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Maestro Health is seeking an experienced Senior Financial and Operational Analyst to assist with a variety of tasks focused on internal reporting and analysis of company performance along with building a financial forecast and operational model.

Working directly with Maestro Health’s CFO and executive management team, the Senior Financial and Operational Analyst will play a key role in the growth and evolution of the company, while learning firsthand how the finance function influences the operation of the business.  This individual will influence and impact our rapidly growing organization by spearheading financial forecasting, budgeting process, operational modeling and operating plan variance analysis.

You will be expected to:

  • Create financial and operational models for senior management
  • Monitor and analyze current and past trends in operational and financial performance metrics, highlighting trends and analyzing causes of unexpected variance(s)
  • Lead company-wide financial planning and forecasting efforts and create efficiencies in these processes.
  • Develop financial models and analyses to support strategic initiatives including new product development, working directly with senior members of the executive management team
  • Develop and refine various reporting templates and financial models; conduct scenario analysis
  • Prepare presentations to the Board of Directors and senior management
  • Oversee the company’s reporting function, ensuring that all internal and external end users receive the reports they need on a regular basis
  • Obtain agreement across key stakeholders on the reports needed by each internal and external end user, develop detailed reporting requirements for each end user report, and work with information technology staff to design each end user report
  • Ensure reports are accurate, high-quality and utilized by end users, updating data collection, report processes, report formatting and report delivery mechanisms as necessary
  • Conduct ad hoc reporting and analysis as requested by senior management team – this includes analysis of existing operations, prospective acquisitions, customer profitability, product profitability, etc.


Desired Skills and Experience

 The Senior Financial and Operational Analyst position requires the following qualifications:

  • 2 - 3 or more years’ experience in a financial, operational or business analyst role
  • Investment banking, private equity, venture capital or consulting experience strongly preferred
  • Results oriented self-starter, who can build positive and productive relationships, have professionalism, practical judgment and integrity
  • Power user of Excel with ability and desire to learn new applications, Strong project management skills including the ability to concurrently drive multiple initiatives and keep to deadlines
  • Advanced analytical/quantitative skills; comfortable working with large sets of data
  • Experience developing budgets, forecasts, scenarios and sensitivity analysis
  • Highest standards of accuracy and precision; highly organized
  • Articulate, with excellent verbal and written communication skills
  • Ability to think creatively, highly-driven and self-motivated
  • Demonstrated ability to roll up sleeves and work with team members
  • Possess high energy levels with willingness to do what it takes to get the job done


“Human” Skills:

Culture is really important to us. We are fast-moving, driven, fun, hard-working, creative, “anti- 9-5 mentality” people, and we are looking for someone who is passionate about joining this type of team and environment.    

The right cultural fit is someone youthful (we don’t mean age, but in spirit) and vibrant who works well in a fast-paced environment; has the experience to hit the ground running and the ability to work quickly.

You will be working with an energetic, passionate team, innovating ways to make the employee benefits experience “people-friendly” again. 


Location:   Chicago office (steps to both Union and Ogilvie train stations)



  • Robust employer-subsidized health benefits program
  • Employer paid life, AD&D, and long-term disability insurance
  • 401k matching
  • Collaborative environment and enjoyable atmosphere
  • Refrigerator full of drinks and healthy snacks
  • Chicago subsidized gym membership (wellness program)
  • Relaxed work/life balance with paid time off/vacation