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Chief of Staff

Chicago, IL
Aug 28, 2022
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Apply before: 
Sep 27, 2022

Monica + Andy is looking for a highly motivated and analytically-minded Chief of Staff to act as right hand to our CEO, Monica Royer. As Chief of Staff, this individual will act as part strategic advisor, part project manager, and part internal communicator. The Chief of Staff will have direct exposure to the Executive team as well as the Board of Directors, and will help shape the strategic direction of Monica + Andy as we move into our next stage of growth.

Who we are

Monica + Andy exists to personalize shopping for moms (and all parents!) by creating joyful experiences and products without compromise. We produce baby and children’s clothing using the softest, safest GOTS certified organic fabrics, and we create and deliver experiences and classes at our various Guideshop locations. We’re committed to helping moms and moms-to-be find their voices and feel confident and supported in their choices because we understand there is no one-size-fits-all approach to motherhood.

M+A’s Core Values:

  1. Self-awareness 2) Empathy 3) Intellectual Honesty 4) Positive Energy 5) Judgment

The Chief of Staff role

The Chief of Staff to the CEO will collaborate with the CEO and management team members to determine, prioritize, and execute on business needs, serving as a trusted liaison for the CEO. The Chief of Staff will be centrally involved in setting and communicating operational and strategic priorities from the CEO, tracking and reporting on progress to key stakeholders (including CEO, management team, Board, etc.). The Chief of Staff will additionally manage coordination of meeting content and follow-ups.

The Chief of Staff to the CEO will:

  • Create presentations and models with and on behalf of the CEO
  • Evaluate Monica + Andy priorities on an ongoing basis, organizing information and decision making processes to facilitate alignment from the CEO and management team
  • Manage and execute on special projects as designated by the CEO
  • Provide a strategic point of view and recommendations to executive leadership team
  • Anticipate potential issues and proactively address them on behalf of the CEO
  • Assist with the hiring process for key positions
  • Act as the main liaison between the CEO and internal and external stakeholders
  • Support the CEO and COO in preparation of board and additional stakeholder presentations
  • Support the CEO in maintaining positive investor relationships and conductive proactive potential investor outreach
  • Identify and implement tools and systems as needed to drive greater structure to scale the business
  • Oversee daily meetings and operations:
  • Track and prioritize CEO task list; review at the end of each business day
  • Liaise with the Executive Assistant to ensure meetings and follow-ups are complete
  • Set agendas / keeping contents of meeting(s) focused
  • Field and draft outreach / communications

Candidate Qualifications

● 2-3 years of experience in management consulting is required

● Commitment to in-person work in Chicago

● Experience translating data into strategic recommendations

● A natural ability to collaborate well with others across the organization and thrive in a fast-paced and highly-fluid environment; highly organized and comfortable managing multiple work streams

● Detail-oriented and takes pride in producing exceptional deliverables

● Hardworking attitude with a “no task is too small” approach

● Ability to operate well in ambiguous situations with limited resources and to successfully execute plans despite roadblocks

● Excellent verbal and written communicator; strong Excel and PowerPoint skills

● Great attention to detail and self motivation

What We Offer


  • Comprehensive Medical, Dental + Vision Plans
  • FSAs + HSAs
  • Life + Disability Benefits
  • EAP + Work/Life Program Services
  • 401(k) Savings Plan
  • Paid Time Off
  • Paid Sick Leave
  • Generous Parental Leave
  • Legal + Identity Protection Plans
  • Pet Discount Plans
  • Auto + Home Insurance


  • Employee Discounts
  • Generous Paid Company Holidays

Monica + Andy is an equal opportunity employer and makes employment decisions on the basis of merit. Monica + Andy policy prohibits unlawful discrimination based on race, color, religious creed, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy, or any other consideration made unlawful by federal, state, or local laws. It also prohibits discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful.

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