, messaging, and business goals into engaging creative concepts and visual storytelling
  • Strong design craft and a deep understanding of typography, layout, visual systems, and brand identity
  • Experience partnering with cross-functional stakeholders and navigating feedback from multiple audiences
  • Excellent communication, presentation, and collaboration skills
  • Ability to balance creative excellence with practical business outcomes
  • Experience working with consumer-facing brands or B2C marketing is preferred, but not required
  • Experience working in technology, SaaS, or high-growth environments is a plus
What We Offer You

Five weeks paid time off (PTO), 11 company paid holidays, unlimited sick days

Generous healthcare packages & mental health benefits

401K plus matching & equity grants for all new Smartlies

Wellness benefit & learning reimbursement opportunities

Volunteer time off days & company donation matching opportunities

And so much more...

The base pay range for this position is as mentioned below per year, plus an annual performance bonus. We take into consideration an individual's background, expertise, and experience in determining final salary. In addition to annual salary, Smartly's total rewards provide employees with stock options, medical/dental/vision insurances, retirement savings benefits, parental leave, 5 weeks vacation, unlimited sick days, life insurance, and disability benefits. This information is provided in accordance with applicable law. Base pay information is based on market location.

Salary in USD: 120,000-150,000

Curious what it's like to work at Smartly? Visit our Careers page to see how we grow, collaborate, and make impact together.

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