Executive Assistant

What’s Up? 

Upfront Healthcare is driven to help every patient get the care they need. We are a high growth Chicago based healthcare technology firm, and we are seeking an exceptional Executive Assistant to strengthen our efficiency.  This role will contribute to the overall effectiveness of our organization by directly supporting our CEO and by providing a range of coordination and support functions to the organization. This role represents a unique opportunity for a highly-motivated individual to assume a wide set of responsibilities and make a significant impact in a fast-paced, entrepreneurial environment.

Why Now? 

What we are doing is working, and we are growing fast!  Through Upfront, patients are engaging and booking necessary care (like COVID Vaccines!) at rates 5 – 10x beyond industry benchmarks and platform utilization is growing rapidly as new products are in the pipeline.  So why now?  We just closed our Series B financing to accelerate our growth, so our product, sales funnel, team and client list are growing.  It is time to create scalable processes to prepare the Company and better support our CEO for this next phase of growth.

Who Are You? 

You are extremely organized and detailed oriented and enjoy using those skills to benefit others. You love to get things done; you like to move fast, but you are flexible because, well, things change fast! You are highly collaborative, love being a key part of a growing team and solving challenges together. You like numbers and while you might lack formal accounting training you aren’t shy to try new things.


  • Provide support to our CEO through extensive calendar management, meeting coordination and travel planning
  • Work closely with the VP of Finance on key accounting processes such as:
    • Code cash and credit card transactions within accounting system
    • Prepare weekly cash reports for management review
    • Reconcile banking and credit card statements for management review
    • Submit and reconcile expense reports
    • Assist with Accounts Payable and Accounts Receivable management
  • Support human resources initiatives including recruiting coordination, on-boarding coordination, and implementation of a performance management program
  • Other responsibilities as assigned


  • At least three years of experience as an executive assistant to top level of management
  • Excellent written and verbal communication skills including strong e-mail etiquette
  • Utmost attention to detail, and timely follow up
  • High degree of maturity with a proven ability to interact with management, team members and external partners
  • Dedication to push things forward throughout the organization —- anticipating needs, troubleshooting issues and responding proactively and calmly under pressure
  • Ability to successfully work in a small, collaborative team environment
  • Fast learner interested in improving processes
  • Fluent in Microsoft Office Suite with strong Excel, PowerPoint and Outlook skills
  • Basic knowledge of accounting and/or finance
  • PLUS: Proficiency in QuickBooks Online
  • PLUS: Proficiency in Microsoft Sharepoint and Teams

Email your resume to [email protected]