Creative Director (Chicago, IL)

| Chicago
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About Leap:

Leap is building the world's largest network of branded retail stores – powered by data, systems and scale. The Leap Platform enables brands to deploy stores that work in concert with eCommerce more rapidly and at significantly reduced cost and risk. Brand stores powered by Leap bring modern brands to life with compelling, immersive customer experience and data driven operations. At Leap, our diverse, growing team is excited by the opportunity to power the next generation of leading consumer brands with a vibrant presence in local communities throughout the country. We're one of the fastest growing companies in the retail/eCommerce space - since launch we've powered stores for dozens of brands, and we're adding more brands and stores each week.

In 2021, our third full calendar year in business, we grew 4x+ by every measure and are heading into 2022 with 50 stores open, 30+ active brands in our store footprint (500+ total registered) and a team of 300+, and poised to grow another 5x in the near term. With new platform capabilities launching, an ambitious revenue plan and operational expansion across existing and new markets, this is a dynamic organization ready to scale its creative capabilities.

Our brand customers are modern brands who lead or aspire to lead their categories today and tomorrow, and *outstanding* people are literally at the core of our product. Our organization is composed of a diverse range of talented individuals and teams. With functions like Real Estate, Store Design & Development, Retail Operations, Marketing, Engineering, Product Management and Data Science, we are a unique company. Our shared ambitions and core values tightly align and drive us to succeed. Our staff are what make our organization so special and honoring our culture and values as we hire, onboard, engage, develop and support our teams is paramount. Come take this leap with us. Your ideas, thinking, and voice are wanted.

Mission for the position:

The Creative Director’s mission is to ensure the Leap brand identity is expressed consistently across all mediums, channels and audiences, from our marketing and investor relations collateral to sales and product user experience for brand customers and employees, and more. The Creative Director will create value by pushing and adding to the thinking of Leap brand/business leaders and managers, and working to translate concepts into clear and compelling visual assets that convey vision and drive desired actions. In this role you will learn everything about Leap and our market (brand customers, consumers i.e. store shoppers, real estate partners i.e. landlords and broker partners) and find creative ways to communicate core/critical business concepts to each, such as why the platform matters, what our products are/do, how the business works, and more. The creative director will be part of the marketing division working across both B2B and B2C marketing workstreams, while also working closely with our CEOs and the product teams as we continue to develop our Platform.


  • Own the Leap brand visual Identity, brand book and art direction
    • Refine Leap’s B2B identity to convey the Platform’s growing value proposition
    • Translate company strategy and Product Marketing concepts into compelling creative
    • Ensure application of brand identity across all platforms: web, app, collateral, slides and more
    • Create and execute visuals for presentation, product content, templates and style guides
    • Curate photographs, artwork, graphics, and designs for company-wide use 
    • Ensure on-time and on-budget project delivery 
  • Help set strategy for and execute brand communication, with particular focus on product, marketing, investor relations and employer brand building assets.
    • Collaborate with product managers to bring Leap’s B2B brand identity to life in internal and external product and platform systems/tools (i.e. the Leap app)
    • Adapt creative to various stages of the customer or prospective customer lifecycle 
    • Develop creative templates collateral and advertising materials for B2B marketing
    • Partner with Brand Management & external agency to define Leap’s B2C identity and ensure brand is consistently brought to life across all touch points (signage, CRM, collateral, etc)
    • Support People & Culture team employer brand building and DEI initiatives
    • Partner with senior executive leadership (our Co-CEO’s, CFO, CTO, et al) to support investor relations work and deliverables

Competencies for Success:

  • Bachelor’s degree or higher, or combination of relevant education, experience and training
  • 7-10 years of related experience in a comparable role – consumer business / technology platform, or brand building experience are both a plus but not required
  • Exceptional Design Portfolio
  • Strong data visualization skills 
  • Excellent written and verbal communication skills
  • Strong business acumen
  • Excellent visual design skills


Outcomes & measures of success:

  • Consistently delivers visual assets that are clear, compelling, reflect strong understanding of the Leap business and strategy, and create value for stakeholders inside and outside of the company
  • Establishes strong relationships with colleagues throughout the company and effectively helps to drive projects and teams, particularly cross-functionally

Why take the leap? 

  • The mission at Leap - to build the world’s largest network of branded retails stores – powered by data, systems and scale, is literally transforming the future of retail, and all Leapers contribute to making this happen.
  • We offer a competitive salary, performance bonus, employee option grants, 401K, paid sabbatical, heritage holidays, charitable donation match, discounts across all of our brands, meaningful health and well being benefits and MORE! 
  • We believe and invest in professional development, employee satisfaction and internal advancement.
  • We offer a work environment that is diverse, inclusive and welcoming to all.

However you identify, whatever your path to get here; Leap celebrates diversity and is committed to maintaining a safe, rewarding and inclusive environment where Leapers thrive individually and as a team. 

In order to achieve our mission, building the world's largest network of branded retail stores – powered by data, systems and scale; we need to work hard to foster a diverse community to support the brands and customers we serve. These aren't just words, this is who we are. We know that our differences are what make our organization special and are paramount to our culture. Your age, skin color, beliefs, sexual orientation, nationality, disability, parental status, vet status, gender identity are valued.

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Technology we use

  • Engineering
    • GolangLanguages
    • JavascriptLanguages
    • PythonLanguages
    • ReactLibraries
    • ReactFrameworks
    • GCPFrameworks
    • FirebaseDatabases
    • BigQueryDatabases
    • LookerDatabases


Our company is located in the heart of River North, a hub of trendy restaurants and bars with easy access to trains and plenty of local parking. The office is the ideal location for commuters and anyone looking to explore fun Chicago culture. There is always something to do!

An Insider's view of Leap

What are some social events your company does?

Work-life balance is great and Leap offers flexibility. As a parent, that is key for me.
While covid was at its height, we were doing virtual hangouts which was great and a nice way to get to know the team. We navigated that part nicely. As the world started opening back up, we incorporated other fun in person social events to our calendar.

Robert Battista

Senior Analytics Engineer

How do you collaborate with other teams in the company?

At Leap, each day is different. We have an opportunity to work closely with each store team and bolster momentum to continue to scale and grow our tech operations. While we do have our every responsibility at Leap, we also have freedom to take on projects. If we see a business need, we can allocate time and resources to puzzle out a process/system.

Bushra Shahid

Support Technician

How has your career grown since starting at the company?

I went to a team of one to a team of two and potentially three.
Over the course of my time here, I've added a managerial role to my position. I’m supporting other team members and their growth. I’m stepping away from minute daily activities and looking at the bigger picture. Over time, that'll grow into helping Leap as a whole, not just my team.

Mark Ellis

Support Manager

How do your team's ideas influence the company's direction?

Our cross-functional product teams design and build the retail platform that powers our network of stores. Every day they generate ideas and make decisions that directly impact our customers, employees, and the overall company direction.

Todd Webb

Vice President of Product

What projects are you most excited about?

Our goal is to fundamentally change how retail works. It feels amazing to have a team that has such innovative ideas for accomplishing this goal. More specifically, we are putting the framework down for automating how stores get on the platform. In time, the technology will configure itself and everything will be plug and play (which is exciting).

Eric Gaydos

Integration Manager

What are Leap Perks + Benefits

Leap Benefits Overview

Did somebody say discount!!? Along with all of our benefits such as health insurance (medical, dental, vision) and employee incentive programs, we also offer many amazing perks., such as a flexible work environment (remote, hybrid, or fully onsite) and hours, unlimited PTO, and product discounts across the brands on our platform. We also strive to maintain a healthy work environment and offer EAP programs and other benefits to support mental health and wellbeing.

Volunteer in local community
Friends outside of work
Eat lunch together
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Unconscious bias training
Unconscious bias training is a part of our onboarding, and it's actually fun and enlightening.
Diversity manifesto
Mean gender pay gap below 10%
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Employee Stock Purchase Plan
Performance Bonus
Match charitable contributions
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Company Outings
Happy Hours
Pet Friendly
Recreational Clubs
Relocation Assistance
Professional Development Benefits
Job Training & Conferences
Diversity Program
Cross functional training encouraged
Promote from within
Time allotted for learning

Additional Perks + Benefits

We have a true open door policy. Our Co-CEOs offer office hours during which employees can have one-on-one time with them for questions, etc. Additionally, we have a store immersion program in which members of corporate spend time shadowing members of field in our stores. We all learn from one another to better help us learn how we fit into the larger picture at Leap!

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