We are an employee health & benefits company with a tech-meets-service platform that simplifies and personalizes how employees and employers shop, enroll and live with their benefits. Our innovative technology makes it easy for employees to choose the right benefits plan while equipping HR with the tools they need through one partner, one service team, one platform, one portal.

Maestronites were brought together with a passion to disrupt the status quo by reimagining employee health and benefits. This passion has driven us to create the first complete platform that optimizes the entire benefits experience for everyone. Our people. passion and platform are united by our mission: to make employee health & benefits people-friendly again.



We are seeking a Graphic Designer to work in our Chicago office. The successful candidate will be responsible for creating visual and print designs for the marketing department. The Graphic Designer will be responsible for designing marketing materials, including ads, brochures, sell sheets, infographics, social media graphics, email design, tradeshow & event graphics, print layouts and more.  This individual will design web layouts and digital media graphics as well.

  • Collaborate with different departments and the marketing team to produce print and digital designs to deliver Maestro’s brand message to a wide prospective audience. ‘Tell a story’ through design.
  • Develop innovative visual concepts to further the company’s edgy brand identity
  • Promote the brand ideas of the company through visual design; communicating a modern, and EDGY aesthetic – that speaks to c-suite executives and young professionals
  • Generate original concepts for visual design projects (vs. being told what to create and then creating it)
  • Collect project requirements and accurately estimate project timelines



  • Delivering edgy and out-of-the-box concepts for campaigns, presentations, event campaigns, etc.
  • Deliver projects on-time
  • Receive public accolades from the company for your work
  • Clients comment on the professionalism and fun of the proposal packages
  • You are recognized for one of our core values: Fun. Preparedness. Teamwork. Humility. Urgency. Bold Thought. Honesty.  



  • 4+ years of print design with at least a year of digital design
  • Expertise in InDesign, Illustrator and Photoshop
  • Experience generating designs consistent with an organization’s brand
  • Mature use of typography, color, and layout to convey concepts/emotion
  • Exceptional communication skills; ability to digest feedback and incorporate that feedback into future iterations
  • The ability to balance several projects at a time
  • The ability to prioritize and work quickly on projects
  • Excellent listening skills
  • Strong attention to detail
  • Ability to work individually or as part of a team
  • Willingness to wear multiple hats when necessary



We have great benefits:

  • Medical
  • Dental
  • Vision
  • 401k match
  • Kashable
  • Figo Pet Insurance

We have great perks in each of our offices, along with a fun, energetic and fast-paced environment, and what will really drive you is our vision. Maestro Health is making employee health & benefits people-friendly again by making healthcare easy to understand, tools easy to use, and costs easy to control. We are aiming to become a household name within the employee health & benefits space.

We can’t do that without great people. We want to hear “WOW! That was the best job and business experience I ever had!” from every Maestronite – past, present, and future. You should be personally challenged, laugh, work your tail off and look forward to coming to work.

Maestro Health is an equal opportunity workplace.  We are committed to equal opportunity regardless of race, color, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, or veteran status.

Are you ready to become a Maestronite? Let’s do this.